prop-2-enyl N-[[(1E)-3-methylbuta-1,3-dienyl]-methylsulfonylamino]-N-prop-2-enoxycarbonylcarbamate | 858940-39-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: prop-2-enyl N-[[(1E)-3-methylbuta-1,3-dienyl]-methylsulfonylamino]-N-prop-2-enoxycarbonylcarbamate
• CAS: 858940-39-3
• 化学式: C₁₄H₂₀N₂O₆S
• 分子量: 344.389
• InChiKey: RESOUIYRWMTRIA-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  prop-2-enyl N-[[(1E)-3-methylbuta-1,3-dienyl]-methylsulfonylamino]-N-prop-2-enoxycarbonylcarbamate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 4 A molecular sieve 、 对甲苯磺酸 、 二乙胺 、 1,2-双(二苯基膦)乙烷 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.5h， 生成 C₁₂H₂₂N₂O₄S
  参考文献：
  名称：

  Design, Synthesis, and Reactivity of 1-Hydrazinodienes for Use in Organic Synthesis

  摘要：

  A new 1-hydrazinodiene (1) has been developed and utilized in Lewis acid catalyzed, intermolecular Diels-Alder reactions with various electron-deficient alkenes. The hydrazine can then be deprotected, and a molecule of methanesulfinic acid is eliminated to provide a putative diazene intermediate (4), which then spontaneously undergoes a suprafacial 1,5-sigmatropic shift to yield stereochemically complex cyclohexenes. This method has been applied to the synthesis of a constitutionally and stereochemically complex decalin derivative.

  DOI：

  10.1021/ja052383c
• 作为产物：
  描述：

  在 吡啶 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 prop-2-enyl N-[[(1E)-3-methylbuta-1,3-dienyl]-methylsulfonylamino]-N-prop-2-enoxycarbonylcarbamate
  参考文献：
  名称：

  Design, Synthesis, and Reactivity of 1-Hydrazinodienes for Use in Organic Synthesis

  摘要：

  A new 1-hydrazinodiene (1) has been developed and utilized in Lewis acid catalyzed, intermolecular Diels-Alder reactions with various electron-deficient alkenes. The hydrazine can then be deprotected, and a molecule of methanesulfinic acid is eliminated to provide a putative diazene intermediate (4), which then spontaneously undergoes a suprafacial 1,5-sigmatropic shift to yield stereochemically complex cyclohexenes. This method has been applied to the synthesis of a constitutionally and stereochemically complex decalin derivative.

  DOI：

  10.1021/ja052383c

文献信息

• Design, Synthesis, and Reactivity of 1-Hydrazinodienes for Use in Organic Synthesis
  作者：Glenn M. Sammis、Eric M. Flamme、Hao Xie、Douglas M. Ho、Erik J. Sorensen

  DOI：10.1021/ja052383c

  日期：2005.6.1

  A new 1-hydrazinodiene (1) has been developed and utilized in Lewis acid catalyzed, intermolecular Diels-Alder reactions with various electron-deficient alkenes. The hydrazine can then be deprotected, and a molecule of methanesulfinic acid is eliminated to provide a putative diazene intermediate (4), which then spontaneously undergoes a suprafacial 1,5-sigmatropic shift to yield stereochemically complex cyclohexenes. This method has been applied to the synthesis of a constitutionally and stereochemically complex decalin derivative.