Category: 456-12-2

Nerdel, Friedrich; John, Ute published an article in 1956, the title of the article was Hydratropic acids. V. Optically active m- and p-substituted homohydratropic acids.Product Details of 456-12-2 And the article contains the following content:

cf. C.A. 49, 13938c. Methylation of p-O2NC6H4CH2CHMeCO2H (I) with CH2N2 in EtOH yields 93% Me ester, b0.002 90°, m. 57° (amide, needles, m. 116°). I (60 g.) in 100 cc. (Me2CH)2O with 50 g. (+)-bornylamine (II) in 50 cc. (Me2CH)2O yields almost 100% II salt, m. 161-3°, [α]D20 11°, which, on fractional crystallization from C6H6 gives 38 g. (-)-salt, m. 168-9°, [α]D20 -3.5°; decomposition of the latter yields (-)-I, needles, m. 107°, [α]D20 -32.4° (EtOH) [Me ester, sirup, [α]D20 -49.1° (EtOH); amide, m. 112-13°, [α]D20 -60.5° (EtOH)]. m-O2NC6H4CH2CHMeCO2Me b0.05 100° (amide, small needles, m. 113°). m-O2NC6H4CH2CHMeCO2H (III) (95 g.) with 65 g. II gives the II salt, m. 144-6° [α]D20 13.4°, which, fractionally crystallized from C6H6, yields 50 g. II salt of (-)-III, m. 159-60°, [α]D20 0°; free (-)-III, m. 69-70°, [α]D20 -24°; quinine salt, m. 83-5°, does not change the rotation; Me ester, b0.001 85°, [α]D20 -40.1°; amide, needles, m. 135°, [α]D20 -61.6°. Reduction of 6.3 g. I in 75 cc. EtOH 20 min. with 0.2 g. PtO2 yields the p-NH2 acid (IV).HCl, pale yellow needles, m. 191° (decomposition); free IV, needles, m. 126°. Reduction of (-)-I in the same way yields (-)-IV, m. 191° (decomposition), [α]D20 -46° (H2O); N-Ac derivative of (-)-IV, prisms, m. 129°, [α]D20 -22.4° (EtOH). Reduction of III with PtO2 in EtOH gives m-H2NC6H4CH2CHMeCO2H (V), m. 99°. Hydrogenation of m-O2NC6H4CH:CMeCO2H gives, after 3 moles H are absorbed, m-H2NC6H4CH:CMeCO2H, m. 137°; further hydrogenation yields V. (-)-V, m. 94°, [α]D20 -14.3°; HCl salt, m. 136°, [α]D20 -42.8°. N-Ac derivative of V, prisms, m. 137°; N-Ac derivative of (-)-V, prisms, m. 123°, [α]D20 -21° (EtOH). Diazotizing IV.HCl at 0° and heating the diazonium solution at 50° give p-HOC6H4CH2CHMeCO2H (VI), needles, m. 102° (-)-VI, m. 99°, [α]D20 -18.5° (EtOH). m-HOC6H4CH2CHMeCO2H (VII) is an oil; (-)-VII, needles, m. 98°, [α]D20 -15.2° (EtOH). Diazotizing a 54% optically pure (-)-IV and heating the diazonium solution with CuH2 yield (-)-PhCH2CHMeCO2H, [α]D20 -14°, corresponding to an [α]D20 of -26° for the optically pure acid. Hydrogenating PhCH:CMeCO2H with NaHg and resolving the acid with quinine yield a quinine salt, m. 122°, [α]D20 116.2°; free (+)-acid, [α]D20 22.9°, d20 1.062; Me ester, b22 230°, d22 1.017, [α]D20 30.1°; (+)-amide, needles, m. 115°. The rotation dispersion of the substituted homohydratropic acids, their esters, and amides are listed in tables and show that the rotation direction is not changed by the entrance of m- and p-substituents. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Product Details of 456-12-2

