2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile

Base Information

Chemical Name:2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile
CAS No.:1225377-71-8
Molecular Formula:C₂₁H₂₆N₂
Molecular Weight:306.451
Hs Code.:

Synonyms:2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile

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Chemical Property of 2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile

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Technology Process of 2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile

There total 10 articles about 2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile 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: 75.0%

: 1225377-69-4
2-((1S,2R,3R,5R)-3-ethynyl-2-(3-hydroxypropyl)-3-(benzylamino)-5-methylcyclohexyl)acetonitrile

: 1225377-71-8
2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile

Guidance literature:: With 1H-imidazole; triphenylphosphine; In tetrachloromethane; for 15h; Inert atmosphere; Heating;
DOI:10.1021/ja101956x

Reference yield:

: 1225377-59-2
(R)-3-(4-methyl-6-oxocyclohex-1-en-1-yl)propyl acetate

: 1225377-71-8
2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / diethyl ether; hexane / 0.68 h / -78 °C / Inert atmosphere

1.2: 0.55 h / -78 °C / Inert atmosphere

2.1: tetrahydrofuran; toluene / 0.58 h / 23 °C / Inert atmosphere

3.1: magnesium(II) perchlorate / 0.5 h / 23 °C / Inert atmosphere

4.1: copper(l) chloride / tetrahydrofuran / 0.5 h / 80 °C / Inert atmosphere

5.1: potassium carbonate / methanol / 7 h / 23 °C / Inert atmosphere

6.1: triphenylphosphine; 1H-imidazole / tetrachloromethane / 15 h / 77 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; magnesium(II) perchlorate; potassium carbonate; triphenylphosphine; copper(l) chloride; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; toluene;
DOI:10.1021/jo400695c

Reference yield:

: 1225377-61-6
3-((1R,2S,4R)-2-(cyanomethyl)-4-methyl-6-oxocyclohexyl)propyl acetate

: 1225377-71-8
2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile

Guidance literature:: Multi-step reaction with 5 steps

1: tetrahydrofuran; toluene / 0.58 h / 23 °C / Inert atmosphere

2: magnesium(II) perchlorate / 0.5 h / 23 °C / Inert atmosphere

3: copper(l) chloride / tetrahydrofuran / 0.5 h / 80 °C / Inert atmosphere

4: potassium carbonate / methanol / 7 h / 23 °C / Inert atmosphere

5: triphenylphosphine; 1H-imidazole / tetrachloromethane / 15 h / 77 °C / Inert atmosphere

With 1H-imidazole; magnesium(II) perchlorate; potassium carbonate; triphenylphosphine; copper(l) chloride; In tetrahydrofuran; methanol; tetrachloromethane; toluene;
DOI:10.1021/jo400695c