5239-43-0

Basic information

• Product Name: 5-oxocyclopent-1-ene-1-heptanoic acid
• Synonyms: 5-oxocyclopent-1-ene-1-heptanoic acid;5-Oxo-1-cyclopentene-1-heptanoic acid;1-Cyclopentene-1-heptanoic acid, 5-oxo-;Ay 16804;Brn 2211467;Einecs 226-039-5
• CAS NO: 5239-43-0
• Molecular Formula: C₁₂H₁₈O₃
• Molecular Weight: 210.26952
• EINECS: 226-039-5
• Mol File: 5239-43-0.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 384.9°Cat760mmHg
• Flash Point: 200.8°C
• Appearance: /
• Density: 1.099g/cm³
• Vapor Pressure: 5.4E-07mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: 5-oxocyclopent-1-ene-1-heptanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-oxocyclopent-1-ene-1-heptanoic acid(5239-43-0)
• EPA Substance Registry System: 5-oxocyclopent-1-ene-1-heptanoic acid(5239-43-0)

Safety Data

• Hazardous Substances Data: 5239-43-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H18O3/c13-11-8-5-7-10(11)6-3-1-2-4-9-12(14)15/h7H,1-6,8-9H2,(H,14,15)

Upstream product

• 33803-57-5 2-(7-hydroxyheptyl)-2-cyclopenten-1-one 
• 52477-96-0 2-(6-carboxyhexyl)-1-methoximino-2-cyclopentene 
• 40098-44-0 2-(6-ethoxycarbonylhexyl)-2-cyclopenten-1-one 
• 41301-73-9 2-(6-carbethoxyhexyl)-1-methoximino-2-cyclopentene 
• 79918-33-5 4-oxo-12-<(tetrahydro-2H-pyran-2-yl)-oxy>dodecanal 
• 64-19-7 acetic acid 
• 105602-58-2 2-(5'-carboxypentyl)cyclohexanone 
• 112-38-9 10-undecenoic acid 
• 14811-73-5 10-oxo-decanoic acid methyl ester 
• 32779-22-9 10,11-dihydroxyundecanoic acid 
• 24724-06-9 methyl 10,11-dihydroxyundecanoate 
• 20530-58-9 1-decene-10-carbomethoxy-1-carboxylic acid 
• 51876-14-3 7-(2-Hydroxy-cyclopentyl)-heptanoic acid 
• 629-41-4 1,8-Octanediol 

Downstream Products

• 34546-57-1 2-(6-methoxycarbonylhexyl)cyclopent-2-en-1-one 
• 40098-26-8 methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoate 
• 40098-44-0 2-(6-ethoxycarbonylhexyl)-2-cyclopenten-1-one 
• 5288-67-5 2-(6-carboxyhexyl)cyclopentanone 
• 40098-24-6 2-(6-methoxycarbonylhexyl)-4-(tetrahydropyran-2-yloxy)cyclopent-2-enone 
• 51876-14-3 7-(2-Hydroxy-cyclopentyl)-heptanoic acid 
• 21269-27-2 7-[(S)-2-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-oxo-cyclopentyl]-heptanoic acid 
• 37786-00-8 Doproston B 
• 40098-40-6 (+/-)-11,15-Didesoxyprostaglandin E⁽¹⁾ 
• 41301-75-1 1-methoximino-2-(7-p-toluenesulfonyloxyheptyl)-2-cyclopentene 
• 52477-97-1 2-(7-butoxycarbonylhexyl)-2-cyclopenten-1-one 
• 64318-56-5 7-[(1S,3R,5S)-3-Hydroxy-5-((E)-(S)-3-hydroxy-oct-1-enyl)-2-oxo-cyclopentyl]-heptanoic acid methyl ester 
• 64318-56-5 (+/-)-11-deoxy-10α-hydroxy-PGE₁ methyl ester 
• 108615-64-1 (+/-)-9-oxo-13-thia-15-hydroxy-16-phenoxy-17,18,19,20-tetranorprostanoic acid 

Relevant articles and documents

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.

A New Synthesis of 8-(ω-Carbomethoxyhexyl)-11-hydroxycyclopent-8(12)-ene-9-one, a Versatile Prostaglandin Intermediate

8-(ω-Carbomethoxyhexyl)-11-hydroxycyclopent-8(12)-ene-9-one (V), a versatile prostaglandin synthon, has been synthesised starting from easily accesible undecylenic acid (VI).The synthesis involves preparation of dihydroxy undecanoic acid (IX) and its methyl ester (X), methyl 9-formylnonanoate (XI), the monoester (XII) and the corresponding unsaturated acid (XIII), γ-lactone (XIV), cyclopentenone acid (XV) and finally the all important PG-intermediate 2-(ω-carbomethoxyhexyl)cyclopentenone (IV).Its reduction with sodium borohydride gives the saturated alcohol (XVI), which via oxidation with Jones' reagent and bromination-dehydrobromination sequence could be converted back to IV.However, IV, on reduction with aluminium isopropoxide gives the allylic alcohol (XXIII), which is converted via acetylation into the acetate (XXIV).Subsequent oxidation of acetate (XXIV) with t-butyl chromate yields the keto-acetate (XXV), which on reduction with aluminium isopropoxide furnishes the hydroxy acetates (XXXII).The hydroxyl group in XXXII is protected as tetrahydropyranyloxy derivative (XXXIII).Hydrolysis of XXXIII with alkali leads to the hydroxy acids (XXXIV).Oxidation of XXXIV with Jones' reagent at low temperature for a short period yields the keto-acid (XXXV), which is esterified to give the ester (XXXVI).Finally, removal of the pyranyloxy group from XXXVI furnishes the versatile synthon (V), identical with the sample prepared by a known procedure.

A NEW ROUTE FOR THE SYNTHESIS OF 1,4-DICARBONYL COMPOUNDS: SYNTHESIS OF JASMONE, DIHYDROJASMONE AND A PROSTAGLANDIN INTERMEDIATE

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