1883-91-6

Basic information

• Product Name: ETHYL TRANS-2-HYDROXYCYCLOHEXANECARBOXYLATE
• Synonyms: trans-2-Carbethoxycyclopentanol.;2-hydroxycyclopentanecarboxylic acid ethyl ester;ethyl 2-hydroxycyclopentane-1-carboxylate;ethyl 2-hydroxycyclopentanecarboxylate;Cyclopentanecarboxylic acid, 2-hydroxy-, ethyl ester, (1R,2R)-rel-
• CAS NO: 1883-91-6
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 172.23
• Mol File: 1883-91-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 68-69 °C
• Boiling Point: 143-144°C/40mm
• Flash Point: 100.2°C
• Appearance: /
• Density: 1.051
• Vapor Pressure: 0.00322mmHg at 25°C
• Refractive Index: 1.481
• PKA: 14.65±0.40(Predicted)
• CAS DataBase Reference: ETHYL TRANS-2-HYDROXYCYCLOHEXANECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL TRANS-2-HYDROXYCYCLOHEXANECARBOXYLATE(1883-91-6)
• EPA Substance Registry System: ETHYL TRANS-2-HYDROXYCYCLOHEXANECARBOXYLATE(1883-91-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 1883-91-6(Hazardous Substances Data)

Usage

General Description

Ethyl trans-2-hydroxycyclohexanecarboxylate is an organic compound which counts amongst the class of cyclohexanecarboxylic acids and derivatives. Its primary role is as an intermediate molecule in the pharmaceutical industry. The molecule is characterized by its cycle of six Carbon atoms, with one of the carbons attached to a carboxylate group (-COOEt) and another attached to a hydroxyl group (-OH). It is the spatial arrangement of these functional groups that equips this molecule with specific chemical properties. As it can be prepared by different methods involving ring-opening of epoxides with alcohol, this compound is versatile for manufacturing a variety of pharmaceuticals and specialty chemicals.

InChI:InChI=1/C9H16O3/c1-2-12-9(11)7-5-3-4-6-8(7)10/h7-8,10H,2-6H2,1H3/t7-,8-/m0/s1

Upstream product

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

Downstream Products

• 130023-71-1 (+/-)-cis-2-hydroxy-cyclopentane-carboxylic acid-⁽¹⁾-hydrazide 
• 130023-71-1 (+/-)-trans-2-hydroxy-cyclopentane-carboxylic acid-⁽¹⁾-hydrazide 
• 63578-04-1 (+/-)-trans-2-(3.5-dinitro-benzoyloxy)-cyclopentane-carboxylic acid-⁽¹⁾-ethyl ester 
• 63578-04-1 (+/-)-cis-2-(3,5-dinitro-benzoyloxy)-cyclopentane-carboxylic acid-⁽¹⁾-ethyl ester 
• 5809-02-9 ethyl cyclopent-2-enyl carboxylate 
• 86984-35-2 N-methyl-cis-2-hydroxycyclopentanecarboxamide 
• 86984-35-2 N-methyl-trans-2-hydroxycyclopentanecarboxamide 
• 61586-79-6 ethyl (1R,2S)-2-hydroxycyclopentanecarboxylate 
• 122331-03-7 ethyl (1S,2S)-2-hydroxycyclopentanecarboxylate 
• 86984-42-1 (4aS,7aS)-3-Methyl-hexahydro-cyclopenta[e][1,3]oxazin-2-one 
• 86984-42-1 (4aR,7aS)-3-Methyl-hexahydro-cyclopenta[e][1,3]oxazin-2-one 
• 130023-81-3 C₁₃H₁₇N₃O₃ 
• 130023-90-4 (1S,2R)-2-(5-Phenylamino-[1,3,4]oxadiazol-2-yl)-cyclopentanol 
• 130023-87-9 (1S,2R)-2-(5-Phenylamino-[1,3,4]thiadiazol-2-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.

Rhodium-catalyzed reformatsky-type reaction

(equation presented) A novel Reformatsky-type reaction was developed using RhCl(PPh3)3 and diethylzinc. Inter- and intramolecular Reformatsky-type reactions were achieved efficiently under mild reaction conditions to give β-hydroxy esters.