trans-Octahydroquinolin-2-one

Base Information

• Chemical Name: trans-Octahydroquinolin-2-one
• CAS No.: 59224-99-6
• Molecular Formula: C9H15NO
• Molecular Weight: 153.224
• DSSTox Substance ID: DTXSID40483111
• Nikkaji Number: J356.796F
• Wikidata: Q82320128
• Mol file: 59224-99-6.mol

Synonyms:trans-Octahydroquinolin-2-one;trans-decahydroquinolone;59224-99-6;trans-Decahydro-2-quinolinone;DTXSID40483111;OBSYXAXPUGVQSN-JGVFFNPUSA-N

Chemical Property of trans-Octahydroquinolin-2-one

Chemical Property:

• Melting Point: 151 °C
• Boiling Point: 321.4±11.0 °C(Predicted)
• PSA: 32.59000
• Density: 1.014±0.06 g/cm3(Predicted)
• LogP: 1.73110
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 153.115364102
• Heavy Atom Count: 11
• Complexity: 167

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2C(C1)CCC(=O)N2
• Isomeric SMILES: C1CC[C@@H]2[C@@H](C1)CCC(=O)N2

Technology Process of trans-Octahydroquinolin-2-one

There total 13 articles about trans-Octahydroquinolin-2-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:

3,4,5,6,7,8-hexahydro-2-quinolinone

trans-2-(methylamino)-3,4,5,6,7,8,9,9a-octahydroquinoline

cyclohexanone-2-propionitrile

2-hydroxyquinoline

Downstream raw materials:

(+/-)-3-(trans-2-amino-cyclohexyl)-propionic acid

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

decahydroquinoline

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