17,18-Dehydrovincamine

Base Information

• Chemical Name: 17,18-Dehydrovincamine
• CAS No.: 32790-09-3
• Molecular Formula: C21H24N2O3
• Molecular Weight: 352.433
• ChEMBL ID: CHEMBL4761192
• DSSTox Substance ID: DTXSID60186455
• Nikkaji Number: J17.469F
• Mol file: 32790-09-3.mol

Synonyms:17,18-Dehydrovincamine;32790-09-3;methyl (15R,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18),13-pentaene-17-carboxylate;14,15-dehydrovincamine;CHEMBL4761192;DTXSID60186455;CHEBI:141861;Eburnamenine-14-carboxylic acid, 17,18-didehydro-14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16alpha)-

Chemical Property of 17,18-Dehydrovincamine

Chemical Property:

• Melting Point: 224-225 °C
• Boiling Point: 508.7±50.0 °C(Predicted)
• PKA: 12.20±0.40(Predicted)
• PSA: 54.70000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 2.66640
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 352.17869263
• Heavy Atom Count: 26
• Complexity: 637

Purity/Quality:

>95% ^*data from raw suppliers

17,18-Dehydrovincamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CC(N3C4=CC=CC=C4C5=C3C1N(CC5)CC=C2)(C(=O)OC)O
• Isomeric SMILES: CC[C@]12C[C@@](N3C4=CC=CC=C4C5=C3[C@H]1N(CC5)CC=C2)(C(=O)OC)O
• Uses: 17,18-Dehydrovincamine is an impurity of Vincamine (V314030) is often used as a nootropic agent to combat the effects of aging, or in conjunction with other nootropics (such as piracetam) for a variety of purposes. Vincamine is a peripheral vasodilator that increases blood flow to the brain.

Technology Process of 17,18-Dehydrovincamine

There total 6 articles about 17,18-Dehydrovincamine 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: 39.0%

(5aR,10aS,11R,12aR,12bS)-5a-Amino-12a-ethyl-11-hydroxy-4,5,5a,10,11,12,12a,12b-octahydro-3H-3a,10-diaza-indeno[1,7-ma]fluorene-11-carboxylic acid methyl ester (112817-47-7) → Δ17-vincamine (32790-09-3) + 14-epi-Δ17-vincamine (32790-10-6)

Guidance literature:

With tert.-butylnitrite; acetic acid; In tetrahydrofuran; for 0.166667h;

DOI:10.1021/jo00240a023

Reference yield: 30.0%

tabersonine (4429-63-4) → Δ17-vincamine (32790-09-3) + 14-epi-Δ17-vincamine (32790-10-6)

Guidance literature:

With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid; In methanol; for 24h; Ambient temperature;

Reference yield: 29.0%

tabersonine (4429-63-4) → C21H22N2O5 (74947-48-1) + Δ17-vincamine (32790-09-3) + 14-epi-Δ17-vincamine (32790-10-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In benzene; at 20 ℃; for 24h;

DOI:10.1016/0040-4020(80)80026-3

upstream raw materials:

tabersonine

(5aR,10aS,11R,12aR,12bS)-5a-Amino-12a-ethyl-11-hydroxy-4,5,5a,10,11,12,12a,12b-octahydro-3H-3a,10-diaza-indeno[1,7-ma]fluorene-11-carboxylic acid methyl ester

C₂₁H₂₅N₃O₃

Downstream raw materials:

criocerine

vincamin

Refernces

• 1、 Palmisano, Giovanni,Danieli, Bruno,Lesma, Giordano,Trupiano, Federica,Pilati, Tullio. "Oxidation of β-Anilinoacrylate Alkaloids Vincadifformine and Tabersonine by Fremy's Salt. A Mechanistic Insight into the Rearrangement of Aspidosperma to Hunteria Alkaloids". . p. 1056 - 1064. Retrieved 1988.
• 2、 Calabi, Luisella,Danieli, Bruno,Lesma, Giordano,Palmisano, Giovanni. "Dye-sensitized Photo-oxygenation of the Aspidosperma Alkaloids Vincadifformine and Tabersonine. A New, Convenient Approach to Vincamine". . p. 1371 - 1380. Retrieved 2007/10/02.