methyl 2-phenyl-2H-indazole-3-carboxylate | 251982-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-phenyl-2H-indazole-3-carboxylate
• 英文别名: 2-phenyl-2H-indazole-3-carboxylic acid methyl ester；methyl 2-phenylindazole-3-carboxylate
• CAS: 251982-42-0
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: DYINUKSGCNWBGN-UHFFFAOYSA-N

物化性质

• 沸点：
  314.1±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-phenyl-2H-indazole-3-carboxylate 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 2-phenyl-2H-indazole-3-carboxylic acid
  参考文献：
  名称：

  Aryl-heteroaromatic compounds, compositions comprising them and use

  摘要：

  本发明揭示并声明了一系列芳基-杂芳化合物，包括它们的组合物和使用方法。本发明特别涉及展现抗癌活性的新型芳基-杂芳化合物，特别是在抑制微管聚合方面的活性。

  公开号：

  US20050020593A1
• 作为产物：
  描述：

  2-phenyl-3-methoxycarbonylindazoline 在 氧气 作用下， 以 甲醇 、 acetate buffer 为溶剂， 生成 methyl 2-phenyl-2H-indazole-3-carboxylate
  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

• Rh(III)-Catalyzed Regio- and Chemoselective [4 + 1]-Annulation of Azoxy Compounds with Diazoesters for the Synthesis of 2<i>H</i>-Indazoles: Roles of the Azoxy Oxygen Atom
  作者：Zhen Long、Zhigang Wang、Danni Zhou、Danyang Wan、Jingsong You

  DOI：10.1021/acs.orglett.7b00631

  日期：2017.6.2

  tandem C–H alkylation/intramolecular decarboxylative cyclization of azoxy compounds with diazoesters for the synthesis of 3-acyl-2H-indazoles is disclosed. The azoxy instead of the azo group enables a distinct approach for cyclative capture, leading to a [4 + 1]-annulation rather than a classic [4 + 2] manner. The azoxy oxygen atom is traceless after annulation, and further removal from the product is

  揭示了用Rh（III）催化的重氮化合物与重氮酸酯的串联C–H烷基化/分子内脱羧环化反应，可合成3-酰基-2 H-吲唑。取代偶氮基团的是偶氮氧基团，从而实现了一种独特的环化捕获方法，从而导致了[4 +1]环化，而不是经典的[4 + 2]方式。环氧化后，z氧基氧原子是无痕的，不需要进一步从产物中除去。该反应具有对不对称的乙氧基苯的完全区域选择性和单芳基二烯氧化物的相容性。
• Metal-Free Synthesis of C-3-Alkoxycarbonylated 2H-Indazoles Using Alkylcarbazates
  作者：Dipti Lai、Suvam Bhattacharjee、Sumit Ghosh、Subrata Sinha、Alakananda Hajra

  DOI：10.1055/a-2316-5066

  日期：——

  A simple, efficient, and environmentally benign method for the direct C-3-alkoxycarbonylation of 2H-indazoles using alkyl carbazates has been developed under metal-free conditions at room temperature. This current protocol represents a facile access to C-3-carboxylic ester derived 2H-indazoles with wide functional group tolerance in good to excellent yields. The mechanistic studies suggest that the

  开发了一种简单、有效且环境友好的方法，用于在室温、无金属条件下使用肼基甲酸烷基酯直接对 2 H-吲唑进行 C-3-烷氧基羰基化。目前的方案代表了以良好至优异的产率轻松获得具有广泛官能团耐受性的 C-3-羧酸酯衍生的 2 H-吲唑。机理研究表明该反应通过自由基途径进行。
• Reissert; Lemmer, Chemische Berichte, 1926, vol. 59, p. 357
  作者：Reissert、Lemmer

  DOI：——

  日期：——
• Synthesis and Electrochemical Behaviour of 2-N-Substituted Indazoles.
  作者：B. A. Frontana-Uribe、C. Moinet、Yves Dory、Jean Marc Chapuzet、Jean Lessard、André Tallec、Tatsuya Shono、H. Toftlund

  DOI：10.3891/acta.chem.scand.53-0814

  日期：——

  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.
• Aryl-heteroaromatic compounds, compositions comprising them and use
  申请人：Mailliet Patrick

  公开号：US20050020593A1

  公开（公告）日：2005-01-27

  A series of aryl-heteroaromatic compounds, compositions comprising them and use thereof are disclosed and claimed. The present invention relates in particular to novel aryl-heteroaromatic compounds exhibiting anticancer activity, and in particular inhibitory activity with regard to tubulin polymerization.

  本发明揭示并声明了一系列芳基-杂芳化合物，包括它们的组合物和使用方法。本发明特别涉及展现抗癌活性的新型芳基-杂芳化合物，特别是在抑制微管聚合方面的活性。