N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas:456-12-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Product Details of 456-12-2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Chakravarti, R. N.; Dasgupta, B. published an article in 1958, the title of the article was Structure of aegelin.Recommanded Product: N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide And the article contains the following content:

cf. C.A. 50, 11281h. Air-dried powd. young leaves (14 kg.) of Aegle marmelos (May-Aug. crop) repeatedly extracted with cold 90% alc. and the extract mixed with filter paper pulp, dried at 80° and extracted 80 hrs. with Et2O, the extract evaporated to 1.5 l. and kept at 0° 1 week, filtered and the product washed with Et2O, crystallized from EtOAc and EtOH-Me2CO and the crystalline product filtered in alc. through Al2O3, the filtrate evaporated and the residue crystallized (alc.) gave 0.15-0.20% aegelin (I), C18H19NO3, m. 178-9°, evolving little H2Se on heating with Se (cf. Chatterjee and Bose, C.A. 47, 10544g), λ 212, 219, 275 mμ (log ε 4.36, 4.36, 4.42) similar to that of trans-PhCH:CHCONHMe, λ 218, 270 mμ (log ε 4.18, 4.39); acetate, m. 123-5°; benzoate, m. 147-8°. I (0.5 g.) in 25 ml. AcOH shaken 4 hrs. at 30° with portionwise addition of 0.2 g. CrO3 and excess AcOH evaporated in vacuo, the residue diluted with H2O and the mixture filtered, gave 0.35 g. aegelone (II), C18H17 159-60° (alc.), λ 280 mμ (log ε 4.67), reducing hot AgNO3NH4OH solution in 1 min., no reaction with Angeli-Rimini or Schiff reagents; semicarbazone, m. 234-5°. I (0.5 g.) hydrogenated 15 min. in 25 ml. AcOH with 50 mg. prereduced PtO2 at 30°/760 mm. and the filtered solution evaporated in vacuo, the residue taken up in H2O and filtered gave 0.33 g. dihydroaegelin (III), m. 140-1° (alc.), similar to I in not reducing AgNO3-NH4OH on heating several min. at 100°, oxidized by CrO3 to the corresponding dihydroaegelone (IV), m. 126-7° (alc.), reducing AgNO3-NH4OH solution; semicarbazone, m. 138-40°. IV was also obtained by partial hydrogenation of 0.5 g. II in 20 ml. AcOH with 50 mg. prereduced PtO2. IV (0.5 g.) in 25 ml. AcOH hydrogenated 30 min. by shaking with 50 mg. prereduced PtO2 and the filtered solution evaporated in vacuo gave III. I (1 g.) in 10 ml. boiling H2O treated portionwise with 4 g. KMnO4 and 0.5 g. KOH in 100 ml. H2O and excess KMnO4 decomposed with MeOH, the solution filtered and concentrated to 20 ml., the cooled concentrate acidified with HCl, and the precipitate (0.4 g.) repeatedly crystallized (hot H2O) gave p-anisic acid, m. 183-4°, and BzOH. Oxidation of I under similar conditions and distillation gave BzH, converted to 60 mg. 2,4-(O2N)2C6H3NHN:CHPh. I (2 g.) refluxed 8 hrs. with 72 ml. 90% alc. and 12 ml. concentrated HCl and the solution steam distilled, the 2nd fraction of the distillate extracted with Et2O and the extract washed with aqueous NaHCO3 and H2O, the dried extract evaporated and the oil (0.427 g.) warmed 0.5 hr. with aqueous H2NNHCONH2.HCl and NaOAc in a min. of alc., kept overnight and decanted, the product washed with H2O and Et2O and the crystalline residue (45 mg.) crystallized (alc.) gave p-MeOC6H4CH:NNHCONH2, m. 203-4°. The oil from the Et2O washings hydrolyzed with 10% alc. KOH and the alc. evaporated, the aqueous solution acidified with HCl and the product crystallized (hot H2O) gave trans-PhCH:CHCO2H (V). The distillation residue steam distilled and extracted with Et2O (extract A) and the aqueous layer (solution B) basified with evolution of NH3, extracted with Et2O and the product (basic crystals) acidified and treated with Meyer reagent gave a creamy precipitate The presence of NH3 in the hydrolysis products of I was confirmed by evaporating solution B to dryness and heating the residue with alkali, adsorbing the evolved gas in alc. and treating the solution with 1,2,4-ClC6H3(NO2)2. Extract A extracted with aqueous NaHCO3 and the extract acidified with HCl gave 0.32 g. V. Hydrogenation of 1.3 g. p-MeC6H4COCN in 15 ml. AcOH 20 min. with 0.1 g. prereduced PtO2 at 30°/760 mm., the dark brown filtered solution treated with 0.46 ml. concentrated H2SO4 and diluted with Et2O gave 1.3 g. p-MeOC6H4COCH2NH2.H2SO4 (VI), m. 167-8° (AcOH) (cf. Kindler and Peschke, C.A. 26, 3785). VI (0.3 g.) and 0.3 ml. trans-PhCH:CHCOCl stirred with gradual addition of 10% NaOH to appearance of pink coloration, the solution stirred with 0.2 ml. trans-PhCH:CHCOCl and the colorless solution made alk. gave 0.2 g. p-MeOC6H4COCH2NHCOCH:CHPh, m. 156-60° (cf. Lister and Robinson, C.A. 7, 326), identical with II, and dehydrated with concentrated H2SO4 to 5-p-methoxyphenyl-2-styryloxazole, showing intense blue fluorescence in solution VI (0.3 g.) and 0.3 ml. PhCH2CH2COCl stirred with cooling with 10% NaOH and the brick-red product crystallized (alc.) gave 0.2 g. p-MeOC6H4COCH2NHCOCH2CH2Ph, m. 126-7°, identical with IV. VI (0.7 g.) in 15 ml. AcOH and 2 ml. H2O hydrogenated 45 min. at 30°/760 mm. with 50 mg. prereduced Pt2O and again hydrogenated 20 min. with 50 mg. catalyst, the filtered solution evaporated in vacuo and the residue in H2O divided, a portion condensed with 0.3 ml. PhCH:CHCOCl to give 0.15 g. I and the other portion condensed with 0.3 ml. PhCH2CH2COCl gave III. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Recommanded Product: N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide

