(2R,3S,4R)-1,4-Dimethyl-3-phenylazetidine-2-carbonitrile | 873669-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (2R,3S,4R)-1,4-Dimethyl-3-phenylazetidine-2-carbonitrile
• 英文别名: (2R,3S,4R)-1,4-dimethyl-3-phenylazetidine-2-carbonitrile
• CAS: 873669-02-4
• 化学式: C₁₂H₁₄N₂
• 分子量: 186.257
• InChiKey: XNSMIWSHJTZDHP-ADEWGFFLSA-N

物化性质

• 沸点：
  316.4±42.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-1,4-Dimethyl-3-phenylazetidine-2-carbonitrile 在 三氟化硼乙醚 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 2.25h， 生成 (2R,3S,4R,5R)-3-amino-1,5-dimethyl-2,4-diphenyl-pyrrolidine
  参考文献：
  名称：

  3-Aminopyrrolidines via Ring Rearrangement of 2-Aminomethylazetidines. Synthesis of (−)-Absouline

  摘要：

  [GRAPHICS]A new entry to enantiopure 3-aminopyrrolidines was developed using a boron trifluoride-mediated rearrangement of 2-aminomethylazetidines. The method is quite general and produces rearranged products in good yield regardless of both substitution pattern and relative stereochemistry of the starting material. A concise stereocontrolled synthesis of (-)-absouline was achieved on the basis of this new method.

  DOI：

  10.1021/ol052388e

文献信息

• Reaction of Azetidines with Chloroformates
  作者：Monica Vargas-Sanchez、Sami Lakhdar、François Couty、Gwilherm Evano

  DOI：10.1021/ol062128c

  日期：2006.11.1

  The reaction of an azetidine with a chloroformate can give either the dealkylated heterocycle or the ring-opened product (gamma-chloroamine), which can further cyclize to the oxazinanone. A general study of this underrated reaction was conducted and revealed that azetidines can undergo smooth nucleophilic ring-opening reactions to highly functionalized gamma-chloroamines in the presence of a variety of alkyl chloroformates under mild reaction conditions. Yields are usually good, and parameters governing this reaction were evaluated.
• 3-Aminopyrrolidines via Ring Rearrangement of 2-Aminomethylazetidines. Synthesis of (−)-Absouline
  作者：Monica Vargas-Sanchez、François Couty、Gwilherm Evano、Damien Prim、Jérome Marrot

  DOI：10.1021/ol052388e

  日期：2005.12.1

  [GRAPHICS]A new entry to enantiopure 3-aminopyrrolidines was developed using a boron trifluoride-mediated rearrangement of 2-aminomethylazetidines. The method is quite general and produces rearranged products in good yield regardless of both substitution pattern and relative stereochemistry of the starting material. A concise stereocontrolled synthesis of (-)-absouline was achieved on the basis of this new method.