3-(3,5-difluorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde | 1223062-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(3,5-difluorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 3-(3,5-Difluorophenyl)-1-phenylpyrazole-4-carbaldehyde
• CAS: 1223062-45-0
• 化学式: C₁₆H₁₀F₂N₂O
• 分子量: 284.265
• InChiKey: IPESYQDYERLCLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,5-difluorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde 在 ammonium acetate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  (1,3-Diphenyl-1H-Pyrazol-4-yl)-Methylamine Analogues as Inhibitors of Dipeptidyl Peptidases

  摘要：

  AbstractA number of pyrazole compounds reported in literatures elicit anti‐hyperglycemic effects. By modifying the side chain of the heterocyclic skeleton, a new chemical class of DPP‐IV inhibitors structurally derived from the (pyrazol‐4‐yl)‐methylamine scaffold have been discovered and evaluated the biological activities of these inhibitors against DPP‐IV, DPP8, DPP‐II and FAP. The SAR studies showed the (1,3‐diphenyl‐1H‐pyrazol‐4‐yl)‐methylamines with 2,4‐dichloro substituents at the 3‐phenyl ring selectively preferred as DPP‐IV inhibitors, whereas with difluoro substituents at the 3‐phenyl ring selectively preferred as DPP8 inhibitors. The binding mode of representative compound 15h at the active site of DPP‐IV was predicted by computer model. In additional, 15h exhibited the ability to significantly decrease the glucose excursion in mice.

  DOI：

  10.1002/jccs.200900152
• 作为产物：
  描述：

  、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 0.5h， 生成 3-(3,5-difluorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  (1,3-Diphenyl-1H-Pyrazol-4-yl)-Methylamine Analogues as Inhibitors of Dipeptidyl Peptidases

  摘要：

  AbstractA number of pyrazole compounds reported in literatures elicit anti‐hyperglycemic effects. By modifying the side chain of the heterocyclic skeleton, a new chemical class of DPP‐IV inhibitors structurally derived from the (pyrazol‐4‐yl)‐methylamine scaffold have been discovered and evaluated the biological activities of these inhibitors against DPP‐IV, DPP8, DPP‐II and FAP. The SAR studies showed the (1,3‐diphenyl‐1H‐pyrazol‐4‐yl)‐methylamines with 2,4‐dichloro substituents at the 3‐phenyl ring selectively preferred as DPP‐IV inhibitors, whereas with difluoro substituents at the 3‐phenyl ring selectively preferred as DPP8 inhibitors. The binding mode of representative compound 15h at the active site of DPP‐IV was predicted by computer model. In additional, 15h exhibited the ability to significantly decrease the glucose excursion in mice.

  DOI：

  10.1002/jccs.200900152

文献信息

• Ionic Liquid [HNMP][HSO₄] Promoted One Pot Synthesis of 1,4- Dihydropyridine Derivatives at Room Temperature
  作者：Gopinath D. Shirole、Ramesh A. Mokal、Sharad N. Shelke

  DOI：10.2174/1570178614666170614085815

  日期：2017.8.22

  a diversity of other functional groups. Conclusion: In summary, we developed a new protocol for the synthesis of various diethyl 1,4- dihydro-2,6-dimethyl-4-(3-aryl-1-phenyl-1H-pyrazol-4-yl)pyridine-3,5-dicarboxylate derivatives using acidic ionic liquid [HNMP] [HSO4] as a highly efficient catalyst. The DHPs 4a-j were obtained by simply stirring at room temperature for appropriate time. A significant

  背景：各种1,4-二氢-2,6-二甲基-4-（3-芳基-1-苯基-1 H-吡唑-4-基）吡啶-3,5-二羧酸二乙酯的高效绿色合成在3-甲基-1-吡咯烷鎓硫酸氢盐[HNMP] [HSO 4 ]存在下，通过3-芳基-1-苯基-1 H-吡唑-4-羧醛，乙酰乙酸乙酯和NH4OAc的多组分缩合反应获得衍生物。作为乙醇中的催化剂。通过在室温下在密封管中简单搅拌合适的时间，已经合成了一系列的1，4-二氢吡啶（DHP）衍生物。该协议具有许多好处，包括简单的后处理程序，出色的产量和环境友好的条件。 方法：在25 mL密封管中装入3-芳基-1-苯基-1 H-吡唑-4-甲醛1（1 mmol），乙酰乙酸乙酯2（0.130 g，2 mmol），NH4OAc 3（0.085）的混合物。（1.2毫摩尔）和100毫克离子液体[HNMP] [HSO 4 ]在10毫升乙醇中的溶液。然后将密封管加盖，并将反应混合物在室温下使用
• Pumice-based sulfonic acid: a sustainable and recyclable acidic catalyst for one-pot synthesis of pyrazole anchored 1,4-dihydropyridine derivatives at room temperature
  作者：Adinath Tambe、Gayatri Sadaphal、Ravindra Dhawale、Gopinath Shirole

  DOI：10.1007/s11164-021-04649-7

  日期：2022.3

  for the synthesis of pyrazole anchored 1,4-dihydropyridine analogs using pumice-based sulfonic acid (pumice@SO3H) as a recyclable solid acid catalyst under simple stirring at room temperature. The present protocol proceeded smoothly with 1,3-diaryl pyrazole-4-carbaldehydes, ethyl acetoacetate, and NH4OAc in ethanol as a solvent with excellent yield. The pumice-based sulfonic acid catalyst is easily

  在本研究中，我们开发了一种高效且环保的方案，用于使用浮石基磺酸 (pumice@SO 3 H) 作为可回收固体酸催化剂，在简单搅拌条件下合成吡唑锚定的 1,4-二氢吡啶类似物。室内温度。本议定书使用 1,3-二芳基 pyrazole-4-carbaldehydes、乙酰乙酸乙酯和 NH 4顺利进行乙醇中的 OAc 作为溶剂，收率极佳。浮石基磺酸催化剂很容易由天然浮石通过与氯磺酸的简单搅拌来制备。该催化剂的主要特点是其非均相性、高孔隙率、无腐蚀、无毒、可回收、在室温下稳定高效。这种催化剂的应用使该协议对环境更加友好。 图形概要
• Shirole; Tambe; Shelke, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, <hi>2020</hi>, vol. 59, # 4, p. 459 - 464
  作者：Shirole、Tambe、Shelke

  DOI：——

  日期：——