3-(4-methoxy-phenyl)-1-phenyl-1H-indazole

• 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-(4-methoxy-phenyl)-1-phenyl-1H-indazole
• 英文别名: 3-(4-methoxyphenyl)-1-phenyl-1H-indazole；3-(4-Methoxyphenyl)-1-phenylindazole
• 化学式: C₂₀H₁₆N₂O
• 分子量: 300.36
• InChiKey: PVQPJHOPGVDBKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-碘吲唑 在 四(三苯基膦)钯 、 copper diacetate 、 碳酸氢钠 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 3-(4-methoxy-phenyl)-1-phenyl-1H-indazole
  参考文献：
  名称：

  First combined selective N- and C-arylations with boronic acids: application to the synthesis of 1,3-diarylindazoles

  摘要：

  3-Iodoindazole allows combined N1- and C3-arylations with boronic acids. These two reactions work independently of one another and can be combined in a one pot procedure. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01650-6

文献信息

• A Synthesis of 1<i>H</i>-Indazoles via a Cu(OAc)₂-Catalyzed N–N Bond Formation
  作者：Cheng-yi Chen、Guangrong Tang、Fengxian He、Zhaobin Wang、Hailin Jing、Roger Faessler

  DOI：10.1021/acs.orglett.6b00611

  日期：2016.4.1

  facile synthesis of 1H-indazoles featuring a Cu(OAc)2-catalyzed N–N bond formation using oxygen as the terminal oxidant is described. The reaction of readily available 2-aminobenzonitriles with various organometallic reagents led to o-aminoaryl N–H ketimine species. The subsequent Cu(OAc)2-catalyzed N–N bond formation in DMSO under oxygen afforded a wide variety of 1H-indazoles in good to excellent

  描述了一种容易合成的1 H-吲唑，其特征在于使用氧作为末端氧化剂，形成Cu（OAc）2催化的N–N键形成。易于获得的2-氨基苯甲腈与各种有机金属试剂的反应产生了邻氨基芳基NH酮亚胺。随后在氧气下在DMSO中形成Cu（OAc）2催化的N–N键，从而以良好或极好的收率提供了多种1 H-吲唑。
• New Synthesis of 1-Substituted-1<i>H</i>-indazoles via 1,3-Dipolar Cycloaddition of <i>in situ</i> Generated Nitrile Imines and Benzyne
  作者：Christian Spiteri、Steve Keeling、John E. Moses

  DOI：10.1021/ol101150t

  日期：2010.8.6

  A new synthesis of 1-substitued-1H-indazoles via 1,3-dipolar cycloaddition of nitrile imines to benzyne is described. The reaction is completed within 5 min, affording the corresponding N(1)−C(3) disubstituted indazoles in moderate to excellent yields.

  描述了通过腈亚胺的1，3-偶极环加成反应生成苯并炔的1-取代-1 H-吲唑的新合成方法。反应在5分钟内完成，以中等至极好的收率得到相应的N（1）-C（3）二取代的吲唑。
• One pot sequential reactions and novel products produced thereby
  申请人：Valsan Mecheril Nandakumar

  公开号：US20060224017A1

  公开（公告）日：2006-10-05

  A method for producing sequenced reaction products comprising performing, in one pot, a first reaction at a lower temperature followed by a second reaction at a higher temperature in the presence of a catalyst system comprising a proazahosphatrane in combination with a palladium compound is provided. In one embodiment, the first reaction is a double amination reaction and the second reaction is an arylation. Use of one pot and a single catalyst system for each set of sequential reactions is efficient and economical. Novel N,N-diarylaminostyrenes and N,N-diarylaminostilbenes are produced according to the methods described herein.

  提供了一种生产序列反应产物的方法，包括在同一个容器中，在存在包括一种临氨基膦杂环丙胺和钯化合物的催化剂体系的情况下，先在较低温度下进行第一反应，然后在较高温度下进行第二反应。在一个实施例中，第一反应是双胺化反应，第二反应是芳基化反应。对于每组顺序反应使用同一个容器和单一催化剂体系是高效且经济的。根据本文描述的方法生产了新颖的N,N-二芳基氨基苯乙烯和N,N-二芳基氨基苯乙烯。
• 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.
• Synthesis of Substituted 1<i>H</i>-Indazoles from Arynes and Hydrazones
  作者：Pan Li、Chunrui Wu、Jingjing Zhao、Donald C. Rogness、Feng Shi

  DOI：10.1021/jo202598e

  日期：2012.4.6

  The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups.