1-(4-fluorophenyl)-2-(4-pyridyl)cyclopentene | 1014718-63-8

• 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: 1-(4-fluorophenyl)-2-(4-pyridyl)cyclopentene
• 英文别名: 2-(4-fluorophenyl)-1-(pyridin-4-yl)cyclopentene；4-(4-Fluorophenyl)-4-oxo-3-(pyridin-4-yl)butanal；4-[2-(4-fluorophenyl)cyclopenten-1-yl]pyridine
• CAS: 1014718-63-8
• 化学式: C₁₆H₁₄FN
• 分子量: 239.292
• InChiKey: ARGQQNXCNPXUIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  C₁₆H₁₆FNO 在 硫酸 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以54%的产率得到1-(4-fluorophenyl)-2-(4-pyridyl)cyclopentene
  参考文献：
  名称：

  Role of the Hydrogen Bonding Heteroatom−Lys53 Interaction between the p38α Mitogen-Activated Protein (MAP) Kinase and Pyridinyl-Substituted 5-Membered Heterocyclic Ring Inhibitors

  摘要：

  In the framework of Investigating the role of heteroatoms in pyridinyl-substituted 5-membered (hetero)cycles as potential p38 alpha MAP kinase inhibitor scaffolds, cyclopentene, pyrrole, furan, and imidazole analogues were synthesized and tested with respect to their ability to inhibit p38a MAP kinase. The vicinal pyridine/4-fluorophenyl pharmacophore was conserved, such as in the prototypical imidazole inhibitor SB203580. The strength of the HB interaction was calculated and compared to the biological data.

  DOI：

  10.1021/jm801467h

文献信息

• A Convenient Synthesis of 1-(4-Fluorophenyl)-2-(4-pyridyl)cyclopentene from Cyclopentanone
  作者：Stefan Laufer、Bassam Abu Thaher、Pierre Koch、Vicente Del Amo、Paul Knochel

  DOI：10.1055/s-2007-1000855

  日期：2008.1

  of pyridyl-substituted five-membered heterocycles as potential p38 mitogen-activated protein kinase inhibitors, we synthesized the disubstituted carbocyclic analogue, 1-(4-fluorophenyl)-2-(4-pyridyl)cyclopentene. A multistep synthesis of this compound starting from cyclopentanone is reported. Cyclopentanone was converted into 1-cy--clo-pentenyl-4-fluorobenzene using a Grignard reaction. The oxidation

  在研究吡啶基取代的五元杂环作为潜在的 p38 丝裂原活化蛋白激酶抑制剂的作用的框架内，我们合成了二取代的碳环类似物 1-(4-fluorophenyl)-2-(4-pyridyl)cyclopentene。报道了从环戊酮开始的这种化合物的多步合成。使用格氏反应将环戊酮转化为 1-环-氯-戊烯基-4-氟苯。该产物用过氧化氢和甲酸氧化得到2-(4-氟苯基)环戊酮。该酮使用钕盐(NdCl 3 ·2LiCl)活化，随后与络合格氏试剂(pyMgCl·LiCl)反应，得到相应的环戊醇衍生物。最后，后一种醇的脱水得到标题化合物。
• Role of the Hydrogen Bonding Heteroatom−Lys53 Interaction between the p38α Mitogen-Activated Protein (MAP) Kinase and Pyridinyl-Substituted 5-Membered Heterocyclic Ring Inhibitors
  作者：Bassam Abu Thaher、Pierre Koch、Verena Schattel、Stefan Laufer

  DOI：10.1021/jm801467h

  日期：2009.4.23

  In the framework of Investigating the role of heteroatoms in pyridinyl-substituted 5-membered (hetero)cycles as potential p38 alpha MAP kinase inhibitor scaffolds, cyclopentene, pyrrole, furan, and imidazole analogues were synthesized and tested with respect to their ability to inhibit p38a MAP kinase. The vicinal pyridine/4-fluorophenyl pharmacophore was conserved, such as in the prototypical imidazole inhibitor SB203580. The strength of the HB interaction was calculated and compared to the biological data.