(3E,6E)-4,6-Diethoxynona-1,3,6,8-tetraen-5-ol | 157642-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3E,6E)-4,6-Diethoxynona-1,3,6,8-tetraen-5-ol
• CAS: 157642-78-9
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: YKLCBIORFOTSNY-WGDLNXRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3E,6E)-4,6-Diethoxynona-1,3,6,8-tetraen-5-ol 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以78%的产率得到(2E,6E)-6-Ethoxy-5-hydroxynona-2,6,8-trien-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 在 lithium aluminium tetrahydride 、 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (3E,6E)-4,6-Diethoxynona-1,3,6,8-tetraen-5-ol
  参考文献：
  名称：

  Intramolecular Reactivity of a Captodative Bis-Diene

  摘要：

  [GRAPHICS]A 1,1-captodative bis-diene (3) has been prepared from crotonaldehyde diethyl acetal through an elimination-metalation sequence. This compound has been reacted with electron-rich and electron-deficient dienophiles. Under both thermal and high-pressure conditions, no intermolecular reaction was observed, the fused (4) and bridged (5) intramolecular bicyclic adducts being recovered. The reduction of the central carbonyl group has led to the corresponding allylic alcohol which, in thermal cycloaddition conditions, also provides an intramolecular adduct that aromatizes in the medium.

  DOI：

  10.1021/ol991000a

文献信息

• 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.
• Intramolecular Reactivity of a Captodative Bis-Diene
  作者：Silvia Aime、Hassan Oulyadi、Jacques Maddaluno、Paolo Venturello

  DOI：10.1021/ol991000a

  日期：1999.11.1

  [GRAPHICS]A 1,1-captodative bis-diene (3) has been prepared from crotonaldehyde diethyl acetal through an elimination-metalation sequence. This compound has been reacted with electron-rich and electron-deficient dienophiles. Under both thermal and high-pressure conditions, no intermolecular reaction was observed, the fused (4) and bridged (5) intramolecular bicyclic adducts being recovered. The reduction of the central carbonyl group has led to the corresponding allylic alcohol which, in thermal cycloaddition conditions, also provides an intramolecular adduct that aromatizes in the medium.