3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-ol | 28795-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-ol
• 英文别名: 3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-ol；1-Phenyl-3,6,6-trimethyl-4-hydroxy-4,5,6,7-tetrahydroindazol；3,6,6-trimethyl-1-phenyl-5,7-dihydro-4H-indazol-4-ol
• CAS: 28795-07-5
• 化学式: C₁₆H₂₀N₂O
• 分子量: 256.348
• InChiKey: GZFQZWPGQSJZQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-ol 在 乙酰氯 作用下， 反应 2.0h， 以87%的产率得到1-Phenyl-3,6,6-trimethyl-6,7-dihydroindazol
  参考文献：
  名称：

  A facile synthesis of 4-acylamino-tetrahydroindazoles via the Ritter reaction

  摘要：

  A new route toward 4-acylamino- and 4-amino-substituted tetrahydroindazoles is disclosed. The title compounds are obtained in good to excellent yields in the Ritter reaction between 4-hydroxy-tetrahydroindazoles and various nitriles. The reactivity of the tetrahydroindazole-derived carbenium ion is both sufficiently high to react with trichloroacetonitrile and sufficiently selective to resist the azide functionality within its structure. The present approach adds a method to the toolbox of tetrahydroindazole chemistry and facilitates the structural modifications of the scaffold, which has found important applications in medicinal chemistry. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.074
• 作为产物：
  描述：

  1-苯基-3,6,6-三甲基-6,7-二氢-1氢-吲哚-4(5氢)-酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以97%的产率得到3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-ol
  参考文献：
  名称：

  A facile synthesis of 4-acylamino-tetrahydroindazoles via the Ritter reaction

  摘要：

  A new route toward 4-acylamino- and 4-amino-substituted tetrahydroindazoles is disclosed. The title compounds are obtained in good to excellent yields in the Ritter reaction between 4-hydroxy-tetrahydroindazoles and various nitriles. The reactivity of the tetrahydroindazole-derived carbenium ion is both sufficiently high to react with trichloroacetonitrile and sufficiently selective to resist the azide functionality within its structure. The present approach adds a method to the toolbox of tetrahydroindazole chemistry and facilitates the structural modifications of the scaffold, which has found important applications in medicinal chemistry. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.074

文献信息

• A facile synthesis of 4-acylamino-tetrahydroindazoles via the Ritter reaction
  作者：Māris Turks、Inta Strakova、Kirils Gorovojs、Sergey Belyakov、Yuri A. Piven、Tatyana S. Khlebnicova、Fedor A. Lakhvich

  DOI：10.1016/j.tet.2012.05.074

  日期：2012.8

  A new route toward 4-acylamino- and 4-amino-substituted tetrahydroindazoles is disclosed. The title compounds are obtained in good to excellent yields in the Ritter reaction between 4-hydroxy-tetrahydroindazoles and various nitriles. The reactivity of the tetrahydroindazole-derived carbenium ion is both sufficiently high to react with trichloroacetonitrile and sufficiently selective to resist the azide functionality within its structure. The present approach adds a method to the toolbox of tetrahydroindazole chemistry and facilitates the structural modifications of the scaffold, which has found important applications in medicinal chemistry. (C) 2012 Elsevier Ltd. All rights reserved.