N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas:456-12-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Recommanded Product: N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Chaudhury, N. Aditya; Chatterjee, A. published an article in 1959, the title of the article was β-Phenylethanolamines. I. New synthesis of aegeline and papaverine.Electric Literature of 456-12-2 And the article contains the following content:

cf. C.A. 52, 14630i. Substituted benzaldehyde cyanohydrins are reduced to the corresponding amines, condensed with piperonal (I), and converted to the N-Me derivatives Thus, 6 g. p-MeOC6H4CH(OH)CN in 50 cc. Et2O is added dropwise to 4 g. LiAlH4 in 200 cc. Et2O at 0°, the mixture stirred at room temperature 5-6 hrs., refluxed 4-5 hrs., the complex decomposed by addition of 5 cc. H2O, 10 cc. 20% aqueous NaOH, and 15 cc. H2O and refluxed 30 min. The solution is filtered hot, extracted with 150 cc. Et2O and β-hydroxy-β-(p-methoxyphenyl)ethylamine (II) (80%), m. 70° (C6H6-petr. ether), isolated by evaporation of the Et2O. II.HCl m. 173°. Equal moles of I and II are refluxed in 95% EtOH 1 hr. and the solvent evaporated in vacuo to give N-piperonylidene-β-hydroxy-β-(p-methoxyphenyl)ethylamine (III) (90-5%), needles, m. 115-16° (C6H6-petr. ether). III (3 g.) in 100 cc. C6H6 is refluxed with 5 cc. MeI 5-6 hrs., the sticky solid product dissolved in 20-5 cc. hot water and 2-3 cc. concentrated HCl, warmed 1 hr., extracted with Et2O, made alk. with 30% NaOH, and extracted with Et2O and then CHCl3. From the combined extracts on distillation in vacuo is obtained N-methyl-β-hydroxy-β-(p-methoxyphenyl)ethylamine (50 %); HCl salt, needles, m. 101° (Me2CO-EtOAc). From the corresponding cyanohydrins are prepared: β-hydroxy-β-(3,4-dimethoxyphenyl)ethylamine (72%), b4 180-2°; HCl salt (IV), m. 163°; its I derivative m. 129-30°; and N-methyl-β-hydroxy-β(3,4-dimethoxyphenyl)ethylamine (46%), HCl salt m. 143-5° (decomposition); also β-hydroxy-β-(3,4-methylenedioxyphenyl)ethylamine (80%), HCl salt m. 181-2°; its I derivative m. 155-6°; and N-methyl-β-hydroxy-β-(3,4-methylene-dioxyphenyl)ethylamine (50%), HCl salt m. 163-5° (decomposition). Homoveratroyl chloride (3 g.) is added to 2 g. IV in the min. amount of H2O, 1.5 g. KOH added, the mixture stirred vigorously 2 hrs., the yellow mass which separates washed with a little H2O, dissolved in the min. amount EtOH containing a few drops dilute NaOH, and allowed to stand 1 day to give 2 g. homoveratroyloxyhomoveratrylamine (V), m. 127-8° (C6H6). V (2 g.) refluxed in PhMe 5 min. with 10 g. P2O5, the PhMe decanted, the residue dissolved in ice H2O, the solution extracted with Et2O, the aqueous portion made alk. with concentrated NaOH, and the resulting emulsion kept 1 day gives 0.51 g. papaverine, m. 147° (CHCl3-petr. ether). Trans-cinnamoyl chloride (3 g.) in 15 cc. Et2O is added dropwise to 2 g. II in 50 cc. Et2O with vigorous stirring, the solution made alk. with dilute NaOH after a solid forms, and dl-trans-N-[β-hydroxy-β-(p-methoxyphenyl)]ethylcinnamide (VI) (1.2 g.), m. 177-8°, filtered, washed (H2O), and recrystallized from EtOAc. VI is identical with natural aegeline. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Electric Literature of 456-12-2

