(2S,3S)-3-methyl-N-(4-methylbenzenesulfonyl)-2-vinylaziridine | 187531-94-8

• 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: (2S,3S)-3-methyl-N-(4-methylbenzenesulfonyl)-2-vinylaziridine
• 英文别名: (2S,3S)-2-ethenyl-3-methyl-1-(4-methylphenyl)sulfonylaziridine
• CAS: 187531-94-8
• 化学式: C₁₂H₁₅NO₂S
• 分子量: 237.323
• InChiKey: BPULHWQMMPQJMI-QDYONFDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-methyl-N-(4-methylbenzenesulfonyl)-2-vinylaziridine 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 2-methyl-N-tosyl-3-vinylaziridine
  参考文献：
  名称：

  An unusual thermodynamic preference of chiral N-arylsulfonyl cis-3-alkyl-2-vinylaziridines over their trans-isomers: palladium(0)-catalysed equilibration reactions

  摘要：

  钯(0)催化的N-烷基磺酰或N-芳基磺酰-3-烷基-2-乙烯基唑烷反应表明，2,3-顺式异构体比相应的2,3-反式异构体更稳定，这与从头计算的结果一致。

  DOI：

  10.1039/cc9960000351
• 作为产物：
  描述：

  (3S)-Methyl-N-p-toluolsulfonylaziridin-(2R)-carbonsaeuremethylester 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (2S,3S)-3-methyl-N-(4-methylbenzenesulfonyl)-2-vinylaziridine
  参考文献：
  名称：

  A Thermodynamic Preference of Chiral N-Methanesulfonyl and N-Arenesulfonyl 2,3-cis-3-Alkyl-2-Vinylaziridines over Their 2,3-Trans-Isomers:  Useful Palladium(0)-Catalyzed Equilibration Reactions for the Synthesis of (E)-Alkene Dipeptide Isosteres

  摘要：

  Palladium(0)-catalyzed reactions of N-methanesulfonyl- or N-(arenesulfonyl)-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations. A highly stereoselective synthetic route to (E)-alkene dipeptide isosteres having desired stereochemistries from 2,3-cis-3-isobutyl-2-vinylaziridine by the use of organocopper chemistry is also presented.

  DOI：

  10.1021/jo961760o

文献信息

• An unusual thermodynamic preference of chiral N-arylsulfonyl cis-3-alkyl-2-vinylaziridines over their trans-isomers: palladium(0)-catalysed equilibration reactions
  作者：Norio Mimura、Toshiro Ibuka、Masako Akaji、Yoshihisa Miwa、Tooru Taga、Kazuo Nakai、Hirokazu Tamamura、Nobutaka Fujii、Yoshinori Yamamoto

  DOI：10.1039/cc9960000351

  日期：——

  Palladium (0)-catalysed reactions of N-alkylsulfonyl- or N-arylsulfonyl-3-alkyl-2-vinyfaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations.

  钯(0)催化的N-烷基磺酰或N-芳基磺酰-3-烷基-2-乙烯基唑烷反应表明，2,3-顺式异构体比相应的2,3-反式异构体更稳定，这与从头计算的结果一致。
• 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.
• A Thermodynamic Preference of Chiral <i>N</i>-Methanesulfonyl and <i>N</i>-Arenesulfonyl 2,3-<i>cis</i>-3-Alkyl-2-Vinylaziridines over Their 2,3-<i>Trans</i>-Isomers:  Useful Palladium(0)-Catalyzed Equilibration Reactions for the Synthesis of (<i>E</i>)-Alkene Dipeptide Isosteres
  作者：Toshiro Ibuka、Norio Mimura、Hiroshi Aoyama、Masako Akaji、Hiroaki Ohno、Yoshihisa Miwa、Tooru Taga、Kazuo Nakai、Hirokazu Tamamura、Nobutaka Fujii、Yoshinori Yamamoto

  DOI：10.1021/jo961760o

  日期：1997.2.1

  Palladium(0)-catalyzed reactions of N-methanesulfonyl- or N-(arenesulfonyl)-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations. A highly stereoselective synthetic route to (E)-alkene dipeptide isosteres having desired stereochemistries from 2,3-cis-3-isobutyl-2-vinylaziridine by the use of organocopper chemistry is also presented.