(1S,2S)-2-hydroxymethyl-1-benzyl-1-methylpyrrolidinium chloride | 1232217-90-1

• 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: (1S,2S)-2-hydroxymethyl-1-benzyl-1-methylpyrrolidinium chloride
• CAS: 1232217-90-1
• 化学式: C₁₃H₂₀NO*Cl
• 分子量: 241.761
• InChiKey: PYEGSDKJDZNLNN-IODNYQNNSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.21
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  氯化苄 、 N-甲基-L-脯氨醇 以 乙醇 为溶剂， 反应 24.0h， 生成 (1R,2S)-2-hydroxymethyl-1-benzyl-1-methylpyrrolidinium chloride 、 (1S,2S)-2-hydroxymethyl-1-benzyl-1-methylpyrrolidinium chloride
  参考文献：
  名称：

  Diasteroselective Structure Directing Effect of (1S,2S)-2-Hydroxymethyl-1-benzyl-1-methylpyrrolidinium in the Synthesis of ZSM-12

  摘要：

  The chiral cation (1S,2S)-2-hydroxymethyl-1-benzyl-1-methylpyrrolidinium (bmpm) and a 50% mixture of this with its diastereoisomer (1R,2S)-2-hydroxymethyl-1-benzyl-1-methylpyrrolidinium have been prepared and tested as structure directing agents (SDAs) in the synthesis of pure-silica zeolites in fluoride medium. The S,S isomer has been shown to efficiently direct the crystallization of zeolite ZSM-12 (MTW); in contrast, the use of a mixture of the two diastereoisomers as a SDA does not lead to the formation of the ZSM-12 structure under the same synthesis conditions, thus suggesting a lower efficiency of the R,S isomer to direct the crystallization of the structure. A computational study based on molecular mechanic simulations allowed explanation of the efficient structure directing role of the S,S isomer in terms of a high host-guest interaction due to a strong structural relationship between the MTW topology and the molecular geometry of the S,S isomer. However, the simulations revealed that the interaction developed by the R,S diasteroisomer with the MTW framework is smaller due to a worse fitting of its molecular structure with the zeolite topology, providing an explanation for the experimental observations.

  DOI：

  10.1021/cm903095q