(cis-4-methylcyclohexyl)phenyl sulfide | 260964-87-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (cis-4-methylcyclohexyl)phenyl sulfide
• CAS: 260964-87-2
• 化学式: C₁₃H₁₈S
• 分子量: 206.352
• InChiKey: DNITZIZHQZIFPU-BJHJDKERSA-N

反应信息

• 作为反应物：
  描述：

  (cis-4-methylcyclohexyl)phenyl sulfide 在 sodium periodate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 以79%的产率得到(cis-4-methylcyclohexyl)phenyl sulfoxide
  参考文献：
  名称：

  Enthalpic and Entropic Contributions to the Conformational Free Energies of Methylthio, Methylsulfinyl, Methylsulfonyl, Phenylthio, Phenylsulfinyl, and Phenylsulfonyl [S(O)_nR, n = 0, 1, 2; R = CH₃, Ph] Groups in Cyclohexane

  摘要：

  A variable-temperature NMR study of (cis-4-methylcyclohexyl)methyl sulfide (1), sulfoxide (2), and sulfone (3), as well as (cis-4-methylcyclohexyl)phenyl sulfide (4), sulfoxide (5), and sulfone (6) allowed determination of the thermodynamic parameters, Delta H degrees and Delta S degrees, for the title groups. Reproduction of the experimental results with Allinger's MM3 program was successfully accomplished in the case of the sulfoxide and sulfide groups. Nevertheless, modification of the original force field torsional parameters was required in order to adequately reproduce the experimentally observed behavior of the sulfonyl derivatives. Rationalization of the enthalpic and entropic contributions to Delta G degrees [S(O)(n)R, n = 0, 1, 2; R = CH3, Ph] is advanced in terms of the steric characteristics of these sulfur-containing groups and the resulting rotameric populations in the axial and equatorial monosubstituted cyclohexanes.

  DOI：

  10.1021/jo991181u
• 作为产物：
  描述：

  苯硫酚 、 trans-4-methylcyclohexyl methanesulfonate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 60.0h， 以97%的产率得到(cis-4-methylcyclohexyl)phenyl sulfide
  参考文献：
  名称：

  Enthalpic and Entropic Contributions to the Conformational Free Energies of Methylthio, Methylsulfinyl, Methylsulfonyl, Phenylthio, Phenylsulfinyl, and Phenylsulfonyl [S(O)_nR, n = 0, 1, 2; R = CH₃, Ph] Groups in Cyclohexane

  摘要：

  A variable-temperature NMR study of (cis-4-methylcyclohexyl)methyl sulfide (1), sulfoxide (2), and sulfone (3), as well as (cis-4-methylcyclohexyl)phenyl sulfide (4), sulfoxide (5), and sulfone (6) allowed determination of the thermodynamic parameters, Delta H degrees and Delta S degrees, for the title groups. Reproduction of the experimental results with Allinger's MM3 program was successfully accomplished in the case of the sulfoxide and sulfide groups. Nevertheless, modification of the original force field torsional parameters was required in order to adequately reproduce the experimentally observed behavior of the sulfonyl derivatives. Rationalization of the enthalpic and entropic contributions to Delta G degrees [S(O)(n)R, n = 0, 1, 2; R = CH3, Ph] is advanced in terms of the steric characteristics of these sulfur-containing groups and the resulting rotameric populations in the axial and equatorial monosubstituted cyclohexanes.

  DOI：

  10.1021/jo991181u