Ethyl apovincaminate

Base Information

• Chemical Name: Ethyl apovincaminate
• CAS No.: 42971-12-0
• Molecular Formula: C₂₂H₂₆N₂O₂
• Molecular Weight: 350.461
• DSSTox Substance ID: DTXSID10904848
• Nikkaji Number: J3.022.983E
• ChEMBL ID: CHEMBL1360725
• Mol file: 42971-12-0.mol

Synonyms:Cavinton;ethyl apovincaminate;ethyl apovincaminate tartrate (1:1);ethyl apovincaminate, (+-)-isomer;ethyl apovincaminate, (16alpha)-isomer;ethyl apovincaminate, (3alpha,16alpha)-isomer;ethyl apovincaminate, 2-oxopentanedioate (1:1);ethyl apovincaminate, 3H-labeled;Kavinton;RGH-4405;TCV-3B;vinpocetine

Chemical Property of Ethyl apovincaminate

Chemical Property:

• Vapor Pressure: 3.02E-07mmHg at 25°C
• Melting Point: 148-151 °C
• Boiling Point: 419.5°C at 760 mmHg
• PKA: 7.87±0.60(Predicted)
• Flash Point: 207.5°C
• PSA: 34.47000
• Density: 1.28g/cm³
• LogP: 4.08620
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 350.199428076
• Heavy Atom Count: 26
• Complexity: 617

Purity/Quality:

NLT 98% ^*data from raw 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=C5N4C(=C2)C(=O)OCC
• Uses: (3R,16R)-Vinpocetine is a diastereomer of Vinpocetine (V332500) which is a derivative of Vincamine with vasodilating activity.

Technology Process of Ethyl apovincaminate

There total 24 articles about Ethyl apovincaminate 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: 73.0%

chloroacetic acid ethyl ester (105-39-5) + (1R*,5S*,12bS*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-carbaldehyde (51152-47-7) → ethyl eburnamenine-14-carboxylate (42971-09-5,42971-12-0,68780-77-8,74924-34-8,77549-94-1,85647-43-4,80038-06-8)

Guidance literature:

With potassium tert-butylate; In benzene; for 2h; Ambient temperature;

Reference yield: 63.1%

(+/-)-3-epivincaminic acid ethyl ester (40163-56-2,66036-68-8,68780-78-9,68780-79-0,74957-84-9,77549-91-8,77549-92-9,77549-93-0,78341-01-2,78341-02-3,93379-89-6) → (+/-)-3-epi-apovincaminic acid ethyl ester (42971-09-5,42971-12-0,68780-77-8,74924-34-8,77549-94-1,85647-43-4,80038-06-8)

Guidance literature:

With sodium hydroxide; acetic anhydride; In water;

Reference yield: 42.0%

(10S,11S,11aS,11bR)-11a-Ethyl-11-hydroxy-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester (74904-40-8,74904-41-9,74924-32-6,74924-33-7,75045-60-2,77027-36-2,79297-53-3) → ethyl eburnamenine-14-carboxylate (42971-09-5,42971-12-0,68780-77-8,74924-34-8,77549-94-1,85647-43-4,80038-06-8)

Guidance literature:

With sodium hydride;

upstream raw materials:

(10R,11R,11aS,11bR)-11a-Ethyl-11-hydroxy-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

chloroacetic acid ethyl ester

(1R*,5S*,12bS*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-carbaldehyde

(10S,11S,11aS,11bR)-11a-Ethyl-11-hydroxy-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

Downstream raw materials:

((4¹S,13aS)-13a-ethyl-2,3,4¹,5,6,13a-hexahydro-1H-indolyl[3,2,1-de]pyridyl[3,2,1-ij][1,5]naphthyridine-12-yl)methanol