[(E)-pent-2-en-4-ynyl] N-(4-methylphenyl)sulfonylcarbamate | 1312930-55-4

• 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: [(E)-pent-2-en-4-ynyl] N-(4-methylphenyl)sulfonylcarbamate
• CAS: 1312930-55-4
• 化学式: C₁₃H₁₃NO₄S
• 分子量: 279.317
• InChiKey: GTORWTACZLEWOU-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(E)-pent-2-en-4-ynyl] N-(4-methylphenyl)sulfonylcarbamate 在 三乙烯二胺 、 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 水 、 sodium hydride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 tert-butyl-[[(2S,3S)-3-ethynyl-1-(4-methylphenyl)sulfonylaziridin-2-yl]methoxy]-dimethylsilane
  参考文献：
  名称：

  Intramolecular 1,4-addition of nitrogen nucleophile and bromine electrophile to conjugated 1,3-enyne

  摘要：

  We have discovered a series of N-bromosuccinimide-promoted 1,4-bromocyclization reactions for conjugated 1,3-enynes. Various nitrogen nucleophiles could be added to conjugated enynes to generate bromoallenyl substituted nitrogen heterocycles. These processes led to simultaneous formation of a highly functionalized axially chiral allene and a stereogenic center under mild conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.039
• 作为产物：
  描述：

  (E)-2-penten-4-yn-1-ol 、 对甲基苯磺酰异氰酸酯 以 二氯甲烷 为溶剂， 以86%的产率得到[(E)-pent-2-en-4-ynyl] N-(4-methylphenyl)sulfonylcarbamate
  参考文献：
  名称：

  Intramolecular 1,4-addition of nitrogen nucleophile and bromine electrophile to conjugated 1,3-enyne

  摘要：

  We have discovered a series of N-bromosuccinimide-promoted 1,4-bromocyclization reactions for conjugated 1,3-enynes. Various nitrogen nucleophiles could be added to conjugated enynes to generate bromoallenyl substituted nitrogen heterocycles. These processes led to simultaneous formation of a highly functionalized axially chiral allene and a stereogenic center under mild conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.039

文献信息

• Intramolecular 1,4-addition of nitrogen nucleophile and bromine electrophile to conjugated 1,3-enyne
  作者：Na Liu、Jenny B. Werness、Ilia A. Guzei、Weiping Tang

  DOI：10.1016/j.tet.2011.02.039

  日期：2011.6

  We have discovered a series of N-bromosuccinimide-promoted 1,4-bromocyclization reactions for conjugated 1,3-enynes. Various nitrogen nucleophiles could be added to conjugated enynes to generate bromoallenyl substituted nitrogen heterocycles. These processes led to simultaneous formation of a highly functionalized axially chiral allene and a stereogenic center under mild conditions. (C) 2011 Elsevier Ltd. All rights reserved.