(1R)-2-Cyclopentene-1α-acetic acid

Base Information

• Chemical Name: (1R)-2-Cyclopentene-1α-acetic acid
• CAS No.: 696-67-3
• Molecular Formula: C7H10O2
• Molecular Weight: 126.155
• Hs Code.: 2916209090
• Mol file: 696-67-3.mol

Synonyms:(R)-2-cyclopentene-1-acetic acid;((R)-cyclopent-2-enyl)-acetic acid;((R)-Cyclopent-2-enyl)-essigsaeure;

Chemical Property of (1R)-2-Cyclopentene-1α-acetic acid

Chemical Property:

• PSA: 37.30000
• LogP: 1.42730

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R)-2-Cyclopentene-1α-acetic acid

There total 2 articles about (1R)-2-Cyclopentene-1α-acetic 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: 93.0%

(R)-Cyclopent-2-enyl-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (161266-92-8) → (-)-(R)-cyclopent-2-en-1-yl-acetic acid (696-67-3) + (-)-8-phenylmenthol (65253-04-5)

Guidance literature:

With sodium hydroxide; In methanol; water; Heating;

DOI:10.1016/0040-4039(94)02216-X

Reference yield:

2',2'-dimethylspiro(bicyclo<4.1.0>heptane-7,5'-<1,3>dioxane)-4',6'-dione → (-)-(R)-cyclopent-2-en-1-yl-acetic acid (696-67-3) + (+)-(S)-cyclohex-2-enylacetic acid (137174-05-1)

Guidance literature:

With hydrogenchloride; hydoxocob(III)alamin hydrochloride; ammonium chloride; zinc; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) THF, water, O deg C, 2 h, ultrasonication, 2) 60 deg C, 22 h, 3) 250 deg C, 400 torr, 15 min;

DOI:10.1002/hlca.19940770502

Reference yield:

(-)-(R)-cyclopent-2-en-1-yl-acetic acid (696-67-3) → (-)-(S)-13-(cyclopent-2-en-1-yl)tridecanoic acid (29106-32-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 84 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / Heating

2.1: 88 percent / tetrabromomethane; triphenylphosphane / CH₂Cl₂ / 0 - 20 °C

3.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3.5 h / Heating

3.2: 58 percent / Li₂CuCl₄ / tetrahydrofuran / -20 °C

With lithium aluminium tetrahydride; carbon tetrabromide; magnesium; ethylene dibromide; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.200200700

upstream raw materials:

(R)-Cyclopent-2-enyl-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Downstream raw materials:

(3aR,6aS)-1-(2,6-dibromo-4-fluorophenyl)-3,3a,4,6a-tetrahydrocyclopenta[b]pyrrol-2(1H)-one

2-[(1R)-cyclopent-2-en-1-yl]-N-(2,6-dibromo-4-fluorophenyl)acetamide

[4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester

laropiprant

Refernces

• 1、 Troxler, Thomas,Scheffold, Rolf. "Asymmetric Catalysis by Vitamin B12: The Isomerization of Achiral Cyclopropanes to Optically Active Olefins". . p. 1193 - 1202. Retrieved 2007/10/02.