120052-54-2

Basic information

• Product Name: METHYL 2-((1S,4S)-4-HYDROXYCYCLOPENT-2-ENYL)ACETATE
• Synonyms: METHYL [(1S,4S)-4-HYDROXYCYCLOPENT-2-EN-1-YL]ACETATE;METHYL 2-((1S,4S)-4-HYDROXYCYCLOPENT-2-ENYL)ACETATE
• CAS NO: 120052-54-2
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.17908
• Mol File: 120052-54-2.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL 2-((1S,4S)-4-HYDROXYCYCLOPENT-2-ENYL)ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-((1S,4S)-4-HYDROXYCYCLOPENT-2-ENYL)ACETATE(120052-54-2)
• EPA Substance Registry System: METHYL 2-((1S,4S)-4-HYDROXYCYCLOPENT-2-ENYL)ACETATE(120052-54-2)

Safety Data

• Hazardous Substances Data: 120052-54-2(Hazardous Substances Data)

Upstream product

• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 
• 108-59-8 malonic acid dimethyl ester 
• 694-97-3 5-norbornene-2-ol 
• 54664-61-8 cis-1,4-diacetoxy-2-cyclopentene 
• 84559-56-8 (S)-methyl 2-(4-oxocyclopent-2-en-1-yl)acetate 
• 67920-82-5 (S)-methyl 2-(cyclopent-2-en-1-yl)acetate 
• 20657-21-0 3-acetoxycyclopent-1-ene 
• 3212-60-0 cyclopent-2-enol 
• 930-30-3 cyclopent-2-enone 
• 16620-79-4 (-)-<1S,4S>bicyclo<2.2.1>heptene-5 one-2 
• 79193-65-0 (+/-)-cis-4-bis(methoxycarbonyl)methyl-2-cyclopentenol 
• 61740-26-9 cis-3-acetoxy-5-hydroxycyclopent-1-ene 
• 694-98-4 norborn-5-en-2-one 
• 426226-00-8 dimethyl 2-((1R,4S)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl)malonate 

Downstream Products

• 1309655-83-1 C₂₃H₂₈O₂Si 
• 483-27-2 (+/-)-dihydrocorynantheol 
• 1382669-33-1 2-((1R,5S)-5-(2-((4-methoxybenzyl)oxy)ethyl)cyclopent-2-en-1-yl)-N,N-dimethylacetamide 
• 1382669-36-4 (3aR,4R,6R,6aR)-6-iodo-4-(2-((4-methoxybenzyl)oxy)ethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 1382669-42-2 (1S,2R,3S)-2-(2-hydroxyethyl)-3-(2-((4-methoxybenzyl)oxy)ethyl)cyclopentanol 
• 1382669-45-5 ((1S,2R,3S)-3-(2-((4-methoxybenzyl)oxy)ethyl)-2-(2-((triethylsilyl)oxy)ethyl)-1-((triethylsilyl)oxy))cyclopentane 
• 1382669-48-8 ((1S,2R,3S)-3-(2-((4-methoxybenzyl)oxy)ethyl)-2-((Z)-pent-2-en-1-yl)-1-((triethylsilyl)oxy))cyclopentane 
• 1382669-39-7 C₁₇H₂₂O₄ 
• 517-81-7 (+)-uleine 

Relevant articles and documents

Enantioselective Total Synthesis of (+)-Nordasycarpidone, (+)-Dasycarpidone, and (+)-Uleine

The structure of uleine type alkaloids is characterized by the presence of a bridged tetracyclic hexahydro-1H-1,5-methanoazocino[4,3-b]indole ring system 1. Various strategies have been developed to access this polycyclic structural motif. We report herein a one-step conversion of appropriately functionalized 1,3,4-trisubstituted cyclopent-1-ene to 1 by way of an integrated oxidation/reduction/cyclization (iORC) process. This domino sequence, initiated by oxidative cleavage of cyclopentene ring, generated subsequently a cyclohexenone, an indole and a 1,3-bridged piperidine ring through formation of one C?C and two C?N bonds. Compound 1 is subsequently converted to nordasycarpidone, dasycarpidone and uleine. The chirality of the molecule was introduced by enzymatic desymmetrization of commercially available meso cis-3,5-diacetoxy-1-cyclopentene.

SYNTHESIS OF DELTA 12-PGJ3 AND RELATED COMPOUNDS

In one aspect, the present invention provides novel derivatives of Δ12-PGJ3 and modular synthetic pathways to obtaining Δ12-PGJ3 and derivatives thereof. In some aspects, the present derivatives of Δ12-PGJ3 are useful as chemotherapeutic agents. The present disclosure also describes compositions of these derivatives as well as methods of use of the derivatives thereof.

Strategy for synthesis of the isoleucine conjugate of epi-jasmonic acid

The TES ether of 2-((1R,2S,3R)-3-hydroxy-2-((Z)-pent-2-enyl)cyclopentyl)acetic acid (5, equal to the reduction product of epi-jasmonic acid) derived from (1R,4S)-4-hydroxycyclopent-2-enyl acetate (19) in 13 steps was activated by using isobutyl chloroformate and was subjected to condensation with isoleucine at room temperature for 48 h. The product was desilylated and oxidized to the isoleucine conjugate of epi-jasmonic acid in 68% yield over three steps. Similarly, allo-isoleucine conjugate of epi-jasmonic acid and three isoleucine conjugates of ent-epi-jasmonic acid, jasmonic acid, and ent-jasmonic acid were synthesized.