Ethyl 4-(benzotriazol-1-yl)-4-ethoxy-3-methyl-5-hexenoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: Ethyl 4-(benzotriazol-1-yl)-4-ethoxy-3-methyl-5-hexenoate
• 英文别名: Ethyl 4-(benzotriazol-1-yl)-4-ethoxy-3-methylhex-5-enoate
• 化学式: C₁₇H₂₃N₃O₃
• 分子量: 317.388
• InChiKey: CADXSCJLPUIZNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙烯醛缩二乙醇 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 6.08h， 生成 Ethyl 4-(benzotriazol-1-yl)-4-ethoxy-3-methyl-5-hexenoate
  参考文献：
  名称：

  N-(.alpha.-Ethoxyallyl)benzotriazole: A Novel Propenoyl Anion Synthon Route to Vinyl Ketones

  摘要：

  Lithiation with butyllithium of N-(alpha-ethoxyallyl)benzotriazole (2) (readily prepared in quantitative yield on a large scale from benzotriazole and acrolein diethyl acetal (9)) followed by reaction of lithio derivative 14 with halides, alpha,beta-unsaturated esters, alpha,beta-unsaturated ketones, and aldehydes gave exclusively alpha-alkylation adducts. These adducts are hydrolyzed under extremely mild conditions, enabling convenient syntheses of vinyl ketones 16 and functionalized vinyl ketones 21, 22, 24, and 27.

  DOI：

  10.1021/jo00128a035

文献信息

• N-(.alpha.-Ethoxyallyl)benzotriazole: A Novel Propenoyl Anion Synthon Route to Vinyl Ketones
  作者：Alan R. Katritzky、Guifen Zhang、Jinlong Jiang

  DOI：10.1021/jo00128a035

  日期：1995.11

  Lithiation with butyllithium of N-(alpha-ethoxyallyl)benzotriazole (2) (readily prepared in quantitative yield on a large scale from benzotriazole and acrolein diethyl acetal (9)) followed by reaction of lithio derivative 14 with halides, alpha,beta-unsaturated esters, alpha,beta-unsaturated ketones, and aldehydes gave exclusively alpha-alkylation adducts. These adducts are hydrolyzed under extremely mild conditions, enabling convenient syntheses of vinyl ketones 16 and functionalized vinyl ketones 21, 22, 24, and 27.