(1S,2S)-3-oxo-2-(2'Z-pentenyl)-cyclopentaneoctanoic acid

Base Information

• Chemical Name: (1S,2S)-3-oxo-2-(2'Z-pentenyl)-cyclopentaneoctanoic acid
• CAS No.: 204135-86-4
• Molecular Formula: C18H30O3
• DSSTox Substance ID: DTXSID30331495
• Metabolomics Workbench ID: 2330
• Nikkaji Number: J1.078.810B
• Wikidata: Q104950756
• Mol file: 204135-86-4.mol

Synonyms:(1S,2S)-3-oxo-2-(2'Z-pentenyl)-cyclopentaneoctanoic acid;204135-86-4;(9S,13S)-10,11-dihydro-12-oxo-15-phytoenoic acid;OPC-8:0;8-[(1R,2R)-3-Oxo-2-{(Z)-pent-2-enyl}cyclopentyl]octanoate;DTXSID30331495;CHEBI:137132;8-[(1S,2S)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]octanoic acid;LMFA02010007;3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid;C04780;(1S,2S)-3-oxo-2-(2Z-pentenyl)cyclopentane-1-octanoic acid;8-{(1S,2S)-3-Oxo-2-[(2Z)-2-penten-1-yl]cyclopentyl}octanoic acid

Chemical Property of (1S,2S)-3-oxo-2-(2'Z-pentenyl)-cyclopentaneoctanoic acid

Chemical Property:

• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 294.21949481
• Heavy Atom Count: 21
• Complexity: 346

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC1C(CCC1=O)CCCCCCCC(=O)O
• Isomeric SMILES: CC/C=C\C[C@H]1[C@H](CCC1=O)CCCCCCCC(=O)O

Technology Process of (1S,2S)-3-oxo-2-(2'Z-pentenyl)-cyclopentaneoctanoic acid

There total 6 articles about (1S,2S)-3-oxo-2-(2'Z-pentenyl)-cyclopentaneoctanoic 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: 75.0%

(1R,2S,3S)-3-(8-Hydroxy-octyl)-2-((Z)-pent-2-enyl)-cyclopentanol (620114-93-4) → (1S,2S)-3-oxo-2-(2Z-pentenyl)cyclopentane-1-octanoic acid (204135-86-4,136845-14-2)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In acetone; at 0 ℃; for 0.5h;

DOI:10.1021/jo0348571

Reference yield:

{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-hydroxy-cyclopentyl}-acetic acid (1027148-88-4) → (1S,2S)-3-oxo-2-(2Z-pentenyl)cyclopentane-1-octanoic acid (204135-86-4,136845-14-2)

Guidance literature:

Multi-step reaction with 6 steps

1: diethyl ether / 0 °C

2: 358 mg / imidazole / dimethylformamide / 1 h / 20 °C

3: 77 percent / DIBAL / CH₂Cl₂; hexane / 0.83 h / -78 °C

4: 96 percent / NaN(TMS)2 / tetrahydrofuran; dimethylformamide / 2 h / 0 - 20 °C

5: 98 percent / TBAF; 4 Angstroem molecular sieves / tetrahydrofuran / 2 h / 60 - 65 °C

6: 75 percent / CrO₃; H₂SO₄ / acetone / 0.5 h / 0 °C

With 1H-imidazole; chromium(VI) oxide; 4 A molecular sieve; sulfuric acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 4: Wittig reaction / 6: Jones oxidation;

DOI:10.1021/jo0348571

Reference yield:

{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-hydroxy-cyclopentyl}-acetic acid methyl ester → (1S,2S)-3-oxo-2-(2Z-pentenyl)cyclopentane-1-octanoic acid (204135-86-4,136845-14-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 358 mg / imidazole / dimethylformamide / 1 h / 20 °C

2: 77 percent / DIBAL / CH₂Cl₂; hexane / 0.83 h / -78 °C

3: 96 percent / NaN(TMS)2 / tetrahydrofuran; dimethylformamide / 2 h / 0 - 20 °C

4: 98 percent / TBAF; 4 Angstroem molecular sieves / tetrahydrofuran / 2 h / 60 - 65 °C

5: 75 percent / CrO₃; H₂SO₄ / acetone / 0.5 h / 0 °C

With 1H-imidazole; chromium(VI) oxide; 4 A molecular sieve; sulfuric acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 3: Wittig reaction / 5: Jones oxidation;

DOI:10.1021/jo0348571

upstream raw materials:

(1R,2S,3S)-3-(8-Hydroxy-octyl)-2-((Z)-pent-2-enyl)-cyclopentanol

{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-hydroxy-cyclopentyl}-acetic acid

{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopentyl}-acetaldehyde

C₄₀H₆₆O₂Si₂

Downstream raw materials:

8-[3-oxo-2-trans-{(Z)-2-pentenyl}cyclopentyl]octanoic acid