1,3,5-三苯基-4,5-二氢-1H-吡唑 | 742-01-8

• 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-4,5-二氢-1H-吡唑
• 英文名称: 1,3,5-triphenyl-4,5-dihydro-1H-pyrazole
• 英文别名: 1,3,5-triphenyl-2-pyrazoline；1,3,5-triphenylpyrazoline；1H-4,5-dihydro-1,3,5-triphenyl-pyrazole；2,3,5-triphenyl-3,4-dihydropyrazole
• CAS: 742-01-8
• 化学式: C₂₁H₁₈N₂
• 分子量: 298.387
• InChiKey: FGCZQOHSWGMVPN-UHFFFAOYSA-N

物化性质

• 熔点：
  139-141℃
• 沸点：
  453.9±48.0 °C(Predicted)
• 密度：
  1.09

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

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-4,5-二氢-1H-吡唑 在 盐酸 、 氧气 、 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 以100%的产率得到2-(4-硝基苯基)-3,5-二苯基-3,4-二氢吡唑
  参考文献：
  名称：

  Electrophilic substitution in N-aryl-2-pyrazolines. 3. Introduction of nitro-, sulfo-, and acyl groups. Reaction with Michler's ketone

  摘要：

  DOI：

  10.1007/bf00506973
• 作为产物：
  描述：

  (E)-3-(2-iodophenyl)-1-phenylprop-2-en-1-one 以 环己烷 为溶剂， 生成 1,3,5-三苯基-4,5-二氢-1H-吡唑
  参考文献：
  名称：

  Grimshaw, James; Silva, A. Prasanna de,, Journal of the Chemical Society. Perkin transactions II, 1983, # 11, p. 1679 - 1686

  摘要：

  DOI：
• 作为试剂：
  描述：

  4-氯苯硫酚 在 三聚氰胺与过氧化氢的化合物 、 1,3,5-三苯基-4,5-二氢-1H-吡唑 作用下， 以 乙腈 为溶剂， 生成 4,4'-二氯二苯二硫醚
  参考文献：
  名称：

  Melamine Hydrogen Peroxide (MHP): Novel and Efficient Reagent for the Chemo- and Homoselective and Transition Metal–Free Oxidation of Thiols and Sulfides

  摘要：

  Melamine hydrogen peroxide (MHP) as a novel hydrogen peroxide adduct was easily prepared. Both chemo- and homoselective oxidation of thiols and sulfides to their corresponding disulfides and sulfoxides occurred by using MHP in moderate to excellent yields. AlCl3 acts as a suitable activator in the oxidation of sulfides with MHP.

  DOI：

  10.1080/10426500902758386

文献信息

• Palladium-Catalyzed Denitrogenative Synthesis of Aryl Ketones from Arylhydrazines and Nitriles Using O₂ as Sole Oxidant
  作者：Xu Wang、Yubing Huang、Yanli Xu、Xiaodong Tang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.6b02697

  日期：2017.2.17

  An efficient and simple palladium-catalyzed approach for the synthesis of aryl ketones from low-cost nitriles and arylhydrazines using molecular oxygen (O2) as sole oxidant via C–N bond cleavage is reported. Various aryl ketones were synthesized in moderate to good yields under mild conditions. A possible mechanism involving the PdII/Pd0 catalytic cycle process is depicted, and a cationic palladium

  据报道，一种有效且简单的钯催化方法可通过低成本的腈和芳肼，使用分子氧（O 2）作为唯一氧化剂通过C–N键断裂来合成芳基酮。在温和的条件下以中等至良好的产率合成了各种芳基酮。描述了涉及Pd II / Pd 0催化循环过程的可能机理，并通过ESI-MS检测了阳离子钯中间体。
• <i>N</i>,<i>N</i>′,<i>N</i>,<i>N</i>′-TETRABROMO-BENZENE-1,3-DISULFONYLAMIDE AS A NOVEL REAGENT FOR OXIDATIVE AROMATIZATION OF 1,3,5-TRISUBSTITUTED PYRAZOLINES UNDER HETEROGENEOUS AND SOLVENT-FREE CONDITIONS
  作者：Ramin Ghorbani-Vaghei、Davood Azarifar、Ardeshir Khazaei、Behrooz Maleki

