| 103873-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 103873-01-4
• 化学式: C₁₂H₁₃NO₂
• 分子量: 207.209
• InChiKey: XDYXDICGEYAHRU-BSFGQKQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  生成 、
  参考文献：
  名称：

  Cis/transstereochemical effects in the negative chemical ionization/OH⁻mass spectra of strained-ring azabicycloalkanes using MIKE and CA/MIKE spectrometry

  摘要：

  AbstractStereospecific decomposition reactions of isomeric (cis and trans) deprotonated molecules from azabicycloalkane derivatives as azetidinols generated under negative chemical ionization (NCI)/OH− have been examined using mass‐analysed ion kinetic energy (MIKE) and collisional activation (CA)/MIKE spectra. These measurements together with the ones obtained on specifically labelled compounds enabled us to determine the origin of the stereochemical effects. The results indicate that the hydroxylic proton constitutes the preferential (≃90%) site for the deprotonation process. Subsequent fragmentations of the deprotonated species observed in the second field‐free region of a reversed geometry instrument are affected by the stereochemistry of the hydroxylic group. The isomer with the hydroxyl group in the cis position relative to the hydrogen at the ring junction mainly loses H2O, while the trans isomer eliminates CH3˙, both processes occurring with high specificity. Labelling studies indicate that two major pathways exist for the elimination of H2O from the cis isomer and the loss of CH3˙ from the trans isomer. The course of the reaction is determined by the ability of the stereoisomers to transfer a proton during the first decomposition step. When the size of the lactam ring is increased from a five‐membered ring to a six‐ or seven‐membered ring, these stereochemical effects tend to become less pronounced.

  DOI：

  10.1002/oms.1210201214
• 作为产物：
  描述：

  乙酰苯-β,β,β-d3 在 Amberlyst A-26 Br₃(-) form 作用下， 以 二氯甲烷 、 重水 为溶剂， 生成
  参考文献：
  名称：

  Cis/transstereochemical effects in the negative chemical ionization/OH⁻mass spectra of strained-ring azabicycloalkanes using MIKE and CA/MIKE spectrometry

  摘要：

  AbstractStereospecific decomposition reactions of isomeric (cis and trans) deprotonated molecules from azabicycloalkane derivatives as azetidinols generated under negative chemical ionization (NCI)/OH− have been examined using mass‐analysed ion kinetic energy (MIKE) and collisional activation (CA)/MIKE spectra. These measurements together with the ones obtained on specifically labelled compounds enabled us to determine the origin of the stereochemical effects. The results indicate that the hydroxylic proton constitutes the preferential (≃90%) site for the deprotonation process. Subsequent fragmentations of the deprotonated species observed in the second field‐free region of a reversed geometry instrument are affected by the stereochemistry of the hydroxylic group. The isomer with the hydroxyl group in the cis position relative to the hydrogen at the ring junction mainly loses H2O, while the trans isomer eliminates CH3˙, both processes occurring with high specificity. Labelling studies indicate that two major pathways exist for the elimination of H2O from the cis isomer and the loss of CH3˙ from the trans isomer. The course of the reaction is determined by the ability of the stereoisomers to transfer a proton during the first decomposition step. When the size of the lactam ring is increased from a five‐membered ring to a six‐ or seven‐membered ring, these stereochemical effects tend to become less pronounced.

  DOI：

  10.1002/oms.1210201214