(1R)-2-methyl-exo,exo-bicyclo<2.2.1>heptane-2,3-dicarboxylic anhydride

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R)-2-methyl-exo,exo-bicyclo<2.2.1>heptane-2,3-dicarboxylic anhydride
• 英文别名: (1R,2S,6R,7S)-2-methyl-4-oxatricyclo[5.2.1.02,6]decane-3,5-dione
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: KURYGOWCQOQZRG-XIVUIJJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R)-2-methyl-exo,exo-bicyclo<2.2.1>heptane-2,3-dicarboxylic anhydride 在 氨 作用下， 生成 (1S)-2-methyl-exo,exo-bicyclo<2.2.1>heptane-2,3-dicarboximide
  参考文献：
  名称：

  Molecular geometry and circular dichroism spectra of bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydrides and imides

  摘要：

  Several tricyclic anhydrides and imides derived from optically active bicyclo[2.2.1]heptane-2,3-dicarboxylic acids were synthesized, and their circular dichroism spectra are reported. On the basis of MNDO calculations it was estalished that despite rigidity of the norbornane system the five-membered rings of succinic anhydride and imide moieties are slightly twisted. The chromophores are flexible and can be more or less skewed depending on solvent polarity. The chromophore nonplanarity significantly influences magnitude and sign of the first Cotton effect associated with the lowest energy n-pi* electronic transition. The sign of the second n-pi* Cotton effect is governed by vicinal effect of substituents. The crystal structures of three N-(S)-1-phenylethylimides were solved to establish the configuration at C-2 of the imide moieties.

  DOI：

  10.1021/jo00063a038
• 作为产物：
  描述：

  (+)-endo-2-methyl-exo,endo-2,3-bicyclo<2.2.1>heptanedicarboxylic acid 以0.82 g的产率得到(1R)-2-methyl-exo,exo-bicyclo<2.2.1>heptane-2,3-dicarboxylic anhydride
  参考文献：
  名称：

  Molecular geometry and circular dichroism spectra of bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydrides and imides

  摘要：

  Several tricyclic anhydrides and imides derived from optically active bicyclo[2.2.1]heptane-2,3-dicarboxylic acids were synthesized, and their circular dichroism spectra are reported. On the basis of MNDO calculations it was estalished that despite rigidity of the norbornane system the five-membered rings of succinic anhydride and imide moieties are slightly twisted. The chromophores are flexible and can be more or less skewed depending on solvent polarity. The chromophore nonplanarity significantly influences magnitude and sign of the first Cotton effect associated with the lowest energy n-pi* electronic transition. The sign of the second n-pi* Cotton effect is governed by vicinal effect of substituents. The crystal structures of three N-(S)-1-phenylethylimides were solved to establish the configuration at C-2 of the imide moieties.

  DOI：

  10.1021/jo00063a038

文献信息

• Molecular geometry and circular dichroism spectra of bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydrides and imides
  作者：Tadeusz Polonski、Maria J. Milewska、Maria Gdaniec、Miroslaw Gilski

  DOI：10.1021/jo00063a038

  日期：1993.5

  Several tricyclic anhydrides and imides derived from optically active bicyclo[2.2.1]heptane-2,3-dicarboxylic acids were synthesized, and their circular dichroism spectra are reported. On the basis of MNDO calculations it was estalished that despite rigidity of the norbornane system the five-membered rings of succinic anhydride and imide moieties are slightly twisted. The chromophores are flexible and can be more or less skewed depending on solvent polarity. The chromophore nonplanarity significantly influences magnitude and sign of the first Cotton effect associated with the lowest energy n-pi* electronic transition. The sign of the second n-pi* Cotton effect is governed by vicinal effect of substituents. The crystal structures of three N-(S)-1-phenylethylimides were solved to establish the configuration at C-2 of the imide moieties.