2630-38-8

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-(3-oxocyclopentyl)acetate is used as a synthetic intermediate for the development of pharmaceuticals. Its unique structure and functional groups make it a valuable building block in the synthesis of various drug molecules, contributing to the discovery and production of new medications.
Used in Chemical Synthesis:
In the chemical industry, methyl 2-(3-oxocyclopentyl)acetate is employed as a versatile intermediate for the synthesis of a wide range of chemical products. Its reactivity and functional groups allow for various chemical reactions, enabling the production of different compounds for various applications.
Used in Research and Development:
Methyl 2-(3-oxocyclopentyl)acetate is also utilized in research and development settings, where it serves as a key component in the exploration of new chemical reactions and the synthesis of novel compounds. Its unique properties make it an essential tool for scientists and researchers working in the fields of organic chemistry and medicinal chemistry.

Upstream product

• 51388-62-6 4-(carboxymethyl)cyclopent-2-en-1-one methyl ester 
• 92775-76-3 ((S)-3-Oxo-cyclopentyl)-trimethylsilanyl-acetic acid methyl ester 
• 125442-80-0 ((R)-3-Oxo-cyclopentyl)-phenylsulfanyl-acetic acid methyl ester 
• 125442-80-0 ((S)-3-Oxo-cyclopentyl)-phenylsulfanyl-acetic acid methyl ester 
• 96999-69-8 [(R)-3-Oxo-2-(toluene-4-sulfinyl)-cyclopentyl]-bis-trimethylsilanyl-acetic acid methyl ester 
• 67-56-1 methanol 
• 2630-37-7 3-(hydroxycarbonylmethyl)cyclopentan-1-one 
• 66972-67-6 3-formylmethylcyclopentan-1-one 
• 930-30-3 cyclopent-2-enone 
• 79681-26-8 2-[(S)-(4-methylphenyl)sulfinyl]cyclopent-2-en-1-one 
• 68366-28-9 (-)-Methyl-2-(methoxycarbonyl)-3-oxocyclopentanacetat 
• 68366-27-8 (1R,2S,3R)-3-Hydroxy-2-(methoxycarbonyl)cyclopentanessigsaeure-methylester 
• 160115-23-1 (S)-3-di(methoxycarbonyl)methyl-1-cyclopentanone 
• 93366-49-5 (+)-(R)-2-(p-tolylsulfinyl)cyclopent-2-enone 

Relevant academic research and scientific papers

Chiroptical Studies of Labile or Difficult-to-Resolve Molecules Generated by Chiral Laser Photochemistry. 2. Products and Steric Course of the Phototransformation of the Racemate

This paper deals with a complex photoresolution of a racemate with circularly polarized light (CPL) which involves the phototransformation of the racemate into a chiral, labile compound.We show here how to obtain both the dichroism for the pure enantiomers and their absolute configuration, besides defining the stereochemical course for the phototransformation.This is exemplified by the irradiation of racemic 1-methoxybicyclohepta-3,6-dien-2-one (1) with ultraviolet, left CPL which led to a mixture containing both the photoresolved (-)(1S,5R)-1, with 0.3percent optical purity and Δεmax(365) = -2.4, and the labile product of the phototransformation of the racemate, (-)(1S,5S)-7-methoxybicyclohepta-3,6-dien-2-one ((-)(1S,5S)-2), with 1.6percent optical purity and Δεmax(350) = -2.0.Acidification of this mixture led to chemically and optically stable methyl (-)(1R)-4-oxo-2-cyclopentene-1-acetate ((-)(1R)-7), with 1.6percent optical purity, Δεmax(320) = -0.39, by selective hydrolysis of 2.The absolute configuration for 2 was assigned by correlation with the product of catalytic reduction of (-)(1R)-7, i.e., methyl (+)-3-oxocyclopentane-1-acetate, whose absolute configuration, (1R), is independently known.The above results show that the 1 -> 2 phototransformation is attained by complete inversion of configuration at the bridgeheads.The Kroning-Kramers theorem helped to elucidate the chiroptical properties for compounds 1, 2, and 7.

Organocatalytic enantioselective Michael additions of malonates to 2-cyclopentenone

The Michael reaction of a dialkyl malonate with a cyclic enone using a chiral diamine-acid combination catalyst gave the desired Michael adduct in high yield with excellent enantiomeric excess in a protic solvent such as methanol and ethanol. The methanol

Asymmetric Michael Addition Reaction of Phosphorus-Stabilized Allyl Anions with Cyclic Enones

The asymmetric Michael addition reaction of chiraly modified P-allyl anions derived from enantiomerically ebriched 2-allyl-1,3,2-oxazaphosphorinane 2-oxides has been investigated with cyclic enones.The racemic 1,3,2-oxazaphosphorinane 2-oxide 3 has been shown to be extremely diastereoselective in the Michael addition to 5-, 6-, and 7-ring enones.With the enantiomerically enriched 2-allyl-1,3,2-oxazaphosphorinane 2-oxides, high regio- and diastereoselectivities (88-90percent diastereomeric excess) have been achieved in the Michael addition reaction of one of the diastereomers (cis series).The Michael reaction of the anions derived from the trans series were not diastereoselective (ca. 10percent diastereomeric excess).The origin of the addition selectivity can be rationalized by (1) consideration of the structure and conformational preferences of the allyl anion (parallel conformation, s-trans, no lithium contact), (2) conformational analysis of the 1,3,2-oxazaphosphorinane 2-oxide ring (chair, equatorial allyl group) and (3) assumption of a 10-membered ring transition state structure with lithium coordination of the enone.

ASYMMETRIC MICHAEL ADDITION REACTION OF METHYL PHENYLTHIOACETATE TO 2-CYCLOPENTENONE CATALYZED BY CHIRAL CROWN-KOtBu COMPLEXES

Asymmetric Michael addition reaction of methyl phenylthioacetate (12) to 2-cyclopentenone (11) using chiral crown ether-KOtBu complexes as catalysts is reported.Crown (7) has been found to give 14 of 71percentee (enantiomeric excess).

ASYMMETRIC MICHAEL ADDITIONS OF ESTER ENOLATES TO ENANTIOMERICALLY PURE VINYLIC SULFOXIDES SYNTHESIS OF 3-SUBSTITUTED GLUTARATE ESTERS IN HIGH ENANTIOMERIC PURITY

Various ester enolate ions add as Michael donors to enantiomerically pure Michael acceptor cycloalkenone sulfoxides 1a and 1b and unsaturated lactone sulfoxides 3a and 3b.The level of asymmetric induction in some cases is extraordinarily high (>=95percent