2-(Benzotriazol-1-yl)-1-(4-methylphenyl)-2-phenoxyethanone | 189343-51-9

• 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)-1-(4-methylphenyl)-2-phenoxyethanone
• CAS: 189343-51-9
• 化学式: C₂₁H₁₇N₃O₂
• 分子量: 343.385
• InChiKey: YZPIXDFRHLGWHI-UHFFFAOYSA-N

物化性质

• 沸点：
  571.4±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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)-1-(4-methylphenyl)-2-phenoxyethanone 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 2-phenoxy-3-(p-tolyl)indole
  参考文献：
  名称：

  Facile Synthesis of Benzotriazines and Indoles by Ring-Scissions of α-Benzotriazol-1-yl Hydrazones

  摘要：

  alpha-(Benzotriazol-1-yl)hydrazones 2a-d and 13a-c were prepared by refluxing the corresponding alpha-(benzotriazol-1-yl)ketones with p-tosyl hydrazide or benzenesulfonyl hydrazide. Treatment of 2a-b with n-butyllithium in the presence of TMEDA gave benzotriazines 6a-b, while lithiation of 13a-c resulted in indole derivatives 16a-c, depending on the structure of the hydrazones.

  DOI：

  10.1080/00397919708005918
• 作为产物：
  描述：

  对甲基苯甲酸甲酯 、 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92%的产率得到2-(Benzotriazol-1-yl)-1-(4-methylphenyl)-2-phenoxyethanone
  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.
• Facile Synthesis of Benzotriazines and Indoles by Ring-Scissions of α-Benzotriazol-1-yl Hydrazones
  作者：Katritzky, Alan R.、Wang, Jin、Karodia, Nazira、Li, Jianqing

  DOI：10.1080/00397919708005918

  日期：1997.11

  alpha-(Benzotriazol-1-yl)hydrazones 2a-d and 13a-c were prepared by refluxing the corresponding alpha-(benzotriazol-1-yl)ketones with p-tosyl hydrazide or benzenesulfonyl hydrazide. Treatment of 2a-b with n-butyllithium in the presence of TMEDA gave benzotriazines 6a-b, while lithiation of 13a-c resulted in indole derivatives 16a-c, depending on the structure of the hydrazones.