162086-59-1

Basic information

• Product Name: 1-Cyclopentene-1-carboxylicacid,3-hydroxy-,methylester(9CI)
• Synonyms: 1-Cyclopentene-1-carboxylicacid,3-hydroxy-,methylester(9CI);methyl 3-hydroxycyclopent-1-enecarboxylate
• CAS NO: 162086-59-1
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.15
• Product Categories: CARBOXYLICESTER
• Mol File: 162086-59-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Cyclopentene-1-carboxylicacid,3-hydroxy-,methylester(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclopentene-1-carboxylicacid,3-hydroxy-,methylester(9CI)(162086-59-1)
• EPA Substance Registry System: 1-Cyclopentene-1-carboxylicacid,3-hydroxy-,methylester(9CI)(162086-59-1)

Safety Data

• Hazardous Substances Data: 162086-59-1(Hazardous Substances Data)

Usage

Explanation

The compound has a total of 8 carbon atoms, 12 hydrogen atoms, and 3 oxygen atoms in its molecular structure.

Explanation

At room temperature, the compound appears as a colorless liquid.

Explanation

The compound is known to have a fruity smell.

Explanation

It is derived from 3-hydroxy-1-cyclopentene-1-carboxylic acid with a methyl group attached to the hydroxyl group.
5. Usage in organic synthesis and chemical research

Explanation

The compound is commonly used as an intermediate or reagent in the synthesis of other organic compounds and in various chemical research applications.
6. Applications in pharmaceuticals, agrochemicals, and fine chemicals

Explanation

The compound is utilized in the production of various pharmaceuticals, agrochemicals, and other fine chemicals, making it a valuable compound in these industries.
7. Use as a fragrance and flavoring agent

Explanation

Due to its fruity odor, the compound can be used as a fragrance or flavoring agent in the food and beverage industry.

Appearance

Colorless liquid

Odor

Fruity

Type

Methyl ester derivative

Upstream product

• 162086-60-4 methyl 2,3-epoxycyclopentane-1-carboxylate 
• 917-54-4 methyllithium 
• 170423-00-4 methyl trans-2,3-epoxy-1-cyclopentancarboxylate 
• 108384-35-6 methyl 3-oxocyclopent-1-enecarboxylate 
• 25662-28-6 1-(carboxymethoxy)cyclopentadiene 
• 2258-56-2 methyl cyclopent-2-ene-1-carboxylate 

Downstream Products

• 172908-33-7 methyl 4-hydroxybicyclo<3.1.0>hexane-1-carboxylate 
• 461406-29-1 cyclohexanecarboxylic acid 3-(tert-butyl-dimethyl-silanyloxy)-cyclopent-1-enylmethyl ester 
• 101244-89-7 (-)-(1S,2S,6S,7S,8S)-8-benzyloxy-1,5-dimethyltricyclo<5.3.0.0^2,6>dec-4-en-3-one 
• 101244-87-5 (+)-(1S,2S,6S,7S,8S)-8-benzyloxy-3-hydroxymethyl-5-methoxy-1,5-dimethyl-4-oxatricyclo<5.3.0.0^2,6>decane 
• 101244-88-6 (+)-(1S,4S,5S)-6,7-diacetyl-4-benzyloxy-1-methylbicyclo<3.2.0>heptane 
• 101244-86-4 (-)-(1S,5R,8S,9S,10S,13S)-8-benzyloxy-11-methoxy-11-methyl-3,12-dioxatetracyclo<8.2.1.0.^5,90^5,13>tridecan-4-one 
• 101244-83-1 (-)-(1S,5R,8S,9S,10S,13S)-8-benzyloxy-3,12-dioxatetracyclo<8.2.1.0.^5,90^5,13>tridecan-4,11-dione 
• 162086-68-2 (-)-(1R,2S,3S,5R,6R,7S,10R)-5-methoxymethoxy-6,10-dimethyltricyclo<5.3.0.0^2,6>decan-3-yl p-toluenesulfonate 
• 108384-35-6 methyl 3-oxocyclopent-1-enecarboxylate 
• 132076-32-5 methyl (1S)-3-oxocyclopentanecarboxylate 
• 32811-75-9 methyl 3-oxocyclopentane-1-carboxylate 
• 132076-27-8 (R)-methyl 3-oxocyclopentanecarboxylate 

Relevant articles and documents

Biocatalytic synthesis of chiral cyclic γ-oxoesters by sequential C-H hydroxylation, alcohol oxidation and alkene reduction

A three-step biocatalytic procedure is described for the conversion of methyl and ethyl cyclopentene- and cyclohexenecarboxylates into both the enantiomers of the corresponding chiral 3-oxoesters, which are useful building blocks for the synthesis of active pharmaceutical ingredients. The allylic hydroxylation of the starting cycloalkenecarboxylates is carried out by using R. oryzae resting cells entrapped in alginate beads, in acetate buffer solution at 25 °C. The oxidation of the intermediate allylic alcohols to unsaturated ketones, performed by the laccase/TEMPO system, and the ene-reductase mediated hydrogenation of the alkene bond were carried out in the same reaction vessel in a sequential mode at 30 °C. Being entirely biocatalytic, our multistep procedure provides considerable advantages in terms of selectivity and environmental impact over reported chemical methods.

