Tag: M.W=200-250

Wu, Y.-Q. published the artcileCyanogen halides, cyanates and their sulfur, selenium, and tellurium analogues, sulfinyl and sulfonyl cyanides, cyanamides, and phosphaalkynes, Related Products of amides-buliding-blocks, the publication is Science of Synthesis (2005), 17-63, database is CAplus.

A review of the preparation of cyanogen halides and cyanates as well as their application to organic synthesis. Sulfur, selenium, and tellurium analogs, sulfinyl and sulfonyl cyanides, cyanamides, and phosphaalkynes are included.

Science of Synthesis published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C9H9F5Si, Related Products of amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Birkofer, Leonhard published the artcileRegularities in the hydrogenative fission of N-benzyl compounds, Recommanded Product: N,N-Dibenzylcyanamide, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1942), 429-41, database is CAplus.

Because of the value of the preparative method of the catalytic removal of the N-CH₂Ph group, a study has been made of the influence of the residue on the N atom upon catalytic debenzylation. All hydrogenations were carried out at room temperature and atm. pressure in EtOH or AcOH, using PdO or PtO₂ as catalyst. PhCH₂NH₂, (PhCH₂)₂NH and PhCH₂NHMe are unchanged in the presence of PdO. (PhCH₂)₃N in AcOH (PdO) or its HCl salt in H₂O (PdO) gives 97% of (PhCH₂)₂NH.HCl; the amine is not reduced by Na and EtOH. Methylcetylbenzylamine in AcOH (PdO) gives 92% of cetylmethylamine-HCl and lauryldibenzylamine gives laurylmethylamine. Dodecyldibenzylamine in AcOH (PtO₂) gives 84% of dodecylhexahydrobenzylamine-HCl, m. 218°. (PhCH₂)₂NNH₂ in absolute EtOH (PdO) yields 88% of PhCH₂NHNH₂; tetrabenzyltetrazene [(PhCH₂)₂NN:]₂ gives (PhCH₂)₂NH. (PhCH₂)₃MeNOH with PdO in EtOH readily yields PhCH₂NHMe (flavianate, m. 190°; picrolonate, m. 210°), whereas (PhCH₂)₃MeNI is not reduced. PhCH₂NPhMe₂Cl gives 90% of cyclohexyldimethylamine. 2-Benzyldihydroisoindole in EtOH (PdO) yields 75% of 1,3-dihydroisoindole, b₃ 100°. 1,4-Dibenzylpiperazine in AcOH (PdO) gives 92% of piperazine diacetate, m. 234°. α-Monobenzylaminotetrazole gives aminotetrazole. PhCH₂NH₂ (1 mol.) in AcOEt is treated with a concentrated aqueous solution of 4 mols. of KCN and then dropwise with 1.1 mols. of Br in AcOEt at 5-10°, and the AcOEt solution shaken with 30% NaOH; the alkali removes the benzylcyanamide, which is polymerized to tribenzylisomelamine (1,3,5-tribenzyl-2,4,6-triimino-1,3,5-triazine) (I), m. 129-30°; short heating with HCl gives NH₃; with H and PdO in EtOH this yields melamine. The elimination of PhCH₂ from 2-imino-1-benzyl-1,2-dihydropyridine is slow and incomplete and is accompanied by nuclear hydrogenation, the products being 2-amino-3,4,5,6-tetrahydropyridine and 2-imino-1-benzylpiperidine (picrate, m. 106°). 2-Benzylaminopyridine does not lose PhCH₂ but is hydrogenated to 2-benzylamino-3,4,5,6-tetrahydropyridine, m. 40-1° (picrate, yellow, m. 131°; picrolonate, yellow, m. 199°). Aromatic rings, CO₂H and CN groups activate the compounds so that PhCH₂ is removed from a sec-N atom. PhNHCH₂Ph in EtOH (PdO) gives 97.5% of PhNH₂ and PhMe, whereas PtO₂ gives mainly cyclohexylhexahydrobenzylamine and small amounts of cyclohexylamine and hexahydrotoluene. PhN(CH₂Ph)₂ with PdO in EtOH gives 89% of PhNH₂ and PhMe. 2-(Dibenzylamino)naphthalene in AcOH (PdO) gives 88% of 2-C₁₀H₇NH₂ and PhMe. ClCH₂CO₂H (9 g.) and 40 g. (PhCH₂)₂NH in 20 cc. dioxane, heated 5 h. at 120°, give 82% of N,N-dibenzylglycocoll, m. 200°; Me ester, m. 41°; hydrogenation in AcOH (PdO) or in EtOH (PdO) gives NH₂CO₂H (95%) or its Me ester (96%). (PhCH₂)₂NCN yields NCNH₂ or I because of polymerization of PhCH₂NHCN if hydrogenation is interrupted before it is complete. (CONHCH₂Ph)₂ and N,N-dibenzylurethane, b₂ 169°, b₄ 181° (82% yield), are stable toward H.

