1-(4-chlorophenyl)-3-methyl-5-phenyl-1H-pyrazole | 94206-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-chlorophenyl)-3-methyl-5-phenyl-1H-pyrazole
• 英文别名: 1-(4-chlorophenyl)-3-methyl-5-phenylpyrazole
• CAS: 94206-80-1
• 化学式: C₁₆H₁₃ClN₂
• mdl: MFCD02642740
• 分子量: 268.746
• InChiKey: WYDINWZOIUBJAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-chlorophenyl)-3-methyl-5-phenyl-1H-pyrazole 在 四氯化碳 、 氯 作用下， 生成 4-chloro-1-(4-chloro-phenyl)-3-methyl-5-phenyl-1H-pyrazole
  参考文献：
  名称：

  230.氯裂解二-（3-甲基-1：5-二苯基-4-吡唑基）二硫化物

  摘要：

  DOI：

  10.1039/jr9580001171
• 作为产物：
  描述：

  1-(4-chlorophenyl)-3-methyl-5-phenylpyrazoline 在 iron(III) chloride 作用下， 以 溶剂黄146 为溶剂， 以95%的产率得到1-(4-chlorophenyl)-3-methyl-5-phenyl-1H-pyrazole
  参考文献：
  名称：

  铁催化的1,3,5-三取代吡唑啉的好氧氧化芳构化

  摘要：

  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。

  DOI：

  10.1016/j.catcom.2013.09.002

文献信息

• Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: synthesis of <i>N</i>-arylpyrazoles
  作者：Jidan Liu、Erjie Xu、Jinyuan Jiang、Zeng Huang、Liyao Zheng、Zhao-Qing Liu

  DOI：10.1039/c9cc09657d

  日期：——

  A general method for the synthesis of structurally diverse N-arylpyrazoles from readily available cyclopropanols and aryldiazonium salts is disclosed. The reaction was conducted at room temperature within minutes with a broad substrate scope and excellent regioselectivity.

  公开了一种由容易获得的环丙醇和芳基重氮盐合成结构多样的N-芳基吡唑的通用方法。该反应在室温下在数分钟内以宽的底物范围和优异的区域选择性进行。
• TBHP/Cu(OAc)₂ mediated oxidation of pyrazolines: A convenient method for the preparation of pyrazoles
  作者：Sai Teja Kolla、Ramya Somanaboina、China Raju Bhimapaka

  DOI：10.1080/00397911.2021.1885716

  日期：2021.5.3

  Abstract An efficient and simple oxidative protocol has been developed for the preparation of pyrazoles from pyrazolines mediated by TBHP/Cu(OAc)2 at room temperature. The present protocol has been successfully applied for the preparation of various pyrazole compounds from heterocyclic pyrazolines.

  摘要 已经开发出一种有效且简单的氧化方案，用于在室温下从由TBHP / Cu（OAc）2介导的吡唑啉制备吡唑。本方案已成功地用于从杂环吡唑啉制备各种吡唑化合物。
• Intramolecular oxidative C–N bond formation under metal-free conditions: One-pot global functionalization of pyrazole ring
  作者：Mohit K. Tiwari、Ashif Iqubal、Parthasarathi Das

  DOI：10.1016/j.tet.2022.133059

  日期：2022.11

  of intermediate free-radical species followed by intramolecular oxidative C–N bond formation afforded the desired pyrazole moiety. The synthetic versatility of this methodology is further highlighted by preparing a diverse range of substrates including di-/tri-/and tetra-substituted pyrazoles, and applying the methodology in the practical synthesis of bioactive scaffolds.

  在此，我们报告了一种有效的 DTBP 促进和 NaI 催化的更环保的方案，用于通过C(sp 2 )-H 键功能化合成高度取代的吡唑。该协议是通用的，并且通过结合使用溶剂t -BuOH 和 EtOH 可以显着提高反应效率，从而以良好至优异的产率产生多种取代的吡唑。包括自由基捕获实验在内的机理研究表明原位中间自由基物质的产生，然后是分子内氧化C-N键的形成，提供了所需的吡唑部分。通过制备包括二/三/和四取代吡唑在内的多种底物，并将该方法应用于生物活性支架的实际合成，进一步突出了该方法的合成多功能性。
• Synthesis of Functionalized Pyrazoles via Vanadium-Catalyzed C–N Dehydrogenative Cross-Coupling and Fluorescence Switch-On Sensing of BSA Protein
  作者：Dinabandhu Sar、Raghunath Bag、Afsana Yashmeen、Subhendu Sekhar Bag、Tharmalingam Punniyamurthy

  DOI：10.1021/acs.orglett.5b02669

  日期：2015.11.6

  Vanadium-catalyzed C-N dehydrogenative cross-coupling of alkenyl hydrazones leading to functionalized pyrazoles is described in a 1:1 mixture of toluene/H2O using air as the terminal oxidant. Significant practical features include use of the commercial nontoxic VOSO4 as a recyclable catalyst, mild reaction conditions, scalability, and the broad substrate scope. Some of the product pyrazoles exhibit interesting photophysical properties. Fluorescence light-up sensing of BSA protein by one of the pyrazoles is also highlighted.
• Oxone-mediated facile access to substituted pyrazoles
  作者：Mitsuhiro Kashiwa、Yoshiyuki Kuwata、Motohiro Sonoda、Shinji Tanimori

  DOI：10.1016/j.tet.2015.11.035

  日期：2016.1

  An Oxone-mediated transition-metal-free oxidative C-N bond formation has been achieved for the regio-selective synthesis of substituted pyrazoles. The reactions accompany the chelation-controlled ortho-oxidation of N-substituted aromatic ring to provide phenol derivatives in some cases. This method displays a facile access to diverse range of substituted pyrazoles from readily accessible hydrazones. (C) 2015 Elsevier Ltd. All rights reserved.