(2R,3S)-N-diphenylphosphinoyl-3-isopropyl-2-vinylaziridine | 214751-90-3

• 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: (2R,3S)-N-diphenylphosphinoyl-3-isopropyl-2-vinylaziridine
• 英文别名: (2R,3S)-1-diphenylphosphoryl-2-ethenyl-3-propan-2-ylaziridine
• CAS: 214751-90-3
• 化学式: C₁₉H₂₂NOP
• 分子量: 311.364
• InChiKey: XCUDGHFYCJFMCK-LFPSWIHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  20.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyllithium-lithium bromide 、 (2R,3S)-N-diphenylphosphinoyl-3-isopropyl-2-vinylaziridine 在 copper(l) iodide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 生成 (Z,3S)-3-(N-diphenylphosphinoyl)amino-2-methylhept-4-ene 、 (E,3S)-3-(N-diphenylphosphinoyl)amino-2-methylhept-4-ene
  参考文献：
  名称：

  Reactions of N-Arylsulfonyl-2,3-cis- and N-Arylsulfonyl-2,3-trans-3-alkyl-2-vinylaziridines with Organocopper Reagents:  Importance of 2,3-cis-Stereochemistry in Controlling Regio- and Stereoselectivity

  摘要：

  Although reactions of 2,3-trans-N-arylsulfonyl-3-alkyl-2-alkenylaziridines with organocopper reagents give a mixture of two or three products, the corresponding 2,3-cis-isomers provide a highly efficient route to synthetically important nonracemic (E)-allylamines. It is also found that the reaction proceeds via the well-known anti-S(N)2' pathway.

  DOI：

  10.1021/jo9810157
• 作为产物：
  描述：

  (3S,4S)-4-(N-diphenylphosphinoyl)amino-5-methylhex-1-en-3-ol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以77%的产率得到(2R,3S)-N-diphenylphosphinoyl-3-isopropyl-2-vinylaziridine
  参考文献：
  名称：

  Reactions of N-Arylsulfonyl-2,3-cis- and N-Arylsulfonyl-2,3-trans-3-alkyl-2-vinylaziridines with Organocopper Reagents:  Importance of 2,3-cis-Stereochemistry in Controlling Regio- and Stereoselectivity

  摘要：

  Although reactions of 2,3-trans-N-arylsulfonyl-3-alkyl-2-alkenylaziridines with organocopper reagents give a mixture of two or three products, the corresponding 2,3-cis-isomers provide a highly efficient route to synthetically important nonracemic (E)-allylamines. It is also found that the reaction proceeds via the well-known anti-S(N)2' pathway.

  DOI：

  10.1021/jo9810157

文献信息

• Reactions of <i>N</i>-Arylsulfonyl-2,3-<i>cis</i>- and <i>N</i>-Arylsulfonyl-2,3-<i>trans</i>-3-alkyl-2-vinylaziridines with Organocopper Reagents:  Importance of 2,3-<i>cis</i>-Stereochemistry in Controlling Regio- and Stereoselectivity
  作者：Ayako Toda、Hiroshi Aoyama、Norio Mimura、Hiroaki Ohno、Nobutaka Fujii、Toshiro Ibuka

  DOI：10.1021/jo9810157

  日期：1998.10.1

  Although reactions of 2,3-trans-N-arylsulfonyl-3-alkyl-2-alkenylaziridines with organocopper reagents give a mixture of two or three products, the corresponding 2,3-cis-isomers provide a highly efficient route to synthetically important nonracemic (E)-allylamines. It is also found that the reaction proceeds via the well-known anti-S(N)2' pathway.