4-ethoxy-2,2-dimethylhepta-4,6-dien-3-ol | 157642-70-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-ethoxy-2,2-dimethylhepta-4,6-dien-3-ol
• 英文别名: (4E)-4-ethoxy-2,2-dimethylhepta-4,6-dien-3-ol
• CAS: 157642-70-1
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: PPKMZLGMZQPONK-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  4-ethoxy-2,2-dimethylhepta-4,6-dien-3-ol 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以85%的产率得到(E)-2,2-Dimethyl-3-hydroxyhept-5-en-4-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
• 作为产物：
  描述：

  反式-2-丁烯醛二乙基缩醛 、 特戊醛 在 potassium tert-butylate 、 重水 、 仲丁基锂 作用下， 生成 4-ethoxy-2,2-dimethylhepta-4,6-dien-3-ol
  参考文献：
  名称：

  Canepa, Carlo; Prandi, Cristina; Sacchi, Luca, Journal of the Chemical Society. Perkin transactions I, 1993, # 16, p. 1875 - 1878

  摘要：

  DOI：

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。