(2S,3S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-(2,4,6-trimethyl-benzenesulfonyl)-3-vinyl-aziridine | 214751-93-6

• 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)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-(2,4,6-trimethyl-benzenesulfonyl)-3-vinyl-aziridine
• 英文别名: tert-butyl-[[(2S,3S)-3-ethenyl-1-(2,4,6-trimethylphenyl)sulfonylaziridin-2-yl]methoxy]-dimethylsilane
• CAS: 214751-93-6
• 化学式: C₂₀H₃₃NO₃SSi
• 分子量: 395.638
• InChiKey: QJNLIRPVPUALLC-GARIHTGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-(2,4,6-trimethyl-benzenesulfonyl)-3-vinyl-aziridine 在 氢氟酸 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 20.0h， 生成 (E,2S)-2-[N-(2,4,6-trimethylbenzene)sulfonyl]amino-3-hexen-1-ol
  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：

  (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-(2,4,6-trimethyl-benzenesulfonyl)-3-vinyl-aziridine 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(2S,3S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-(2,4,6-trimethyl-benzenesulfonyl)-3-vinyl-aziridine
  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

• Regio- and stereoselectivity in reactions of 2,3-cis- and trans-3-alkyl-2-vinylaziridines with organocopper reagents: Importance of 2,3-cis-stereochemistry in controlling selectivity
  作者：Hiroshi Aoyama、Norio Mimura、Hiroaki Ohno、Kiyonori Ishii、Ayako Toda、Hirokazu Tamamura、Akira Otaka、Nobutaka Fujii、Toshiro Ibuka

  DOI：10.1016/s0040-4039(97)01726-7

  日期：1997.10

  By treatment with organocopper reagents, N-activated 2,3-cis-3-alkyl-2-vinylaziridines produced exclusively (E)-allyl amines in high yields, presumably via an anti-SN2′ reaction pathway. On the other hand, under otherwise identical conditions, N-activated 2,3-trans-3-alkyl-2-vinylaziridines gave an 85-96:15-4 mixture of (E)- and (Z)-allyl amines. In reactions of certain N-activated2,3-trans-3-alkyl-2-vinylaziridines

  通过用有机铜试剂处理，N-活化的2,3-顺-3-烷基-2-乙烯基氮丙啶类化合物可能通过反-S N 2'反应途径以高收率专门生产了（E）-烯丙基胺。另一方面，在其他相同条件下，N-活化的2，3-反式-3-烷基-2-乙烯基氮丙啶给出了（E）-和（Z）-烯丙基胺的85-96：15-4混合物。在某些经N活化的2,3-反式-3-烷基-2-乙烯基氮丙啶的反应中，仅以2-3％的产率获得了N 2反应产物。