  DOI：10.1080/10426500490466797

  日期：2004.9

  1,3,5-Trisubstituted pyrazolines were converted to the corresponding pyrazoles in good yields under heterogeneous and solvent-free conditions by N,N′,N,N′-tetrabromo-benzene-1,3-disulfonylamide [TBBDA] at ambient temperature.

  在环境温度下，N,N',N,N'-四溴-苯-1,3-二磺酰胺 [TBBDA] 在非均相和无溶剂条件下将 1,3,5-三取代的吡唑啉以良好的产率转化为相应的吡唑.
• Mild Oxidation of 1,3,5-Trisubstituted Pyrazolines with N-Bromo-sulphonamides
  作者：Ramin Ghorbani-Vaghei、Davood Azarifar、Behrooz Maleki

  DOI：10.1002/jccs.200400200

  日期：2004.12

  1,3,5-Trisubstituted pyrazolines to pyrazoles are carried out efficiently in the presence of new reagents N,N,N',N'-tetrabromo-benzene-1,3-disulfonylamine [TBBDA] and N,N'-dibromo-N,N'-1,2-ethanediylbis-(p-toluenesulphonamide) [BNBTS] in solvent-free conditions with catalytic amounts of SiO 2 under microwave irradiation in high yields.

  在新试剂 N,N,N',N'-四溴苯-1,3-二磺酰胺 [TBBDA] 和 N,N'-二溴- N,N'-1,2-乙二基双-(对甲苯磺酰胺) [BNBTS] 在无溶剂条件下和催化量的 SiO 2 在微波照射下以高产率。
• Iron-catalyzed aerobic oxidative aromatization of 1,3,5-trisubstituted pyrazolines
  作者：Guddekoppa S. Ananthnag、Adithya Adhikari、Maravanji S. Balakrishna

  DOI：10.1016/j.catcom.2013.09.002

  日期：2014.1

  A simple and high yielding method for the synthesis of tri-substituted pyrazoles via iron(III) catalyzed aerobic oxidative aromatization of pyrazolines has been reported. The process demonstrates a variety of functional group tolerance.

  已经报道了一种简单且高产率的方法，该方法通过铁（III）催化的吡唑啉的需氧氧化芳构化合成三取代的吡唑。该过程证明了多种功能基团的耐受性。
• Unexpected ring opening of pyrazolines with activated alkynes: synthesis of 1<i>H</i>-pyrazole-4,5-dicarboxylates and chromenopyrazolecarboxylates
  作者：Sai Teja Kolla、Nageswara Rao Rayala、Balasubramanian Sridhar、China Raju Bhimapaka

  DOI：10.1039/d1ob01727f

  日期：——

  prepared by reacting pyrazolines with activated alkynes under neat conditions without a catalyst. The products were formed via unexpected ring opening of pyrazolines with the elimination of styrene/ethylene. These types of transformations are unknown and the products formed were confirmed using their spectral/analytical data. In addition, the structures of compounds 5e and 5n were confirmed by single-crystal

  1 H -Pyrazole-4,5-dicarboxylates 和 chromenopyrazole carboxylates 是通过在没有催化剂的纯净条件下使吡唑啉与活化的炔烃反应制备的。产物是通过吡唑啉的意外开环和苯乙烯/乙烯的消除而形成的。这些类型的转化是未知的，并且使用它们的光谱/分析数据确认了所形成的产物。此外，化合物5e和5n的结构通过单晶X射线分析证实。进行了对照实验以支持所提出的反应机理。

表征谱图