4-acetoxy-2-phenylpent-2-ene | 99942-95-7

• 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: 4-acetoxy-2-phenylpent-2-ene
• CAS: 99942-95-7
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: LRUHEFIUDVBQBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-acetoxy-2-phenylpent-2-ene 在 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 3-methyl-3-phenylhex-4-enoic acid
  参考文献：
  名称：

  Ireland-Claisen rearrangement of secondary allyl acetate revisited: inevitable C-silylation circumvented by one-pot application of excessive LDA/TMSCl and TBAF

  摘要：

  Yield lowering C-silylation was found to be inevitable in all the six tested examples of stoichiometric LDA/TMSCl promoted Ireland-Claisen rearrangement of secondary allyl acetates. In order to circumvent this problem, a higher yielding protocol was devised after the isolated by-products were found to be excellent substrates for further rearrangement. Thus, excessive LDA/TMSCl was applied to achieve complete 3,3'-sigmatropic shift of the substrates, and the resulting mixtures of normal and alpha-silylated gamma,delta-unsaturated carboxylic acids was then desilylated by one-pot application of TBAF. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.071
• 作为产物：
  描述：

  (E/Z)-2-phenylpent-2-ene 、 溶剂黄146 在 cobalt(III) acetate 作用下， 反应 14.0h， 以32%的产率得到3-acetoxy-2-phenylpentan-2-ol
  参考文献：
  名称：

  Morimoto, Takashi; Hirano, Masao; Koyama, Tsuyoshi, Journal of the Chemical Society. Perkin transactions II, 1985, p. 1109 - 1116

  摘要：

  DOI：

文献信息

• Morimoto, Takashi; Hirano, Masao; Koyama, Tsuyoshi, Journal of the Chemical Society. Perkin transactions II, 1985, p. 1109 - 1116
  作者：Morimoto, Takashi、Hirano, Masao、Koyama, Tsuyoshi

  DOI：——

  日期：——
• Ireland-Claisen rearrangement of secondary allyl acetate revisited: inevitable C-silylation circumvented by one-pot application of excessive LDA/TMSCl and TBAF
  作者：Di Liu、Xiaoming Yu

  DOI：10.1016/j.tetlet.2012.02.071

  日期：2012.4

  Yield lowering C-silylation was found to be inevitable in all the six tested examples of stoichiometric LDA/TMSCl promoted Ireland-Claisen rearrangement of secondary allyl acetates. In order to circumvent this problem, a higher yielding protocol was devised after the isolated by-products were found to be excellent substrates for further rearrangement. Thus, excessive LDA/TMSCl was applied to achieve complete 3,3'-sigmatropic shift of the substrates, and the resulting mixtures of normal and alpha-silylated gamma,delta-unsaturated carboxylic acids was then desilylated by one-pot application of TBAF. (c) 2012 Elsevier Ltd. All rights reserved.