ethyl (1R,3aS,5S,7aR)-5-cyclohexyl-3a-hydroxy-7a-methylperhydroindene-1-yl-(E)-metacrylate

Base Information

Chemical Name:ethyl (1R,3aS,5S,7aR)-5-cyclohexyl-3a-hydroxy-7a-methylperhydroindene-1-yl-(E)-metacrylate
CAS No.:392235-27-7
Molecular Formula:C₂₂H₃₆O₃
Molecular Weight:348.526
Hs Code.:

Synonyms:ethyl (1R,3aS,5S,7aR)-5-cyclohexyl-3a-hydroxy-7a-methylperhydroindene-1-yl-(E)-metacrylate

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Chemical Property of ethyl (1R,3aS,5S,7aR)-5-cyclohexyl-3a-hydroxy-7a-methylperhydroindene-1-yl-(E)-metacrylate

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Technology Process of ethyl (1R,3aS,5S,7aR)-5-cyclohexyl-3a-hydroxy-7a-methylperhydroindene-1-yl-(E)-metacrylate

There total 12 articles about ethyl (1R,3aS,5S,7aR)-5-cyclohexyl-3a-hydroxy-7a-methylperhydroindene-1-yl-(E)-metacrylate 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:

: 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

: 392235-27-7
ethyl (1R,3aS,5S,7aR)-5-cyclohexyl-3a-hydroxy-7a-methylperhydroindene-1-yl-(E)-metacrylate

Guidance literature:: Multi-step reaction with 9 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 / 0.5 h / 0 °C

9.2: tetrahydrofuran / 2 h / 20 °C

With borane; potassium tert-butylate; hydrogen; oxalic acid; nickel; sodium hydride; toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; 5percent Rh/Al₂₀₃; In tetrahydrofuran; 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

: 392235-27-7
ethyl (1R,3aS,5S,7aR)-5-cyclohexyl-3a-hydroxy-7a-methylperhydroindene-1-yl-(E)-metacrylate

Guidance literature:: Multi-step reaction with 5 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 / 0.5 h / 0 °C

5.2: tetrahydrofuran / 2 h / 20 °C

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

Reference yield:

: 178379-39-0
(1S,3aS,7aR)-1-hydroxymethyl-3a-hydroxy-7a-methyl-5-perhydroindenone

: 392235-27-7
ethyl (1R,3aS,5S,7aR)-5-cyclohexyl-3a-hydroxy-7a-methylperhydroindene-1-yl-(E)-metacrylate

Guidance literature:: Multi-step reaction with 5 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 / 0.5 h / 0 °C

5.2: tetrahydrofuran / 2 h / 20 °C

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