96382-85-3

Basic information

• Product Name: CIS-3-CARBOMETHOXYCYCLOPENTANE-1-CARBOXYLIC ACID
• Synonyms: CIS-3-CARBOMETHOXYCYCLOPENTANE-1-CARBOXYLIC ACID;(1R,3S)-rel-1,3-Cyclopentanedicarboxylic acid 1-methyl ester;cis-1,3-Cyclopentanedicarboxylic acid monomethyl ester;(1R,3S)-rel-3-(Methoxycarbonyl)cyclopentanecarboxylic acid;-rel-3-(Methoxycarbonyl)
• CAS NO: 96382-85-3
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• Mol File: 96382-85-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 286℃
• Flash Point: 115℃
• Appearance: /
• Density: 1.242
• Vapor Pressure: 0.000677mmHg at 25°C
• Refractive Index: 1.49
• PKA: 4.51±0.40(Predicted)
• CAS DataBase Reference: CIS-3-CARBOMETHOXYCYCLOPENTANE-1-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-3-CARBOMETHOXYCYCLOPENTANE-1-CARBOXYLIC ACID(96382-85-3)
• EPA Substance Registry System: CIS-3-CARBOMETHOXYCYCLOPENTANE-1-CARBOXYLIC ACID(96382-85-3)

Safety Data

• Hazardous Substances Data: 96382-85-3(Hazardous Substances Data)

Usage

General Description

CIS-3-CARBOMETHOXYCYCLOPENTANE-1-CARBOXYLIC ACID, also known as cis-3-carbomethoxycyclopentanecarboxylic acid, is a chemical compound with the molecular formula C9H14O4. It is a cyclic compound with a carboxylic acid functional group and a carbomethoxy substituent at the cis-3 position. CIS-3-CARBOMETHOXYCYCLOPENTANE-1-CARBOXYLIC ACID is commonly used as a building block in organic synthesis and pharmaceutical research, particularly in the development of drugs and biologically active compounds. It has potential applications in medicinal chemistry, as well as in the production of chiral intermediates and pharmaceutical ingredients. Its unique structure and functional groups make it a valuable precursor for the synthesis of various complex molecules with potential biological activity.

InChI:InChI=1/C8H12O4/c1-12-8(11)6-3-2-5(4-6)7(9)10/h5-6H,2-4H2,1H3,(H,9,10)/t5-,6+/m1/s1

Upstream product

• 67-56-1 methanol 
• 876-05-1 cis-1,3-cyclopentanedicarboxylic acid 
• 39590-04-0 (1R,3S)-dimethyl cyclopentane-1,3-dicarboxylate 
• 6054-16-6 cyclopentane-1,3-dicarboxylic acid anhydride 
• 6054-16-6 cis-1,3-cyclopentanedicarboxylic acid anhydride 
• 124-41-4 sodium methylate 
• 498-66-8 norborn-2-ene 

Downstream Products

• 116891-16-8 (+/-)-1--5-methyl-2,4(1H,3H)-pyrimidinedione benzoate 
• 116891-20-4 (+/-)-1--2,4(1H,3H)-pyrimidinedione benzoate 
• 116891-18-0 (+/-)-2,3-dihydro-1--2-thioxo-4(1H)-pyrimidinone benzoate 
• 116940-94-4 Benzoic acid (1S,3R)-3-(4-chloro-5-methyl-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester 
• 116940-95-5 Benzoic acid (1S,3R)-3-(4-chloro-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester 
• 116940-85-3 (+/-)-cis-3-(hydroxymethyl)cyclopentanecarboxamide 
• 78795-25-2 (+/-)-1--5-methyl-2,4(1H,3H)-pyrimidinedione 
• 78795-20-7 (+/-)-cis-3-aminocyclopentanemethanol 
• 85174-63-6 (+/-)-methyl cis-3-(chloromethanoyl)cyclopentanecarboxylate 

Relevant articles and documents

Conformational Restriction and Enantioseparation Increase Potency and Selectivity of Cyanoguanidine-Type Histamine H4 Receptor Agonists

2-Cyano-1-[4-(1H-imidazol-4-yl)butyl]-3-[2-(phenylsulfanyl)ethyl]guanidine (UR-PI376, 1) is a potent and selective agonist of the human histamine H4 receptor (hH4R). To gain information on the active conformation, we synthesized analogues of 1 with a cyclopentane-1,3-diyl linker. Affinities and functional activities were determined at recombinant hHxR (x: 1-4) subtypes on Sf9 cell membranes (radioligand binding, [35S]GTPγS, or GTPase assays) and in part in luciferase assays on human or mouse H4R (HEK-293 cells). The most potent H4R agonists among 14 racemates were separated by chiral HPLC, yielding eight enantiomerically pure compounds. Configurations were assigned based on X-ray structures of intermediates and a stereocontrolled synthetic pathway. (+)-2-Cyano-1-{[trans-(1S,3S)-3-(1H-imidazol-4-yl)cyclopentyl]methyl}-3-[2-(phenylsulfanyl)ethyl]guanidine ((1S,3S)-UR-RG98, 39a) was the most potent H4R agonist in this series (EC50 11 nM; H4R vs H3R, >100-fold selectivity; H1R, H2R, negligible activities), whereas the optical antipode proved to be an H4R antagonist ([35S]GTPγS assay). MD simulations confirmed differential stabilization of the active and inactive H4R state by the enantiomers.

Enantioselective synthesis of (+) and (-)-cis-3-aminocyclopentanecarboxylic acids by enzymatic asymmetrization

Both enantiomers of cis-3-aminocyclopentanecarboxylic acid (GABA analogs, inhibitory neurotransmitter) have been prepared via enzymatic asymmetrization of cis -1,3-cyclopentanedicarboxylic acid.

Synthesis of cyclopentane analogs of 1-(2',3'-dideoxy-β-glycero-pentofuranosyl)pyrimidine nucleosides

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