5-[(3R,3aR,4R,6aS,8R,9bR)-3,6,8-trimethyl-2,3a,4,6a,7,8,9,9b-octahydro-3H-benzo[de]quinolin-4-yl]benzene-1,3-diol

Base Information

Chemical Name:5-[(3R,3aR,4R,6aS,8R,9bR)-3,6,8-trimethyl-2,3a,4,6a,7,8,9,9b-octahydro-3H-benzo[de]quinolin-4-yl]benzene-1,3-diol
CAS No.:936368-39-7
Molecular Formula:C₂₁H₂₇NO₂
Molecular Weight:325.451
Hs Code.:

Synonyms:5-[(3R,3aR,4R,6aS,8R,9bR)-3,6,8-trimethyl-2,3a,4,6a,7,8,9,9b-octahydro-3H-benzo[de]quinolin-4-yl]benzene-1,3-diol

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Chemical Property of 5-[(3R,3aR,4R,6aS,8R,9bR)-3,6,8-trimethyl-2,3a,4,6a,7,8,9,9b-octahydro-3H-benzo[de]quinolin-4-yl]benzene-1,3-diol

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Technology Process of 5-[(3R,3aR,4R,6aS,8R,9bR)-3,6,8-trimethyl-2,3a,4,6a,7,8,9,9b-octahydro-3H-benzo[de]quinolin-4-yl]benzene-1,3-diol

There total 15 articles about 5-[(3R,3aR,4R,6aS,8R,9bR)-3,6,8-trimethyl-2,3a,4,6a,7,8,9,9b-octahydro-3H-benzo[de]quinolin-4-yl]benzene-1,3-diol 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: 84.0%

: 936368-38-6
(3R,3aR,4R,6aS,8R,9bR)-4-(3,5-dimethoxyphenyl)-3,6,8-trimethyl-2,3a,4,6a,7,8,9,9b-octahydro-3H-benzo[de]quinoline

: 936368-39-7
5-[(3R,3aR,4R,6aS,8R,9bR)-3,6,8-trimethyl-2,3a,4,6a,7,8,9,9b-octahydro-3H-benzo[de]quinolin-4-yl]benzene-1,3-diol

Guidance literature:: (3R,3aR,4R,6aS,8R,9bR)-4-(3,5-dimethoxyphenyl)-3,6,8-trimethyl-2,3a,4,6a,7,8,9,9b-octahydro-3H-benzo[de]quinoline; With boron tribromide; In dichloromethane; at -80 - 0 ℃;

With sodium hydrogencarbonate; In dichloromethane; water; Further stages.;
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

: 936368-39-7
5-[(3R,3aR,4R,6aS,8R,9bR)-3,6,8-trimethyl-2,3a,4,6a,7,8,9,9b-octahydro-3H-benzo[de]quinolin-4-yl]benzene-1,3-diol

Guidance literature:: Multi-step reaction with 9 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

6.1: 94 percent / camphorsulfonic acid / benzene / 10 h / 80 °C

7.1: LiAlH₄ / diethyl ether / 24 h / 23 °C

8.1: 490 mg / aq. HCl / tetrahydrofuran / 2 h / 50 °C

9.1: boron tribromide / CH₂Cl₂ / -80 - 0 °C

9.2: 84 percent / NaHCO₃ / H₂O; CH₂Cl₂

With hydrogenchloride; lithium aluminium tetrahydride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; boron tribromide; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; benzene; 5.1: Dess-Martin oxidation;
DOI:10.1021/ol070049a

Reference yield:

: 936368-44-4
[(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]methyl methanesulfonate

: 936368-39-7
5-[(3R,3aR,4R,6aS,8R,9bR)-3,6,8-trimethyl-2,3a,4,6a,7,8,9,9b-octahydro-3H-benzo[de]quinolin-4-yl]benzene-1,3-diol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 98 percent / dimethylsulfoxide / 72 h / 50 °C

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

2.2: 87 percent / hexane; tetrahydrofuran / 0.5 h / -80 °C

3.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 23 °C

4.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 23 °C

5.1: 94 percent / camphorsulfonic acid / benzene / 10 h / 80 °C

6.1: LiAlH₄ / diethyl ether / 24 h / 23 °C

7.1: 490 mg / aq. HCl / tetrahydrofuran / 2 h / 50 °C

8.1: boron tribromide / CH₂Cl₂ / -80 - 0 °C

8.2: 84 percent / NaHCO₃ / H₂O; CH₂Cl₂

With hydrogenchloride; lithium aluminium tetrahydride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; boron tribromide; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; benzene; 4.1: Dess-Martin oxidation;
DOI:10.1021/ol070049a