1-(1-Ethoxy-4,4-diphenylbuta-1,3-dienyl)benzotriazole | 190603-18-0

• 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: 1-(1-Ethoxy-4,4-diphenylbuta-1,3-dienyl)benzotriazole
• CAS: 190603-18-0
• 化学式: C₂₄H₂₁N₃O
• 分子量: 367.45
• InChiKey: CWWBSMRCKVKWKU-UHFFFAOYSA-N

物化性质

• 沸点：
  560.2±60.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-Ethoxy-4,4-diphenylbuta-1,3-dienyl)benzotriazole 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以79%的产率得到5,5-dipropyldihydrofuran-2-one
  参考文献：
  名称：

  Stereoselective Syntheses of β,γ-Unsaturated Esters and γ-Lactones:  1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene, a Protected CCH₂CO₂Et Synthon Equivalent

  摘要：

  1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene (3), prepared from N-(alpha-ethoxy-allyl)benzotriazole (1), underwent selective Horner reactions with aldehydes to give substituted dienes. Subsequent hydrolysis of these intermediates readily produced beta,gamma-unsaturated esters 2a-c in good yields. Similar reactions with ketones followed by hydrolysis of 10 produced, depending on the conditions, either the corresponding gamma,gamma-disubstituted beta,gamma-unsaturated esters 11a-d or gamma-lactones 9a-c and 13. A double lithiation process provided beta,gamma,gamma-trisubstituted beta,gamma-unsaturated esters 15, 18, and beta,gamma,gamma-trisubstituted gamma-lactone 14.

  DOI：

  10.1021/jo9701647
• 作为产物：
  描述：

  丙烯醛缩二乙醇 在 正丁基锂 、 双氧水 作用下， 以 正己烷 为溶剂， 反应 23.17h， 生成 1-(1-Ethoxy-4,4-diphenylbuta-1,3-dienyl)benzotriazole
  参考文献：
  名称：

  Stereoselective Syntheses of β,γ-Unsaturated Esters and γ-Lactones:  1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene, a Protected CCH₂CO₂Et Synthon Equivalent

  摘要：

  1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene (3), prepared from N-(alpha-ethoxy-allyl)benzotriazole (1), underwent selective Horner reactions with aldehydes to give substituted dienes. Subsequent hydrolysis of these intermediates readily produced beta,gamma-unsaturated esters 2a-c in good yields. Similar reactions with ketones followed by hydrolysis of 10 produced, depending on the conditions, either the corresponding gamma,gamma-disubstituted beta,gamma-unsaturated esters 11a-d or gamma-lactones 9a-c and 13. A double lithiation process provided beta,gamma,gamma-trisubstituted beta,gamma-unsaturated esters 15, 18, and beta,gamma,gamma-trisubstituted gamma-lactone 14.

  DOI：

  10.1021/jo9701647

文献信息

• Stereoselective Syntheses of β,γ-Unsaturated Esters and γ-Lactones:  1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene, a Protected CCH₂CO₂Et Synthon Equivalent
  作者：Alan R. Katritzky、Daming Feng、Hengyuan Lang

  DOI：10.1021/jo9701647

  日期：1997.6.13

  1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene (3), prepared from N-(alpha-ethoxy-allyl)benzotriazole (1), underwent selective Horner reactions with aldehydes to give substituted dienes. Subsequent hydrolysis of these intermediates readily produced beta,gamma-unsaturated esters 2a-c in good yields. Similar reactions with ketones followed by hydrolysis of 10 produced, depending on the conditions, either the corresponding gamma,gamma-disubstituted beta,gamma-unsaturated esters 11a-d or gamma-lactones 9a-c and 13. A double lithiation process provided beta,gamma,gamma-trisubstituted beta,gamma-unsaturated esters 15, 18, and beta,gamma,gamma-trisubstituted gamma-lactone 14.