trans-(1-benzyl-4-methylpyrrolidin-3-yl)methanol

• 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: trans-(1-benzyl-4-methylpyrrolidin-3-yl)methanol
• 英文别名: rac-trans-(4-methyl-3-pyrrolidinyl)methanol；[(3R,4R)-1-benzyl-4-methylpyrrolidin-3-yl]methanol
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: MQIQTRXCBIVWTN-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-(1-benzyl-4-methylpyrrolidin-3-yl)methanol 在 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 13.5h， 生成 tert-butyl (3R,4R)-3-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Diastereodivergent Access to Syn and Anti 3,4-Substituted β-Fluoropyrrolidines: Enhancing or Reversing Substrate Preference

  摘要：

  A practical diastereodivergent access to beta-fluoropyrrolidines with two adjacent stereocenters has been demonstrated, by either enhancing or completely reversing the substrate control, in the diastereoselective fluorination of a series of diverse pyrrolidinyl carbaldehydes using organocatalysis. Furthermore, enamine catalysis has been successfully utilized for kinetic resolution, obtaining a fluorinated beta-prolinol analogue with two adjacent tetrasubstituted chiral centers in 95% ee from a racemic substrate.

  DOI：

  10.1021/acs.orglett.6b00293

文献信息

• Diastereodivergent Access to <i>Syn</i> and <i>Anti</i> 3,4-Substituted β-Fluoropyrrolidines: Enhancing or Reversing Substrate Preference
  作者：Kasper Fjelbye、Mauro Marigo、Rasmus Prætorius Clausen、Karsten Juhl

  DOI：10.1021/acs.orglett.6b00293

  日期：2016.3.4

  A practical diastereodivergent access to beta-fluoropyrrolidines with two adjacent stereocenters has been demonstrated, by either enhancing or completely reversing the substrate control, in the diastereoselective fluorination of a series of diverse pyrrolidinyl carbaldehydes using organocatalysis. Furthermore, enamine catalysis has been successfully utilized for kinetic resolution, obtaining a fluorinated beta-prolinol analogue with two adjacent tetrasubstituted chiral centers in 95% ee from a racemic substrate.