Methyl (E)-2-ethoxypenta-2,4-dienoate | 157642-72-3

• 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: Methyl (E)-2-ethoxypenta-2,4-dienoate
• 英文别名: methyl (2E)-2-ethoxypenta-2,4-dienoate
• CAS: 157642-72-3
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: FZSAJTKDMICVRX-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl (E)-2-ethoxypenta-2,4-dienoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (E)-2-Ethoxypenta-2,4-dien-1-ol
  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
• 作为产物：
  描述：

  碳酸二甲酯 以70%的产率得到
  参考文献：
  名称：

  Prandi Cristina, Venturello Paolo, J. Org. Chem., 59 (1994) N 18, S 5458-5462

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Heck Reaction on 1-Alkoxy-1,3-dienes:  A Regioselective γ-Arylation of α,β-Unsaturated Carbonyl Compounds
  作者：Annamaria Deagostino、Cristina Prandi、Paolo Venturello

  DOI：10.1021/ol035258j

  日期：2003.10.1

  [reaction: see text] alpha,beta-Unsaturated acetals afford, in the presence of the LIC-KOR superbase, 1-alkoxybuta-1,3-dienes. These substrates cross couple with aryl derivatives in the presence of Pd catalyst (Heck conditions) in a regio- and stereoselective mode. With dialkyl acetals, the reaction affords arylated dienes; on the other hand, in the case of 1,3-dioxane derivatives, the final outcome

  [反应：见正文]在LIC-KOR超碱存在下，α，β-不饱和乙缩醛可提供1-烷氧基丁1,3-二烯。这些底物在Pd催化剂存在下（Heck条件）以区域选择性和立体选择性方式与芳基衍生物交叉偶联。用二烷基乙缩醛，反应得到芳基化的二烯; 另一方面，在1，3-二恶烷衍生物的情况下，该方法的最终结果形式上对应于起始的α，β-不饱和物质的直接γ-芳基化反应。
• Prandi Cristina, Venturello Paolo, J. Org. Chem., 59 (1994) N 18, S 5458-5462
  作者：Prandi Cristina, Venturello Paolo

  DOI：——

  日期：——
• .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.