octahydroquinolin-2(1H)-one

Base Information

• Chemical Name: octahydroquinolin-2(1H)-one
• CAS No.: 4169-27-1
• Molecular Formula: C9H15 N O
• Molecular Weight: 153.224
• Hs Code.: 2933790090
• Mol file: 4169-27-1.mol

Synonyms:Carbostyril,3,4,4a,5,6,7,8,8a-octahydro- (7CI); Carbostyril, octahydro- (8CI); NSC 250941;Octahydro-2(1H)-quinolinone; Octahydrocarbostyril; Perhydroquinolin-2-one

Chemical Property of octahydroquinolin-2(1H)-one

Chemical Property:

• Vapor Pressure: 0.000298mmHg at 25°C
• Boiling Point: 321.4°Cat760mmHg
• Flash Point: 186.7°C
• PSA: 29.10000
• Density: 1.014g/cm³
• LogP: 1.78400

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of octahydroquinolin-2(1H)-one

There total 19 articles about octahydroquinolin-2(1H)-one 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: 96.0%

3,4-dihydro-2(1H)-quinolone (553-03-7) → cis-3,4,4a,5,6,7,8,8a-Octahydro-2(1H)-quinolinone (4169-27-1,37088-57-6,58887-53-9,58887-63-1,59224-99-6,131348-81-7,131348-82-8)

Guidance literature:

With Rh-CAAC; hydrogen; In 2,2,2-trifluoroethanol; at 50 ℃; under 37503.8 Torr; diastereoselective reaction; Molecular sieve; Autoclave; Schlenk technique;

DOI:10.1021/acs.orglett.0c03427

Reference yield: 64.0%

2-hydroxyquinoline (59-31-4) → cis-3,4,4a,5,6,7,8,8a-Octahydro-2(1H)-quinolinone (4169-27-1,37088-57-6,58887-53-9,58887-63-1,59224-99-6,131348-81-7,131348-82-8)

Guidance literature:

With C₃₃H₄₉ClNRh; hydrogen; In 2,2,2-trifluoroethanol; water; at 70 ℃; for 24h; under 37503.8 Torr; Autoclave;

DOI:10.1021/jacs.5b05868

Reference yield: 60.0%

3,4,5,6,7,8-hexahydro-2-quinolinone (10333-11-6) → cis-3,4,4a,5,6,7,8,8a-Octahydro-2(1H)-quinolinone (4169-27-1,37088-57-6,58887-53-9,58887-63-1,59224-99-6,131348-81-7,131348-82-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In 1,4-dioxane; ethanol; for 48h; under 760.051 Torr; Inert atmosphere;

DOI:10.1021/jacs.5b07201

upstream raw materials:

(E)-methyl 2-nitrocinnamate

3-(2-benzoylamino-cyclohexyl)-propionic acid

ethanol

acetic acid

Downstream raw materials:

3-(2-benzoylamino-cyclohexyl)-propionic acid

(4aS,8aS)-3-Chloro-octahydro-quinolin-2-one

decahydroquinoline

(+/-)-(2R,3aS,7aS)-octahydroindole-2-carboxylic acid

Refernces

• 1、 Wanner, Benedikt,Kreituss, Imants,Gutierrez, Osvaldo,Kozlowski, Marisa C.,Bode, Jeffrey W.. "Catalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights". supporting information. p. 11491 - 11497. Retrieved 2015/09/21.
• 2、 Guthikonda, Ravindra N.,Shah, Shrenik K.,Pacholok, Stephen G.,Humes, John L.,Mumford, Richard A.,Grant, Stephan K.,Chabin, Renee M.,Green, Barbara G.,Tsou, Nancy,Ball, Richard,Fletcher, Daniel S.,Luell, Silvi,Euan MacIntyre,MacCoss, Malcolm. "Bicyclic amidine inhibitors of nitric oxide synthase: Discovery of perhydro-iminopyrindine and perhydro-iminoquinoline as potent, orally active inhibitors of inducible nitric oxide synthase". . p. 1997 - 2001. Retrieved 2007/10/03.