(E)-2-Ethoxypenta-2,4-dienoic acid

• 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: (E)-2-Ethoxypenta-2,4-dienoic acid
• 英文别名: (2E)-2-ethoxypenta-2,4-dienoic acid
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: BLRFVNGJODXOPK-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  反式-2-丁烯醛二乙基缩醛 、 二氧化碳 在 potassium tert-butylate 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 以48%的产率得到(E)-2-Ethoxypenta-2,4-dienoic acid
  参考文献：
  名称：

  .alpha.,.beta.-Unsaturated Acetals as Precursors of .alpha.-Substituted Ethoxy Dienes. Useful Reagents for Nucleophilic Acylation

  摘要：

  The reaction of (E)-1,1-diethoxybut-2-ene (1a) and 1,1-diethoxy-3-methylbut-2-ene (1b) with 2 equiv of sec-butyllithium complexed with potassium tert-butoxide (Schlosser's base) in THF at -95 degrees C gives 1-metalated 1-ethoxy 1,3-dienes that are synthetically equivalent to acyl anions. Subsequent reaction with suitable electrophiles, such as alkyl halides, aldehydes, ketones, carbon dioxide, and carboxylic acid derivatives, affords (E)-1-substituted 1-ethoxy 1,3-dienes 2a-i. Experimental procedures are given for the reaction of the carbanionic intermediates with the electrophiles. Some typical examples for the conversion of the produced alpha-substituted alkoxy dienes into the corresponding alpha,beta-unsaturated carbonyl compounds are also reported. In particular, in the case in which crotonaldehyde is used as an electrophile, the addition product 2c undergoes acid-catalyzed conversion to compounds 4c, 5c, and 6c as a function of the experimental conditions.

  DOI：

  10.1021/jo00097a059

文献信息

• .alpha.,.beta.-Unsaturated Acetals as Precursors of .alpha.-Substituted Ethoxy Dienes. Useful Reagents for Nucleophilic Acylation
  作者：Cristina Prandi、Paolo Venturello

  DOI：10.1021/jo00097a059

  日期：1994.9

  The reaction of (E)-1,1-diethoxybut-2-ene (1a) and 1,1-diethoxy-3-methylbut-2-ene (1b) with 2 equiv of sec-butyllithium complexed with potassium tert-butoxide (Schlosser's base) in THF at -95 degrees C gives 1-metalated 1-ethoxy 1,3-dienes that are synthetically equivalent to acyl anions. Subsequent reaction with suitable electrophiles, such as alkyl halides, aldehydes, ketones, carbon dioxide, and carboxylic acid derivatives, affords (E)-1-substituted 1-ethoxy 1,3-dienes 2a-i. Experimental procedures are given for the reaction of the carbanionic intermediates with the electrophiles. Some typical examples for the conversion of the produced alpha-substituted alkoxy dienes into the corresponding alpha,beta-unsaturated carbonyl compounds are also reported. In particular, in the case in which crotonaldehyde is used as an electrophile, the addition product 2c undergoes acid-catalyzed conversion to compounds 4c, 5c, and 6c as a function of the experimental conditions.