1-(4-氟苯基)-3,5-二甲基-1H-吡唑-4-甲醛 | 890626-54-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(4-氟苯基)-3,5-二甲基-1H-吡唑-4-甲醛
• 中文别名: 1-(4-氟苯基)-3,5-二甲基-吡唑-4-甲醛；1-(4-氟-苯基)-3,5-二甲基-1H-吡唑-4-甲醛；1-(4-氟苯基)-3,5-二甲基-4-吡唑甲醛
• 英文名称: 1-(4-fluorophenyl)-3,5-dimethyl-4-pyrazolaldehyde
• 英文别名: 1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazole-4-carbaldehyde；1-(4-fluorophenyl)-3,5-dimethylpyrazole-4-carbaldehyde
• CAS: 890626-54-7
• 化学式: C₁₂H₁₁FN₂O
• mdl: MFCD06655672
• 分子量: 218.231
• InChiKey: AXOXHQSHPSKAID-UHFFFAOYSA-N

物化性质

• 沸点：
  335.0±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933199090
• 危险标志：
  GHS07
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  1-(4-氟苯基)-3,5-二甲基-1H-吡唑-4-甲醛 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  芳基吡唑啉荧光探针的聚集诱导发光增强、阴离子传感、溶剂选择性荧光猝灭

  摘要：

  已合成并表征了 28 种含有吡唑单元的新型吡唑啉化合物。C 1和B 6的晶体结构表明，这些吡唑啉衍生物可以通过芳环的面对面堆叠形成3D层状结构，并且在不良溶剂中更倾向于形成H型聚集体。选择化合物C 4作为标准样品，研究其在THF/环己烷中的聚集诱导发射增强(AIEE)和可逆机械色致发光(MFC)行为。结果表明形成H型聚集，聚集状态下的RIR和RIV现象导致高fc下的强荧光发射行为溶剂。荧光发射光谱分析表明，C 4的荧光发射可以被氯仿选择性猝灭。同时，化合物C 4可以选择性地识别CH 2 Cl 2 中的NO 3 -。荧光猝灭机理研究表明，化合物C 4在CHCl 3溶剂或NO 3 -存在下，可被空气中的氧气氧化生成新的化合物C 4-1，导致C 4的荧光猝灭. 密度泛函理论计算也证实了这一结果。

  DOI：

  10.1016/j.dyepig.2021.110014

文献信息

• Synthesis of quinoline derivatives containing pyrazole group and investigation of their crystal structure and spectroscopic properties in relation to acidity and alkalinity of mediums
  作者：Tiegang Ren、Jie Wang、Guihui Li、Hongbin Cheng、Yongzhe Li

  DOI：10.1016/j.saa.2014.03.018

  日期：2014.8

  Two series of quinoline derivatives containing pyrazole group were synthesized and characterized by means of 1H NMR, FT-IR, MS, elemental analysis and X-ray single crystal diffraction, and their UV–vis absorption behavior and fluorescence properties were also measured. Moreover, the effects of acetic acid and triethylamine on the spectroscopic properties of synthesized products were examined with compounds

  合成了两个含吡唑基的喹啉衍生物，并通过1 H NMR，FT-IR，MS，元素分析和X射线单晶衍射对其进行了表征，并测量了它们的紫外可见吸收性能和荧光性质。此外，用化合物3a和5a检验了乙酸和三乙胺对合成产物光谱性质的影响作为例子。已经发现，所有合成的喹啉衍生物在303nm处显示最大吸收峰并且在445nm附近显示发射峰。此外，乙酸和三乙胺均可改变介质的酸度，从而影响合成产品的紫外可见吸收光谱和荧光光谱。此外，理论研究表明，喹啉环的H +和N原子的整合有利于在乙酸存在下形成新产物，这种情况下获得的产物在400 nm处显示出新的UV-vis吸收峰。
• Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3-alkyl-2-(alkylimino)thiazolidin-4-one chemotype
  作者：Mariangela Urbano、Miguel Guerrero、Subash Velaparthi、Melissa Crisp、Peter Chase、Peter Hodder、Marie-Therese Schaeffer、Steven Brown、Hugh Rosen、Edward Roberts

  DOI：10.1016/j.bmcl.2011.09.049

  日期：2011.11

  High affinity and selective S1P(4) receptor (S1P(4)-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P(4)-R agonist hit distinct from literature S1P(4)-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P(4)-R agonist activity and exquisite selectivity over the other S1P(1-3,5)-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P(4)-R signaling cascade and elucidate the molecular basis of the receptor function. (C) 2011 Elsevier Ltd. All rights reserved.
• Smoothened antagonists for hair inhibition
  作者：Jie Jack Li、Veerabahu Shanmugasundaram、Satya Reddy、Laura L. Fleischer、Zenquan Wang、Yvonne Smith、William G. Harter、Wen-Song Yue、Manju Swaroop、Ling Li、Christy Xiaodong Ji、Danielle Dettling、Bella Osak、Laura R. Fitzgerald、Robert Conradi

  DOI：10.1016/j.bmcl.2010.06.033

  日期：2010.8

  A series of aminomethylpyrazoles were prepared and evaluated using cell-based Smoothened beta-lactamase reporter assay and Smoothened binding assay. Potent Smoothened antagonists 10k and 10l were found to inhibit hair growth in vivo in the C3H/HeN mouse hair growth model. The more selective compound 10l was tested negative in the 3T3 NRU assay, indicating a low risk for causing photo-irritation and was efficacious using the C3H/HeN mouse hair growth model although it was slightly less efficacious than that of the reference compound eflornithine (7). (c) 2010 Elsevier Ltd. All rights reserved.
• Aggregation-induced luminescence enhancement, anion sensing, solvent-selective fluorescence quenching of arylpyrazoline fluorescent probe
  作者：Qiushuo Huang、Tiantian Liu、Danyang Ma、Junxia Liu、Tiegang Ren、Wenpeng Wu、Jinglai Zhang

  DOI：10.1016/j.dyepig.2021.110014

  日期：2022.2

  28 Novel pyrazoline compounds containing pyrazole units have been synthesized and characterized. The crystal structures of C1 and B6 showed that these pyrazoline derivatives could form 3D layered structures through face-to-face stacking of aromatic rings, and they were more inclined to form H-type aggregation in poor solvent. Compound C4 was selected as the standard sample to study their properties

  已合成并表征了 28 种含有吡唑单元的新型吡唑啉化合物。C 1和B 6的晶体结构表明，这些吡唑啉衍生物可以通过芳环的面对面堆叠形成3D层状结构，并且在不良溶剂中更倾向于形成H型聚集体。选择化合物C 4作为标准样品，研究其在THF/环己烷中的聚集诱导发射增强(AIEE)和可逆机械色致发光(MFC)行为。结果表明形成H型聚集，聚集状态下的RIR和RIV现象导致高fc下的强荧光发射行为溶剂。荧光发射光谱分析表明，C 4的荧光发射可以被氯仿选择性猝灭。同时，化合物C 4可以选择性地识别CH 2 Cl 2 中的NO 3 -。荧光猝灭机理研究表明，化合物C 4在CHCl 3溶剂或NO 3 -存在下，可被空气中的氧气氧化生成新的化合物C 4-1，导致C 4的荧光猝灭. 密度泛函理论计算也证实了这一结果。