4-(5-oxo-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzonitrile | 118049-54-0

• 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: 4-(5-oxo-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzonitrile
• 英文别名: 4-(5-oxo-3-phenyl-4H-pyrazol-1-yl)benzonitrile
• CAS: 118049-54-0
• 化学式: C₁₆H₁₁N₃O
• mdl: MFCD13638280
• 分子量: 261.283
• InChiKey: KIDROXHDSAMXBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  211-212 °C(Solv: methanol (67-56-1))
• 沸点：
  452.3±47.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-oxo-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzonitrile 在 吡啶 、 (-)-(5aS,10bR)-5a,10b-二氢-2-(2,4,6-三甲基苯基)-4H,6H-茚并[2,1-b][1,2,4]三唑[4,3-d][1,4]氯化恶唑鎓一水合物 、 3,3',5,5'-四叔丁基-4,4'-联苯醌 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 48.17h， 生成 (S)-4-(1,10-dioxo-4,6,8-triphenyl-2,3-diazaspiro[4.5]deca-3,6,8-trien-2-yl)benzonitrile
  参考文献：
  名称：

  NHC催化的Enals的形式[3 + 3]环状反应对映体合成螺环己二酮

  摘要：

  在氧化的N-杂环卡宾（NHC）催化下，α，β-不饱和醛与α-亚芳基吡唑啉酮的反应证明了吡唑啉酮稠合的螺环己二酮的对映选择性。这种原子经济和正式的[3 + 3]环状反应通过乙烯基迈克尔加成/螺环化/脱氢级联反应进行，以中等到良好的产率和优异的ee值提供具有全碳四元立体中心的螺环化合物。该反应成功的关键是由NHC协同产生的手性α，β-不饱和酰基偶氮鎓和碱基介导的吡唑啉酮类的二烯酸酯/烯酸酯中间体的串联生成。

  DOI：

  10.1002/anie.201507802
• 作为产物：
  描述：

  4-肼苯腈 、 苯甲酰乙酸乙酯 在 溶剂黄146 作用下， 反应 8.0h， 生成 4-(5-oxo-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzonitrile
  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

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 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.
• Identification, synthesis and evaluation of SARS-CoV and MERS-CoV 3C-like protease inhibitors
  作者：Vathan Kumar、Kian-Pin Tan、Ying-Ming Wang、Sheng-Wei Lin、Po-Huang Liang

  DOI：10.1016/j.bmc.2016.05.013

  日期：2016.7

  Severe acute respiratory syndrome (SARS) led to a life-threatening form of atypical pneumonia in late 2002. Following that, Middle East Respiratory Syndrome (MERS-CoV) has recently emerged, killing about 36% of patients infected globally, mainly in Saudi Arabia and South Korea. Based on a scaffold we reported for inhibiting neuraminidase (NA), we synthesized the analogues and identified compounds with low micromolar inhibitory activity against 3CL(pro) of SARS-CoV and MERS-CoV. Docking studies show that a carboxylate present at either R-1 or R-4 destabilizes the oxyanion hole in the 3CL(pro). Interestingly, 3f, 3g and 3m could inhibit both NA and 3CL(pro) and serve as a starting point to develop broad-spectrum antiviral agents. (C) 2016 Elsevier Ltd. All rights reserved.
• Identification, Synthesis, and Evaluation of New Neuraminidase Inhibitors
  作者：Vathan Kumar、Chih-Kang Chang、Kian-Pin Tan、Young-Sik Jung、Shih-Hsun Chen、Yih-Shyun E. Cheng、Po-Huang Liang

  DOI：10.1021/ol502410x

  日期：2014.10.3

  High-throughput screening was performed on similar to 6800 compounds to identify KR-72039 as an inhibitor of H1N1 and H5N1 neuraminidases (NAs). Structureactivity relationship studies led to 3e, which inhibited H5N1 NA with an IC50 of 2.8 mu M and blocked viral replication. Docking analysis shows that compounds bind to loop-430 around the NA active site. Compound 3l additionally inhibited H7N9 NA, making it a dual inhibitor of N1- and N2-type NAs.
• 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。