1-(4-甲基苯基)吲唑 | 92160-67-3

• 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-(4-甲基苯基)吲唑
• 英文名称: 1-(p-tolyl)-1H-indazole
• 英文别名: 1H-Indazole, 1-(4-methylphenyl)-；1-(4-methylphenyl)indazole
• CAS: 92160-67-3
• 化学式: C₁₄H₁₂N₂
• 分子量: 208.263
• InChiKey: FUROWUQNJZNRIL-UHFFFAOYSA-N

物化性质

• 熔点：
  70-70.5 °C
• 沸点：
  291.5±23.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 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：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-甲基苯基)吲唑 在 正丁基锂 作用下， 以 四氢呋喃 、 环己烷 、 甲苯 为溶剂， 反应 27.0h， 生成 3-methyl-1-(p-tolyl)quinazoline-2,4(1H,3H)-dithione
  参考文献：
  名称：

  Syntheses of Acridines and Quinazoline-2,4(1H,3H)-dithiones by Rearrangements of N-Heterocyclic Carbenes of Indazole

  摘要：

  N-Heterocyclic carbenes of indazole which are arylated at N1 (1-aryl-indazol-3-ylidenes) have been generated by deprotonation of the corresponding indazolium salts. On deprotonation with potassium carbonate, potassium phosphate or tert-butanolate in dioxane or toluene at reflux temperature, a rearrangement to acridines took place. Deprotonation with n-butyllithium in THF at room temperature in the presence of carbon disulfide gave quinazoline-2,4(1H,3H)-dithiones by a new rearrangement reaction.

  DOI：

  10.3987/com-14-13082
• 作为产物：
  描述：

  3-trimethylsilylindazole 在 吡啶 、 氢氧化钾 、 copper diacetate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 1-(4-甲基苯基)吲唑
  参考文献：
  名称：

  Regioselective synthesis of 1-arylindazoles via N-arylation of 3-trimethylsilylindazoles

  摘要：

  The copper(II)-catalyzed cross-coupling reaction of 3-trimethylsilylindazoles bearing substituents on the benzene ring with arylboronic acids regioselectively gave the corresponding 1-aryl-3-trimethylsilylindazoles and no 2-aryl isomers were formed at all. Moreover, the trimethylsilyl group of the resulting indazoles was easily removed by treatment with ethanolic KOH to give 1-arylindazoles. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.157

文献信息

• Microwave-assisted palladium mediated decarbonylation reaction: synthesis of eulatachromene
  作者：Akanksha、Debabrata Maiti

  DOI：10.1039/c2gc35622h

  日期：——

  Microwave-assisted decarbonylation reactions were investigated using a palladium catalyst. A large number of aldehydes can be decarbonylated efficiently with lower catalyst loadings and under shorter reaction times compared to conventional heating. A successful decarbonylation led to the synthesis of natural product eulatachromene in three steps starting from easily available materials.

  通过使用钯催化剂，对微波辅助脱羰反应进行了研究。与传统加热方式相比，许多醛类可以在较低的催化剂用量和较短的反应时间内高效地进行脱羰反应。成功的脱羰反应使得从易得原料出发，通过三个步骤合成了天然产物eulatachromene。
• A general and efficient aldehyde decarbonylation reaction by using a palladium catalyst
  作者：Atanu Modak、Arghya Deb、Tuhin Patra、Sujoy Rana、Soham Maity、Debabrata Maiti

  DOI：10.1039/c2cc31144e

  日期：——

  A facile decarbonylation reaction of aldehydes has been developed by employing Pd(OAc)2. A wide variety of substrates are decarbonylated, without using any exogenous ligand for palladium as well as CO-scavenger.

  通过使用Pd(OAc)2，开发了一种简便的醛脱羰反应。多种底物可进行脱羰处理，无需使用任何外源配体或CO清除剂。
• An efficient dehydroxymethylation reaction by a palladium catalyst
  作者：Atanu Modak、Togati Naveen、Debabrata Maiti

  DOI：10.1039/c2cc36951f

  日期：——

  A general method for selective dehydroxymethylation has been discovered by using widely available Pd(OAc)(2). The present study offers a new synthetic strategy for the regioselective functionalization by employing the steric, electronic and coordinating nature of the hydroxymethyl (-CH(2)OH) group temporarily.

  通过使用广泛可用的Pd（OAc）（2），发现了一种选择性脱羟甲基化的一般方法。本研究通过暂时使用羟甲基（-CH（2）OH）基团的空间，电子和配位性质，为区域选择性功能化提供了一种新的合成策略。
• Copper−Diamine-Catalyzed <i>N</i>-Arylation of Pyrroles, Pyrazoles, Indazoles, Imidazoles, and Triazoles
  作者：Jon C. Antilla、Jeremy M. Baskin、Timothy E. Barder、Stephen L. Buchwald

  DOI：10.1021/jo049658b

  日期：2004.8.1

  This paper details the copper-catalyzed N-arylation of π-excessive nitrogen heterocycles. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate functional groups such as

  本文详细介绍了铜催化的π-过量氮杂环的N-芳基化反应。芳基碘化物或芳基溴化物与常见的氮杂环（吡咯，吡唑，吲唑，咪唑和三唑）的偶联成功地用衍生自二胺配体和CuI的催化剂进行了高收率的偶联。发现一般条件可耐受芳基卤化物或杂环上的官能团，例如醛，酮，醇，伯胺和腈。使用本文报道的条件，受阻的芳基卤化物或杂环也被发现是合适的底物。
• N-Picolinamides as ligands for Ullmann-type C N coupling reactions
  作者：Fehmi Damkaci、Abdulkhaliq Alawaed、Erik Vik

  DOI：10.1016/j.tetlet.2016.04.017

  日期：2016.5

  N-phenyl-2-pyridincarboxamide-1-oxide as a ligand with Cu2O in Ullmann type CN bond formations between aryl halides and N-heteroaryls in common solvents, such as MeCN, DMF, and DMSO at 82–120 °C has been successfully demonstrated. The ligand is effective when only 4% equiv is used relative to the substrate. The reaction provided the corresponding products in coupling of electron-rich, electron poor, and

  使用N-苯基-2-吡啶甲酰胺-1-氧化物作为Cu 2 O的配体，在普通溶剂（例如MeCN，DMF和DMSO）中于82- ℃下在芳基卤化物和N-杂芳基之间的Ullmann C型N键形成中120°C已被成功证明。当相对于底物仅使用4％当量时，配体是有效的。该反应以良好或非常好的收率提供了富电子，电子贫乏和邻位取代的芳基卤化物（包括邻位芳基氯化物）偶联的相应产物。当邻位时，在苄基位置选择性地优选N-芳基化-卤化物苄基溴化物与一当量的吡唑反应。然而，当使用2.5当量的吡唑时，以非常高的产率实现二-N-芳基化，从而提供了对偶联反应的化学计量控制。