3-((S)-4-Oxo-1-vinyl-cyclohex-2-enyl)-propionic acid

Base Information

• Chemical Name: 3-((S)-4-Oxo-1-vinyl-cyclohex-2-enyl)-propionic acid
• CAS No.: 503000-34-8
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• Mol file: 503000-34-8.mol

Synonyms:3-((S)-4-Oxo-1-vinyl-cyclohex-2-enyl)-propionic acid

Chemical Property of 3-((S)-4-Oxo-1-vinyl-cyclohex-2-enyl)-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((S)-4-Oxo-1-vinyl-cyclohex-2-enyl)-propionic acid

There total 17 articles about 3-((S)-4-Oxo-1-vinyl-cyclohex-2-enyl)-propionic acid 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: 91.0%

(1S,4R)-4-(3-Hydroxy-propyl)-4-vinyl-cyclohex-2-enol (503000-53-1) → 3-((S)-4-Oxo-1-vinyl-cyclohex-2-enyl)-propionic acid (503000-34-8)

Guidance literature:

With jones reagent; In acetone; at 20 ℃; for 0.333333h;

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) → 3-((S)-4-Oxo-1-vinyl-cyclohex-2-enyl)-propionic acid (503000-34-8)

Guidance literature:

Multi-step reaction with 12 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

12.1: 91 percent / Jones reagent / acetone / 0.33 h / 20 °C

With 1H-imidazole; hydrogenchloride; tert.-butylhydroperoxide; Grubbs catalyst first generation; jones reagent; 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; acetone; benzene; 4.1: Wittig reaction / 6.1: Katsuki-Sharpless asymmetric epoxidation / 12.1: Jones oxidation;

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) → 3-((S)-4-Oxo-1-vinyl-cyclohex-2-enyl)-propionic acid (503000-34-8)

Guidance literature:

Multi-step reaction with 8 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

8.1: 91 percent / Jones reagent / acetone / 0.33 h / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; Grubbs catalyst first generation; jones reagent; 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; acetone; benzene; 2.1: Katsuki-Sharpless asymmetric epoxidation / 8.1: Jones oxidation;

DOI:10.1021/ol034020s

upstream raw materials:

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

(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

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