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Recommanded Product: N,N-Dibenzylcyanamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Gelfand, Erwin W. published the artcileImportance of the leukotriene B4-BLT1 and LTB4-BLT2 pathways in asthma, Recommanded Product: [(2-Hexylcyclopentylidene)amino]thiourea, the publication is Seminars in Immunology (2017), 44-51, database is CAplus and MEDLINE.

For several decades, the leukotriene pathways have been implicated as playing a central role in the pathophysiol. of asthma. The presence and elevation of numerous metabolites in the blood, sputum, and bronchoalveolar lavage fluid from asthmatics or exptl. animals adds support to this notion. However, targeting of the leukotriene pathways has had, in general, limited success. The single exception in asthma therapy has been targeting of the cysteinyl leukotriene receptor 1, which clin. has proven effective but only in certain clin. situations. Interference with 5-lipoxygenase has had limited success, in part due to adverse drug effects. The importance of the LTB4-BLT1 pathway in asthma pathogenesis has extensive exptl. support and findings, albeit limited, from clin. samples. The LTB4-BLT1 pathway was shown to be important as a neutrophil chemoattractant. Despite observations made more than two decades ago, the LTB4-BLT1 pathway has only recently been shown to exhibit important activities on subsets of T lymphocytes, both as a chemoattractant and on lymphocyte activation, as well as on dendritic cells, the major antigen presenting cell in the lung. The role of BLT2 in asthma remains unclear. Targeting of components of the LTB4-BLT1 pathway offers innovative therapeutic opportunities especially in patients with asthma that remain uncontrolled despite intensive corticosteroid treatment.

Seminars in Immunology published new progress about 321673-30-7. 321673-30-7 belongs to amides-buliding-blocks, auxiliary class Immunology/Inflammation,Scavenger receptor, name is [(2-Hexylcyclopentylidene)amino]thiourea, and the molecular formula is C12H23N3S, Recommanded Product: [(2-Hexylcyclopentylidene)amino]thiourea.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Misner, Jerry W. published the artcileAn improved method for the decyanation of N,N-disubstituted cyanamides, Synthetic Route of 2451-91-4, the publication is Journal of Organic Chemistry (1987), 52(14), 3166-8, database is CAplus.

The cleavage of N,N-disubstituted cyanamides, e.g. the ergoline I (R = cyano), to secondary amines, e.g. I (R = H), is effected rapidly and in high yields with NaOH or KOH in ethylene glycol at temperature greater than 120°. The products can usually be isolated easily as either the free amines or as their salts so long as they are reasonably hydrophobic. This procedure is an excellent alternative to other methods, especially with acid sensitive substrates.

Journal of Organic Chemistry published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Synthetic Route of 2451-91-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Nobuaki, Miyahara published the artcileLTB4 and Allergies, Recommanded Product: [(2-Hexylcyclopentylidene)amino]thiourea, the publication is Arerugi, Men’eki (2018), 25(3), 362-370, database is CAplus.

