1-Phenylpent-1-en-3-yl acetate | 94421-30-4

• 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: 1-Phenylpent-1-en-3-yl acetate
• 英文别名: 1-phenylpent-1-en-3-yl acetate
• CAS: 94421-30-4
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: IZHDTKCQQSJEGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  5
• 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
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Phenylpent-1-en-3-yl acetate 在 三甲基氯硅烷 、 lithium diisopropyl amide 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以86%的产率得到
  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：

  (1-chloro-3-phenylprop-2-enyl) acetate 、 乙基溴化镁 在 (R)-1-[(S_P)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine 、 噻吩-2-甲酸亚铜(I) 作用下， 以 二氯甲烷 为溶剂， 以35%的产率得到1-Phenylpent-1-en-3-yl acetate
  参考文献：
  名称：

  铜催化的手性烯醇乙酸酯和β-取代醛的区域选择性和对映选择性合成

  摘要：

  α,β-不饱和醛原位转化为 α-氯代烯丙基乙酸酯，随后铜催化的区域选择性和对映选择性（高达 94% ee）烯丙基烷基化与格氏试剂一起提供手性烯醇乙酸酯和手性 β-取代醛- 锅协议。

  DOI：

  10.1021/ja105585y

文献信息

• Copper-Catalyzed Regio- and Enantioselective Synthesis of Chiral Enol Acetates and β-Substituted Aldehydes
  作者：Martín Fañanás-Mastral、Ben L. Feringa

  DOI：10.1021/ja105585y

  日期：2010.9.29

  The in situ transformation of α,β-unsaturated aldehydes into α-chloroallylic acetates and subsequent copper-catalyzed regio- and enantioselective (up to 94% ee) allylic alkylation with Grignard reagents provides chiral enol acetates and chiral β-substituted aldehydes in a one-pot protocol.

  α,β-不饱和醛原位转化为 α-氯代烯丙基乙酸酯，随后铜催化的区域选择性和对映选择性（高达 94% ee）烯丙基烷基化与格氏试剂一起提供手性烯醇乙酸酯和手性 β-取代醛- 锅协议。
• 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.