(1R,3aS,5S,7aR)-1-(E)-acrylaldehyde-5-cyclohexyl-7a-methylperhydroindene-3a-ol

Base Information

Chemical Name:(1R,3aS,5S,7aR)-1-(E)-acrylaldehyde-5-cyclohexyl-7a-methylperhydroindene-3a-ol
CAS No.:178379-82-3
Molecular Formula:C₁₉H₃₀O₂
Molecular Weight:290.446
Hs Code.:

Synonyms:(1R,3aS,5S,7aR)-1-(E)-acrylaldehyde-5-cyclohexyl-7a-methylperhydroindene-3a-ol

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Chemical Property of (1R,3aS,5S,7aR)-1-(E)-acrylaldehyde-5-cyclohexyl-7a-methylperhydroindene-3a-ol

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Technology Process of (1R,3aS,5S,7aR)-1-(E)-acrylaldehyde-5-cyclohexyl-7a-methylperhydroindene-3a-ol

There total 12 articles about (1R,3aS,5S,7aR)-1-(E)-acrylaldehyde-5-cyclohexyl-7a-methylperhydroindene-3a-ol 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%

: 392235-38-0
(1R,3aS,5S,7aR)-1-(E)-allyl alcohol-5-cyclohexyl-7a-methylperhydroindene-3a-ol

: 178379-82-3
(1R,3aS,5S,7aR)-1-(E)-acrylaldehyde-5-cyclohexyl-7a-methylperhydroindene-3a-ol

Guidance literature:: With manganese(IV) oxide; In 1,4-dioxane; at 20 ℃; for 3h;
DOI:10.1021/jm011001k

Reference yield:

: 33879-04-8,51065-67-9
(+)-(3aS,7aS)-2,3,3a,4,7,7a-hexahydro-3a-hydroxy-7a-methyl-1H-indene-1,5(6H)-dione

: 178379-82-3
(1R,3aS,5S,7aR)-1-(E)-acrylaldehyde-5-cyclohexyl-7a-methylperhydroindene-3a-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 83 percent / oxalic acid / acetonitrile / 16 h

2.1: 77 percent / t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Heating

3.1: BH₃ / tetrahydrofuran / 1 h / 20 °C

3.2: 20 percent / NaBO₃; aq. NaOH / 16 h / 20 °C

4.1: 68 percent / 1 N pTSA / acetonitrile; H₂O / 16 h

5.1: 82 percent / tetrahydrofuran; cyclohexane; diethyl ether / 1 h / -78 - 0 °C

6.1: 82 percent / Raney-Ni / ethanol; H₂O / 3 h / Heating

7.1: 100 percent / H₂ / 5percent Rh/Al₂₀₃ / methanol / 4 h / 3268.22 Torr

8.1: 100 percent / IBX / dimethylsulfoxide / 1.5 h

9.1: NaH / tetrahydrofuran / 1 h / 0 °C

9.2: 100 percent / tetrahydrofuran / 2 h / 20 °C

10.1: DIBAH / tetrahydrofuran / 16 h / -78 - 20 °C

11.1: 96 percent / MnO₂ / dioxane / 3 h / 20 °C

With manganese(IV) oxide; borane; potassium tert-butylate; hydrogen; oxalic acid; nickel; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; 5percent Rh/Al₂₀₃; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; cyclohexane; water; dimethyl sulfoxide; acetonitrile; tert-butyl alcohol; 2.1: Wittig reaction / 9.2: Horner-Emmons reaction;
DOI:10.1021/jm011001k

Reference yield:

: 591-51-5
phenyllithium

: 178379-82-3
(1R,3aS,5S,7aR)-1-(E)-acrylaldehyde-5-cyclohexyl-7a-methylperhydroindene-3a-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 82 percent / tetrahydrofuran; cyclohexane; diethyl ether / 1 h / -78 - 0 °C

2.1: 82 percent / Raney-Ni / ethanol; H₂O / 3 h / Heating

3.1: 100 percent / H₂ / 5percent Rh/Al₂₀₃ / methanol / 4 h / 3268.22 Torr

4.1: 100 percent / IBX / dimethylsulfoxide / 1.5 h

5.1: NaH / tetrahydrofuran / 1 h / 0 °C

5.2: 100 percent / tetrahydrofuran / 2 h / 20 °C

6.1: DIBAH / tetrahydrofuran / 16 h / -78 - 20 °C

7.1: 96 percent / MnO₂ / dioxane / 3 h / 20 °C

With manganese(IV) oxide; hydrogen; nickel; sodium hydride; diisobutylaluminium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; 5percent Rh/Al₂₀₃; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; cyclohexane; water; dimethyl sulfoxide; 5.2: Horner-Emmons reaction;
DOI:10.1021/jm011001k