(2S,3S)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-ethynyl-2-methyl-1-tosylaziridine

• 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-(((tert-butyldimethylsilyl)oxy)methyl)-2-ethynyl-2-methyl-1-tosylaziridine
• 英文别名: tert-butyl-[[(2S,3S)-3-ethynyl-3-methyl-1-(4-methylphenyl)sulfonylaziridin-2-yl]methoxy]-dimethylsilane
• 化学式: C₁₉H₂₉NO₃SSi
• 分子量: 379.596
• InChiKey: JUMJLBACCMKCPI-MVGXFMOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 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)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-ethynyl-2-methyl-1-tosylaziridine 在 copper(I) bromide dimethylsulfide complex 、 二甲基硫 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Reactions of carbon nucleophiles with 2,2,3-trisubstituted ethynylaziridines

  摘要：

  Carbon nucleophiles were used to open a 2,2,3-trisubstituted ethynylaziridine. A cyanide nucleophile opened the ring at the more substituted carbon, proceeding regioselectively with inversion of configuration. In an attempt to expand upon the scope of the reaction, Normant cuprates were reacted with a 2,2,3-trisubstituted ethynylaziridine. This reaction produced chiral allenes via an anti-S(N)2' pathway. X-ray analysis of a derivative allowed the absolute stereochemistry of the anti-allenes to be assigned as P. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2013.08.009
• 作为产物：
  描述：

  (R)-4-((R)-1-hydroxy-1-methylprop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 盐酸 、 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 水 、 sodium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (2S,3S)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-ethynyl-2-methyl-1-tosylaziridine
  参考文献：
  名称：

  Reactions of carbon nucleophiles with 2,2,3-trisubstituted ethynylaziridines

  摘要：

  Carbon nucleophiles were used to open a 2,2,3-trisubstituted ethynylaziridine. A cyanide nucleophile opened the ring at the more substituted carbon, proceeding regioselectively with inversion of configuration. In an attempt to expand upon the scope of the reaction, Normant cuprates were reacted with a 2,2,3-trisubstituted ethynylaziridine. This reaction produced chiral allenes via an anti-S(N)2' pathway. X-ray analysis of a derivative allowed the absolute stereochemistry of the anti-allenes to be assigned as P. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2013.08.009

文献信息

• Reactions of carbon nucleophiles with 2,2,3-trisubstituted ethynylaziridines
  作者：Brandon T. Kelley、Madeleine M. Joullié

  DOI：10.1016/j.tetasy.2013.08.009

  日期：2013.10

  Carbon nucleophiles were used to open a 2,2,3-trisubstituted ethynylaziridine. A cyanide nucleophile opened the ring at the more substituted carbon, proceeding regioselectively with inversion of configuration. In an attempt to expand upon the scope of the reaction, Normant cuprates were reacted with a 2,2,3-trisubstituted ethynylaziridine. This reaction produced chiral allenes via an anti-S(N)2' pathway. X-ray analysis of a derivative allowed the absolute stereochemistry of the anti-allenes to be assigned as P. Published by Elsevier Ltd.