122331-03-7

Basic information

• Product Name: (1S,2S)-TRANS-2-HYDROXY-CYCLOPENTANECARBOXYLIC ACID ETHYL ESTER
• Synonyms: ETHYL (1S,2S)-TRANS-2-HYDROXYCYCLOPENTANECARBOXYLATE;(1S,2S)-TRANS-2-HYDROXY-CYCLOPENTANECARBOXYLIC ACID ETHYL ESTER;ETHYL (1S 2S)-TRANS-2-HYDROXYCYCLOPENTAN
• CAS NO: 122331-03-7
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.19
• Product Categories: Chiral Building Blocks;Esters;Organic Building Blocks;Chiral Alcohols
• Mol File: 122331-03-7.mol
• Article Data: 27

Chemical Properties

• Appearance: /
• Refractive Index: n20/D 1.457
• CAS DataBase Reference: (1S,2S)-TRANS-2-HYDROXY-CYCLOPENTANECARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-TRANS-2-HYDROXY-CYCLOPENTANECARBOXYLIC ACID ETHYL ESTER(122331-03-7)
• EPA Substance Registry System: (1S,2S)-TRANS-2-HYDROXY-CYCLOPENTANECARBOXYLIC ACID ETHYL ESTER(122331-03-7)

Safety Data

• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 122331-03-7(Hazardous Substances Data)

Usage

General Description

The chemical (1S,2S)-trans-2-hydroxy-cyclopentanecarboxylic acid ethyl ester is an organic compound with the molecular formula C9H16O3. It is a colorless liquid with a faint odor and is commonly used as a building block in organic synthesis. (1S,2S)-TRANS-2-HYDROXY-CYCLOPENTANECARBOXYLIC ACID ETHYL ESTER is a chiral molecule, meaning it has non-superimposable mirror images, and is often used in the production of pharmaceuticals and agrochemicals. It can also be used as a flavoring agent or fragrance ingredient in various products. Additionally, it has potential applications in the field of medicinal chemistry and drug development.

Upstream product

• 5299-60-5 6-hydroxy-hexanoic acid ethyl ester 
• 294212-80-9 2-bromo-6-triethylsilanyloxy-hexanoic acid ethyl ester 
• 294212-79-6 ethyl 6-triethylsilyloxyhexanoate 
• 294212-81-0 ethyl 2-bromo-6-hydroxyhexanoate 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 294212-87-6 ethyl 2-bromo-6-oxohexanoate 
• 63578-04-1 (+/-)-trans-2-(3.5-dinitro-benzoyloxy)-cyclopentane-carboxylic acid-⁽¹⁾-ethyl ester 
• 124668-80-0 (E)-ethyl 6-[(methylsulfonyl)oxy]hex-2-enoate 
• 13038-15-8 (E)-6-hydroxy-hex-2-enoic acid ethyl ester 
• 1092929-40-2 (Z)-6-hydroxy-hex-2-enoic acid ethyl ester 
• 63578-04-1 (+/-)-cis-2-(3,5-dinitro-benzoyloxy)-cyclopentane-carboxylic acid-⁽¹⁾-ethyl ester 
• 1373216-32-0 tris(4-isopropylphenyl)silyl chloride 
• 1883-91-6 ethyl trans-2-hydroxy-1-cyclopentane carboxylate 
• 108-05-4 vinyl acetate 

Downstream Products

• 61586-79-6 ethyl (1R,2S)-2-hydroxycyclopentanecarboxylate 
• 110611-67-1 ethyl (1R,2R)-2-hydroxycyclopentanecarboxylate 
• 124150-23-8 (1R,2S)-2-methoxycarbonylcyclopentan-1-ol 
• 110611-68-2 ethyl syn-(1S,2R)-2-hydroxycyclopentanecarboxylate 
• 169868-13-7 (1S,2R)-2-hydroxycyclopentane-1-carboxylic acid 
• 130023-77-7 C₁₃H₁₇N₃O₂S 
• 130023-83-5 (1R,2S)-2-(5-Mercapto-4-phenyl-4H-[1,2,4]triazol-3-yl)-cyclopentanol 

Relevant articles and documents

Investigation of Electrostatic Interactions towards Controlling Silylation-Based Kinetic Resolutions

Electrostatic interactions between a silylated isothiourea intermediate and an ester π system were explored by determining how variations in sterics and electronics affect the selectivity of a silylation-based kinetic resolution. Sterics on the π systems affect the selectivity factors of alkyl 2-hydroxycyclohexanecarboxylates, resulting in a strong correlation of selectivity factors to Charton values. Induction effects of electron-withdrawing substituents on phenyl esters significantly enhance selectivity supporting an edge to face π–π interaction. The linear free energy relationships that were uncovered will aid in future incorporation of intermolecular electrostatic interactions towards controlling asymmetric reactions.

Candida antarctica lipase B-catalyzed reactions of β-hydroxy esters: Competition of acylation and hydrolysis

The ester function of ethyl cis-(±)-2-hydroxycyclopentane-1- carboxylate [(±)-1] and ethyl (±)-5-hydroxycyclopent-1- enecarboxylate [(±)-2] was demonstrated to undergo hydrolysis, as a side-reaction, during asymmetric (E > 200) O-acylation with Candida antarctica lipase B (CAL-B) as catalyst and vinyl acetate as acyl donor in t-BuOMe at 30 C. This competition of acylation and undesirable hydrolysis draws attention to CAL-B-catalyzed non-hydrolytic resolutions where the substrates contain any hydrolysable functions. Enantiomerically enriched cis-2-hydroxycyclopentane-1-carboxylic acid (ee = 90%) and 5-hydroxycyclopent-1- enecarboxylic acid (ee = 47%) were prepared through de novo CAL-B-catalyzed hydrolysis of (±)-1 and (±)-2 with added H2O in t-BuOMe at 30 C.

Chiral Diphosphonites as Ligands in the Ruthenium-Catalyzed Enantioselective Reduction of Ketones, B-Ketoesters and Ketimines

Chiral ruthenium complexes are disclosed, obtained by reaction of a ruthenium salt with a chiral diphosphonite. Chiral diols with the general structure given in scheme 1 are preferably used as chiral diphosphonites. Said ruthenium complexes can be simply and economically obtained and provide high enantioselectivity on reduction of ketones, β-ketoesters and ketimines.