Molecular Hybridization of Potent and Selective γ-Hydroxybutyric Acid (GHB) Ligands: Design, Synthesis, Binding Studies, and Molecular Modeling of Novel 3-Hydroxycyclopent-1-enecarboxylic Acid (HOCPCA) and trans-γ-Hydroxycrotonic Acid (T-HCA) Analogs

γ-Hydroxybutyric acid (GHB) is a neuroactive substance with specific high-affinity binding sites. To facilitate target identification and ligand optimization, we herein report a comprehensive structure-affinity relationship study for novel ligands targeting these binding sites. A molecular hybridization strategy was used based on the conformationally restricted 3-hydroxycyclopent-1-enecarboxylic acid (HOCPCA) and the linear GHB analog trans-4-hydroxycrotonic acid (T-HCA). In general, all structural modifications performed on HOCPCA led to reduced affinity. In contrast, introduction of diaromatic substituents into the 4-position of T-HCA led to high-affinity analogs (medium nanomolar Ki) for the GHB high-affinity binding sites as the most high-affinity analogs reported to date. The SAR data formed the basis for a three-dimensional pharmacophore model for GHB ligands, which identified molecular features important for high-affinity binding, with high predictive validity. These findings will be valuable in the further processes of both target characterization and ligand identification for the high-affinity GHB binding sites.

Achieving Regio- and Enantioselectivity of P450-Catalyzed Oxidative CH Activation of Small Functionalized Molecules by Structure-Guided Directed Evolution

Directed evolution of the monooxygenase P450-BM3 utilizing iterative saturation mutagenesis at and near the binding site enables a high degree of both regio- and enantioselectivity in the oxidative hydroxylation of cyclohexene-1-carboxylic acid methyl est

Parallel kinetic resolution of tert-butyl (RS)-3-oxy-substituted cyclopent-1-ene-carboxylates for the asymmetric synthesis of 3-oxy-substituted cispentacin and transpentacin derivatives

tert-Butyl (RS)-3-methoxy- and (RS)-3-tert-butyldiphenylsilyloxy-cyclopent- 1-ene-carboxylates display excellent levels of enantiorecognition in mutual kinetic resolutions with both lithium (RS)-N-benzyl-N-(α-methylbenzyl) amide and lithium (RS)-N-3,4-dim

Studies aimed at the total synthesis of azadirachtin. A modeled connection of C-8 and C-14 in azadirachtin

(figure presented) Studies on the connection between the right and left segments of azadirachtin are described. The Ireland-Claisen rearrangement of Li-enolate of the modeled ester with dichlorodimethylsilane in toluene afforded the desired limonoid frame

Ring Opening of Cyclopropylketones Induced by Photochemical Electron Transfer

Depending on the substitution pattern of cyclopropylketones, the photochemically induced electron transfer of tertiary amines to cyclopropylketones leads either to the formation of 3-substituted cycloalkanones or to ring expanded products.

Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 9. Synthesis and ring opening reactions of cis- and trans-oxides derived from 3-(benzyloxymethyl)cyclopentene and methyl 2- cyclopenten-1-carboxylate

The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in the oxirane systems derived from cyclopentene bearing a polar functionality (CH2OBn or COOMe) in a homoallylic relationship to the oxirane ring. The cis/trans diastereoisomeric epoxide pairs 7-8 and 9-10 derived from 3- (benzyloxymethyl)cyclopentene and methyl 2-cyclopenten-1-carboxylate, respectively, were prepared and some of their opening reactions were studied. The regioselectivity observed turned out to depend on the opening reaction protocol (standard or metal-assisted), suggesting the efficacious incursion, under the appropriate conditions, of chelate bidentate species in the opening process.

Enantioselective total synthesis of (+)-stoechospermol via stereoselective intramolecular (2+2) photocycloaddition of the chiral butenolide

Enantioselective total synthesis of (+)-stoechospermol 2, a representative of spatane diterpenes having a cis,anti,cis-tricyclo[5.2.0.02,6]decane skeleton, was achieved by employing a stereo- and regioselective intramolecular (2+2) photocycloaddition of (S)-γ-hydroxymethyl-γ-butenolide-derived ester 10.

ASYMMETRIC TOTAL SYNTHESIS OF STOECHOSPERMOL USING INTRAMOLECULAR (2+2) PHOTOCYCLOADDITION REACTION

The first asymmetric total synthesis of stoechospermol, a representative spatane diterpene having cis, anti, cis-tricyclo2,6>decane ring system, was achieved.Using the intramolecular asymmetric (2+2) photocycloaddition reaction of the diastereomeric ester 11, the readily available butenolide 9 was transformed into the optically active dilactone 12a and 12b.Subsequent construction of tricyclic carbon ring system and introduction of substituents in a right stereochemistry gave rise to optically pure stoechospermol 1.