endo-3-(Trimethylsilyl)-2-norbornyl 2,4-dinitrobenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: endo-3-(Trimethylsilyl)-2-norbornyl 2,4-dinitrobenzoate
• 英文别名: [(1R,2R,3S,4S)-3-trimethylsilyl-2-bicyclo[2.2.1]heptanyl] 2,4-dinitrobenzoate
• 化学式: C₁₇H₂₂N₂O₆Si
• 分子量: 378.457
• InChiKey: MYIUMRBAZIARBA-CJTUPEFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4-二硝基苯甲酰氯 、 endo-3-(trimethylsilyl)-endo-2-norborneol 在 吡啶 作用下， 以32%的产率得到endo-3-(Trimethylsilyl)-2-norbornyl 2,4-dinitrobenzoate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00114a021

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.