(2E,4Z)-3-(2-Phenyl-propionyl)-hexa-2,4-dienedioic acid dimethyl ester | 144053-90-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,4Z)-3-(2-Phenyl-propionyl)-hexa-2,4-dienedioic acid dimethyl ester
• 英文别名: dimethyl (2E,4Z)-3-(2-phenylpropanoyl)hexa-2,4-dienedioate
• CAS: 144053-90-7
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: HVJSGXZQGSMMQU-TVFNDYRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(3,4-Dimethoxyphenyl)-2-phenylpropane 在 Fe^III(TF5PS4P) 、 tartrate buffer 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 水 、 乙腈 为溶剂， 以30%的产率得到(2E,4Z)-3-(2-Phenyl-propionyl)-hexa-2,4-dienedioic acid dimethyl ester
  参考文献：
  名称：

  Selective oxidative cleavage of 1,2-dimethoxyarenes to muconic diesters catalysed by an iron β-sulfonated-tetrakis(pentafluorophenyl)porphyrin

  摘要：

  水溶性铁(III)[TF5PS4P=美索-四(五氟苯基)-β-四磺酸卟啉]催化了通过一氢过氧邻苯二甲酸镁（或H2O2）对带有电子吸引取代基（CN、CHO、COR）的1,2-二甲氧基芳烃的选择性氧化，形成的穆康酸二甲酯产率为30-40%，并且在CH2Cl2提取后，这是获得的唯一反应产物。

  DOI：

  10.1039/c39920001036

文献信息

• Iron porphyrin-catalyzed oxidation of 1,2-dimethoxyarenes: a discussion of the different reactions involved and the competition between the formation of methoxyquinones or muconic dimethyl esters
  作者：Isabelle Artaud、Khaled Ben-Aziza、Daniel Mansuy

  DOI：10.1021/jo00064a026

  日期：1993.6

  This paper describes the oxidation of an alpha,beta-diarylpropane lignin dimer model and other dimethoxyarenes by several iron porphyrin-based biomimetic systems. From l-(3,4-dimethoxyphenyl)-2-phenylpropanol (1), three types of products are identified: the 3,4-dimethoxybenzaldehyde derived from the C(alpha)-C(beta) cleavage of the propyl side chain and either quinones or muconic dimethyl esters resulting from oxidations at the level of the dimethoxyaryl group. The selectivity of the reaction is discussed with respect to the nature and reactivity of the high-valent iron-oxo species formed upon reaction of the oxidants, H2O2 or magnesium monoperoxyphthalate (MMP), with the iron porphyrins. Fe(TF5PP)CI-catalyzed oxidation of 1 by H2O2 in an aprotic medium (CH3CN/CH2Cl2), yields a clean ''lignin peroxidase-like'' reaction with selective formation of the aldehyde. In an aqueous buffered solution, MMP oxidation of para-substituted 1,2-dimethoxyarenes catalyzed by an iron tetrakis(pentafluorophenyl)-beta-tetrasulfonatoporphyrin, Fe(TF5PS4P), clearly depends on the electronic properties of the para-substituent. The reaction is selective for para-quinone formation in the case of an electron-releasing group and for muconic dimethyl ester formation in the case of an electron-withdrawing group.