2-(Benzotriazol-1-ylmethyl)-4-phenylthiazole | 168697-95-8

• 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: 2-(Benzotriazol-1-ylmethyl)-4-phenylthiazole
• 英文别名: 1-[(4-phenyl-thiazol-2-yl)-methyl]-1H-benzotriazole；2-(benzotriazol-1-ylmethyl)-4-phenyl-1,3-thiazole
• CAS: 168697-95-8
• 化学式: C₁₆H₁₂N₄S
• 分子量: 292.364
• InChiKey: HJLSULXKUXUWJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(Benzotriazol-1-ylmethyl)-4-phenylthiazole 在 正丁基锂 作用下， 以 四氢呋喃 、 环己烷 、 甲苯 为溶剂， 反应 28.0h， 生成 1,2-Diphenyl-2-(4-phenylthiazol-2-yl)propane
  参考文献：
  名称：

  1-(Cyanomethyl)benzotriazole as a Convenient Precursor for the Synthesis of 2-Substituted Thiazoles

  摘要：

  Treatment of 1-(cyanomethyl)benzotriazole with hydrogen peroxide followed by a Lawesson reagent afforded by a Lawesson reagent afforded (benzotriazol-1-yl)thioacetamide which condensed with alpha-halo carbonyl compounds (Hantzsch thiazole synthesis) to give the corresponding 2-(benzotriazol-1-ylmethyl)thiazoles. Lithiation of 2-(benzotriazol-1-ylmethyl)-4-phenylthiazole with butyllithium occurred exclusively at the methylene group, and subsequent quenching of the resulting anion with alkyl halides produced the corresponding alkylated products in good yields. Treatment of these intermediates with Grignard reagents in toluene or with electron-rich heterocycles in the presence of zinc bromide resulted in the displacement of benzotriazole to afford the corresponding thiazoles with elaborated 2-substituents.

  DOI：

  10.1021/jo00122a053
• 作为产物：
  描述：

  1H-苯并三唑-1-乙腈 在 劳森试剂 、 双氧水 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 为溶剂， 反应 7.5h， 生成 2-(Benzotriazol-1-ylmethyl)-4-phenylthiazole
  参考文献：
  名称：

  1-(Cyanomethyl)benzotriazole as a Convenient Precursor for the Synthesis of 2-Substituted Thiazoles

  摘要：

  Treatment of 1-(cyanomethyl)benzotriazole with hydrogen peroxide followed by a Lawesson reagent afforded by a Lawesson reagent afforded (benzotriazol-1-yl)thioacetamide which condensed with alpha-halo carbonyl compounds (Hantzsch thiazole synthesis) to give the corresponding 2-(benzotriazol-1-ylmethyl)thiazoles. Lithiation of 2-(benzotriazol-1-ylmethyl)-4-phenylthiazole with butyllithium occurred exclusively at the methylene group, and subsequent quenching of the resulting anion with alkyl halides produced the corresponding alkylated products in good yields. Treatment of these intermediates with Grignard reagents in toluene or with electron-rich heterocycles in the presence of zinc bromide resulted in the displacement of benzotriazole to afford the corresponding thiazoles with elaborated 2-substituents.

  DOI：

  10.1021/jo00122a053

文献信息

• Structure based design of a series of potent and selective non peptidic PTP-1B inhibitors
  作者：Cheuk K. Lau、Christopher I. Bayly、Jacques Yves Gauthier、Chun Sing Li、Michel Therien、Ernest Asante-Appiah、Wanda Cromlish、Yves Boie、Farnaz Forghani、Sylvie Desmarais、Qingping Wang、Kathryn Skorey、Deena Waddleton、Paul Payette、Chidambaram Ramachandran、Brian P. Kennedy、Giovana Scapin

  DOI：10.1016/j.bmcl.2003.11.076

  日期：2004.2

  A series of benzotriazole phenyldifluoromethylphosphonic acids were found to be potent PTP-1B inhibitors. Molecular modeling on the X-ray crystal structure of the lead structure led to the design of potent PTP-1B inhibitors that show moderate selectivity against TC-PTP, a very closely related protein tyrosine phosphatase. (C) 2004 Elsevier Ltd. All rights reserved.
• 1-(Cyanomethyl)benzotriazole as a Convenient Precursor for the Synthesis of 2-Substituted Thiazoles
  作者：Alan R. Katritzky、Jie Chen、Zhijun Yang

  DOI：10.1021/jo00122a053

  日期：1995.9

  Treatment of 1-(cyanomethyl)benzotriazole with hydrogen peroxide followed by a Lawesson reagent afforded by a Lawesson reagent afforded (benzotriazol-1-yl)thioacetamide which condensed with alpha-halo carbonyl compounds (Hantzsch thiazole synthesis) to give the corresponding 2-(benzotriazol-1-ylmethyl)thiazoles. Lithiation of 2-(benzotriazol-1-ylmethyl)-4-phenylthiazole with butyllithium occurred exclusively at the methylene group, and subsequent quenching of the resulting anion with alkyl halides produced the corresponding alkylated products in good yields. Treatment of these intermediates with Grignard reagents in toluene or with electron-rich heterocycles in the presence of zinc bromide resulted in the displacement of benzotriazole to afford the corresponding thiazoles with elaborated 2-substituents.