(1R,3R,6S)-3-<(E)-5-formyl-3-methyl-2-pentenyl>-1,6-dimethyl-2-methylenecyclohexanebutyronitrile

Base Information

Chemical Name:(1R,3R,6S)-3-<(E)-5-formyl-3-methyl-2-pentenyl>-1,6-dimethyl-2-methylenecyclohexanebutyronitrile
CAS No.:150930-65-7
Molecular Formula:C₂₀H₃₁NO
Molecular Weight:301.472
Hs Code.:

Synonyms:(1R,3R,6S)-3-<(E)-5-formyl-3-methyl-2-pentenyl>-1,6-dimethyl-2-methylenecyclohexanebutyronitrile

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Chemical Property of (1R,3R,6S)-3-<(E)-5-formyl-3-methyl-2-pentenyl>-1,6-dimethyl-2-methylenecyclohexanebutyronitrile

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Technology Process of (1R,3R,6S)-3-<(E)-5-formyl-3-methyl-2-pentenyl>-1,6-dimethyl-2-methylenecyclohexanebutyronitrile

There total 19 articles about (1R,3R,6S)-3-<(E)-5-formyl-3-methyl-2-pentenyl>-1,6-dimethyl-2-methylenecyclohexanebutyronitrile 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: 92.0%

: 4-[(1R,3R,6S)-1,6-Dimethyl-2-methylene-3-(3-methyl-2-vinyloxy-but-3-enyl)-cyclohexyl]-butyronitrile

: 150930-65-7
(1R,3R,6S)-3-<(E)-5-formyl-3-methyl-2-pentenyl>-1,6-dimethyl-2-methylenecyclohexanebutyronitrile

Guidance literature:: In benzene; at 170 ℃; for 20h;
DOI:10.1021/ja00087a023

Reference yield:

: 150930-58-8
(1S,8aR)-1,2,3,7,8,8a-hexahydro-6-methoxy-1,8a-dimethylnaphthalene

: 150930-65-7
(1R,3R,6S)-3-<(E)-5-formyl-3-methyl-2-pentenyl>-1,6-dimethyl-2-methylenecyclohexanebutyronitrile

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) MCPBA, 2.) silica gel / 1.) benzene, hexanes, 0 deg C - RT, 30 min, 2.) benzene, hexanes, 40 min

2: 59 percent / NaBH₄ / methanol / 0.33 h / 0 °C

3: 91 percent / imidazole / dimethylformamide / 2 h

4: 98 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

5: 81 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6: 4 percent / 18-crown-6 / dimethylformamide / 16 h / 45 °C

7: 70 percent / Hg(OCOCF₃)2, Et₃N / 20 h / Ambient temperature

8: 25 percent / xylene / 14 h / 210 °C

9: tetrahydrofuran / 1 h / -78 °C

10: Hg(OCOCF₃)2, Et₃N / 24 h / Ambient temperature

11: 92 percent / benzene / 20 h / 170 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; 18-crown-6 ether; mercury(II) trifluoroacetate; silica gel; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; xylene; benzene;
DOI:10.1021/ja00087a023

Reference yield:

: 105088-15-1
(4aR,5S)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone

: 150930-65-7
(1R,3R,6S)-3-<(E)-5-formyl-3-methyl-2-pentenyl>-1,6-dimethyl-2-methylenecyclohexanebutyronitrile

Guidance literature:: Multi-step reaction with 12 steps

1: 89 percent / p-TsOH / dimethylformamide; methanol / 24 h

2: 1.) MCPBA, 2.) silica gel / 1.) benzene, hexanes, 0 deg C - RT, 30 min, 2.) benzene, hexanes, 40 min

3: 59 percent / NaBH₄ / methanol / 0.33 h / 0 °C

4: 91 percent / imidazole / dimethylformamide / 2 h

5: 98 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

6: 81 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

7: 4 percent / 18-crown-6 / dimethylformamide / 16 h / 45 °C

8: 70 percent / Hg(OCOCF₃)2, Et₃N / 20 h / Ambient temperature

9: 25 percent / xylene / 14 h / 210 °C

10: tetrahydrofuran / 1 h / -78 °C

11: Hg(OCOCF₃)2, Et₃N / 24 h / Ambient temperature

12: 92 percent / benzene / 20 h / 170 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; 18-crown-6 ether; mercury(II) trifluoroacetate; silica gel; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; xylene; benzene;
DOI:10.1021/ja00087a023