3-phenyl-1-(4-isopropylphenyl)pyrazol-5(4H)-one | 1078132-25-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-phenyl-1-(4-isopropylphenyl)pyrazol-5(4H)-one
• 英文别名: 5-phenyl-2-(4-propan-2-ylphenyl)-4H-pyrazol-3-one
• CAS: 1078132-25-8
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: JJTGXUTYDAEYJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenyl-1-(4-isopropylphenyl)pyrazol-5(4H)-one 在 吡啶 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.17h， 生成 2-(4-isopropylphenyl)-4,9-diphenyl-6,7-di-p-tolyl-2,3-diazaspiro[4.4]nona-3,6,8-trien-1-one
  参考文献：
  名称：

  Rh（III）催化的形式sp 3 C–H活化/环合反应合成螺戊二烯吡唑啉酮

  摘要：

  已经开发了用Rh催化烯醇定向的形式sp 3 C–H活化/环炔基的α-亚芳基吡唑啉酮。该反应提供了在室温下以良好至优异的产率合成螺戊二烯吡唑啉酮的便利途径，表现出良好的官能团耐受性，克可扩展性和高区域选择性。值得注意的是，α-亚芳基吡唑啉酮是在C–H活化/环化反应中作为新型C3合成子引入的。

  DOI：

  10.1021/acs.orglett.7b00930
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 、 4-异丙基苯肼盐酸盐 在 溶剂黄146 、 三乙胺 作用下， 反应 20.0h， 以81%的产率得到3-phenyl-1-(4-isopropylphenyl)pyrazol-5(4H)-one
  参考文献：
  名称：

  Synthesis and evaluation of pyrazolone compounds as SARS-coronavirus 3C-like protease inhibitors

  摘要：

  A series of pyrazolone compounds as possible SARS-CoV 3CL protease inhibitors were designed, synthesized, and evaluated by in vitro protease assay using fluorogenic substrate peptide in which several showed potent inhibition against the 3CL protease. Interestingly, one of the inhibitors was also active against 3C protease from coxsackievirus B3. These inhibitors could be potentially developed into anti-coronaviral and anti-picornaviral agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.050

文献信息

• A highly diastereoselective (5+1) annulation of allenoates and pyrazolones catalyzed by CH₃OK
  作者：Jingxiong Lai、You Huang

  DOI：10.1039/d3cc05751h

  日期：——

  A CH₃OK catalyzed [5+1] annulation was developed using a newly designed allene with 1,5-biselectroephilic properties.

  利用一种新设计的具有 1,5 双嗜酸特性的烯烃，开发了一种 CH3OK 催化的 [5+1] 环化反应。
• Synthesis, biological evaluation and SAR study of novel pyrazole analogues as inhibitors of Mycobacterium tuberculosis
  作者：Daniele Castagnolo、Alessandro De Logu、Marco Radi、Beatrice Bechi、Fabrizio Manetti、Matteo Magnani、Sibilla Supino、Rita Meleddu、Lorenza Chisu、Maurizio Botta

  DOI：10.1016/j.bmc.2008.08.016

  日期：2008.9

  As a continuation of our previous work that turned toward the identification of antimycobacterial compounds with innovative structures, two series of pyrazole derivatives were synthesized by parallel solution-phase synthesis and were assayed as inhibitors of Mycobacterium tuberculosis (MTB), which is the causative agent of tuberculosis. One of these compounds showed high activity against MTB (MIC = 4 mu g/mL). The newly synthesized pyrazoles were also computationally investigated to analyze their fit properties to the pharmacophoric model for antitubercular compounds previously built by us and to re. ne structure-activity relationship analysis. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Spiropentadiene Pyrazolones by Rh(III)-Catalyzed Formal sp³ C–H Activation/Annulation
  作者：Jiuan Zheng、Panpan Li、Meng Gu、Aijun Lin、Hequan Yao

  DOI：10.1021/acs.orglett.7b00930

  日期：2017.6.2

  pyrazolones with alkynes has been developed. This reaction provides a convenient route to synthesize spiropentadiene pyrazolones in good to excellent yields at room temperature, exhibiting good functional group tolerance, gram scalability, and high regioselectivity. Of note, the α-arylidene pyrazolone was introduced as a novel C3 synthon in C–H activation/annulation.

  已经开发了用Rh催化烯醇定向的形式sp 3 C–H活化/环炔基的α-亚芳基吡唑啉酮。该反应提供了在室温下以良好至优异的产率合成螺戊二烯吡唑啉酮的便利途径，表现出良好的官能团耐受性，克可扩展性和高区域选择性。值得注意的是，α-亚芳基吡唑啉酮是在C–H活化/环化反应中作为新型C3合成子引入的。
• Synthesis and evaluation of pyrazolone compounds as SARS-coronavirus 3C-like protease inhibitors
  作者：R. Ramajayam、Kian-Pin Tan、Hun-Ge Liu、Po-Huang Liang

  DOI：10.1016/j.bmc.2010.09.050

  日期：2010.11.15

  A series of pyrazolone compounds as possible SARS-CoV 3CL protease inhibitors were designed, synthesized, and evaluated by in vitro protease assay using fluorogenic substrate peptide in which several showed potent inhibition against the 3CL protease. Interestingly, one of the inhibitors was also active against 3C protease from coxsackievirus B3. These inhibitors could be potentially developed into anti-coronaviral and anti-picornaviral agents. (C) 2010 Elsevier Ltd. All rights reserved.