(E)-2-ethoxy-1-phenylpenta-2,4-dien-1-ol | 157642-79-0

• 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-ol
• 英文别名: (E)-1-Phenyl-2-ethoxypenta-2,4-dien-1-ol；(2E)-2-ethoxy-1-phenyl-2,4-pentadien-1-ol；(2E)-2-ethoxy-1-phenylpenta-2,4-dien-1-ol
• CAS: 157642-79-0
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: YEYKPXBWGQOHME-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 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-ol 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以81%的产率得到1-Hydroxy-1-phenylpent-3-en-2-one
  参考文献：
  名称：

  1-Substituted 1-ethoxy dienes obtained by reaction of 1,1-diethoxybut-2-ene with electrophiles in the presence of the mixed metal base LICKOR

  摘要：

  The mixture of sec-butyllithium and potassium tert-butoxyde (LICKOR reagent) in THF at -95 degrees C, promotes smooth 1,4-eliminative process in 1,1-diethoxybut-2-ene (1) to afford conjugate (E)-1-ethoxybuta-1-3-diene (2). Moreover, when 2 equivalents of the mixed base are sued for 1 equivalent of the substrate, further metallation of the derivative 2 takes place affording the corresponding alpha-substituted derivatives 4a-e. Intermediates 4b-c and 4e can be converted by aqueous methanolic hydrochloric acid into the corresponding carbonyl compounds 5b-c and 5e. On the other hand, in mild acid (E)-3-tert-butyl-4-ethoxy-2,2-dimethylthepta-4,6-dien-3-ol (4d) cyclizes in a one-pot synthetic sequence to 2,2-di-tert-butyl-3-ethoxy-5-methyl-2,5-dihydrofuran (5d).

  DOI：

  10.1016/s0040-4020(01)89552-1
• 作为产物：
  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

文献信息

• A Short and Efficient New Synthesis of γ-Halo-Substituted α,β-Unsaturated Acetals and Carbonyl Compounds
  作者：Annamaria Deagostino、Paolo Balma Tivola、Cristina Prandi、Paolo Venturello

  DOI：10.1055/s-1999-2933

  日期：1999.11

  Treatment with N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS) of 1-subsituted 1-alkoxy-1,3-dienes, obtained by reaction of α,β-unsaturated acetals with LICKOR superbase, affords γ-brominated (chlorinated) α,β-unsaturated acetals or carbonyl compounds, according to the selected experimental conditions.

  用N-溴代琥珀酰亚胺（NBS）或N-氯代琥珀酰亚胺（NCS）处理由α,β-不饱和醛与LICKOR超级碱反应得到的1-取代1-烷氧基-1,3-二烯，能够根据选定的实验条件获得γ-溴化（氯化）α,β-不饱和醛或羰基化合物。
• Prandi Cristina, Venturello Paolo, J. Org. Chem., 59 (1994) N 18, S 5458-5462
  作者：Prandi Cristina, Venturello Paolo

  DOI：——

  日期：——
• Prandi Cristina, Venturello Paolo, Tetrahedron, 50 (1994) N 43, S 1263-1268
  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.
• 1-Substituted 1-ethoxy dienes obtained by reaction of 1,1-diethoxybut-2-ene with electrophiles in the presence of the mixed metal base LICKOR
  作者：Cristina Prandi、Paolo Venturello

  DOI：10.1016/s0040-4020(01)89552-1

  日期：1994.1

  The mixture of sec-butyllithium and potassium tert-butoxyde (LICKOR reagent) in THF at -95 degrees C, promotes smooth 1,4-eliminative process in 1,1-diethoxybut-2-ene (1) to afford conjugate (E)-1-ethoxybuta-1-3-diene (2). Moreover, when 2 equivalents of the mixed base are sued for 1 equivalent of the substrate, further metallation of the derivative 2 takes place affording the corresponding alpha-substituted derivatives 4a-e. Intermediates 4b-c and 4e can be converted by aqueous methanolic hydrochloric acid into the corresponding carbonyl compounds 5b-c and 5e. On the other hand, in mild acid (E)-3-tert-butyl-4-ethoxy-2,2-dimethylthepta-4,6-dien-3-ol (4d) cyclizes in a one-pot synthetic sequence to 2,2-di-tert-butyl-3-ethoxy-5-methyl-2,5-dihydrofuran (5d).