5239-43-0

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

• 51551-01-0 9,12-Dioxo-dodecanoic acid 
• 5288-67-5 2-(6-carboxyhexyl)cyclopentanone 
• 79918-34-6 2-<7-<(tetrahydro-2H-pyran-2-yl)oxy>heptyl>cyclopent-2-en-1-one 
• 110066-09-6 7-(1-Bromo-2-oxo-cyclopentyl)-heptanoic acid 
• 105602-58-2 2-(5'-carboxypentyl)cyclohexanone 
• 108-94-1 cyclohexanone 
• 53596-83-1 1-tetrahydropyranyloxy-8-iodooctane 
• 51876-14-3 7-(2-Hydroxy-cyclopentyl)-heptanoic acid 
• 1931-63-1 methyl ester of azelaic acid aldehyde 
• 629-41-4 1,8-Octanediol 
• 79918-30-2 1-(phenylsulfonyl)-8-<(tetrahydro-2H-pyran-2-yl)oxy>octane 
• 41301-95-5 1-methoximino-2-(5-hydroxypentyl)-2-cyclopentene 
• 52477-92-6 1-methoximino-2-(5-acetoxypentyl)-2-cyclopentene 
• 35074-08-9 2-(4-carboxybutyl)cyclopentan-1-one 

Downstream Products

• 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 
• 40098-26-8 methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoate 
• 51876-14-3 7-(2-Hydroxy-cyclopentyl)-heptanoic acid 
• 52477-97-1 2-(7-butoxycarbonylhexyl)-2-cyclopenten-1-one 
• 41301-75-1 1-methoximino-2-(7-p-toluenesulfonyloxyheptyl)-2-cyclopentene 
• 34546-57-1 2-(6-methoxycarbonylhexyl)cyclopent-2-en-1-one 
• 40098-40-6 (+/-)-11,15-Didesoxyprostaglandin E⁽¹⁾ 
• 37786-00-8 Doproston B 
• 21269-27-2 7-[(S)-2-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-oxo-cyclopentyl]-heptanoic acid 
• 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 academic research and scientific papers

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.

MICROBIOLOGICAL SYNTHESIS OF S(-)-2-(4-CARBOXY-3-HYDROXYBUTYL)-2-CYCLOPENTEN-1-ONE AND SOME OF ITS PROPERTIES

A microbiological synthesis of S(-)-2-(4-carboxy-3-hydroxybutyl)-2-cyclopenten-1-one was undertaken.Its methyl ether undergoes enantiospecific cyclization to 2-methoxycarbonylmethyl-5-oxocyclopentatetrahydropyran with the total asymmetric induction of two new S-chiral centers.The chiroptical characteristics of the compounds are examined.

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.

EINFACHE, REGIOSPECIFISCHE SYNTHESE VON CYCLOALKENONEN AUS LACTONEN

The reaction of lithiumalkylphosphonates with γ- or δ-lactones followed by oxidation leads to 2,5- or 2,6-dioxophosphonates, which can be cyclized to cyclopentanones or cyclohexanones, respectively, constituting an easy, regiospecific route to cycloalkanones from lactones.

Synthesis of Prostanoid Synthon and an Analogue

2-(ω-Carboxyhexyl)cyclopent-2-en-1-one (VI), a prostanoid synthon and 2-(ω-carboxypentyl)cyclopent-2-en-1-one (IX) have been synthesized from aleuritic acid.

SYNTHESIS OF 2-(6'-CARBOXYHEXYL)CYCLOPENT-2-EN-1-ONE (PROSTAGLANDIN SYNTHON) BY CYCLIZATION OF 5-HYDROXYDODECANE-1,12-DIOIC ACID

The oxidation of 2-(6'-carboxyhexyl)cyclopentanone by persulfuric acid leads to a mixture of 5-hydroxydodecane-1,12-dioic acid and the corresponding δ-lactone.Cyclodehydration of the latter with polyphosphoric acid gives 2-(6'-carboxyhexyl)cyclopent-2-en-1-one (prostaglandin synthon) with an overall yield of 41percent.

Prostaglandins Part 7. Synthesis of (+/-)-11-Deoxy-10-hydroxy- and (+/-)-11-Deoxy-10-oxoprostaglandins

The epoxides of 2-alkylcyclopent-2-enones (I) react with acetic acid to give 5-acetoxy-2-alkylcyclopent-2-enones (II) which afford (+/-)-11-deoxy-10-hydroxyprostaglandins via conjugate-addition reactions.The 11-deoxy-10-hydroxyprostaglandin (IXa) readily undergoes base-catalysed autoxidation to the 11-deoxy-10-oxoprostaglandin (XIII).