34546-57-1

Basic information

• Product Name: methyl 5-oxocyclopent-1-ene-1-heptanoate
• Synonyms: methyl 5-oxocyclopent-1-ene-1-heptanoate;5-Oxo-1-cyclopentene-1-heptanoic acid methyl ester
• CAS NO: 34546-57-1
• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 224.2961
• EINECS: 252-080-3
• Mol File: 34546-57-1.mol

Chemical Properties

• Boiling Point: 327.2°Cat760mmHg
• Flash Point: 141.5°C
• Appearance: /
• Density: 1.035g/cm³
• Vapor Pressure: 0.000205mmHg at 25°C
• Refractive Index: 1.481
• CAS DataBase Reference: methyl 5-oxocyclopent-1-ene-1-heptanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-oxocyclopent-1-ene-1-heptanoate(34546-57-1)
• EPA Substance Registry System: methyl 5-oxocyclopent-1-ene-1-heptanoate(34546-57-1)

Safety Data

• Hazardous Substances Data: 34546-57-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 100, p. 1267, 1978 DOI: 10.1021/ja00472a039Tetrahedron Letters, 24, p. 555, 1983 DOI: 10.1016/S0040-4039(00)81462-8Synthetic Communications, 8, p. 319, 1978 DOI: 10.1080/00397917808065628

InChI:InChI=1/C13H20O3/c1-16-13(15)10-5-3-2-4-7-11-8-6-9-12(11)14/h8H,2-7,9-10H2,1H3

Upstream product

• 74017-20-2 12-Oxo-dodec-8-ynoic acid methyl ester 
• 67-56-1 methanol 
• 5239-43-0 7-(5-oxo-1-cyclopenten-1-yl)heptanoic acid 
• 74-85-1 ethene 
• 7003-48-7 non-8-ynoic acid methyl ester 
• 1026696-24-1 7-(1-Chloro-2,6-dioxo-cyclohexyl)-heptanoic acid methyl ester 
• 35851-47-9 dimethyl 3-oxoundecane-1,11-dioate 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 53279-37-1 4-hydroxydodecanedioic acid γ-lactone 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 75964-11-3 Methyl 7-<2-(mesitylenesulfonyloxy)-5-oxo-1-cyclopentenyl>heptanoate 
• 67136-06-5 Methyl 7-(2,5-dioxocyclopentyl)heptanoate 
• 23535-03-7 Methyl 7-(2-methoxy-5-oxo-1-cyclopentenyl)heptanoate 
• 30828-10-5 4-ketododecanedioic acid dimethyl ester 

Downstream Products

• 40098-40-6 (+/-)-11,15-Didesoxyprostaglandin E⁽¹⁾ 
• 84700-67-4 methyl rac-9-(ethylidenedioxy)-15-(phenylsulfenyl)-14(E)-prostanoate 
• 84700-68-5 rac-9-(ethylidenedioxy)-15-(phenylsulfenyl)-14(E)-prostanoic acid 
• 856865-45-7 cis-2-(4-[1-(R)-(tert-butyldimethylsilyloxy)hexyl]phenyl)-5-oxo-cyclopentaneheptanoic acid methyl ester 
• 856865-45-7 trans-2-(4-[1-(R)-(tert-butyldimethylsilyloxy)hexyl]phenyl)-5-oxo-cyclopentaneheptanoic acid methyl ester 
• 40098-26-8 methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoate 
• 77970-40-2 7-[(1S,2R)-2-(Bis-p-tolylsulfanyl-methyl)-5-oxo-cyclopentyl]-heptanoic acid methyl ester 
• 77970-40-2 7-[(1S,2R)-2-(Bis-p-tolylsulfanyl-methyl)-5-oxo-cyclopentyl]-heptanoic acid methyl ester 
• 51876-14-3 7-(2-Hydroxy-cyclopentyl)-heptanoic acid 
• 5288-67-5 2-(6-carboxyhexyl)cyclopentanone 
• 40098-24-6 2-(6-methoxycarbonylhexyl)-4-(tetrahydropyran-2-yloxy)cyclopent-2-enone 
• 84700-65-2 methyl rac-9-oxo-15-(phenylsulfinyl)-14(E)-prostanoate 
• 77852-90-5 7-{(1S,5R)-2-Oxo-5-[((S)-toluene-4-sulfinyl)-p-tolylsulfanyl-methyl]-cyclopentyl}-heptanoic acid methyl ester 
• 77852-93-8 7-{5-Hydroxy-5-[((S)-toluene-4-sulfinyl)-p-tolylsulfanyl-methyl]-cyclopent-1-enyl}-heptanoic acid methyl ester 

Relevant articles and documents

Synthesis of (±)-15-thia-15-deoxy-PGE1 methyl ester

The 15-thia-15-deoxy analogue of prostaglandin E1 methyl ester has been prepared by the zirconocene chloride mediated conjugate addition of an n-pentyl ethynyl sulfide derived anion to an appropriately substituted cyclopentenone. Similar methodology has also been used to prepare other 3-(3'-thia-1'-octenyl)-cyclopentanones.

