1-苯基-1H-吲唑-3-羧酸乙酯 | 7716-35-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-苯基-1H-吲唑-3-羧酸乙酯
• 英文名称: 3-ethoxycarbonyl-1-phenyl-1H-indazole
• 英文别名: ethyl N-phenyl-1H-indazole-3-carboxylate；ethyl 1-phenyl-1H-indazole-3-carboxylate；3-Ethoxycarbonyl-1-phenyl-imidazol；1-phenyl-1H-indazole-3-carboxylic acid ethyl ester；ethyl 1-phenylindazole-3-carboxylate
• CAS: 7716-35-0
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: TWDDWHHKQWOVSF-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  375.3±25.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Ethyl 4-hydroxy-1-phenyl-4,5,6,7-tetrahydroindazole-3-carboxylate 在 palladium on activated charcoal 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以85%的产率得到1-苯基-1H-吲唑-3-羧酸乙酯
  参考文献：
  名称：

  A Convenient Synthesis of Indazoles

  摘要：

  DOI：

  10.1055/s-1984-31048

文献信息

• Facile and efficient synthesis of indazole derivatives by 1,3-cycloaddition of arynes with diazo compounds and azomethine imides
  作者：Tienan Jin、Fan Yang、Yoshinori Yamamoto

  DOI：10.1135/cccc2009014

  日期：——

  N-Unsubstituted indazoles 3 and 1-arylindazoles 4 are readily available in good to high yields through [3+2] cycloaddition of 2-(trimethylsilyl)aryl triflates 1 and diazo compounds in the presence of KF or CsF under mild reaction conditions. Furthermore, we found that azomethine imides also underwent cycloaddition reaction with 2-(trimethylsilyl)phenyl triflates (1a) in the presence of KF to afford indazolone derivatives 6 in moderate yields.

  N-未取代吲唑3和1-芳基吲唑4可通过2-(三甲基硅基)芳基三氟甲烷磺酸酯1和重氮化合物在KF或CsF存在下在温和反应条件下进行[3+2]环加成反应，以良好至高产率方便获得。此外，我们发现偶氮亚甲基亚胺也可在KF存在下与2-(三甲基硅基)苯基三氟甲烷磺酸酯（1a）发生环加成反应，得到吲唑酮衍生物6，产率中等。
• Synthesis of Indazoles by the [3+2] Cycloaddition of Diazo Compounds with Arynes and Subsequent Acyl Migration
  作者：Zhijian Liu、Feng Shi、Pablo D. G. Martinez、Cristiano Raminelli、Richard C. Larock

  DOI：10.1021/jo702062n

  日期：2008.1.1

  The [3+2] cycloaddition of a variety of diazo compounds with o-(trimethylsilyl)aryl triflates in the presence of CsF or TBAF at room temperature provides a very direct, efficient approach to a wide range of potentially biologically and pharmaceutically interesting substituted indazoles in good to excellent yields under mild reaction conditions. Simple diazomethane derivatives afford N-unsubstituted

  在室温下，在CsF或TBAF存在下，各种重氮化合物与邻-（三甲基甲硅烷基）芳基三氟甲酸酯的[3 + 2]环加成反应，提供了一种直接，有效的方法，可用于处理许多潜在的生物学和药学上令人关注的取代的吲唑在温和的反应条件下，收率好至极好。简单的重氮甲烷衍生物根据试剂的化学计量和反应条件而提供N-未取代的吲唑或1-芳基化的吲唑，而含二羰基的重氮化合物进行羰基迁移以选择性地提供1-酰基或1-烷氧基羰基的吲唑。
• Assembly of <i>N</i>,<i>N</i>-Disubstituted Hydrazines and 1-Aryl-1<i>H</i>-indazoles via Copper-Catalyzed Coupling Reactions
  作者：Xiaodong Xiong、Yongwen Jiang、Dawei Ma

  DOI：10.1021/ol300847v

  日期：2012.5.18

  CuI-catalyzed coupling of N-acyl-N′-substituted hydrazines with aryl iodides takes place at 60–90 °C to afford N-acyl-N′,N′-disubstituted hydrazines regioselectively and thereby gives a facile method for assembling N,N-diaryl hydrazines. N-Acyl-N′-substituted hydrazines can also react with 2-bromoarylcarbonylic compounds at 60–125 °C under the catalysis of CuI/4-hydroxy-l-proline to provide 1-aryl-1H-indazoles

  N-酰基-N'-取代的肼与芳基碘化物的CuI催化偶联在60-90°C下进行，可选择性地提供N-酰基-N '，N'-双取代的肼，从而提供了一种简便的组装N的方法，N-二芳基肼。在CuI / 4-羟基-1-脯氨酸的催化下，N-酰基-N'-取代的肼还可在60-125°C下与2-溴芳基羰基化合物反应，生成1-芳基-1 H-吲唑。
• An efficient transition-metal-free synthesis of 1H-indazoles from arylhydrazones with montmorillonite K-10 under O2 atmosphere
  作者：Jin Yu、Jin Woo Lim、Su Yeon Kim、Jimin Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2015.01.183

  日期：2015.3

  An efficient transition-metal-free synthetic method of 1H-indazoles has been developed. The reaction of arylhydrazones in the presence of montmorillonite K-10 in 1,2-dichlorobenzene at 130 degrees C afforded 1Hindazoles in good yields most likely via a sequential intramolecular nucleophilic cyclization and an aerobic oxidation pathway. (C) 2015 Elsevier Ltd. All rights reserved.
• An Efficient, Facile, and General Synthesis of 1H-Indazoles by 1,3-Dipolar Cycloaddition of Arynes with Diazomethane Derivatives
  作者：Tienan Jin、Yoshinori Yamamoto

  DOI：10.1002/anie.200700101

  日期：2007.4.27