(1S,4R)-4-(3-Hydroxy-propyl)-4-vinyl-cyclohex-2-enol

Base Information

• Chemical Name: (1S,4R)-4-(3-Hydroxy-propyl)-4-vinyl-cyclohex-2-enol
• CAS No.: 503000-53-1
• Molecular Formula: C₁₁H₁₈O₂
• Molecular Weight: 182.263
• Mol file: 503000-53-1.mol

Synonyms:(1S,4R)-4-(3-Hydroxy-propyl)-4-vinyl-cyclohex-2-enol

Chemical Property of (1S,4R)-4-(3-Hydroxy-propyl)-4-vinyl-cyclohex-2-enol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R)-4-(3-Hydroxy-propyl)-4-vinyl-cyclohex-2-enol

There total 16 articles about (1S,4R)-4-(3-Hydroxy-propyl)-4-vinyl-cyclohex-2-enol 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: 94.0%

(1S,4R)-4-[3-(tert-butyldiphenylsiloxy)propyl]-4-vinyl-2-cyclohexen-1-ol (503000-26-8) → (1S,4R)-4-(3-Hydroxy-propyl)-4-vinyl-cyclohex-2-enol (503000-53-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1021/ol034020s

Reference yield:

1-[3-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxy)-3-vinyl-hexylselanyl]-2-nitro-benzene (503000-47-3) → (1S,4R)-4-(3-Hydroxy-propyl)-4-vinyl-cyclohex-2-enol (503000-53-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 91 percent / H₂O₂ / tetrahydrofuran / 1 h / 20 °C

2.1: 100 percent / aq. HCl / ethanol / 2 h / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 89 percent / benzene / 5 h / Heating

5.1: 100 percent / DIBAl-H / tetrahydrofuran; hexane / 0.5 h / 0 °C

6.1: 92 percent / L-(+)-DIPT; molecular sieves 4 Angstroem; TBHP / Ti(i-PrO)4 / CH₂Cl₂ / -25 - 20 °C

7.1: 95 percent / triphenylphosphine; I₂; imidazole / benzene / 0.5 h / 20 °C

8.1: 96 percent / Zn; acetic acid / 0.5 h / 50 °C

9.1: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

10.1: (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 48 h / 20 °C

10.2: 87 percent / aq. HCl / tetrahydrofuran / 0.5 h / 20 °C / Acid hydrolysis

11.1: 94 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

With 1H-imidazole; hydrogenchloride; tert.-butylhydroperoxide; Grubbs catalyst first generation; oxalyl dichloride; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; titanium(IV) isopropylate; In tetrahydrofuran; ethanol; hexane; dichloromethane; benzene; 4.1: Wittig reaction / 6.1: Katsuki-Sharpless asymmetric epoxidation;

DOI:10.1021/ol034020s

Reference yield:

6-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-vinyl-octa-2,7-dienoic acid ethyl ester (503000-50-8) → (1S,4R)-4-(3-Hydroxy-propyl)-4-vinyl-cyclohex-2-enol (503000-53-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 100 percent / DIBAl-H / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.1: 92 percent / L-(+)-DIPT; molecular sieves 4 Angstroem; TBHP / Ti(i-PrO)4 / CH₂Cl₂ / -25 - 20 °C

3.1: 95 percent / triphenylphosphine; I₂; imidazole / benzene / 0.5 h / 20 °C

4.1: 96 percent / Zn; acetic acid / 0.5 h / 50 °C

5.1: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

6.1: (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 48 h / 20 °C

6.2: 87 percent / aq. HCl / tetrahydrofuran / 0.5 h / 20 °C / Acid hydrolysis

7.1: 94 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; Grubbs catalyst first generation; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; iodine; diisobutylaluminium hydride; acetic acid; triethylamine; triphenylphosphine; zinc; titanium(IV) isopropylate; In tetrahydrofuran; hexane; dichloromethane; benzene; 2.1: Katsuki-Sharpless asymmetric epoxidation;

DOI:10.1021/ol034020s

upstream raw materials:

(1S,4R)-4-[3-(tert-butyldiphenylsiloxy)propyl]-4-vinyl-2-cyclohexen-1-ol

6-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-vinyl-octa-2,7-dienoic acid ethyl ester

tert-Butyl-{4-[2-((2S,3R)-3-iodomethyl-oxiranyl)-ethyl]-4-vinyl-hex-5-enyloxy}-diphenyl-silane

1-[3-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxy)-3-vinyl-hexylselanyl]-2-nitro-benzene

Downstream raw materials:

(4S)-4-(2-carbamoylethyl)-4-vinyl-2-cyclohexene-1-one

(3¹S,6aR,9aR)-6a-ethyloctahydro-1H-pyrrolo[3,2,1-ij]quinolin-9(2H)-one

C₁₁H₁₅O₂NH₂C₂H₆

N-(6a-ethyl-decahydro-pyrrolo[3,2,1-ij]quinolin-9-ylidene)-N'-(2-methoxy-phenyl)-hydrazine