Synthesis of Methyl ο-(5-Oxo-1-cyclopentenyl)alkanoates Starting from 2-Nitrocycloalkanones

A convenient synthesis of methyl ο-(5-oxo-1-cyclopentenyl)alkanoates 1 is described. 2-Nitrocycloalkanones 2 are converted to 2-(3,3-dimethoxypropyl)-2-nitrocycloalkanones 4.Treatment of 4 with MeOH/MeONa led to the ring-opened nitronates 5 which underwent a Nef reaction to form the corresponding oxo derivatives 6.Partial hydrolysis of 6 followed by base-catalyzed aldol reaction gave the desired products in high yields.

CUPRIC BROMIDE UTILIZATION IN THE SYNTHESIS OF PROSTANOID INTERMEDIATES

An effective, one-step procedure using CuBr2 is reported for the introduction of a double bond into the prostanoid nucleus.

A Short Route to 2-(6-Methoxycarbonylhexyl)-cyclopent-2-en-1-one

The prostaglandin intermediate 2-(6-methoxycarbonylhexyl)-cyclopent-2-en-1-one (5) has been prepared by a short synthetic sequence, consisting of the reaction of 2-(1,3-dioxolan-2-yl)-ethylmagnesium bromide (1) with methyl 9-chloro-9-oxononanoate (2), followed by cleavage of the dioxolane ring of 3 and base-induced cyclisation of 4.

EP2 RECEPTOR AGONISTS

A compound selected from Formula (iv) or Formula (iii); (iv) (1R,2S)-2[4-1(S)-hydroxyhexyl)phenyl]-5-oxo-cyclopentaneheptanoic acid [RSS] or (iii) (1R,2S)-2[4-1(R)-hydroxyhexyl)phenyl]-5-oxo-cyclopentaneheptanoic acid [RSR] or a salt, solvate, chemically protected form or prodrug thereof, and its use in treating conditions alleviated by agonism of an EP2 receptor.

Synthons for 11-Deoxyprostaglandins of Series I and Their 11-Methyl-substituted Analogues Based on 2-Acylcyclohexane-1,3-diones

A convenient method for the synthesis of cyclopentenone synthons for 11-deoxyprostanoids including their 11-methyl-suhstituted analogues has been developed. 2-[ω-(Methoxycarbonyl)alkyl]cyclohexane-1,3-diones prepared by ionic hydrogenation of 2-[ω-(methoxycarbonyl)alkanoyl]cyclohexane-1,3-diones were chlorinated with tert-butyl hypochlorite, and the chlorination products were treated with anhydrous sodium carbonate to give the corresponding 2-alkyl-2-cyclopenten-1-ones and their 4-methyl-substituted derivatives as a result of the Favorskii rearrangement.

Preparation of 2-(6-carboxyhexyl)- and 2-(6-methoxycarbonylhexyl)cyclopent-2-en-1-one using free radical reactions

Two short and simple synthetic routes to the prostaglandin synthons 2-(6-carboxyhexyl)- and 2-(6-methoxycarbonylhexyl)cyclopent-2-en-1-one have been developed. The first is based on a cyclohexanone oxidative transformation with hydrogen peroxide and di-tert-butyl peroxide, the second on the free radical addition reaction of methyl 9-oxononanoate to acrylaldehyde diacylal.

Process for preparing 7-(2-hexyl-5-hydroxy-cyclopentyl)-heptanoic acid

A multistep process for preparing 7-(2-hexyl-5-hydroxy-cyclopentyl)-heptanoic acid is described. Novel intermediates are also described.

A New Method of Synthesizing 7-(2-Hydroxy-5-oxo-1-cyclopentenyl)heptanoic Acid and Related Compounds

A useful prostanoid synthon, 7-(2-hydroxy-5-oxo-1-cyclopentenyl)heptanoic acid (3), was prepared from commercially available cyclooctanone in two steps.Nine other related cyclopentanoids which are also valuable synthons for prostaglandins were obtained from 3 in reasonable yields via several steps.The procedure is capable of generating these synthons on a laboratory scale.

A NEW FACILE SYNTHESIS OF 2-ALKYLCYCLOPENT-2-ENONES

A new, simple and short route to 2-alkylcyclopent-2-enones starting from inxpensive terminal epoxides is described.