(+)-Dihydroeburnamenine

Base Information

• Chemical Name: (+)-Dihydroeburnamenine
• CAS No.: 47122-74-7
• Molecular Formula: C19H24N2
• Molecular Weight: 280.40726
• Mol file: 47122-74-7.mol

Synonyms:Dihydroeburnamenine;14,15-Dihydro-eburnamenin;14,15-dihydro-eburnamenine;eburnamenine;(11aR,11bR)-11a-Ethyl-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene;

Chemical Property of (+)-Dihydroeburnamenine

Chemical Property:

• PSA: 8.17000
• LogP: 4.07230

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+)-Dihydroeburnamenine

There total 34 articles about (+)-Dihydroeburnamenine 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: 91.0%

(3R,16R)-14,15-dihydroeburnamenin-19-one (690993-33-0) → Dihydroeburnamenine (47122-74-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 70 ℃; for 0.5h;

DOI:10.1016/j.tet.2004.02.015

Reference yield: 90.0%

(5aR,11aS)-11a-Ethyl-1,2,3,5,5a,10,11,11a-octahydro-3a,9b-diaza-benzo[cd]fluoranthen-4-one → d,l-Epidihydroeburnamenin (47122-74-7,53946-80-8,53955-88-7,65026-49-5,96896-20-7,124222-39-5)

Guidance literature:

With sodium tetrahydroborate; trifluoroacetic acid; In 1,4-dioxane; Heating;

DOI:10.1021/jo970847m

Reference yield: 90.0%

11a-Ethyl-1,2,3,5,5a,10,11,11a-octahydro-3a,9b-diaza-benzo[cd]fluoranthen-4-one → d,l-Epidihydroeburnamenin (47122-74-7,53946-80-8,53955-88-7,65026-49-5,96896-20-7,124222-39-5)

Guidance literature:

With sodium tetrahydroborate; trifluoroacetic acid; In 1,4-dioxane; for 8h; Heating;

DOI:10.1016/0040-4039(95)02166-3

upstream raw materials:

(+) eburnamenine

(3R,16R)-14,15-dihydroeburnamenin-19-one

(3R)-3-ethyldihydro-3-(2-propenyl)-2(3H)-furanone

(3R)-3-ethyltetrahydro-2-methoxy-3-(2-propenyl)furan

Refernces

• 1、 Padwa, Albert,Harring, Scott R.,Semones, Mark A.. "Cycloaddition Reaction of Mesoionic Betaines as an Approach toward Trialkylindoline Alkaloids". . p. 44 - 54. Retrieved 2007/10/03.
• 2、 Takano, Seiichi,Hatakeyama, Susumi,Ogasawara, Kunio. "Synthetic Approach to (+/-)- Vincamine via Cleavage of an α-Diketone Monothioacetal. Alternative Synthesis of (+/-)-Eburnamine, (+/-)-Isoeburnamine, and (+/-)-Eburnamenine". . p. 457 - 461. Retrieved 2007/10/02.