1,2-Didehydro-17-methoxyaspidospermidine

Base Information

• Chemical Name: 1,2-Didehydro-17-methoxyaspidospermidine
• CAS No.: 2912-26-7
• Molecular Formula: C20H26N2O
• Molecular Weight: 310.439
• Mol file: 2912-26-7.mol

Synonyms:(+)-N-Deacetyl-1,2-didehydroaspidospermine;1,2-Didehydro-17-methoxyaspidospermidine;17-Methoxyeburenine

Chemical Property of 1,2-Didehydro-17-methoxyaspidospermidine

Chemical Property:

• PSA: 24.83000
• LogP: 3.45090

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Didehydro-17-methoxyaspidospermidine

There total 17 articles about 1,2-Didehydro-17-methoxyaspidospermidine 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: 66.0%

(31S,6aR,9aR)-6a-ethyloctahydro-1H-pyrrolo[3,2,1-ij]quinolin-9(2H)-one (4724-62-3,502614-34-8,502614-35-9) + 2-methoxyphenylhydrazine hydrochloride (6971-45-5,57396-67-5) → (+)-dehydrodeacetylaspidospermine (2912-26-7)

Guidance literature:

(3¹S,6aR,9aR)-6a-ethyloctahydro-1H-pyrrolo[3,2,1-ij]quinolin-9(2H)-one; 2-methoxyphenylhydrazine hydrochloride; With sodium carbonate; In ethanol; at 20 ℃; for 0.5h;

With acetic acid; at 95 ℃; for 1h;

DOI:10.1021/acs.orglett.7b01292

Reference yield:

C20H26N2O2 → (+)-dehydrodeacetylaspidospermine (2912-26-7)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 7h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.8b01428

Reference yield:

N-(6a-ethyl-decahydro-pyrrolo[3,2,1-ij]quinolin-9-ylidene)-N'-(2-methoxy-phenyl)-hydrazine (503000-58-6) → (+)-dehydrodeacetylaspidospermine (2912-26-7)

Guidance literature:

With acetic acid; at 95 ℃;

DOI:10.1021/ol034020s

upstream raw materials:

N-(6a-ethyl-decahydro-pyrrolo[3,2,1-ij]quinolin-9-ylidene)-N'-(2-methoxy-phenyl)-hydrazine

3-ethyl-5-bromo-2-pyrone

(3¹S,6aR,9aR)-6a-ethyloctahydro-1H-pyrrolo[3,2,1-ij]quinolin-9(2H)-one

2-methoxyphenylhydrazine hydrochloride

Downstream raw materials:

(+)-deacetylaspidospermine

vallesine

aspidospermine

Refernces

• 1、 Wang, Nengzhong,Du, Shuo,Li, Dong,Jiang, Xuefeng. "Divergent Asymmetric Total Synthesis of (+)-Vincadifformine, (-)-Quebrachamine, (+)-Aspidospermidine, (-)-Aspidospermine, (-)-Pyrifolidine, and Related Natural Products". . p. 3167 - 3170. Retrieved 2017/06/23.