<5-(4-methoxyphenyl)-1H-pyrazol-3-yl>acetonitrile | 134161-75-4

• 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-methoxyphenyl)-1H-pyrazol-3-yl>acetonitrile
• 英文别名: 2-(5-(4-methoxyphenyl)-1H-pyrazol-3-yl)acetonitrile；2-[3-(4-methoxyphenyl)-1H-pyrazol-5-yl]acetonitrile
• CAS: 134161-75-4
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: ZVGCJBIDARLIMB-UHFFFAOYSA-N

物化性质

• 熔点：
  150 °C
• 沸点：
  460.3±40.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <5-(4-methoxyphenyl)-1H-pyrazol-3-yl>acetonitrile 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.5h， 生成 2′-deoxy-1′-(5-cyanomethyl-3-p-methoxyphenyl)pyrazolyl-β-D-ribofuranose
  参考文献：
  名称：

  新型吡唑核苷的合成、结构和抗癌活性评价研究

  摘要：

  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。

  DOI：

  10.3390/molecules24213922
• 作为产物：
  描述：

  6-(4-methoxyphenyl)-3-cyano-4-methylsulfanyl-2H-pyran-2-one 在 一水合肼 作用下， 以 甲醇 为溶剂， 生成 <5-(4-methoxyphenyl)-1H-pyrazol-3-yl>acetonitrile
  参考文献：
  名称：

  取代的苯并[ h ]喹唑啉，苯并[ g ]吲唑，吡唑，2,6-二芳基吡啶作为抗结核药的研究

  摘要：

  各种取代的5,6-二氢-8-甲氧基苯并[ h ]喹唑啉-2-胺，1-（3-（4-烷氧基苯基）-7-甲氧基-3,3a，4,5-四氢-2 H苯并[ g通过有效的方法以高收率合成了吲唑-2-基）乙酮，吡唑和2,6-二芳基吡啶衍生物。合成的化合物（4 - 23），用于对它们的体外抗结核病活性进行了评估结核分枝杆菌分枝杆菌H37Rv菌株。化合物6a，6c，8a，19a和19e在MIC值为50、100、50、25和100μM的浓度下表现出显着的抗结核活性。使用THP-1细胞的体外细胞毒性数据表明，大多数活性化合物19a都是安全的，因为其MIC值远低于细胞毒性值。

  DOI：

  10.1016/j.bmcl.2013.08.101

文献信息

• Photophysical and electrochemical studies of highly fluorescent pyrazole and imidazole containing heterocycles
  作者：Hardesh K. Maurya、Ch. Pavan Kumar、M. Chandrasekharam、Atul Gupta

  DOI：10.1016/j.dyepig.2016.09.030

  日期：2017.1

  Highly congested pyrazole and imidazole ring containing heterocycles were studied for their photophysical and electrochemical properties. TDDFT calculations of the molecules were carried out using B3LYP/G(d,p) level theory in DMF medium and the results were in good agreement with the experimental values. The imidazole derivatives showed a red shifted absorption peak (λmax, 455–474 nm) and higher molar

  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。
• Choline chloride as an efficient catalyst for the synthesis of styryl-pyrazoles
  作者：Hardesh K. Maurya、Kripa Shankar Nainawat、Atul Gupta

  DOI：10.1080/00397911.2016.1185124

  日期：2016.6.17

  ABSTRACT An efficient and green methodology for syntheses of various styryl-pyrazoles (3) from the reaction of 2-(5-phenyl-1H-pyrazol-3-yl)acetonitriles (1) with substituted benzaldehydes (2) by the use of biodegradable, nonhazardous, naturally occurring, and inexpensive choline chloride and NaOH under an environmentally benign medium has been described. GRAPHICAL ABSTRACT

  摘要 利用可生物降解的 2-(5-苯基-1H-吡唑-3-基)乙腈 (1) 与取代苯甲醛 (2) 反应合成各种苯乙烯基-吡唑 (3) 的高效绿色方法已经描述了在环境无害的介质下使用无害、天然存在且价格低廉的氯化胆碱和 NaOH。图形概要
• 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.
• Synthesis of E - and Z -Pyrazolylacrylonitriles and their evaluation as novel antioxidants
  作者：Virinder S Parmar、Ajay Kumar、Ashok K Prasad、Sanjay K Singh、Naresh Kumar、Shubhasish Mukherjee、Hanumantharao G Raj、Sanjay Goel、William Errington、Mohindar S Puar

  DOI：10.1016/s0968-0896(99)00056-5

  日期：1999.7

  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.