(-)-(14alpha)-Dihydrovinpocetine

Base Information

• Chemical Name: (-)-(14alpha)-Dihydrovinpocetine
• CAS No.: 57327-92-1
• Molecular Formula: C22H28N2O2
• Molecular Weight: 352.47
• Hs Code.: 2939800000
• UNII: 1E09UMT0FC
• DSSTox Substance ID: DTXSID001100499
• Nikkaji Number: J675.684K
• Wikidata: Q27252308
• Mol file: 57327-92-1.mol

Synonyms:57327-92-1;(-)-Dihydroapovincaminic acid ethyl ester;(-)-(14alpha)-Dihydrovinpocetine;Dihydrovinpocetine, (-)-(14alpha)-;UNII-1E09UMT0FC;1E09UMT0FC;(-)-(14alpha)-Dihydrovinpocetine-d5;1H-Indolo(3,2,1-de)pyrido(3,2,1-ij)(1,5)naphthyridine-12-carboxylic acid, 13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-, ethyl ester, (12R,13aS,13bS)-;Ethyl (12R,13aS,13bS)-13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-1H-indolo(3,2,1-de)pyrido(3,2,1-ij)(1,5)naphthyridine-12-carboxylate;ethyl (15S,17R,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate;1H-Indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylic acid, 13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-, ethyl ester, (12R,13aS,13bS)-;(?)-Dihydrovinpocetine;SCHEMBL10571107;DTXSID001100499;(-)-(14.ALPHA.)-DIHYDROVINPOCETINE;DIHYDROVINPOCETINE, (-)-(14.ALPHA.)-;Q27252308

Chemical Property of (-)-(14alpha)-Dihydrovinpocetine

Chemical Property:

• Boiling Point: 497.4±45.0 °C(Predicted)
• PKA: 8.66±0.60(Predicted)
• PSA: 34.47000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 4.17650
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 352.215078140
• Heavy Atom Count: 26
• Complexity: 566

Purity/Quality:

NLT 98% ^*data from raw suppliers

(-)-DihydroapovincaminicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(C2)C(=O)OCC
• Isomeric SMILES: CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4[C@H](C2)C(=O)OCC
• Uses: (-)-Dihydroapovincaminic Acid Ethyl Ester, can be used as a chiral modifier in enantioselective heterogeneous catalytic hydrogenations. It is also structurally related to Vinpocetine (V332500), a Vasodilator (cerebral). (-)-Dihydroapovincaminic Acid Ethyl Ester, can be used as a chiral modifier in enantioselective heterogeneous catalytic hydrogenations. It is also structurally related to Vinpocetine (V332500), a Vasodilator (cerebral). Vinpocetine USP Related Compound D

Technology Process of (-)-(14alpha)-Dihydrovinpocetine

There total 4 articles about (-)-(14alpha)-Dihydrovinpocetine 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:

3β-apovincaminic acid ethyl ester (77549-94-1,80038-06-8) → 14-Ethoxycarbonyl-14,15-dihydro-3β,16α-eburnamenin (57327-92-1,57517-54-1,59684-94-5,68779-70-4,68779-72-6,78216-19-0,96245-05-5,96245-06-6)

Guidance literature:

With ammonium hydroxide; formic acid; palladium; In N-methyl-acetamide; ethanol; dichloromethane; water;

Reference yield:

Vinpocetine (42971-09-5,80038-06-8) → 3α-deoxyvincaminic acid ethyl ester (57327-92-1) + 3α-deoxyepivincaminic acid ethyl ester (57517-54-1)

Guidance literature:

With hydrogen; Rh on carbon; In methanol; at 25 ℃; under 4500.4 Torr; Yield given. Yields of byproduct given;

DOI:10.1016/0957-4166(95)00317-I

Reference yield:

→ 14-Ethoxycarbonyl-14,15-dihydro-3β,16α-eburnamenin (57327-92-1,57517-54-1,59684-94-5,68779-70-4,68779-72-6,78216-19-0,96245-05-5,96245-06-6)

Guidance literature:

14-Ethoxycarbonyl-3,4-dehydro-14,15-dihydro-eburnamenin-perchlorat, NaBH4;

upstream raw materials:

3β-apovincaminic acid ethyl ester

Vinpocetine