1,3,5-三苯基-1H-吡唑 | 2183-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1,3,5-三苯基-1H-吡唑
• 英文名称: 1,3,5-triphenyl-1H-pyrazole
• 英文别名: 1,3,5-triphenylpyrazole
• CAS: 2183-27-9
• 化学式: C₂₁H₁₆N₂
• mdl: MFCD00159617
• 分子量: 296.371
• InChiKey: YQDSXDPQYUXRDP-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

• 作为反应物：
  描述：

  1,3,5-三苯基-1H-吡唑 在 乙醇 、 sodium 作用下， 生成 1,3,5-三苯基-4,5-二氢-1H-吡唑
  参考文献：
  名称：

  Knorr; Laubmann, Chemische Berichte, 1888, vol. 21, p. 1207

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-dichloro-1,3-diphenylpropan-1-one 在 乙醇 、 potassium acetate 、 溶剂黄146 作用下， 生成 1,3,5-三苯基-1H-吡唑
  参考文献：
  名称：

  v. Auwers; Huegel, Journal fur praktische Chemie (Leipzig 1954), 1935, vol. <2> 143, p. 157,166

  摘要：

  DOI：
• 作为试剂：
  描述：

  2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 在 吡啶 、 2,4,6-三甲基吡啶 、 甲醇 、 tris-(dibenzylideneacetone)dipalladium(0) 、 1,3,5-三苯基-1H-吡唑 、 氢溴酸 、 sodium methylate 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 、 溶剂黄146 、 sodium t-butanolate 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (2R,4aR,6R,7R,8R,8aS)-7-(benzo[c][1,2,5]oxadiazol-4-ylamino)-2-phenyl-6-(2-(trimethylsilyl)ethoxy)hexahydropyrano[3,2-d][1,3]dioxin-8-ol
  参考文献：
  名称：

  Syntheses of 2-NBDG analogues for monitoring stereoselective uptake of d -glucose

  摘要：

  2-NBDG is a widely used fluorescent tracer for monitoring D-glucose uptake into single living cells. However, 2-NBDG alone is not sufficient for monitoring the net stereoselective uptake of D-glucose, unless its possible non-stereoselective uptake is properly evaluated. L-Glucose derivatives, which emit fluorescence distinct from that of 2-NBDG, should provide valuable information on the stereoselective uptake, when used with 2-NBDG in combination. In the present study, we synthesized Texas Red (sulforhodamine 101 acid)-coupled and [2-(benz-2-oxa-1,3-diazol-4-yl)amino]-coupled 2-deoxy-D-glucose, referred to as [2-TRG] and [2-BDG], respectively. These derivatives showed emission wavelength longer and shorter than that of 2-NBDG, respectively. 2-TRLG, an antipode of 2-TRG, proved to be an effective tracer for evaluating the extent of non-stereoselective uptake of 2-NBDG when used simultaneously with 2-NBDG. On the other hand, 2-BDG exhibited very weak fluorescence, but the application of a novel cross coupling in the presence of a benzoxadiazole group may be useful for the future development of effective glucose tracers. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.148

文献信息

• Pyrrole and Pyrazole Ring Closure in Heterogeneous Media
  作者：F. Texier-Boullet、B. Klein、J. Hamelin

  DOI：10.1055/s-1986-31655

  日期：——

  Pyrroles and pyrazoles may be conveniently prepared by dispersing primary amines or hydrazines and 1,4- or 1,3-diketones, respectively, on alumina or clay (montmorillonite K 10) without solvent, keeping the mixture at 20°C or higher temperatures for 1-26 h, and then eluting the product with dichloromethane.

