1-Methylcyclohexene

1-methylcyclohexene.svg 120 1-Methylcyclohex-1-ene 2,3,4,5-Tetrahydrotoluene 1-Methyl-1-cyclohexene 1304483 591-49-1 TE4P8Q2044 229299 11086 DTXSID70862258 DTXSID10862257 209-718-0 1S/C7H12/c1-7-5-3-2-4-6-7/h5H,2-4,6H2,1H3 CTMHWPIWNRWQEG-UHFFFAOYSA-N 11574 CC1=CCCCC1 3295 colorless liquid 110 0.811 g/mL at 20 °C 1.44 7 12 -120.4 0.052 g/kg for 1-methylcyclohexene MSDS (1-methylcyclohexene) -3 02 07 08 Warning 225 304 315 319 335 210 233 240 241 242 243 261 264 271 280 301+310 302+352 303+361+353 304+340 305+351+338 312 321 331 332+313 337+313 362 370+378 403+233 403+235 405 501 1-Methylcyclohexene is an organic compound consisting of cyclohexene with a methyl group substituent attached to the alkene group. Two other structural isomers are known: 3-methylcyclohexene and 4-methylcyclohexene. All are colorless volatile liquids. They are specialized reagents. Methylcyclohexenes are a cyclic olefins. Synthesis and reactions Methylcyclohexenes are formed by the partial hydrogenation of toluene to methylcyclohexane over ruthenium catalyst.Belohlav, H. Kluson, P. Cerveny, L. 1997 Partial Hydrogenation of Toluene Over A Ruthenium Catalyst, A Model Treatment of A Deactivation Process Res. Chem. Intermed. 32 2 161–168 10.1163/156856797X00312 95532469 Ozonolysis of 1-methylcyclohexene results in ring-opening.Atkinson Roger. Tuazon Ernesto C. Aschmann Sara M. Products of the Gas-Phase Reactions of O3 with Alkenes Environmental Science & Technology 1995 29 7 1860–1866 10.1021/es00007a025 1995EnST...29.1860A Stereochemical probe 1-Methylcyclohexene is used as a probe of the stereochemistry of reactions involving alkenes because it is prochiral and the two sp2-carbon atoms differ. thumb|left|"Hydrosilylation of Cyclohexene" The regioselectivity and stereoselectivity of hydrosilylation of 1-methylcyclohexene with chloro(methyl)silanes depends on the number of chlorine atoms in the hydrosilylating agent.December 2004 Hydrosilylation of Cyclohexene, 1-Methylcyclohexene, and Isopropylidenecyclohexane Russian Journal of General Chemistry M. Voronkov etal 74 12 1895–1899 10.1007/s11176-005-0114-4 98097289 Using chlorodimethylsilane produces a mixture of seven different products including cis- and trans-isomers of 2-, 3-, 4-chlorodimethyl(methylcyclohexyl)silanes and chlorodimethyl(cyclohexylmethyl)silane. The poor selectivity is due to the migration of the double bond in the cyclohexene ring. Reaction with dichloromethylsilane is more regioselective and stereoselective, only giving three of the seven products obtained from monochlorodimethylsilane. With trichloromethylsilane, trichlorocyclohexylmethylsilane is the only possible product and is obtained at 60 percent yield. All these products can be further reacted with Grignard reagents such as ethynylmagnesium bromide to synthesize ethynyl derivatives. Oxidation of 1-methylcyclohexene catalyzed by cytochrome P450 yields a 2:1 mixture of hydroxylation to epoxidation products.Khan, M. M. T. Rao, A. P. Bhatt, S. D. Merchant, R. R. Epoxidation of cyclohexene, methylcyclohexene and cis-cyclooctene by molecular oxygen using ruthenium(III) aquo ion as catalyst: A kinetic study 1990 Journal of Molecular Catalysis 62 3 265–276 10.1016/0304-5102(90)85222-4 The stereochemistry of hydroformylation has been examined using 1-methylcyclohexene. The main product has the formyl group on the less substituted alkene-carbon, trans with respect to the methyl substituent.10.1002/9781119390541.ch7 Carbonylation and Carboxylation Hydrocarbon Chemistry 2017 509–568 978-1-119-39051-0 Árpád Molnár George A. Olah G. K. Surya Prakash Wiley References Category:Cyclohexenes