(cis-4-methylcyclohexyl)methyl sulfoxide | 60260-76-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: (cis-4-methylcyclohexyl)methyl sulfoxide
• 英文别名: cis-4-Methyl-cyclohexyl-methylsulfoxid
• CAS: 60260-76-6
• 化学式: C₈H₁₆OS
• 分子量: 160.28
• InChiKey: XUWMCNYZIYWLST-JWHQNHQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  4-methylcyclohexanethiol 在 sodium hydroxide 、 sodium periodate 作用下， 生成 (cis-4-methylcyclohexyl)methyl sulfoxide
  参考文献：
  名称：

  Conformational analysis. 32. Conformational energies of methyl sulfide, methyl sulfoxide, and methyl sulfone groups

  摘要：

  DOI：

  10.1021/jo00886a026

文献信息

• Enthalpic and Entropic Contributions to the Conformational Free Energies of Methylthio, Methylsulfinyl, Methylsulfonyl, Phenylthio, Phenylsulfinyl, and Phenylsulfonyl [S(O)<i>_n</i>R, <i>n</i> = 0, 1, 2; R = CH₃, Ph] Groups in Cyclohexane
  作者：Eusebio Juaristi、Victoria Labastida、Sandra Antúnez

  DOI：10.1021/jo991181u

  日期：2000.2.1

  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.