A review. Mouth leukotriene B₄ (LTB₄) is a bioactive lipid derived from arachidonic acid. Since the identification of the high-affinity receptor BLT1 and the low-affinity receptor BLT2 of LTB₄, their involvement in various allergic diseases has been elucidated. LTB₄-BLT1 pathway has been suggested to be involved in bronchial apol., especially in severe acute infarct steroid-resistant apnea, and in atopic dermatitis, allergic rhinitis, conjunctivitis, etc : LTB₄-BLT1 regulation of the pathway is expected as a new bureaucracy for allergic diseases.

Arerugi, Men’eki published new progress about 321673-30-7. 321673-30-7 belongs to amides-buliding-blocks, auxiliary class Immunology/Inflammation,Scavenger receptor, name is [(2-Hexylcyclopentylidene)amino]thiourea, and the molecular formula is C12H23N3S, Recommanded Product: [(2-Hexylcyclopentylidene)amino]thiourea.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Chen, Jian published the artcileNickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes, COA of Formula: C11H22N2O4, the publication is Journal of the American Chemical Society (2021), 143(35), 14089-14096, database is CAplus and MEDLINE.

A nickel-catalyzed, multicomponent regio- and enantioselective coupling via sequential hydroformylation and carbonylation from readily available starting materials has been developed. This modular multicomponent hydrofunctionalization strategy enables the straightforward reductive hydrocarbonylation of a broad range of unactivated alkenes to produce a wide variety of unsym. dialkyl ketones bearing a functionalized α-stereocenter, including enantioenriched chiral α-aryl ketones and α-amino ketones. It uses chiral bisoxazoline as a ligand, silane as a reductant, chloroformate as a safe CO source, and a racemic secondary benzyl chloride or an N-hydroxyphthalimide (NHP) ester of a protected α-amino acid as the alkylation reagent. The benign nature of this process renders this method suitable for late-stage functionalization of complex mols.

Journal of the American Chemical Society published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, COA of Formula: C11H22N2O4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Zhou, Min published the artcileSynthesis of poly-α/β-peptides with tunable sequence via the copolymerization on N-carboxyanhydride and N-thiocarboxyanhydride, Computed Properties of 2418-95-3, the publication is iScience (2021), 24(10), 103124, database is CAplus and MEDLINE.

The fascinating functions of proteins and peptides in biol. systems have attracted intense interest to explore their mimics using polymers, including polypeptides synthesized from polymerization The folding, structures and functions of proteins and polypeptides are largely dependent on their sequence. However, sequence-tunable polymerization for polypeptide synthesis is a long-lasting challenge. The application of polypeptides is also greatly hindered by their susceptibility to enzymic degradation Although poly-α/β-peptide has proven to be an effective strategy to address the stability issue, the synthesis of poly-α/β-peptide from polymerization is not available yet. Hereby, we demonstrate a living and controlled copolymerization on α-NCA and β-NTA to prepare sequence-tunable poly-α/β-peptides. This polymerization strategy shows a prominent solvent-driven characteristic, providing random-like copolymers of poly-α/β-peptides in THF and block-like copolymers of poly-α/β-peptides in a mixed solvent of CHCl₃/H₂O (95/5, volume/volume), and opens new avenues for sequence-tunable polymerization and enables facile synthesis of proteolysis tunable poly-α/β-peptides for diverse applications.

iScience published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C14H26O2, Computed Properties of 2418-95-3.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Dubovtsev, Alexey Yu. published the artcileAcid-catalyzed [2+2+2] cycloaddition of two cyanamides and one ynamide: highly regioselective synthesis of 2,4,6-triaminopyrimidines, Quality Control of 2451-91-4, the publication is Organic & Biomolecular Chemistry (2021), 19(20), 4577-4584, database is CAplus and MEDLINE.