N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas:456-12-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Electric Literature of 456-12-2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Arthur, H. R.; Ng, Y. L. published an article in 1959, the title of the article was Examination of the rutaceae of Hong Kong. IV. Synthesis of dihydronitidine.Category: amides-buliding-blocks And the article contains the following content:

Dihydronitidine (I) was synthesized and the structures for nitidine (II) and oxynitidine (III) proposed in the earlier work confirmed. Acetopiperone (25 g.) and 30 g. veratraldehyde treated with 150 ml. alc. with 30 ml. 10% aqueous NaOH gave 30 g. 3,4-dimethoxy-3′,4′-methylenedioxychalcone (IV), m. 135° (alc.). IV (30 g.) in 110 ml. EtOCH2CH2OH containing 6.5 ml. AcOH treated 3 min. at 100° with 12.5 g. KCN in 45 ml. H2O, heating continued 10 min., 150 ml. H2O added, and the mixture cooled gave 30 g. α-(3,4-dimethoxyphenyl)-γ-(3,4-methylenedioxyphenyl)-α-oxobutyronitrile (V), yellow needles, m. 146° (alc.). V (30 g.) in 200 ml. AcOH treated gradually with 30 ml. concentrated H2SO4 gave 25 g. α-(3,4-dimethoxyphenyl)-γ-(3,4-methylenedioxyphenyl)-γ-oxobutyramide (VI), m. 177° (alc.). VI (25 g.) in 350 ml. 7% aqueous NaOH and 200 ml. alc. refluxed 10 hrs. and then acidified gave 22 g. α-(3,4-dimethoxyphenyl)-γ-(3,4-methylenedioxyphenyl)-γ-oxobutyric acid (VII), needles, m. 172° (alc.). VII (11 g.) in 110 ml. AcOH containing 2 ml. 70% HClO4 hydrogenated during 2 hrs. at 60°/1 atm. over 2 g. 5% Pd-C, most of the solvent removed, H2O added, the oily product extracted with C6H6, the 8 g. brown oil [α-(3,4-dimethoxyphenyl)-γ-(3,4-methylenedioxyphenyl)-butyric acid] refluxed 4 min. with 20 ml. POCl3, the mixture poured on ice, the solid dissolved in CHCl3, washed with aqueous NaOH, H2O, dried, and evaporated gave 6.5 g. 2-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydro-6,7-methylenedioxy-1-oxonaphthalene (VIII), m. 165° (alc.). VIII(6 g.) in 15 ml. HCONH2 and 0.8 ml. HCO2H heated 3 hrs. at 180° with 0.8 g. (NH4)2SO4, 0.8 ml. HCO2H added hourly, the mixture cooled, diluted with H2O, extracted with CHCl3, washed, and evaporated gave 3.5 g. 2-(3,4-dimethoxyphenyl)-1-formamido-1,2,3,4-tetrahydro-6,7-methylenedioxynaphthalene (IX), m. 178° (dioxane-alc.). IX (1.5 g.) refluxed 15 min. with 3 ml. POCl3 in 10 ml. PhMe gave a solid which suspended in MeOH and basified gave 1 g. 3,4,11,12-tetrahydro-6,7-di-methoxy-2′,3′-methylenedioxy-1,2-benzophenanthridine (X), m. 188-9° (MeOH). X (0.9 g.) heated 0.5 hr. at 240° with 0.2 g. 30% Pd-C and extracted with CHCl3 gave 0.6 g. 6,7-dimethoxy-2′,3′-methylenedioxy-1,2-benzophenanthridine (XI), m. 273° (C5H5N). XI (0.5 g.) in 5 ml. xylene and 10 ml. PhNO2 refluxed a few min. with 1 ml. Me2SO4 gave the methosulfate of XI, m. 306-7° (decomposition) (aqueous alc.). XI methosulfate (0.4 g.) in 60 ml. H2O and 4 ml. concentrated HCl refluxed 5 hrs. with 8 g. Zn powder under argon, 3 ml. more HCl added after each hr., the solution cooled to 0-5°, sealed 12 hrs. under argon, the solid washed, shaken with CHCl3 and NH3, the extract washed, dried, and evaporated gave 0.2 g. I, prisms, m. 208-11° (alc.). Simple transformations used for I led to syntheses of II and III. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Category: amides-buliding-blocks

