2-(Benzotriazol-1-yl)-2-phenoxy-1-phenylethanone | 189343-53-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(Benzotriazol-1-yl)-2-phenoxy-1-phenylethanone
• CAS: 189343-53-1
• 化学式: C₂₀H₁₅N₃O₂
• 分子量: 329.358
• InChiKey: JEVCAMGICHQDNN-UHFFFAOYSA-N

物化性质

• 沸点：
  561.4±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(Benzotriazol-1-yl)-2-phenoxy-1-phenylethanone 以 乙醚 、 苯 为溶剂， 反应 60.5h， 生成 1-苯基-1-丙炔 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  A Novel Transformation of Esters to Alkynes with 1-Substituted Benzotriazoles

  摘要：

  Reactions of lithio benzotriazol-1-yl derivatives 2, 11, and 25 with aromatic and aliphatic esters 3, 12, and 26 gave alpha-(benzotriazol-1-yl) ketones 4, 13, and 27, respectively, in high yields. Alternatively, alpha-(benzotriazol-1-yl) ketones 22 can be accessed by the reaction of alpha-(benzotriazol-1-yl) esters 20 with Grignard reagents. Condensation of 4, 13, 22, and 27 with (p-toluenesulfonyl)hydrazine provided p-tosylhydrazones 5, 14, 21, and 28. Treatment of hydrazones 5, 21, and 28 with n-butyllithium in diethyl ether resulted in the elimination of the tosyl group, dinitrogen, and benzotriazolyl group to afford the corresponding acetylenes 9, 23, and 29 in good yields. When alpha-(benzotriazol-1-yl) 1-alpha-phenoxy hydrazones 14 were treated with methyllithium, n-butyllithium, or phenyllithium, alkynes 18 were obtained, in which phenoxy groups were replaced by the lithium reagents.

  DOI：

  10.1021/jo962291t
• 作为产物：
  描述：

  苯甲酸甲酯 、 1-(苯氧基甲基)-1H-苯并噻唑 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.0h， 以95%的产率得到2-(Benzotriazol-1-yl)-2-phenoxy-1-phenylethanone
  参考文献：
  名称：

  A Novel Transformation of Esters to Alkynes with 1-Substituted Benzotriazoles

  摘要：

  Reactions of lithio benzotriazol-1-yl derivatives 2, 11, and 25 with aromatic and aliphatic esters 3, 12, and 26 gave alpha-(benzotriazol-1-yl) ketones 4, 13, and 27, respectively, in high yields. Alternatively, alpha-(benzotriazol-1-yl) ketones 22 can be accessed by the reaction of alpha-(benzotriazol-1-yl) esters 20 with Grignard reagents. Condensation of 4, 13, 22, and 27 with (p-toluenesulfonyl)hydrazine provided p-tosylhydrazones 5, 14, 21, and 28. Treatment of hydrazones 5, 21, and 28 with n-butyllithium in diethyl ether resulted in the elimination of the tosyl group, dinitrogen, and benzotriazolyl group to afford the corresponding acetylenes 9, 23, and 29 in good yields. When alpha-(benzotriazol-1-yl) 1-alpha-phenoxy hydrazones 14 were treated with methyllithium, n-butyllithium, or phenyllithium, alkynes 18 were obtained, in which phenoxy groups were replaced by the lithium reagents.

  DOI：

  10.1021/jo962291t

文献信息

• A Novel Transformation of Esters to Alkynes with 1-Substituted Benzotriazoles
  作者：Alan R. Katritzky、Jin Wang、Nazira Karodia、Jianqing Li

  DOI：10.1021/jo962291t

  日期：1997.6.13

  Reactions of lithio benzotriazol-1-yl derivatives 2, 11, and 25 with aromatic and aliphatic esters 3, 12, and 26 gave alpha-(benzotriazol-1-yl) ketones 4, 13, and 27, respectively, in high yields. Alternatively, alpha-(benzotriazol-1-yl) ketones 22 can be accessed by the reaction of alpha-(benzotriazol-1-yl) esters 20 with Grignard reagents. Condensation of 4, 13, 22, and 27 with (p-toluenesulfonyl)hydrazine provided p-tosylhydrazones 5, 14, 21, and 28. Treatment of hydrazones 5, 21, and 28 with n-butyllithium in diethyl ether resulted in the elimination of the tosyl group, dinitrogen, and benzotriazolyl group to afford the corresponding acetylenes 9, 23, and 29 in good yields. When alpha-(benzotriazol-1-yl) 1-alpha-phenoxy hydrazones 14 were treated with methyllithium, n-butyllithium, or phenyllithium, alkynes 18 were obtained, in which phenoxy groups were replaced by the lithium reagents.