Triflic acid (10 mol%) catalyzes the highly regioselective [2+2+2] cycloaddition between two cyanamides and one ynamide to grant the 2,4,6-triaminopyrimidine core. The developed synthetic method is effective for the preparation of a family of the diversely substituted heterocyclic products (30 examples; yields up to 94%). The synthesis can be easily scaled up and conducted in gram quantities. As demonstrated by the post-functionalizations involving the amino-substituents, the obtained heterocycles represent a useful platform for the construction of miscellaneous pyrimidine-based frameworks. The performed d. functional theory calculations verified a particular role of H⁺, functioning as an electrophilic activator, in the regioselectivity of the cycloaddition

Organic & Biomolecular Chemistry published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Quality Control of 2451-91-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Bany, T. published the artcileChloroalkylamines, drugs paralyzing the endings of the sympathetic system, Name: N,N-Dibenzylcyanamide, the publication is Acta Poloniae Pharmaceutica (1955), 223-32, database is CAplus.

Derivatives of N,N-dibenzyl-β-chloroethylamine (Dibenamine) containing Br, I, or F and substituents other than benzyl are described as having possible paralyzing properties of the sympathetic system and action against malignant growth. FCH₂CH₂OH (I), b. 100-2°, was prepared in about 40% yield by adding with stirring 80 g. ClCH₂CH₂OH to a mixture of 87 g. KF (dried at 170°) and 110 g. HOCH₂CH₂OH heated at 210° at such a rate that a fraction b. 95-105° is distilled from the mixture, treating the distillate with 2 g. NaF, filtering and redistilling. FCH₂CH₂Cl (II), b₇₅₀ 57°, d₂₃ 1.1764, n_D²³ 1.3842 was obtained in 30% yield by adding 145 g. SOCl₂ to 60 g. I, refluxing 3 hrs. on a water bath, adding water, washing the resulting oil with NaHCO₃ and water, drying over CaCl₂ and distilling FCH₂CH₂Br (III), b₇₄₃ 72°, was obtained in a 23.7% yield by heating 7 g. I with 65 g. PBr₅ 3 hrs., washing the oil with water and Na₂CO₃, taking up in ether, drying and distilling (PhCH₂)₂NH.HCl (IV), not m. below 350°, was obtained by refluxing a mixture of 10 g. Na₂NCN, 45 g. water, 55 g. EtOH, and 25.2 g. PhCH₂Cl 36 hrs., distilling water and EtOH, crystallizing from petr. ether the resulting (PhCH₂)₂NCN, m. 112°, boiling it with 16 g. H₂SO₄ and 48 g. water 6 hrs., adding 26 g. NaOH in 48 g. water, steam distilling the amine, extracting the distillate with ether, treating the extract with HCl and filtering the precipitate (PhCH₂)₂NCH₂CH₂F.HCl (V), m. 248-50°, was prepared in 53% yield by heating 8 g. (PhCH₂)₂NH and 4 g. II in a sealed tube at 120-60° 24 hrs. and crystallizing from EtOH. (PhCH₂)₂NCH₂CH₂Br.HBr (VI), m. 181-2°, was obtained in 68% yield by adding HBr to 5 g. (PhCH₂)₂NCH₂CH₂OH (VII), filtering and drying the VII.HBr (m. 164°), heating it on a water bath 2 hrs. with 8.4 g. PBr₃ and 20 ml. CHCl₃, distilling the CHCl₃, adding EtOH, filtering the mixture, distilling the EtOH, and crystallizing from EtOH. Refluxing 6 g. VI and 5 g. NaI.2H₂O in 100 ml. AcOMe 2 hrs., evaporating to 0.5 volume, and cooling gave 7.2 g. (PhCH₂)₂NCH₂CH₂I.HI, m. 173-4° (from EtOH). (PhCH₂CH₂)₂NCH₂CH₂Cl.HCl (VIII), m. 153-4°, was obtained in 86.2% yield by refluxing 4 g. (PhCH₂CH₂)₂NCH₂CH₂OH in 20 ml. CHCl₃ with 2.5 g. SOCl₂ 4 hrs., removing CHCl₃, crystallizing the residue from EtOH-Et₂O and recrystallizing from AcOMe. (PhCH₂CH₂)₂NCH₂CH₂I.HI, m. 159-60°, was prepared in 85.7% yield by refluxing 1 g. VIII and 1.5 g. NaI.2H₂O in 25 ml. AcOMe 2 hrs., filtering off the precipitate, distilling the filtrate, taking up the residue in CHCl₃, filtering again, concentrating the filtrate and recrystallizing the solid from absolute EtOH. (α-C₁₀H₇CH₂)₂NCH₂CH₂Cl.HCl (IX), m. 185-6°, was prepared in 89.6% yield by refluxing 5 g. (α-C₁₀H₇CH₂)₂NCH₂CH₂OH and 2.7 g. SOCl₂ in 25 ml. CHCl₃ 4 hrs., distilling the CHCl₃, cooling, filtering off the precipitate, and crystallizing from absolute EtOH. (α-C₁₀H₇CH₂)₂NCH₂CH₂Br.HBr, m. 199-200°, was obtained in 82.5% yield by heating a solution of 1 g. IX in 5 ml. absolute EtOH with 1.2 g. CaBr₂.6H₂O in a min. quantity of absolute EtOH 6 hrs., cooling and recrystallizing from absolute EtOH. (α-C₁₀H₇CH₂)₂NCH₂CH₂I.HI, m. 181-2°, was obtained in 82.7% yield by heating 2 g. IX and 1.55 g. NaI.2H₂O in EtOH 8 hrs., cooling, filtering off the NaCl, concentrating the filtrate, and recrystallizing from MeOH. The piperidine derivative, C₅H₁₀NCH₂CH₂Cl.HCl (X), m. 234°, was obtained in 28.4% yield by heating on a water bath 13 g. C₅H₁₀NH with 12 g. ClCH₂CH₂OH 6 hrs., adding 50 ml. CHCl₃ and 23 g. SOCl₂, refluxing an addnl. 3 hrs., distilling the CHCl₃ and crystallizing from absolute EtOH. C₅H₁₀NCH₂CH₂Br.HBr, m. 219-20°, was obtained in 5.6% yield by refluxing 2 g. X and 2 g. CaBr₂.6H₂O in EtOH 6 hrs., distilling EtOH and crystallizing from AcOMe. C₅H₁₀NCH₂CH₂I.HI, m. 212-13°, was prepared in 5% yield by refluxing 2 g. X and 3 g. NaI.2H₂O in EtOH 6 hrs. and crystallizing from MeOH. C₅H₁₀NCH₂CH₂F.HCl (not m. below 350°) was prepared by heating 5 g. C₅H₁₀NH and 5 g. II 12 hrs. in a sealed tube at 140-60° and crystallizing from dilute EtOH.

Acta Poloniae Pharmaceutica published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Name: N,N-Dibenzylcyanamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Tian, Zi-You published the artcileA moisture-tolerant route to unprotected α/β-amino acid N-carboxyanhydrides and facile synthesis of hyperbranched polypeptides, SDS of cas: 2418-95-3, the publication is Nature Communications (2021), 12(1), 5810, database is CAplus and MEDLINE.

A great hurdle in the production of synthetic polypeptides lies in the access of N-carboxyanhydrides (NCA) monomers, which requires dry solvents, Schlenk line/gloveboxe, and protection of side-chain functional groups. Here we report a robust method for preparing unprotected NCA monomers in air and under moisture. The method employs epoxy compounds as ultra-fast scavengers of hydrogen chloride to allow assisted ring-closure and prevent NCA from acid-catalyzed decomposition under moist conditions. The broad scope and functional group tolerance of the method are demonstrated by the facile synthesis of over 30 different α/β-amino acid NCAs, including many otherwise inaccessible compounds with reactive functional groups, at high yield, high purity, and up to decagram scales. The utility of the method and the unprotected NCAs is demonstrated by the facile synthesis of two water-soluble polypeptides that are promising candidates for drug delivery and protein modification. Overall, our strategy holds great potential for facilitating the synthesis of NCA and expanding the industrial application of synthetic polypeptides.

Nature Communications published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C3H6BrNaO3S, SDS of cas: 2418-95-3.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics