(E,Z)-1-phenyl-2,5-dimethyl-1,4-pentadien-3-one | 217076-67-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E,Z)-1-phenyl-2,5-dimethyl-1,4-pentadien-3-one
• 英文别名: (1E,4Z)-2-methyl-1-phenylhexa-1,4-dien-3-one
• CAS: 217076-67-0
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: OFXFORQZLRYINW-NNLZZCHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E,Z)-1-phenyl-2,5-dimethyl-1,4-pentadien-3-one 在 四氯化钛 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 2,4-dimethyl-3-phenyl-cyclopentanone
  参考文献：
  名称：

  The reductive Nazarov cyclization

  摘要：

  Tri- and tetrasubstituted 1,4-dien-3-ones 1 were treated with Lewis acid in the presence of triethylsilane, furnishing either silyl enol ethers 4 or cyclopentanones 5 in good yields, depending upon work-up conditions. This reaction is presumed to occur through oxyallyl intermediate 3, which undergoes intermolecular hydride transfer and O-silylation to give 4. In most cases, only 2 equiv. of silane was required, and catalytic amounts of Lewis acid could be used. Trienone substrate 7 was found to undergo clean conversion to tricyclic ether 8, indicating fast capture of the oxyallyl intermediate by the pendant olefin. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01934-0
• 作为产物：
  描述：

  α-甲基肉桂醛 在 barium permanganate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (E,Z)-1-phenyl-2,5-dimethyl-1,4-pentadien-3-one
  参考文献：
  名称：

  Ionic Hydrogenation of Oxyallyl Intermediates: The Reductive Nazarov Cyclization

  摘要：

  Cyclization of tri- and tetrasubstituted dienones 1 under Lewis acidic conditions in the presence of triethylsilane led to formation of either silyl enol ethers 6 or cyclopentanones 7 in good to excellent yields, depending on work-up conditions. The proposed mechanism involves initial Nazarov cyclization to give oxyallyl intermediates 5, which are intercepted via intermolecular transfer of hydride. The reactions proceeded cleanly with as little as 2 equiv. of silane and in most cases catalytic amounts of Lewis acid could be used. Trapping with Et3SiD occurs at the less substituted terminus in unsymmetrical cases. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00866-8