(E)-pent-2-enyl (toluene-4-sulfonyl)acetate

• 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-enyl (toluene-4-sulfonyl)acetate
• 英文别名: [(E)-pent-2-enyl] 2-(4-methylphenyl)sulfonylacetate
• 化学式: C₁₄H₁₈O₄S
• 分子量: 282.361
• InChiKey: FDQIGJUNPLLMDM-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-pent-2-enyl (toluene-4-sulfonyl)acetate 、 (E)-cinnamyl 4-nitrophenyl carbonate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以56%的产率得到(+/-)-[(E)-cinnamyl]((2E)-pent-2-enyl)-2-(toluene-4-sulfonyl)malonate
  参考文献：
  名称：

  Highly regioselective decarboxylative Claisen rearrangement reactions of diallyl 2-sulfonylmalonates

  摘要：

  The decarboxylative Claisen rearrangement of a range of substituted diallyl 2-sulfonylmalonates is described. The substrates are made by C-carboxylation of the corresponding allyl sulfonylacetates with allyl para-nitrophenyl carbonates. The reactions display a high degree of regioselectivity, with allylic substituents possessing electron-rich substituents at the allyl three-position rearranging preferentially. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.130
• 作为产物：
  描述：

  反-2-戊烯-1-醇 、 对甲苯磺酰乙酸 在 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以91%的产率得到(E)-pent-2-enyl (toluene-4-sulfonyl)acetate
  参考文献：
  名称：

  Highly regioselective decarboxylative Claisen rearrangement reactions of diallyl 2-sulfonylmalonates

  摘要：

  The decarboxylative Claisen rearrangement of a range of substituted diallyl 2-sulfonylmalonates is described. The substrates are made by C-carboxylation of the corresponding allyl sulfonylacetates with allyl para-nitrophenyl carbonates. The reactions display a high degree of regioselectivity, with allylic substituents possessing electron-rich substituents at the allyl three-position rearranging preferentially. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.130

文献信息

• Highly regioselective decarboxylative Claisen rearrangement reactions of diallyl 2-sulfonylmalonates
  作者：Donald Craig、Mark I. Lansdell、Simon E. Lewis

  DOI：10.1016/j.tetlet.2007.08.130

  日期：2007.10

  The decarboxylative Claisen rearrangement of a range of substituted diallyl 2-sulfonylmalonates is described. The substrates are made by C-carboxylation of the corresponding allyl sulfonylacetates with allyl para-nitrophenyl carbonates. The reactions display a high degree of regioselectivity, with allylic substituents possessing electron-rich substituents at the allyl three-position rearranging preferentially. (C) 2007 Elsevier Ltd. All rights reserved.