Ethyl 2-hydroxycyclopentanecarboxylate

Base Information

• Chemical Name: Ethyl 2-hydroxycyclopentanecarboxylate
• CAS No.: 1883-91-6
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.197
• NSC Number: 122560,122559
• DSSTox Substance ID: DTXSID30940324
• Nikkaji Number: J1.476.908K
• Mol file: 1883-91-6.mol

Synonyms:Ethyl 2-hydroxycyclopentanecarboxylate;54972-10-0;ethyl 2-hydroxycyclopentane-1-carboxylate;1883-91-6;2-hydroxy-cyclopentanecarboxylic acid ethyl ester;MFCD02093827;Ethyl2-Hydroxycyclopentanecarboxylate;Cyclopentanecarboxylic acid, 2-hydroxy-, ethyl ester;1-cyclopentanecarboxylic acid, 2-hydroxy-, ethyl ester;SCHEMBL1611567;DTXSID30940324;NSC122559;NSC122560;AKOS006228274;ethyl 2-hydroxycyclopentane-carboxylate;NSC-122559;NSC-122560;SB45796;SB83951;Ethyl 2-hydroxycyclopentanecarboxylate #;SY056771;TS-02104;FT-0626255;FT-0771012;FT-0772851;2-hydroxy-cyclopentylcarboxylic acid ethyl ester;A913943;ETHYL(1R,2S)-CIS-2-HYDROXYCYCLOPENTANECARBOXYLATE

Chemical Property of Ethyl 2-hydroxycyclopentanecarboxylate

Chemical Property:

• Vapor Pressure: 0.00322mmHg at 25°C
• Melting Point: 68-69 °C
• Boiling Point: 143-144°C/40mm
• PKA: 14.65±0.40(Predicted)
• Flash Point: 100.2°C
• PSA: 46.53000
• Density: 1.051
• LogP: 0.71050
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 144

Purity/Quality:

98%,99%, ^*data from raw suppliers

ETHYL TRANS-2-HYDROXYCYCLOPENTANECARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: R36/37/38:
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CCCC1O

Technology Process of Ethyl 2-hydroxycyclopentanecarboxylate

There total 22 articles about Ethyl 2-hydroxycyclopentanecarboxylate 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: 89.0%

ethyl 2-cis-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopentanecarboxylate → ethyl cis-(±)-2-hydroxycyclopentane-1-carboxylate (1883-91-6,2315-21-1,54972-10-0,61586-79-6,63599-14-4,63599-15-5,110611-67-1,110611-68-2,122331-03-7)

Guidance literature:

With sodium perborate tetrahydrate; In tetrahydrofuran; water; at 27 ℃; Inert atmosphere;

DOI:10.1039/c7ob01382e

Reference yield: 71.0%

2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → ethyl cis-(±)-2-hydroxycyclopentane-1-carboxylate (1883-91-6,2315-21-1,54972-10-0,61586-79-6,63599-14-4,63599-15-5,110611-67-1,110611-68-2,122331-03-7) + ethyl trans-2-hydroxy-1-cyclopentane carboxylate (1883-91-6,2315-21-1,54972-10-0,61586-79-6,63599-14-4,63599-15-5,110611-67-1,110611-68-2,122331-03-7)

Guidance literature:

With zinc(II) tetrahydroborate; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1016/S0957-4166(03)00366-5

Reference yield: 71.0%

2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → ethyl cis-(±)-2-hydroxycyclopentane-1-carboxylate (1883-91-6,2315-21-1,54972-10-0,61586-79-6,63599-14-4,63599-15-5,110611-67-1,110611-68-2,122331-03-7) + ethyl trans-2-hydroxy-1-cyclopentane carboxylate (1883-91-6,2315-21-1,54972-10-0,61586-79-6,63599-14-4,63599-15-5,110611-67-1,110611-68-2,122331-03-7)

Guidance literature:

With zinc(II) tetrahydroborate; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1016/S0957-4166(03)00366-5

upstream raw materials:

2-ethoxycarbonyl-1-cyclopentanone

(+/-)-cis-2-(3,5-dinitro-benzoyloxy)-cyclopentane-carboxylic acid-⁽¹⁾-ethyl ester

ethyl 2-bromo-6-oxohexanoate

ethyl 2-bromo-6-hydroxyhexanoate

Downstream raw materials:

(+/-)-cis-2-hydroxy-cyclopentane-carboxylic acid-⁽¹⁾-hydrazide

N-methyl-cis-2-hydroxycyclopentanecarboxamide

ethyl (1R,2S)-2-hydroxycyclopentanecarboxylate

(+/-)-trans-2-hydroxy-cyclopentane-carboxylic acid-⁽¹⁾-hydrazide

Refernces

• 1、 Zuo, Ya-Jie,Chang, Xiao-Tong,Hao, Zhi-Ming,Zhong, Chong-Min. "Copper-catalyzed, stereoconvergent,: Cis -diastereoselective borylative cyclization of ω -mesylate- α, β -unsaturated esters and ketones". supporting information. p. 6323 - 6327. Retrieved 2017/08/10.
• 2、 Levy, Laura M.,Dehli, Juan R.,Gotor, Vicente. "Lipase-catalysed resolution of cyclic cis- and trans-β-hydroxy esters". . p. 2053 - 2058. Retrieved 2007/10/03.