(E)-2-Ethoxy-1-phenylpenta-2,4-dien-1-one

• 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: (E)-2-Ethoxy-1-phenylpenta-2,4-dien-1-one
• 英文别名: (2E)-2-Ethoxy-1-phenylpenta-2,4-dien-1-one
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: HAFSUWMAUBQQNY-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  5
• 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

• 作为反应物：
  描述：

  (E)-2-Ethoxy-1-phenylpenta-2,4-dien-1-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (E)-2-ethoxy-1-phenylpenta-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：

  反式-2-丁烯醛二乙基缩醛 、 苯甲酸乙酯 在 potassium tert-butylate 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 以65%的产率得到(E)-2-Ethoxy-1-phenylpenta-2,4-dien-1-one
  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

• Alkoxydienylstannanes via metalation of α,β-unsaturated and α-phenyl acetals: preparation and synthetic uses in the Stille cross-coupling reaction
  作者：Paolo Balma Tivola、Anna Deagostino、Cristina Prandi、Paolo Venturello

  DOI：10.1039/b007500k

  日期：——

  Treatment of α,β-unsaturated (1 and 2) and α-phenyl (3) acetals with an equimolar mixture of butyllithium and potassium tert-butoxide (Schlosser’s reagent LIC–KOR) gives α-metalated 1,3-dienes and vinyl ethers that readily react with chlorotributyltin affording (Z)-functionalized alkoxyvinylstannanes 4–6. Stille cross-coupling reaction between these reactants and allyl bromide, iodobenzene, or benzoyl chloride produces derivatives 7–13 that can be moreover converted into carbonyl compounds 14–19 according to an umpolung approach.

  用丁基锂和叔丁醇钾的等摩尔混合物（Schlosserâs 试剂 LICâKOR）处理δ,δ-不饱和（1 和 2）和δ-苯基（3）乙醛，可得到δ-金属化的 1,3-二烯和乙烯基醚，它们很容易与氯代三丁基锡反应，生成 (Z) 功能化的烷氧基乙烯基锡 4â6。这些反应物与烯丙基溴、碘苯或苯甲酰氯发生斯蒂尔交叉偶联反应，生成衍生物 7â13，根据umpolung 方法，这些衍生物还可以转化为羰基化合物 14â19。
• 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.