7712-68-7

Basic information

• Product Name: (1S)-2-Isopropylidene-5β-methylcyclopentane-1α-carboxylic acid
• Synonyms: (1S)-2-Isopropylidene-5β-methylcyclopentane-1α-carboxylic acid;(1S)-2α-Methyl-5-isopropylidenecyclopentanecarboxylic acid;(1S,2R)-2-Methyl-5-(1-methylethylidene)cyclopentanecarboxylic acid;Pulegenic acid
• CAS NO: 7712-68-7
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• Mol File: 7712-68-7.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S)-2-Isopropylidene-5β-methylcyclopentane-1α-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-2-Isopropylidene-5β-methylcyclopentane-1α-carboxylic acid(7712-68-7)
• EPA Substance Registry System: (1S)-2-Isopropylidene-5β-methylcyclopentane-1α-carboxylic acid(7712-68-7)

Safety Data

• Hazardous Substances Data: 7712-68-7(Hazardous Substances Data)

Upstream product

• 3391-90-0 (S)-(-)-pulegone 
• 623935-92-2 ethyl (2R)-2-methyl-5-(propan-2-ylidene)cyclopentanecarboxylate 
• 89-82-7 pulegone 
• 30165-01-6 trans-methyl pulegenate 

Downstream Products

• 876152-54-4 tert-butyl(((1S,2R)-2-methyl-5-(propan-2-ylidene)cyclopentyl)methoxy)diphenylsilane 
• 1268265-29-7 (5aS,8R,8aS)-1-(methoxymethoxy)-5a,7,8-trimethyl-4-phenyl-8,8a-dihydro-5aH-cyclopenta[4,5]furo[3,2-c]pyridine 
• 864448-19-1 (5aS,8R,8aS)-5a,7,8-trimethyl-4-phenyl-2,5a,8,8a-tetrahydro-1H-cyclopenta[4,5]furo[3,2-c]pyridin-1-one 
• 1268265-28-6 (5aS,8R,8aS)-7-(1,3-dithiolan-2-yl)-5a,8-dimethyl-4-phenyl-2,5a,8,8a-tetrahydro-1H-cyclopenta[4,5]furo[3,2-c]pyridin-1-one 
• 1268265-27-5 (5aS,8R,8aS)-5a,8-dimethyl-1-oxo-4-phenyl-2,5a,8,8a-tetrahydro-1H-cyclopenta[4,5]furo[3,2-c]pyridine-7-carbaldehyde 
• 1268265-26-4 (5aR,6R,7R,8R,8aS)-7-(hydroxymethyl)-6-iodo-5a,8-dimethyl-4-phenyl-2,5a,6,7,8,8a-hexahydro-1H-cyclopenta[4,5]furo[3,2-c]pyridin-1-one 
• 1268265-24-2 (5aR,6R,7R,8R,8aS)-7-(((tert-butyldiphenylsilyl)oxy)methyl)-6-iodo-5a,8-dimethyl-4-phenyl-2,5a,6,7,8,8a-hexahydro-1H-cyclopenta[4,5]furo[3,2-c]pyridin-1-one 
• 1268265-17-3 3-((1R,4S,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,5-dimethylcyclopent-2-en-1-yl)-4-hydroxy-5-phenylpyridin-2(1H)-one 
• 1268265-23-1 ethyl 2-((1S,4S,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,5-dimethylcyclopent-2-en-1-yl)-3-oxo-3-((E)-styrylamino)propanoate 
• 1268265-19-5 (1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-en-1-yl methyl carbonate 
• 1268265-22-0 (1S,4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-enol 
• 1268265-21-9 (4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-enone 
• 1268265-30-0 (4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-4-methylcyclopent-2-enone 
• 1268265-20-8 (4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-methylcyclopent-2-enone 

Relevant articles and documents

Pheromone synthesis. Part 264: Synthesis of the core 3-oxabicyclo[3.3.0]octane structures of gomadalactones A, B and C, the components of the contact sex pheromone of the white-spotted longicorn beetle, Anoplophora malasiaca

The core bicyclic cyclopentanelactone structures of gomadalactones A, B and C with α-hydroxyketone system were synthesized from (R)-pulegone, employing deconjugation of an α,β-unsaturated lactone as the key step. Comparison of the CD spectra of the synthetic compounds with those of the natural products confirmed the absolute configuration of the natural pheromone components as proposed in 2007. X-ray crystallographic analysis of the model compound of gomadalactone B core structure was carried out.

Total synthesis of citridone A

The first total synthesis of citridone A has been achieved through regioselective intramolecular iodocyclization and regio-and stereoselective Pd(0)-catalyzed coupling as key reactions.(Figure Presented)

Terpenes and Terpene Derivatives, XXIX Synthesis and Olfactive Properties of (-)- and rac-Silphiperfol-5-en-3-ol and of Some Tris-nor Derivatives

The new sesquiterpene alcohols silphiperfol-5-en-3-ol and the corresponding 7-epi compound (+)-1b, important constituents of the essential oil of Artemisia laciniata have been synthesized in 13 steps by starting from (R)-(+)-pulegone (6) in an overall yield of 8percent.The key reaction is the copper-catalyzed 1,4-Grignard addition of the iodo acetal 34 to the enone (+)-4 in the presence of TMSCl and TMEDA to give the silyl ether 38.Hydrolysis with spontaneous aldol cyclization and dehydration leads to the silphiperfolenones (+)-2a,b which are separable by flash chromatgraphy.The reduction with L-selectrideR gives the alcohols (-)-1a and (+)-1b which are identical in all physical properties with the isolated natural compound.With LiAlH4 the diastereoisomers 42a,b are formed.Olfactive evaluation of the isomers (-)-1a and (+)-1b has shown that the odor of the naturally occuring mixture of 1a,b with the descriptors woody, ambergris, slightly camphoraceous is correctly assigned. (-)-1a represents the more woody and camphoraceous, (+)-1b the more animal facette of ambergris.The odor of rac-1a,b, of the diasteroisomers 42a,b and of the ketones (+)-2a,b is also described as well as that of the tris-nor-silphiperfolene derivatives 29-31. Key Words: Artemisia laciniata / Sesquiterpene alcohols, tricyclic / Structure-odor correlation / (R)-(+)-Pulegone / 1,4-Grignard reaction