ethyl (E)-3-methyl-4-oxonon-5-enoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl (E)-3-methyl-4-oxonon-5-enoate
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: TXVDPPYQOQADFP-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  反式-2-己烯醛二乙缩醛 以 正己烷 为溶剂， 反应 6.0h， 生成 ethyl (E)-3-methyl-4-oxonon-5-enoate
  参考文献：
  名称：

  Benzotriazole- and 1,2,4-Triazole-Stabilized Allylic Anions:  Applications in Syntheses of Functionalized α,β-Unsaturated Ketones, γ-Lactones, γ-Lactams, and β-Substituted Esters

  摘要：

  Deprotonated 1-(benzotriazol-1-yl)-1-ethoxy-2-hexene (7) reacted with alkyl halides, aldehydes, ketones, imines, and alpha-beta-unsaturated esters to give exclusively the alpha-alkylated products 8a-c, 10a,b, 12, 14, 16, and 18a,b, respectively. Without isolation, these products were hydrolyzed under mild conditions to generate the corresponding simple or functionalized alpha,beta-unsaturated ketones 9a-c, 11a,b, 13, 15, 17, and 19a,b. Similar reactions with the phenyl-substituted analog 3-(benzotriazol-1-yl)-3-ethoxy-1-phenyl-1-propene (21) also gave the analogous alpha-products, but they were accompanied by small amount of the gamma-products in most cases. By contrast, deprotonation of the corresponding triazole derivative 29 with butyllithium followed by reactions with alkyl halides, aldehydes, ketones, or imines yielded exclusively gamma-alkylated adducts 32, 34, 36, 38, 40, and 42. Intermediates 32, 34, 36, 38, 40, and 42 were readily converted into beta-substituted esters 33a-c, gamma-lactones 35a,b, 39, 41, and 43, and gamma-lactams 37a-c on hydrolysis.

  DOI：

  10.1021/jo961396t