<5-(4-fluorophenyl)-1H-pyrazol-3-yl>acetonitrile | 153391-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: <5-(4-fluorophenyl)-1H-pyrazol-3-yl>acetonitrile
• 英文别名: 2-(5-(4-fluorophenyl)-1H-pyrazol-3-yl)acetonitrile；2-[3-(4-fluorophenyl)-1H-pyrazol-5-yl]acetonitrile
• CAS: 153391-41-4
• 化学式: C₁₁H₈FN₃
• 分子量: 201.203
• InChiKey: YUEINQRCAODONE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <5-(4-fluorophenyl)-1H-pyrazol-3-yl>acetonitrile 在 sodium t-butanolate 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 (E)-2-[5-(4-Fluoro-phenyl)-1H-pyrazol-3-yl]-3-(1H-pyrrol-2-yl)-acrylonitrile
  参考文献：
  名称：

  Synthesis of E - and Z -Pyrazolylacrylonitriles and their evaluation as novel antioxidants

  摘要：

  A facile synthesis of (Z)- and (E)-2-(5-arylpyrazol-3-yl)-3-(pyrrol-2-yl)acrylonitriles and (Z)-2-(1,3-diarylpyrazol-5-yl)-3-(pyrrol-2-yl)acrylonitriles, and isomerisation of (Z)-2-(5-arylpyrazolyl)acrylonitriles to (E)-2-(5-arylpyrazolyl)acrylonitriles under basic conditions have been reported. (Z)-2-(1,3-Diarylpyrazolyl)acrylonitrile did not undergo isomerisation under the similar conditions. New compounds were identified on the basis of their spectral data (H-1-, C-13-, H-1-H-1 COSY, NOESY, NOE, HMQC NMR, IR, UV and EI mass). The structures of one acrylonitrile and five of their precursor 6-arylpyran-2-ones and cyanomethylpyrazoles were confirmed by X-ray crystallographic studies. Effects of pyrazolylacrylonitriles and their precursors on rat liver-microsomal lipid peroxidation were evaluated in vitro with a view to establish structure-activity relationship and to identify a lead compound. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00056-5
• 作为产物：
  描述：

  4-氟苯乙酮 在 potassium hydroxide 、 肼 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 <5-(4-fluorophenyl)-1H-pyrazol-3-yl>acetonitrile
  参考文献：
  名称：

  高荧光吡唑和咪唑杂环的光物理和电化学研究

  摘要：

  研究了高度稠合的吡唑和咪唑环含杂环的光物理和电化学性质。在DMF介质中使用B3LYP / G（d，p）能级理论对分子进行TDDFT计算，结果与实验值吻合良好。咪唑衍生物显示出红移吸收峰（λ最大，455-474纳米）和较高的摩尔消光系数大于吡唑衍生物。在从吡唑到咪唑的π共轭增加的情况下，观察到发射最大值（537nm-565nm）中的红移。吸收和发射光谱的这些初步结果表明，这些分子可能具有有机应用的潜力。

  DOI：

  10.1016/j.dyepig.2016.09.030

文献信息

• Synthetic, Structural, and Anticancer Activity Evaluation Studies on Novel Pyrazolylnucleosides
  作者：Yadav、Sharma、Kaushik、Kumar、Jha、Prasad、Len、Malhotra、Wengel、Parmar

  DOI：10.3390/molecules24213922

  日期：——

  The synthesis of novel pyrazolylnucleosides 3a–e, 4a–e, 5a–e, and 6a–e are described. The structures of the regioisomers were elucidated by using extensive NMR studies. The pyrazolylnucleosides 5a–e and 6a–e were screened for anticancer activities on sixty human tumor cell lines. The compound 6e showed good activity against 39 cancer cell lines. In particular, it showed significant inhibition against

  描述了新型吡唑基核苷 3a-e、4a-e、5a-e 和 6a-e 的合成。通过使用广泛的核磁共振研究阐明了区域异构体的结构。吡唑基核苷 5a-e 和 6a-e 已在 60 种人类肿瘤细胞系中筛选抗癌活性。化合物6e对39种癌细胞系显示出良好的活性。特别是，它对肺癌细胞系 Hop-92 (GI50 9.3 µM) 和乳腺癌细胞系 HS 578T (GI50 3.0 µM) 显示出显着的抑制作用。
• Kumar, Ajay; Husain, Mofazzal; Prasad, Ashok K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 8, p. 1950 - 1957
  作者：Kumar, Ajay、Husain, Mofazzal、Prasad, Ashok K.、Singh, Ishwar、Vats, Archana、Sharma, Nawal K.、Sharma, Sunil K.、Gupta, Rajinder K.、Olsend, Carl E.、Bracke, Marc E.、Gross, Richard A.、Parmar, Virinder S.

  DOI：——

  日期：——
• A carbanion induced synthesis of highly congested pyrazole and imidazole containing heterocycles
  作者：Hardesh K. Maurya、Atul Gupta

  DOI：10.1016/j.tetlet.2014.01.095

  日期：2014.3

  An efficient approach to the synthesis of highly congested di, penta and hexacyclic pyrazoles as well as imidazole fragment containing novel heterocyclic molecule has been developed through a carbanion induced transformation of suitably functionalized 2H-pyran-2-ones, benzo[h]chromene and thiochromeno[4,3-b]pyrans. Due to the presence of fluorescence, we report their prime application metal sensor as off/on switching in ferric ions. (C) 2014 Elsevier Ltd. All rights reserved.
• Parmar, Virinder S.; Jain, Subhash C.; Jha, Amitabh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 10, p. 872 - 879
  作者：Parmar, Virinder S.、Jain, Subhash C.、Jha, Amitabh、Kumar, Naresh、Kumar, Ajay、Vats, Archana、Jha, Hriday N.、Mukherjee, Shubhasish、Singh, Sanjay K.、Jennings, Keith R.、Summerfield, Scott G.、Errington, William、Olsen, Carl E.

  DOI：——

  日期：——
• Ram, Vishnu Ji; Haque, Navedul; Singh, Sanjay Kumar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 9, p. 924 - 928
  作者：Ram, Vishnu Ji、Haque, Navedul、Singh, Sanjay Kumar、Hussaini, Falak Anwer、Shoeb, Aboo

  DOI：——

  日期：——