1,3,4-三苯基-1H-吡唑 | 1666-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1,3,4-三苯基-1H-吡唑
• 英文名称: 1,3,4-triphenyl-1H-pyrazole
• 英文别名: 1,3,4-triphenylpyrazole；1,3,4-triphenyl-1H-pyrazole；1,3,4-Triphenyl-1H-pyrazol；1,3,4-Triphenyl-pyrazol；1,3,4-Triphenylpyrazol
• CAS: 1666-85-9
• 化学式: C₂₁H₁₆N₂
• 分子量: 296.371
• InChiKey: AXRVRVKZFJPHBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933199090

反应信息

• 作为产物：
  描述：

  3,3-bis(methylthio)-1,2-diphenylprop-2-en-1-one 在 potassium tert-butylate 、 镍 作用下， 以 乙醇 、 叔丁醇 为溶剂， 生成 1,3,4-三苯基-1H-吡唑
  参考文献：
  名称：

  Regioselective Synthesis of 1-Aryl-3,4-substituted/annulated-5-(methylthio)pyrazoles and 1-Aryl-3-(methylthio)-4,5-substituted/annulated Pyrazoles

  摘要：

  Highly efficient and regioselective synthesis of 1-aryl-3,4-substituted/annulated-5-(methylthio)-pyrazoles and 1-aryl-3-(methylthio)-4,5-substituted/annulated pyrazoles has been reported via cyclocondensation of arylhydrazines with either alpha-oxoketene dithioacetals or beta-oxodithioesters.

  DOI：

  10.1021/jo051771u

文献信息

• Synthesis of 3<i>H</i>-Pyrazolo[3,4-<i>c</i>]isoquinolines and Thieno[3,2-<i>c</i>]isoquinolines via Cascade Imination/Intramolecular Decarboxylative Coupling
  作者：Garima Pandey、Subhendu Bhowmik、Sanjay Batra

  DOI：10.1021/ol4023722

  日期：2013.10.4

  A general approach for the synthesis of 3H-pyrazolo[3,4-c]isoquinolines and thieno[3,2-c]isoquinolines is described involving the implementation of a cascade imination/intramolecular decarboxylative coupling between potassium 2-amino(hetero)benzoates and 2-haloarylaldehydes. The reactions of pyrazole-based substrates require a Pd–Cu bimetallic system for superior yields whereas the thienyl-based substrates

  为3合成的一般方法ħ -吡唑并[3,4- c ^ ]异喹啉和噻吩并[3,2- C ^ ]异喹啉，描述涉及级联亚胺化/分子内脱羧耦合钾之间2-氨基（杂）的实施苯甲酸酯和2-卤代芳基醛。吡唑基底物的反应需要Pd-Cu双金属系统才能获得更高的收率，而噻吩基的底物仅使用Pd催化剂即可提供优异的收率。
• Cu(OAc)2·H2O-catalyzed N-arylation of nitrogen-containing heterocycles
  作者：Zhong-Lin Xu、Hong-Xi Li、Zhi-Gang Ren、Wei-Yuan Du、Wei-Chang Xu、Jian-Ping Lang

  DOI：10.1016/j.tet.2011.05.025

  日期：2011.7

  In the absence of any additional ligands, the efficient N-arylation of nitrogen-containing heterocycles with aryl iodides catalyzed by relative low catalyst amount of Cu(OAc)2·H2O was developed. This simple catalytic system is involved in the C–N cross-coupling reaction and works for a variety of pyrazole, pyrrole, imidazole, triazole, indole, benzoimidazole, benzotriazole, carbazole, and anilines

  在没有任何其他配体的情况下，开发了由相对较低的催化剂量的Cu（OAc）2 ·H 2 O催化的含氮杂环与芳基碘的有效N-芳基化反应。这种简单的催化系统参与C–N交叉偶联反应，适用于各种电子性质不同的各种吡唑，吡咯，咪唑，三唑，吲哚，苯并咪唑，苯并三唑，咔唑和苯胺以及碘代芳基碘。建立了高效的铜（II）催化的N-芳基化方案。
• Regioselective rapid analog synthesis of 1,3-(or 1,5-)diphenyl-4-aryl/heteroaryl-5-(or 3-)(methylthio)pyrazoles via Suzuki cross-coupling
  作者：Taukeer A. Khan、Sarvesh Kumar、Chelvam Venkatesh、Hiriyakkanavar Ila

  DOI：10.1016/j.tet.2011.02.043

  日期：2011.4

  Regioselective routes for the synthesis of 1,3-(or 1,5-)diphenyl-4-aryl/heteroaryl-5-(or 3-)(methylthio)pyrazoles via Suzuki cross-coupling of 4-bromo (or 4-iodo)-1,3-(or 1,5-)diphenyl-5-(or 3-)(methylthio)pyrazoles have been reported.

  通过4-溴（或4-碘）的Suzuki交叉偶联合成1，3-（或1，5-）二苯基-4-芳基/杂芳基-5-（或3-）（甲硫基）吡唑的区域选择性路线已经报道了）-1，3-（或1，5-）二苯基-5-（或3-）（甲硫基）吡唑。
• Copper-catalyzed synthesis of 1,3,4-trisubstituted and 1,3,4,5-tetrasubstituted pyrazoles via [3+2] cycloadditions of hydrazones and nitroolefins
  作者：Chong Shi、Chaowei Ma、Haojie Ma、Xiaoqiang Zhou、Jinhui Cao、Yuxing Fan、Guosheng Huang

  DOI：10.1016/j.tet.2016.05.034

  日期：2016.7

  A highly economical and efficient copper(I)-catalyzed regioselective method for the synthesis of 1,3,4-trisubstituted and 1,3,4,5-tetrasubstituted pyrazoles via [3+2] cycloaddition of hydrazones and nitroolefins has been reported. This process displays excellent applicability with a wide range of substrates under mild conditions.

  已经报道了通过economic和硝基烯烃的[3 + 2]环加成反应来合成1,3,4-三取代和1,3,4,5-四取代的吡唑的一种非常经济和高效的铜（I）催化区域选择性方法。在温和的条件下，该方法在各种基材上均显示出极好的适用性。
• Pd-catalyzed cross-coupling reactions of halogenated 1-phenylpyrazol-3-ols and related triflates
  作者：Eglė Arbačiauskienė、Gytė Vilkauskaitė、Gernot A. Eller、Wolfgang Holzer、Algirdas Šačkus

  DOI：10.1016/j.tet.2009.07.017

  日期：2009.9

  1-Phenyl-1H-pyrazol-3-ol was used as a versatile synthon for the preparation of various 1-phenyl-1H-pyrazole derivatives substituted at C-3 and C-4 of the pyrazole nucleus and at the phenyl ring para-position. Treatment of 1-phenyl-1H-pyrazol-3-ol with triflic anhydride in the presence of base gave 3-trifloyloxy pyrazole, while bromination and iodination yielded the corresponding halogenated derivatives

  1-苯基-1 H-吡唑-3-醇被用作通用的合成子，用于制备在吡唑核的C-3和C-4以及在苯环上取代的各种1-苯基-1 H-吡唑衍生物对位。在碱存在下用三氟甲磺酸酐处理1-苯基-1 H-吡唑-3-醇，得到3-三氟甲酰氧基吡唑，而溴化和碘化则得到相应的卤代衍生物。获得的支架用于碳-碳键形成的Pd催化的交叉偶联反应中，生成（杂）芳基和碳官能取代的1-苯基-1 H-吡唑。