  吡咯和吡唑可以通过将伯胺或肼以及1,4-或1,3-二酮分别分散在氧化铝或粘土（蒙脱石K 10）上，无需溶剂，在20°C或更高温度下保持混合物1至26小时，然后用二氯甲烷洗脱产物来方便地制备。
• A Regioselective Approach to Trisubstituted Pyrazoles via Palladium-Catalyzed Oxidative Sonogashira-Carbonylation of Arylhydrazines
  作者：Yongliang Tu、Zhenming Zhang、Tao Wang、Jiamei Ke、Junfeng Zhao

  DOI：10.1021/acs.orglett.7b01447

  日期：2017.7.7

  A palladium-catalyzed oxidative carbonylation of arylhydrazines and alkynes with balloon pressure CO/O2 to afford trisubstituted pyrazoles in a one-pot manner has been developed. The formation of trisubstituted pyrazoles involves a sequential C–N bond cleavage, carbonylation, Sonogashira coupling, Michael addition, and intramolecular condensation cyclization tandem process. An unprecedented oxidative

  已经开发了用球罐压力CO / O 2进行钯催化的芳基肼和炔烃的氧化羰基化反应，以一锅法得到三取代的吡唑。三取代吡唑的形成涉及连续的C–N键断裂，羰基化，Sonogashira偶联，迈克尔加成和分子内缩合环化串联过程。芳基肼的空前的氧化Sonogashira-羰基化反应在如此简便的吡唑方法中起着关键作用。
• A General and Convenient Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides
  作者：Xiao-Feng Wu、Helfried Neumann、Matthias Beller

  DOI：10.1002/chem.201001864

  日期：2010.10.25

  Convenient carbonylations: An efficient methodology for the carbonylative Sonogashira reaction of aryl bromides has been developed (see scheme). Contrary to known procedures, inexpensive aryl bromides can be applied as substrates to give the desired compounds in moderate to good yields (47–88 %).

  方便的羰基化：已开发出一种有效的方法用于芳基溴的羰基化Sonogashira反应（请参见方案）。与已知方法相反，廉价的芳基溴化物可以用作底物，以中等至良好的收率（47–88％）得到所需化合物。
• Alternative Biarylphosphinesfor Use in the Palladium-Catalyzed Amination of Aryl Halides
  作者：Robert Singer、Stephane Caron、Ruth McDermott、Patrice Arpin、Nga Do

  DOI：10.1055/s-2003-40881

  日期：2003.8

  Two families of biarylphosphine ligands were prepared for use in the Pd-catalyzed amination reaction. The first series investigated was derived from N-phenylpyrroles, and the second, was derived from N-phenylpyrazoles. While the pyrrole ligands were not as general in substrate scope, one of the readily prepared pyrazole ligands (R = t-Bu) was found to have a fairly broad substrate scope.

  制备了两类联芳基膦配体用于 Pd 催化的胺化反应。研究的第一个系列衍生自 N-苯基吡咯，第二个系列衍生自 N-苯基吡唑。虽然吡咯配体在底物范围上并不普遍，但发现一种容易制备的吡唑配体 (R = t-Bu) 具有相当广泛的底物范围。
• Novel synthesis of di-imines by the transformation of 1-aryl-4,6-disubstituted pyrimidin-2(1H)-ones
  作者：Takehiko Nishio、Yoshimori Omote

  DOI：10.1039/p19820002149

  日期：——

  The di-imines (4), which are versatile starting materials for the synthesis of heterocycles, are obtained in fair yields when the 1-aryl-4,6-disubstituted pyrimidin-2(1H)-ones (3) are treated with alkoxide, both photochemically and thermally. The di-imines (4) thus obtained, when treated with carbon disulphide, give the 1,3-thiazine-2-thiones (8) and/or the 1-arylpyrimidine-2(1H)-thiones (9).

  当将1-芳基-4,6-二取代的嘧啶2-2（1 H）-酮（3）处理后，二价亚胺（4）是合成杂环的通用起始原料，并以合理的收率获得。光化学和热的醇盐。如此获得的二亚胺（4），当用二硫化碳处理时，得到1，3-噻嗪-2-硫酮（8）和/或1-芳基嘧啶-2（1H）-硫酮（9）。