N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas:456-12-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Category: amides-buliding-blocks

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Tian, Min; Zhou, Shenzhi; Li, Wei; Li, Jiaru; Yang, Lan; Peng, Ying; Zheng, Jiang published an article in 2021, the title of the article was Metabolic activation of aegeline mediated by CYP2C19.Name: N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide And the article contains the following content:

Aegeline (AGL) is a natural alkaloidal amide mainly isolated from the leaves and fruits of tropical plant Aegle marmelos, with multiple pharmacol. activities. As one component of several dietary supplements, AGL caused a series of acute and chronic liver injuries. Nevertheless, the mechanisms of AGL-induced hepatotoxicity remain unclear. This study was conducted to identify reactive metabolite(s), to determine related metabolic pathways, and define the possible association of the bioactivation with AGL cytotoxicity. A demethylation metabolite (M1) and a GSH conjugate (M2) were detected in rat liver microsomal incubations containing AGL and GSH. The two metabolites were both found in bile of rats and rat primary hepatocytes after AGL administration. Recombinant P 450 enzyme incubations showed that CYP2C19 was the principal enzyme catalyzing this metabolic activation. Ticlopidine, a selective inhibitor of CYP2C19, decreased the formation of M1 and M2 in hepatocytes and attenuated the susceptibility of hepatocytes to the cytotoxicity of AGL. The results suggest that AGL was metabolized to a p-quinone methide intermediate which could in part participate in AGL-induced cytotoxicity. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Name: N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide

The Article related to aegeline cytochrome p metabolic activation, aegeline, cyp2c19, cytotoxicity, metabolic activation, quinone methide intermediate, Placeholder for records without volume info and other aspects.Name: N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Chatterjee, Asima; Bose, Sukumar published an article in 1952, the title of the article was The active principles of the leaves of Aegle marmelos.Recommanded Product: N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide And the article contains the following content:

cf. C.A. 43, 2993g. From the leaves of Aegle marmelos have been isolated skimmianine (I) and a sterol, aegelin (II), C18H18O4. I is characterized by the preparation of 7 salts and by its ultraviolet absorption spectrum. II from EtOAc, then Me2CO or EtOH, m. 174-5°. It gives a yellow Liebermann-Burchard test, a yellow-to-pink Salkowsky test, and a red Lifschütz test. II with Ac2O-pyridine gives a mono-Ac derivative m. 159-60°. Se dehydrogenation of II gives no identifiable product. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Recommanded Product: N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide

N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas:456-12-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Recommanded Product: N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Chatterjee, Asima; Chaudhuri, Narayan Aditya published an article in 1957, the title of the article was New synthesis of β-hydroxy-β-(p-methoxyphenyl)ethylamine and aegelin, the alkaloid of Aegle marmelos correa.Recommanded Product: N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide And the article contains the following content:

KCN and HCl (sp. gr. 1.85) added alternately in small quantities to anisaldehyde cooled in a freezing mixture gave anisaldehyde cyanohydrin (I), m. 67°. I was smoothly reduced by LiAlH4 (65% yield) to DL-β-hydroxy-β-(p-methoxyphenyl)ethylamine (II). Dry HCl gas added to II dissolved in Et2O gave II.HCl, m. 172-3°. An ethereal solution of II added to an ethereal solution of trans-cinnamoyl chloride (III) gave DL-trans-N-[β-hydroxy-β-(p-methoxyphenyl)] ethyl cinnamide (IV), m. 178-9°, identical with aegelin; this was confirmed by infrared spectra and Rf values. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Recommanded Product: N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide

