114507-67-4

Basic information

• Product Name: (Z)-(1S^*,2S^*,3R^*)-1-<(2,3-benzo-2-cyclohexylidene)methyl>-2-isopropyl-5-methylcyclohexanol
• CAS NO: 114507-67-4
• Molecular Weight: 298.469
• Mol File: 114507-67-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-(1S^*,2S^*,3R^*)-1-<(2,3-benzo-2-cyclohexylidene)methyl>-2-isopropyl-5-methylcyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-(1S^*,2S^*,3R^*)-1-<(2,3-benzo-2-cyclohexylidene)methyl>-2-isopropyl-5-methylcyclohexanol(114507-67-4)
• EPA Substance Registry System: (Z)-(1S^*,2S^*,3R^*)-1-<(2,3-benzo-2-cyclohexylidene)methyl>-2-isopropyl-5-methylcyclohexanol(114507-67-4)

Safety Data

• Hazardous Substances Data: 114507-67-4(Hazardous Substances Data)

Upstream product

• 91092-18-1 1-(dichloromethylene)-1,2,3,4-tetrahydronaphthalene 
• 491-07-6 (+/-)-menthone 

Relevant articles and documents

Stereochemical Aspects in the Insertion by Alkylidenemethylene Carbenoids into the α-C-H Bond of Alkoxides

Primary alkoxides (R1CH2OM; M=K or Li) when treated with haloalkenes (R3R4C=CXY; X=Cl or Br, Y=H or Cl) in the presence of n-BuLi in THF at 0 deg C gave allylic alcohols (R1CH(OH)CH=CR3R4) through the insertion reaction of the corresponding alkylidenemethylene carbenoid () into the α-C-H bond of alkoxides.Secondary alkoxides (R1R2CHOM), under similar reaction conditions, gave butyl adducts (R1R2C(OH)C4H9) in addition to the insertion products.In particular, the C-H insertion of menthyl oxide proceeded without stereospecificity to give a mixture of the axial and equatorial insertion products.These results provided evidence for the hydride abstraction-recombination mechanism in the carbenoid insertion reaction.The regioselective, nonstereospecific insertion reaction was also observed when alkoxides were treated with separately prepared ((2,3-benzo-2-cyclohexylidene)chloromethyl)lithium at temperatures from -95 to -40 deg C.The absence of H-D scrambling in crossover experiments under these reaction conditions clearly showed that the hydride abstraction-recombination mechanism proceeded within a solvent cage.An inversion of configuration on the carbenoid carbon in the hydride abstraction step was proposed on the basis of the E/Z stereoselectivity in the insertion products.