Benzoic acid, 2-[[(2-nitrophenyl)methylene]amino]-, methyl ester | 61144-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid, 2-[[(2-nitrophenyl)methylene]amino]-, methyl ester
• 英文别名: methyl 2-[(2-nitrophenyl)methylideneamino]benzoate
• CAS: 61144-88-5
• 化学式: C₁₅H₁₂N₂O₄
• 分子量: 284.271
• InChiKey: HHRKYCFRLVFDAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Benzoic acid, 2-[[(2-nitrophenyl)methylene]amino]-, methyl ester 在 三丁基膦 作用下， 以 异丙醇 为溶剂， 反应 16.0h， 以143 mg的产率得到methyl 2-(2H-indazol-2-yl)benzoate
  参考文献：
  名称：

  Regioselective Synthesis of 2H-Indazoles Using a Mild, One-Pot Condensation–Cadogan Reductive Cyclization

  摘要：

  An operationally simple and efficient one-pot synthesis of 2H-indazoles from commercially available reagents is reported. Ortho-imino-nitrobenzene substrates, generated via condensation, undergo reductive cyclization promoted by tri-n-butylphosophine to afford substituted 2H-indazoles under mild reaction conditions. A variety of electronically diverse ortho-nitrobenzaldehydes and anilines were examined. To further extend the scope of the transformation, aliphatic amines were also employed to form N2-alkyl indazoles selectively under the optimized reaction conditions.

  DOI：

  10.1021/ol5012423
• 作为产物：
  描述：

  邻氨基苯甲酸甲酯 、 邻硝基苯甲醛 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 Benzoic acid, 2-[[(2-nitrophenyl)methylene]amino]-, methyl ester
  参考文献：
  名称：

  Johnston, David; Smith, David M.; Shepherd, Thomas, Journal of the Chemical Society. Perkin transactions I, 1987, p. 495 - 500

  摘要：

  DOI：

文献信息

• Johnston, David; Smith, David M.; Shepherd, Thomas, Journal of the Chemical Society. Perkin transactions I, 1987, p. 495 - 500
  作者：Johnston, David、Smith, David M.、Shepherd, Thomas、Thompson, David

  DOI：——

  日期：——
• Regioselective Synthesis of 2<i>H</i>-Indazoles Using a Mild, One-Pot Condensation–Cadogan Reductive Cyclization
  作者：Nathan E. Genung、Liuqing Wei、Gary E. Aspnes

  DOI：10.1021/ol5012423

  日期：2014.6.6

  An operationally simple and efficient one-pot synthesis of 2H-indazoles from commercially available reagents is reported. Ortho-imino-nitrobenzene substrates, generated via condensation, undergo reductive cyclization promoted by tri-n-butylphosophine to afford substituted 2H-indazoles under mild reaction conditions. A variety of electronically diverse ortho-nitrobenzaldehydes and anilines were examined. To further extend the scope of the transformation, aliphatic amines were also employed to form N2-alkyl indazoles selectively under the optimized reaction conditions.