(4R,9aR)-Octahydro-4-methyl-2H-quinolizin-2-one

Base Information

Chemical Name:(4R,9aR)-Octahydro-4-methyl-2H-quinolizin-2-one
CAS No.:66835-10-7
Molecular Formula:C10H17NO
Molecular Weight:167.251
Hs Code.:
UNII:KZG62E68A9
DSSTox Substance ID:DTXSID601242796
Nikkaji Number:J19.966D

Synonyms:66835-10-7;(4R,9aR)-Octahydro-4-methyl-2H-quinolizin-2-one;(+)-Myrtine;Myrtine, (+)-;SCHEMBL546576;KZG62E68A9;DTXSID601242796;2H-Quinolizin-2-one, octahydro-4-methyl-, (4R,9aR)-;2H-Quinolizin-2-one, octahydro-4-methyl-, (4R-cis)-;(4R,9aR)-4-methyl-1,3,4,6,7,8,9,9a-octahydroquinolizin-2-one;InChI=1/C10H17NO/c1-8-6-10(12)7-9-4-2-3-5-11(8)9/h8-9H,2-7H2,1H3/t8-,9-/m1/s

Suppliers and Price of (4R,9aR)-Octahydro-4-methyl-2H-quinolizin-2-one

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 3 raw suppliers

Chemical Property of (4R,9aR)-Octahydro-4-methyl-2H-quinolizin-2-one

Chemical Property:

XLogP3:1.1
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:0
Exact Mass:167.131014166
Heavy Atom Count:12
Complexity:190

Purity/Quality:: 99% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC1CC(=O)CC2N1CCCC2
Isomeric SMILES:C[C@@H]1CC(=O)C[C@@H]2N1CCCC2

Technology Process of (4R,9aR)-Octahydro-4-methyl-2H-quinolizin-2-one

There total 4 articles about (4R,9aR)-Octahydro-4-methyl-2H-quinolizin-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:

: 87905-98-4
5-<(benzyloxycarbonyl)amino>pentanol

: 66835-10-7
(4R,9aR)-hexahydro-4-methyl-1H-quinolizin-2(6H)-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.17 h / -78 °C / Inert atmosphere

1.2: 0.5 h / 20 °C / Inert atmosphere

2.1: toluene / 20 °C

3.1: (8α, 9S)-9-amine-6'-methoxycinchonan; trifluoroacetic acid / tetrahydrofuran / 20 °C

4.1: N-ethyl-N,N-diisopropylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 20 °C

4.2: 2 h / 20 °C

5.1: toluene / 16 h / 20 °C

6.1: tetrahydrofuran / 7 h / 20 °C

7.1: acetic acid; hydrogen bromide / dichloromethane / 4 h / 0 - 20 °C

7.2: 0 °C

With oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; hydrogen bromide; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; (8α, 9S)-9-amine-6'-methoxycinchonan; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1002/ejoc.201900477

Reference yield:

: 505-18-0
2,3,4,5-tetrahydropyridine

: 66835-10-7
(4R,9aR)-hexahydro-4-methyl-1H-quinolizin-2(6H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: L-proline / dimethyl sulfoxide; water / 1 h / 20 °C

2.1: sodium carbonate / water; dichloromethane / 0 - 20 °C

3.1: N-ethyl-N,N-diisopropylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 20 °C

3.2: 2 h / 20 °C

4.1: toluene / 16 h / 20 °C

5.1: tetrahydrofuran / 7 h / 20 °C

6.1: acetic acid; hydrogen bromide / dichloromethane / 4 h / 0 - 20 °C

6.2: 0 °C

With trimethylsilyl trifluoromethanesulfonate; hydrogen bromide; sodium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; L-proline; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene;
DOI:10.1002/ejoc.201900477

Reference yield:

: 505-18-0
2,3,4,5-tetrahydropyridine

: 3102-33-8
trans-3-penten-2-one

: 66835-10-7,66900-13-8,66900-14-9,82111-00-0,82111-01-1,82111-02-2,106818-38-6,106818-39-7
(9aβH)-4β-methyloctahydro-2H-quinolizin-2-one

: 66835-10-7,66900-13-8,66900-14-9,82111-00-0,82111-01-1,82111-02-2,106818-38-6,106818-39-7
(9aβH)-4α-methyloctahydro-2H-quinolizin-2-one

Guidance literature:: trans-3-penten-2-one; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

2,3,4,5-tetrahydropyridine; With boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; hexane; at -78 - 20 ℃; for 2h;

With sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; hexane; water; at 0 - 20 ℃; Overall yield = 64 mg;
DOI:10.1021/acs.orglett.0c04024