endo-3-(trimethylsilyl)-endo-2-norborneol | 129849-99-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: endo-3-(trimethylsilyl)-endo-2-norborneol
• 英文别名: (1R,2R,3S,4S)-3-trimethylsilylbicyclo[2.2.1]heptan-2-ol
• CAS: 129849-99-6；129938-41-6
• 化学式: C₁₀H₂₀OSi
• 分子量: 184.354
• InChiKey: SCFLNULUTPNJGS-RGOKHQFPSA-N

物化性质

• 沸点：
  234.5±23.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  endo-3-(trimethylsilyl)-endo-2-norborneol 在 吡啶 、 二甲基二环氧乙烷 作用下， 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  endo-3-Trimethylsilyl-2-norbornyl 2-Nitrobenzenesulfinate

  摘要：

  The structure of the title compound, C16H23NO4SSi, was solved in order to determine the C(alkyl)-O(ester) bond distance for comparison purposes. There exists a close contact [O3 . . . S 2.766 (2) Angstrom] between one of the nitro O atoms and the sulfinate S atom. The C-O bond distance is 1.464 (3) Angstrom.

  DOI：

  10.1107/s0108270197003521
• 作为产物：
  描述：

  endo-3-(trimethylsilyl)-2-norcamphor 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.5h， 以67%的产率得到endo-3-(trimethylsilyl)-endo-2-norborneol
  参考文献：
  名称：

  Lambert, Joseph B.; Chelius, Erik C., Journal of the American Chemical Society, 1990, vol. 112, # 22, p. 8120 - 8126

  摘要：

  DOI：

文献信息

• Ground State Stereoelectronic Effects of Silicon: A Comparison of the Effects of Synperiplanar and Antiperiplanar Silicon on C-O Bond Lengths at the .beta. Position
  作者：Alison J. Green、Yew-leong Kuan、Jonathan M. White

  DOI：10.1021/jo00114a021

  日期：1995.5

  Results from low-temperature crystal structure analyses of beta-trimethylsilyl esters with synperiplanar and antiperiplanar geometry are reported. These studies reveal a significant response of the C(alkyl)-O(ester) bond length to the electron demand of the ester function when the beta-trimethylsilyl substituent is antiperiplanar to the ester. However, when the geometry is synperiplanar, the C-O bond lengths are not significantly different from those of the corresponding nonsilylated derivatives. This is interpreted in terms of more effective overlap between the sigma(C-Si) orbital and the sigma*(C-O) antibonding orbital in the antiperiplanar geometry than in the synperiplanar geometry.