(19Z)-Anhydrovobasinediol

Base Information

• Chemical Name: (19Z)-Anhydrovobasinediol
• CAS No.: 19452-84-7
• Molecular Formula: C20H24N2O
• Molecular Weight: 308.41736
• Mol file: 19452-84-7.mol

Synonyms:Taberpsychine;(19Z)-taberpsychine;

Chemical Property of (19Z)-Anhydrovobasinediol

Chemical Property:

• Melting Point: 20So C (dec.).
• PSA: 28.26000
• LogP: 3.61600

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: An alkaloid which occurs in Tabernaemontana psychotrifolia H.B.K., this base is laevorotatory having [α]>D - 243° and gives an ultraviolet spectrum with absorption maxima at 222, 2S0 and 296 mp. with a shoulder at 272 mil. The alkaloid may be purified by recrystallization from Me2CO followed by sublima_x0002_tion. It yields a crystalline methiodide, m.p. 272-4°C (dec.) which has an ultraviolet spectrum containing an absorption maximum at 222 mp. and a shoulder at 276 mp.. On catalytic hydrogenation with Pt02 as catalyst it gives the dihydro derivative, m.p. 191-3°C, furnishing a methiodide, m.p. 265-SoC (dec.). Zn dust distillation yields 3-ethylpyridine and 3-methyl-5-ethylpyridine.

Technology Process of (19Z)-Anhydrovobasinediol

There total 70 articles about (19Z)-Anhydrovobasinediol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

C22H23Cl3N2O3 (137032-29-2) → (19Z)-taberpsychine (19452-84-7,113973-32-3,119322-72-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1.5h; Ambient temperature;

Reference yield: 73.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + des-N4-methyl (19Z)-taberpsychine → (19Z)-taberpsychine (19452-84-7,113973-32-3,119322-72-4)

Guidance literature:

With sodium cyanoborohydride; In methanol; water; at 21 ℃; for 0.5h;

DOI:10.1021/jacs.8b05095

Reference yield: 70.0%

N-carbomethoxy-N-desmethyl taberpsychine (119184-35-9) → (+)-taberpsychine (19452-84-7,113973-32-3,119322-72-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 22 ℃;

DOI:10.1021/ja00184a086

upstream raw materials:

N-carbomethoxytaberpsychine

(6R,10R)-(+)-5-benzyl-9-oxo-12-(prop-2-ynyl)-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

(S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester

(6R,10R)-(+)-5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Refernces

• 1、 Kitajima, Mariko,Takayama, Hiromitsu,Sakai, Shin-ichiro. "Stereoselective Transformation of Ajmaline into Three Minor Gelsemium Alkaloids, Koumidine, (19Z)-Anhydrovobasinediol and N-Demethoxyrankinidine and their Absolute Configuration". . p. 1773 - 1779. Retrieved 2007/10/02.
• 2、 Magnus,Mugrage,DeLuca,Cain. "Total synthesis of (+)-koumine, (+)-taberpsychine, and (+)-koumidine". . p. 786 - 789. Retrieved 2007/10/02.