(2Z,4E)-methyl 2-methyl-5-phenylpenta-2,4-dienoate | 20430-17-5

• 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: (2Z,4E)-methyl 2-methyl-5-phenylpenta-2,4-dienoate
• 英文别名: methyl (2Z,4E)-2-methyl-5-phenylpenta-2,4-dienoate
• CAS: 20430-17-5
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: DXEMFHFZAKHOKR-QZTBCQRESA-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：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl (E)-3-acetoxy-2-methylene-5-phenylpent-4-enoate 在 palladium diacetate 、 甲酸 、 三乙胺 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以61%的产率得到(2Z,4E)-methyl 2-methyl-5-phenylpenta-2,4-dienoate
  参考文献：
  名称：

  Palladium catalysed regio and stereoselective reduction of Baylis-Hillman coupling products derived allylic acetates

  摘要：

  Acetates derived front a variety of the Baylis-Hillman products undergo reduction with HCOOH in the presence of Et3N. Pd(OAc)(2), and dppe (or tri-isopropylphosphite) to yield the corresponding trisubstituted Z-olefins in good yields displaying high regio and stereoselectivity. (C) 1998 Published by Elsevier Science Ltd. All lights reserved.

  DOI：

  10.1016/s0040-4039(98)01049-1

文献信息

• Synthese stereoselective d'esters α,β- ethyleniques α-methyles Z ou E par la reaction de wittig-horner a partir de phosphonates ou d'oxydes de phosphine
  作者：Guita Etemad-Moghadam、Jacqueline Seyden-Penne

  DOI：10.1016/s0040-4020(01)91264-5

  日期：1984.1
• Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group
  作者：Satoshi Mochida、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo200509m

  日期：2011.5.6

  The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. alpha,beta-Unsaturated carboxylic acids such as methacrylic acid also undergo the olefination at the beta-position. Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-carboxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarene derivatives.