5288-67-5

Basic information

• Product Name: 7-(2-oxocyclopentyl)heptanoic acid
• CAS NO: 5288-67-5
• Molecular Formula: C₁₂H₂₀O₃
• Molecular Weight: 212.2854
• Mol File: 5288-67-5.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 369.8°C at 760 mmHg
• Flash Point: 191.6°C
• Density: 1.061g/cm³
• Vapor Pressure: 1.76E-06mmHg at 25°C
• Refractive Index: 1.484
• CAS DataBase Reference: 7-(2-oxocyclopentyl)heptanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(2-oxocyclopentyl)heptanoic acid(5288-67-5)
• EPA Substance Registry System: 7-(2-oxocyclopentyl)heptanoic acid(5288-67-5)

Safety Data

• Hazardous Substances Data: 5288-67-5(Hazardous Substances Data)

Usage

General Description

7-(2-oxocyclopentyl)heptanoic acid is a chemical compound with the molecular formula C11H18O3. It is a derivative of heptanoic acid, containing a cyclopentyl group and a ketone group. 7-(2-oxocyclopentyl)heptanoic acid is used in the synthesis of other organic compounds and may also have potential industrial or pharmaceutical applications. Its properties and uses make it an important chemical in various fields such as organic chemistry, pharmaceuticals, and materials science.

Upstream product

• 29823-18-5 ethyl 7-bromoheptanoate 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 54696-27-4 2-ethoxycarbonyl-2-<6',6'-bis(ethoxycarbonyl)hexyl>cyclopentanone 
• 58707-68-9 2-carboxyethoxy-2-(6'-methoxycarbonylhexyl)-cyclopentanone 
• 74845-09-3 5-(6-carbethoxyhexyl)-2-carbethoxycyclopentanone 
• 51876-14-3 7-(2-Hydroxy-cyclopentyl)-heptanoic acid 
• 1119-60-4 hept-6-enoic acid 
• 120-92-3 cyclopentanone 
• 5239-43-0 7-(5-oxo-1-cyclopenten-1-yl)heptanoic acid 
• 40491-73-4 Decahydro-cyclopentacyclononene-3a,4-diol 
• 111-24-0 1,5-dibromo-pentane 
• 1906-95-2 5-bromopentylmalonic acid diethyl ester 
• 54049-24-0 methyl 7-bromoheptanoate 
• 502-42-1 cycloheptanone 

Downstream Products

• 5239-43-0 7-(5-oxo-1-cyclopenten-1-yl)heptanoic acid 
• 40098-26-8 methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoate 
• 40098-24-6 2-(6-methoxycarbonylhexyl)-4-(tetrahydropyran-2-yloxy)cyclopent-2-enone 
• 34546-57-1 2-(6-methoxycarbonylhexyl)cyclopent-2-en-1-one 
• 85745-91-1 2-(6'-carboxy-1'E-hexylidene)cyclopentanone 
• 85421-76-7 2-(6-carboxyhexyl)cyclopentanone hexylhydrazone 

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.

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.

PRACTICAL SYNTHESIS OF 2-(6'-METHOXYCARBONYLHEXYL)CYCLOPENT-2-EN-1-ONE (PROSTAGLANDIN SYNTHON)

2-(6'-Methoxycarbonylhexyl)cyclopentanone was obtained by alkylation of the 2-(ethoxycarbonyl)cyclopentanone potassium salt with diethyl 5-bromopentylmalonate followed by acid cleavage of the obtained triester and esterification.Its bromination with copper bromide and dehydrobromination with collidine lead to 2-(6'-methoxycarbonylhexyl)cyclopent-2-en-1-one (a known prostaglandin synthon) with an overall yield of 28percent.The use of molecular bromine for bromination leads to the production of the 5-bromo analog of the synthon.