(R, E)-6-cyclohexyl-3-methyl-5-methylenehex-2-ene-1,6-diol

Base Information

Chemical Name:(R, E)-6-cyclohexyl-3-methyl-5-methylenehex-2-ene-1,6-diol
CAS No.:1404458-86-1
Molecular Formula:C₁₄H₂₄O₂
Molecular Weight:224.343
Hs Code.:

Synonyms:(R, E)-6-cyclohexyl-3-methyl-5-methylenehex-2-ene-1,6-diol

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Chemical Property of (R, E)-6-cyclohexyl-3-methyl-5-methylenehex-2-ene-1,6-diol

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Technology Process of (R, E)-6-cyclohexyl-3-methyl-5-methylenehex-2-ene-1,6-diol

There total 5 articles about (R, E)-6-cyclohexyl-3-methyl-5-methylenehex-2-ene-1,6-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: 99.0%

: 1404458-83-8
(R,E)-6-(tert-butyldiphenylsilyloxy)-1-cyclohexyl-4-methyl-2-methylenehex-4-en-1-ol

: 1404458-86-1
(R, E)-6-cyclohexyl-3-methyl-5-methylenehex-2-ene-1,6-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 13h; Inert atmosphere;
DOI:10.1021/ol302751b

Reference yield:

: (E)-3-methylhex-2-en-5-yn-1-ol

: 1404458-86-1
(R, E)-6-cyclohexyl-3-methyl-5-methylenehex-2-ene-1,6-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium carbonate / methanol / 2 h / 20 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 2 h / 0 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -40 °C / Inert atmosphere

3.2: 2.5 h / -78 °C / Inert atmosphere

4.1: N-iodo-succinimide / dichloromethane / 0.17 h / 0 °C

5.1: N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; chromium dichloride; lithium chloride; manganese; C₁₀H₁₀O₄*NiCl₂; zirconocene dichloride / acetonitrile / 3 h / 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 13 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; chromium dichloride; manganese; N-iodo-succinimide; n-butyllithium; zirconocene dichloride; N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; C₁₀H₁₀O₄*NiCl₂; tetrabutyl ammonium fluoride; potassium carbonate; lithium chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; 5.1: |Nozaki-Hiyama-Kishi Reaction;
DOI:10.1021/ol302751b

Reference yield:

: 24529-80-4
(E)-1-O-acetyl-4-chloro-3-methyl-2-buten-1-ol

: 1404458-86-1
(R, E)-6-cyclohexyl-3-methyl-5-methylenehex-2-ene-1,6-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: potassium carbonate; tetra-(n-butyl)ammonium iodide; copper(l) iodide / acetonitrile / 27 h / 20 °C / Inert atmosphere

2.1: potassium carbonate / methanol / 2 h / 20 °C / Inert atmosphere

3.1: 1H-imidazole / dichloromethane / 2 h / 0 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -40 °C / Inert atmosphere

4.2: 2.5 h / -78 °C / Inert atmosphere

5.1: N-iodo-succinimide / dichloromethane / 0.17 h / 0 °C

6.1: N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; chromium dichloride; lithium chloride; manganese; C₁₀H₁₀O₄*NiCl₂; zirconocene dichloride / acetonitrile / 3 h / 20 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 13 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; chromium dichloride; manganese; N-iodo-succinimide; copper(l) iodide; n-butyllithium; zirconocene dichloride; N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; C₁₀H₁₀O₄*NiCl₂; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium carbonate; lithium chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; 6.1: |Nozaki-Hiyama-Kishi Reaction;
DOI:10.1021/ol302751b