[S,(-)]-3-Oxocyclopentaneacetic acid

Base Information

• Chemical Name: [S,(-)]-3-Oxocyclopentaneacetic acid
• CAS No.: 2630-37-7
• Molecular Formula: C7H10O3
• Molecular Weight: 142.15
• Mol file: 2630-37-7.mol

Synonyms:(1S)-3-Oxocyclopentane-1-acetic acid;[S,(-)]-3-Oxocyclopentaneacetic acid;(S)-2-(3-Oxocyclopentyl)acetic acid

Chemical Property of [S,(-)]-3-Oxocyclopentaneacetic acid

Chemical Property:

• Boiling Point: 316.5±15.0 °C(Predicted)
• PKA: 4.52±0.10(Predicted)
• PSA: 54.37000
• Density: 1.210±0.06 g/cm3(Predicted)
• LogP: 0.83030
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

(S)-2-(3-Oxocyclopentyl)aceticacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [S,(-)]-3-Oxocyclopentaneacetic acid

There total 5 articles about [S,(-)]-3-Oxocyclopentaneacetic 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: 33.0%

phenylthioacetylene (6228-98-4) + 2-carbomethoxycyclopent-2-enone (36601-73-7) → 3-(hydroxycarbonylmethyl)cyclopentan-1-one (2630-44-6) + 3-(hydroxycarbonylmethyl)cyclopentan-1-one (2630-37-7)

Guidance literature:

phenylthioacetylene; 2-carbomethoxycyclopent-2-enone; With 2,2'-bis(picolinoyloxy)-(1S)-1,1'-binaphthalene; silver hexafluoroantimonate; copper dichloride; In dichloromethane; at -78 ℃; for 3h;

With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.5h;

With hydrogenchloride; In methanol; at 60 ℃; for 12h; Title compound not separated from byproducts;

DOI:10.1016/j.tet.2006.01.050

Reference yield:

norbornane-2,6-dione → 3-(hydroxycarbonylmethyl)cyclopentan-1-one (2630-44-6) + 3-(hydroxycarbonylmethyl)cyclopentan-1-one (2630-37-7)

Guidance literature:

With 6-oxocamphor hydrolase from Rhodococcus sp. NCIMB 9784; In water; at 20 ℃; for 2h; pH=7.0; Title compound not separated from byproducts;

DOI:10.1002/1521-3773(20010316)40:6<1111::AID-ANIE11110>3.0.CO;2-2

Reference yield:

(1R,2S,3R)-3-Hydroxy-2-(methoxycarbonyl)cyclopentanessigsaeure-methylester (68366-27-8) → 3-(hydroxycarbonylmethyl)cyclopentan-1-one (2630-37-7)

Guidance literature:

Multi-step reaction with 2 steps

1: CrO₃, aq. H₂SO₄ / acetone

2: aq. HCl

With chromium(VI) oxide; hydrogenchloride; sulfuric acid; In acetone;

DOI:10.1021/jo01317a034

upstream raw materials:

(-)-Methyl-2-(methoxycarbonyl)-3-oxocyclopentanacetat

ethyl 5-oxocyclopent-1-en-1-carboxylate

1-(tert-butyldimethylsilyloxy)-1-tert-butoxyethylene

phenylthioacetylene

Downstream raw materials:

(S)-(-)-methyl 3-oxocyclopentylacetate