N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas:456-12-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Recommanded Product: N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Conroy, Harold; Bernasconi, Raymond; Brook, Peter R.; Ikan, Raphael; Kurtz, Roberta; Robinson, Keith W. published an article in 1960, the title of the article was Structure of echitamine.Related Products of 456-12-2 And the article contains the following content:

Accumulated data favor formulation of echitamine (I) in compatability with the theory of alkaloid biogenesis and in close resemblance to intermediates of the strychnine-vomicine group. Echitamine chloride (II), C22H29ClN2O4, ν 1740, shows no infrared N+-H peak and no :C:N+: absorption at 1680 cm.-1 The aqueous solution is neutral, apparent pKa 11, and treatment with aqueous NaOH gives I, C22H28N2O4, readily crystallized as the C6H6 solvate, m. 139-40° (transition at 98-101°). The 60 Mc. high resolution nuclear magnetic resonance (n.m.r.) spectrum gives intense singlets at τ 6.30, 7.76 for O-Me and N-Me, indicating that I is not a quaternary ammonium hydroxide; a doublet at τ 8.39 for allylic C-Me; a 1,3,3,1 sym. quartet at τ 4.56 for the olefinic proton; and a one-proton singlet near τ 5.1 ascribed to a single OH group. Formation of I α-methiodide, m. 226-9° (decomposition) (absolute alc.), with 2 N-Me groups indicates normal behavior as a tertiary base. The reconversion of I to II is sufficiently slow at 25° so that titration of I gives a pKa 7.8 in 60% aqueous alc. and this hysteresis is well accommodated by the equilibrium I ⇌ II. II treated with Me3COK in absolute Me3COH yields alloechitamine (III), C21H26NO3, m. 191° (MeOH), ν 1736, 1689 cm.-1, n.m.r, spectra showing presence of O-Me, N-Me, and MeCH: groups; MeI salt, showing loss of 1689 cm.-1 peak due to transannular interaction. I in alc. hydrogenated with Pt gives a high yield of echitinolide (IV), C21H26N2O3, m. 140-4° (Et2O), m. 154-7° (C6H6), pKa, 5.4 (60% alc.), n.m.r. τ 7.53 (singlet, N-Me), 7.76 (singlet, C-Me), 8.48 (doublet, C-Me), ν 1742 cm.-1; O-monoacetate, m. 210-14°, 1754 cm.-1 IV heated with HCl gives an isomer, isoechitinolide (V), m. 149-54° (Et2O), ν 1754 cm.-1 I and II show almost identical ultraviolet absorption [λ 235, 295 mμ (log ε 3.93, 3.55)], even in strongly alk. solution IV and V absorb at longer wave lengths [λ 248, 309 mμ (log ε 3.91, 3.55)] but acidification causes downward displacement. All compounds with low wave length absorption have Na equatorial with respect to the C carbocyclic six-membered ring, whereas absorption above 240 mμ (and 300 mμ) can be consistently related with structures in which Na has axial conformation. The Hofmann degradation of IV MeI salt gives the methine, C22H30N2O4, reduced by Zn-HCl to the lactone, deoxyneodihydroechitamine methine, λ247, 307 mμ (log ε 3.97, 3.59), unchanged in acidic solution The Zn dust and Se degradations leading to echitamyrine and dimethylpyrrolo-2′,3′;3,4-quinoline might proceed through the intermediate (VI) which could arise from the iminium cation of IV by 1,2 migration of the indoline α-C. It is suggested that the specific biogenetic derivation of I involves the precursor (VII) in Mannich cyclization. (CA 53, 22033i). A close relation to the quaternary alkaloid C-fluorocurarine is apparent, and the noncyclized system retaining the CO2H residue is present in corynoxeine and rhyncophylline. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Related Products of 456-12-2

