2-(4-cyanophenyl)indazoline | 205309-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 2-(4-cyanophenyl)indazoline
• 英文别名: 4-(1,3-Dihydroindazol-2-yl)benzonitrile；4-(1,3-dihydroindazol-2-yl)benzonitrile
• CAS: 205309-86-0
• 化学式: C₁₄H₁₁N₃
• 分子量: 221.261
• InChiKey: MXFVVCWBPLETLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  39.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-cyanophenyl)indazoline 在 氧气 作用下， 以 甲醇 、 acetate buffer 为溶剂， 生成 4-(2H-indazol-2-yl)benzonitrile
  参考文献：
  名称：

  Synthesis and Electrochemical Behaviour of 2-N-Substituted Indazoles.

  摘要：

  A new 2-N-aryl-3-methoxycarbonylindazole synthesis from the 6 F mol(-1) reduction of appropriately substituted aryl-nitrones has been developed. The indazoles bearing an electron withdrawing group in the 2-position are electroreducible compounds at high negative potentials producing selectively the corresponding 2-N-substituted indazolines in aqueous alcoholic medium. The nitrile and ester groups are not reduced under the reaction conditions. Three new 2-N-aryl-indazolines were synthesized and characterized. A second electron withdrawing group attached at the 3-position leads to a less cathodic reduction of the 2-N-aryl-3-methoxycarbonylindazole. An appropriately substituted indazoline was used to generate ill situ a new tetracyclic heterocycle.

  DOI：

  10.3891/acta.chem.scand.53-0814
• 作为产物：
  描述：

  4-(2H-indazol-2-yl)benzonitrile 以 甲醇 、 acetate buffer 为溶剂， 以90%的产率得到2-(4-cyanophenyl)indazoline
  参考文献：
  名称：

  Synthesis and Electrochemical Behaviour of 2-N-Substituted Indazoles.

  摘要：

  A new 2-N-aryl-3-methoxycarbonylindazole synthesis from the 6 F mol(-1) reduction of appropriately substituted aryl-nitrones has been developed. The indazoles bearing an electron withdrawing group in the 2-position are electroreducible compounds at high negative potentials producing selectively the corresponding 2-N-substituted indazolines in aqueous alcoholic medium. The nitrile and ester groups are not reduced under the reaction conditions. Three new 2-N-aryl-indazolines were synthesized and characterized. A second electron withdrawing group attached at the 3-position leads to a less cathodic reduction of the 2-N-aryl-3-methoxycarbonylindazole. An appropriately substituted indazoline was used to generate ill situ a new tetracyclic heterocycle.

  DOI：

  10.3891/acta.chem.scand.53-0814

文献信息

• 2-Substituted indazoles from electrogenerated ortho-nitrosobenzylamines
  作者：Bernardo A. Frontana-Uribe、Claude Moinet

  DOI：10.1016/s0040-4020(98)00058-1

  日期：1998.3

  An electrochemical methodology for an efficient access to ortho-nitrosobenzylamines has been developed. These products cyclize intramolecularly producing the desired 2-substituted indazoles in high yields. The electrochemical procedure overcomes limitations of previous chemical methods. (C) 1998 Elsevier Science Ltd. All rights reserved.