(2Z,4E)-2-methyl-5-phenylpenta-2,4-dienoic acid | 20430-16-4

• 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: (2Z,4E)-2-methyl-5-phenylpenta-2,4-dienoic acid
• 英文别名: 2-Methyl-5-phenyl-pentadien-(2cis.4trans)-saeure；2-Methyl-5-phenyl-2-cis-4-trans-pentadienoic acid；2-Methyl-5-phenyl-2-cis-4-trans-pentadiensaeure
• CAS: 20430-16-4
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: WHEIBFYABJHSOM-POQLCMLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-2-methyl-5-phenylpenta-2,4-dienoic acid 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (2Z,4E)-methyl 2-methyl-5-phenylpenta-2,4-dienoate
  参考文献：
  名称：

  Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group

  摘要：

  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.

  DOI：

  10.1021/jo200509m
• 作为产物：
  描述：

  ethyl (2Z,4E)-5-phenyl-2-[(trimethylsilyl)methyl]penta-2,4-dienoate 在 氢氧化钾 、 水 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以90%的产率得到(3E,5E)-2-Methyl-5-phenyl-2,4-pentadiensaeure
  参考文献：
  名称：

  碱水溶液中2-[（（三甲基甲硅烷基）甲基]丙烯酸酯衍生物的水解和甲硅烷基化的相关性

  摘要：

  研究了2-[（（三甲基甲硅烷基）甲基]丙烯酸（= 2-[（（三甲硅烷基）甲基]丙-2-烯酸酯）衍生物的水解和脱甲硅基反应，以评估是否存在其他偶联取代基的效果（方案3和4以及表1和2）。在丙烯酸​​酯部分具有非共轭取代基的底物在稀碱条件下是稳定的，并在浓碱条件下提供简单的水解产物。相反，水解和去甲硅烷基化反应都发生在丙烯酸酯骨架上带有共轭取代基的底物上。反应性的差异可以用中间阴离子的稳定性来解释。

  DOI：

  10.1002/hlca.200890093

文献信息

• One step synthesis of γ-alkylidenebutenolides from simple vinyl carboxylic acids and alkenes
  作者：Chunbing Yu、Jian Zhang、Guofu Zhong

  DOI：10.1039/c7cc04973k

  日期：——

  a straightforward and atom-economical protocol for the synthesis of a wide range of valuable γ-alkylidenebutenolides. This method is of particular interest because of employing widely available and low cost vinyl carboxylic acids and electron-deficient alkenes as building blocks. Moreover, the methodology can be applied to a gram scale synthesis with 1 mol% catalyst loading.

  描述了通过铑化学进行的第一个串联交叉偶联/ oxa-Michael加成/脱氢工艺，它为合成各种有价值的γ-亚烷基丁烯内酯提供了直接且原子经济的方案。由于采用广泛可用且低成本的乙烯基羧酸和缺电子烯烃作为构建基块，因此该方法特别受关注。而且，该方法可以应用于具有1mol％催化剂负载的克级合成。
• 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.
• Correlation of Hydrolysis and Desilylation of 2-[(Trimethylsilyl)methyl]acrylate Derivatives in Aqueous Alkali Solutions
  作者：Chiaki Kuroda、Takeshi Sunakawa、Yuichi Muguruma

  DOI：10.1002/hlca.200890093

  日期：2008.5

  Hydrolysis and desilylation reaction of 2-[(trimethylsilyl)methyl]acrylate (=2-[(trimethylsilyl)methyl]prop-2-enoate) derivatives were studied to evaluate the effect of the presence/absence of a further conjugating substituent (Schemes 3 and 4 and Tables 1 and 2). The substrates having a nonconjugating substituent at the acrylate moiety were stable to dilute alkali conditions, and afforded simple hydrolysis

  研究了2-[（（三甲基甲硅烷基）甲基]丙烯酸（= 2-[（（三甲硅烷基）甲基]丙-2-烯酸酯）衍生物的水解和脱甲硅基反应，以评估是否存在其他偶联取代基的效果（方案3和4以及表1和2）。在丙烯酸​​酯部分具有非共轭取代基的底物在稀碱条件下是稳定的，并在浓碱条件下提供简单的水解产物。相反，水解和去甲硅烷基化反应都发生在丙烯酸酯骨架上带有共轭取代基的底物上。反应性的差异可以用中间阴离子的稳定性来解释。