N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas:456-12-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Related Products of 456-12-2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Chatterjee, A.; Bose, S.; Srimany, S. K. published an article in 1959, the title of the article was Constitution, stereochemistry, and synthesis of aegeline, an alkaloidal amide of Aegle marmelos.Synthetic Route of 456-12-2 And the article contains the following content:

cf. CA 47, 10544g. Aegeline (I), C18H19NO3, was shown to be N-β-hydroxy-β-p-methoxyphenylethylcinnamamide by degradation and synthesis and its trans configuration established spectrometrically. Powd. sun-dried leaves of A. marmelos (5 kg.) extracted 72 hrs. with 8 l. Et2O and the deep green extract concentrated to 500 ml., washed with 1% HCl and 5% aqueous NaOH and the dried concentrate refrigerated 2 weeks, the precipitate (3.6 g.) triturated with C6H6 and Me2CO and the residue crystallized from alc. gave I, m. 173-5°. The mother liquors evaporated and the residue chromatographed in C6H6 on 4 kg. Al2O3, the column eluted with 200 ml. EtOAc and the fraction (2.4 g.) recrystallized (alc. and EtOAc) yielded pure I, m. 176°; mono-Ac derivative, m. 124°. I (0.3 g.) in 30 ml. aldehyde-free alc. hydrogenated 2 hrs. with 0.09 g. prereduced PtO2 and the filtered solution evaporated gave dihydroaegeline, C18H21NO3, m. 140° (alc. and EtOAc). I (0.25 g.) in 10 ml. EtOAc and 2 ml. AcOH ozonized 50 min. at -75° and the ozonide decomposed reductively overnight with 0.5 g. Mg powder in 10 ml. 1:1 AcOH-H2O, the mixture diluted with 50 ml. H2O and shaken 3 times with 30 ml. CHCl3, the organic layer washed twice with 2N HCl and once with H2O and the dried (anhydrous Na2SO4) solution evaporated (N atm.), the residual oil taken up in 2 ml. alc. and treated 40 hrs. with Brady’s reagent, the precipitate taken up in 1:1 C6H6-AcOEt and chromatographed over Al2O3, eluted with C6H6 and the fraction recrystallized 3 times from alc. gave authentic 2,4-(O2N)2C6H3NHN:CHPh (II), m. 235°. I (0.15 g.) in 150 ml. MeOH treated 4 hrs. with 2 g. HIO4 and the mixture steam-distilled, the distillate (800 ml.) extracted 4 times with 250 ml. Et2O and the extract washed with aqueous NaHSO3, the iodine-free extract evaporated and the residue treated with 2,4-(O2N)2C6H3NHNH2, the precipitate (m. 225-47°) chromatographed in 15 ml. 1:1 C6H6-EtOAc over Al2O3 and eluted with 45 ml. C6H6 yielded 80 mg. II. Further elution with 30 ml. EtOAc gave 40 mg. 2,4-(O2N)2C6H3NHN:CHC6H4OMe-p (III), m. 250°. I (0.5 g.) in 5 ml. alc. and 5 ml. concentrated HCl heated 60 hrs. in a sealed tube at 120° (oil bath) and the cooled mixture diluted with 50 ml. H2O, extracted 3 times with 100 ml. Et2O and the aqueous phase evaporated, the residue decomposed with alkali and the evolved gas adsorbed in 10 ml. 2N aqueous HCl, the solution evaporated and the residue taken up in 1 ml. H2O, treated with a few drops of aqueous picric acid gave H2NMe picrate, m. 209°. The H2O-washed Et2O layer shaken with aqueous NaHCO3 and the alk. solution acidified with HCl gave 0.159 g. PhCH:CHCO2H. The acid-free Et2O evaporated and the residue taken up in 3 ml. alc., the solution treated with 2,4-(O2N)2C6H3NHNH2 and the precipitate (60 mg.) chromatographed in 10 ml. EtOAc over Al2O3 and eluted with 45 ml. C6H6 and 30 ml. EtOAc gave III from the latter eluant. I (1 g.) fused 30 min. with 6.0 g. KOH in a Ni crucible at 250° with evolution of MeNH2 and the cooled mass digested in 200 ml. H2O containing 10.0 g. NH4Cl, the filtered solution shaken 5 times with 100 ml. Et2O and the cooled aqueous solution acidified with HCl, extracted 3 times with 100 ml. Et2O and the washed and dried extract evaporated gave a mixture of 30 mg. p-MeOC6H4CO2H and 170 mg. BzOH. The probability that I suffered hydramine fission and that the basic fragment was a p-MeOC6H4CH(OH)CH2NH2 derivative was finally substantiated by a simple straight forward synthesis. Prolonged hydrolysis of ω-phthalimido-p-methoxyacetophenone with refluxing concentrated HCl gave p-MeOC6H4COCH2NH2.HCl, taken up (1 g.) in 3 ml. H2O and treated with 3 ml. aqueous solution of 1.24 g. SnCl4.4H2O containing 1 ml. HCl, the mixture stirred and the crystalline precipitate (2.0 g.) taken up in 20 ml. hot H2O, the solution cooled to 37° and stirred with 2.0 g. molten PhCH:CHCOCl, the mixture treated dropwise with 25 ml. 10% aqueous KOH until red and the stirring continued until the solution became colorless, the addition of alkali resumed and the alternate process continued until the red coloration persisted, the pyrazine-free solution stored 2 hrs. and the H2O-washed crystals recrystallized (EtOAc), gave ω-cinnamoylamino-p-methoxyacetophenone, m. 153-4°. The ketone (0.5 g.) in 50 ml. MeOH treated with 5.0 g. NaBH4 and the mixture kept 24 hrs., the solution concentrated and diluted with 100 ml. H2O, extracted 3 times with 200 ml. Et2O and the washed and dried extract evaporated yielded 60% authentic I, m. 176° (EtOAc). The absorption maximum λ 217, 223, 275 mμ (log ε 4.5328, 4.5177, 4.6053) were indicative of a trans double bond to the carboxyamide group and this assignment was in agreement with the strong absorption in the infrared spectrum at “trans-band region” (intense band at 982 cm.-1 with a shoulder at 990 cm.-1). Comparative data for other trans α,β-unsaturated amides were tabulated (compound and ν in cm.-1 given): I, 3250, 3060, 2830, 1665, 1627, 1580, 1520, 1062, 1040, 990, 982; trans-N-2-p-methoxyphenylethyl-N-methylcinnamamide, 1655, 1610, 1576, 1509, 1036, 1027, 991, 982; trans-N-methylcinnamamide, 3280, 3100, 2860, 1660, 1625, 1580, 1500, 953. I contained an asym. C atom but was optically inactive and it seemed that the linkage of the trans-cinnamoyl group to the optically active N-β-hydroxy-β-p-methoxyphenylethylamine caused an inversion at the asym. center. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Synthetic Route of 456-12-2

