(4aR,8aS)-3,3-Dimethyloctahydroquinoxalin-2(1H)-one

Base Information

• Chemical Name: (4aR,8aS)-3,3-Dimethyloctahydroquinoxalin-2(1H)-one
• CAS No.: 71029-05-5
• Molecular Formula: C₁₀H₁₈N₂O
• Molecular Weight: 182.266
• DSSTox Substance ID: DTXSID20512337
• Wikidata: Q82371528
• Mol file: 71029-05-5.mol

Synonyms:71029-05-5;(4aR,8aS)-3,3-Dimethyloctahydroquinoxalin-2(1H)-one;DTXSID20512337;WCIJYVHCHODWEJ-JGVFFNPUSA-N;cis-3,3-dimethyl-decahydroquinoxalin-2-one

Chemical Property of (4aR,8aS)-3,3-Dimethyloctahydroquinoxalin-2(1H)-one

Chemical Property:

• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 182.141913202
• Heavy Atom Count: 13
• Complexity: 225

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(=O)NC2CCCCC2N1)C
• Isomeric SMILES: CC1(C(=O)N[C@H]2CCCC[C@H]2N1)C

Technology Process of (4aR,8aS)-3,3-Dimethyloctahydroquinoxalin-2(1H)-one

There total 4 articles about (4aR,8aS)-3,3-Dimethyloctahydroquinoxalin-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: 91.0%

1,2,3,4-tetrahydro-3,3-dimethylquinoxalin-2-one (80636-30-2) → cis-3,3-Dimethyldecahydro-2-quinoxalinone (71029-04-4,71029-05-5,99976-77-9)

Guidance literature:

With hydrogen; rhodium; In methanol; at 150 ℃; for 4h; under 83600.1 Torr;

DOI:10.1055/s-1982-29706

Reference yield:

1,2-diamino-benzene (95-54-5) → cis-3,3-Dimethyldecahydro-2-quinoxalinone (71029-04-4,71029-05-5,99976-77-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / aq. NaOH / benzyltriethylammonium chloride / CH₂Cl₂ / 10 °C / overnight

2: 91 percent / H₂ / Rhodium catalyst / methanol / 4 h / 150 °C / 83600.1 Torr

With sodium hydroxide; hydrogen; N-benzyl-N,N,N-triethylammonium chloride; rhodium; In methanol; dichloromethane;

DOI:10.1055/s-1982-29706

Reference yield:

rac-diaminocyclohexane (694-83-7) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → (4aR,8aR)-3,3-Dimethyl-octahydro-quinoxalin-2-one (71029-04-4,71029-05-5,99976-77-9) + cis-3,3-Dimethyldecahydro-2-quinoxalinone (71029-04-4,71029-05-5,99976-77-9)

Guidance literature:

In water; at 120 ℃; Yield given; overnight;

DOI:10.1055/s-1982-29706

upstream raw materials:

rac-diaminocyclohexane

2-hydroxy-2-methylpropanenitrile

1,2,3,4-tetrahydro-3,3-dimethylquinoxalin-2-one

1,2-diamino-benzene