Tetracyclohexylmethane | 1593-07-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 饱和烃
• 英文名称: Tetracyclohexylmethane
• 英文别名: Tetracyclohexylmethan；Tricyclohexylmethylcyclohexane
• CAS: 1593-07-3
• 化学式: C₂₅H₄₄
• 分子量: 344.624
• InChiKey: PNKNNZNGLWDMFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  四苯基甲烷 在 Rh on carbon 氢气 作用下， 100.0 ℃ 、8.62 MPa 条件下， 生成 Tetracyclohexylmethane
  参考文献：
  名称：

  Tetracyclohexylmethane

  摘要：

  DOI：

  10.1021/jo01016a514

文献信息

• Tetracyclohexylmethane
  作者：Glen R. Buell、Leonard Spialter

  DOI：10.1021/jo01016a514

  日期：1965.5
• Molecular Structure and Internal Rotations of Tetracyclohexylmethane
  作者：Ishay Columbus、Silvio E. Biali

  DOI：10.1021/jo00105a034

  日期：1994.12

  The stereochemistry of tetracyclohexylmethane (2), obtained by catalytic hydrogenation of tetraphenylmethane, is analyzed. The Cahn-Ingold-Prelog conformational descriptors of the ideal conformers of tetrasubstituted methanes are reevaluated and an alternative method presented. Methane 2 exists in the crystal in a (g/a/-g) conformation (of approximate Sq symmetry) in which all the rings are in a chair arrangement and are skewed from their perfectly staggered D(2)d conformation. Molecular mechanics (MM) calculations indicate that the crystallographic conformation is the lowest energy form. Analysis of the H-1 and C-13 NMR data indicates that, even at low temperatures, the molecule undergoes a fast rotational process which exchanges the ortho and meta groups. On the basis of the MM calculations it is concluded that the preferred rotational pathway involves libration of the four rings via a transition state of D(2)d symmetry in which all the rings are perfectly staggered.