N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas:456-12-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Synthetic Route of 456-12-2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Martin, R. Bruce; Edsall, John T.; Wetlaufer, Donald B.; Hollingworth, Barbara R. published an article in 1958, the title of the article was A complete ionization scheme for tyrosine and the ionization constants of some tyrosine derivatives.Application of 456-12-2 And the article contains the following content:

cf. preceding abstract Each of the 3 ionizing groups in the tyrosine mol. is characterized by 4 acidic constants (microconsts.) since the tendency of each group to accept or donate a proton depends upon the state of charge on the other 2 groups. Values for these 12 microconsts. were obtained for different ionic strengths, from spectrophotometric measurements at different pH values, from studies on the ionization of tyrosine derivatives, and from math. relations between the constants From the charge interactions between the NH4 and phenolic groups, a distance of 7.0 A. between the groups is calculated, by use of an ellipsoidal model of the type proposed by Kirkwood and Westheimer (C.A. 32, 82449). The distance between the carboxyl and phenolic protons was calculated to be 7.7 A. in the same manner. These values are compatible with those derived from mol. models, with the use of correct interatom. distances and bond angles. Tyrosine (10 g.) dissolved in about 300 ml. absolute MeOH with just enough 40% alc. NaOH, the mixture treated with about 30 ml. Mel, warmed in the dark, the precipitate dissolved by addition of just enough 40% alc. NaOH, the mixture held 2 hrs., cooled, filtered, the precipitate dissolved in H2O, adsorbed on Dowex 50-X8 (H), eluted with N NH4OH, evaporated to dryness, the residue in H2O adsorbed on Dowex 1-X8 (OH), eluted with 0.5N AcOH, the acetate salt evaporated to dryness, exchanged changed on Dowex 50, and the solution taken to dryness yielded N-trimethyltyrosine (I), m. approx. 260° (decomposition). pK values are reported for I, O-methyltyrosine, tyrosine Et ester, O-methyltyrosine Et ester, and tyrosinamide. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Application of 456-12-2

N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas:456-12-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Application of 456-12-2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics