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