6-oxo-6-phenyl-(2Z,4E)-2,4-hexadienoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 6-oxo-6-phenyl-(2Z,4E)-2,4-hexadienoic acid
• 英文别名: (2Z,4E)-6-oxo-6-phenylhexa-2,4-dienoic acid
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: ZXJCDKFZBKBKNP-HXGSSHHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲硅氧基-2-呋喃 、 2-二氮杂-1-苯乙酮 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到6-oxo-6-phenyl-(2Z,4E)-2,4-hexadienoic acid
  参考文献：
  名称：

  Metal carbenoid mediated ring opening of furan-2-yloxy derivatives. Stereoselective synthesis of 2,4-hexadienedioic acid and 6-aryl-1-oxo-2,4-hexadienoic acid derivatives

  摘要：

  2-Methoxy- and 2-trimethylsilyloxyfuran undergo facile ring opening reaction upon treatment with metal carbenoid. Treatment of 2-methoxyfuran with ethyl diazoacetate and aryl-alpha -diazocarbonyl compounds under metal catalysis afforded (2Z,4E)-hexadienedioate and 6-aryl-6-oxo-(2Z,4E)-hexadienoates respectively. When 2-trimethylsilyloxyfuran was used, desilylation occurred to give directly the monoprotected (Z,E)-muconic acid and 6-aryl-6-oxo-(2Z,4E)-hexadienoic acids. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00691-3

文献信息

• Metal carbenoid mediated ring opening of furan-2-yloxy derivatives. Stereoselective synthesis of 2,4-hexadienedioic acid and 6-aryl-1-oxo-2,4-hexadienoic acid derivatives
  作者：Po Chuen Shieh、Chi Wi Ong

  DOI：10.1016/s0040-4020(01)00691-3

  日期：2001.8

  2-Methoxy- and 2-trimethylsilyloxyfuran undergo facile ring opening reaction upon treatment with metal carbenoid. Treatment of 2-methoxyfuran with ethyl diazoacetate and aryl-alpha -diazocarbonyl compounds under metal catalysis afforded (2Z,4E)-hexadienedioate and 6-aryl-6-oxo-(2Z,4E)-hexadienoates respectively. When 2-trimethylsilyloxyfuran was used, desilylation occurred to give directly the monoprotected (Z,E)-muconic acid and 6-aryl-6-oxo-(2Z,4E)-hexadienoic acids. (C) 2001 Elsevier Science Ltd. All rights reserved.