(2R)-2-[(1R,2R,4aS,6R,8aR)-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

Base Information

Chemical Name:(2R)-2-[(1R,2R,4aS,6R,8aR)-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile
CAS No.:936368-46-6
Molecular Formula:C₂₃H₂₉NO₃
Molecular Weight:367.488
Hs Code.:

Synonyms:(2R)-2-[(1R,2R,4aS,6R,8aR)-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

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Chemical Property of (2R)-2-[(1R,2R,4aS,6R,8aR)-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

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Technology Process of (2R)-2-[(1R,2R,4aS,6R,8aR)-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

There total 11 articles about (2R)-2-[(1R,2R,4aS,6R,8aR)-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile 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%

: 936368-45-5
(2R)-2-[(1R,2R,4aS,6R,8S,8aR)-2-(3,5-dimethoxyphenyl)-8-hydroxy-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

: 936368-46-6
(2R)-2-[(1R,2R,4aS,6R,8aR)-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 0 - 23 ℃;
DOI:10.1021/ol070049a

Reference yield:

: 936368-33-1
ethyl (2E,4S,6R,8E)-4-{[tert-butyl(dimethyl)silyl]oxy}-6,9-dimethyl-10-oxodeca-2,8-dienoate

: 936368-46-6
(2R)-2-[(1R,2R,4aS,6R,8aR)-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

Guidance literature:: Multi-step reaction with 7 steps

1.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C

1.2: tetrahydrofuran / -80 - 0 °C

1.3: CHCl₃ / 2 h / 60 °C

2.1: 1.610 g / diisobutylaluminium hydride / CH₂Cl₂ / -20 - 23 °C

3.1: 94 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

4.1: 98 percent / dimethylsulfoxide / 72 h / 50 °C

5.1: lithium diisopropylamide / hexane; tetrahydrofuran / 1 h / -80 °C

5.2: 87 percent / hexane; tetrahydrofuran / 0.5 h / -80 °C

6.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 23 °C

7.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 23 °C

With potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 7.1: Dess-Martin oxidation;
DOI:10.1021/ol070049a

Reference yield:

: 936368-43-3
[(1S,2S,4aS,6R,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol

: 936368-46-6
(2R)-2-[(1R,2R,4aS,6R,8aR)-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]propanenitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: 94 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

2.1: 98 percent / dimethylsulfoxide / 72 h / 50 °C

3.1: lithium diisopropylamide / hexane; tetrahydrofuran / 1 h / -80 °C

3.2: 87 percent / hexane; tetrahydrofuran / 0.5 h / -80 °C

4.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 23 °C

5.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 23 °C

With tetrabutyl ammonium fluoride; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 5.1: Dess-Martin oxidation;
DOI:10.1021/ol070049a