3-chloro-5-(trifluoromethyl)(2-pyridyl) phenyl ketone | 339010-42-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-chloro-5-(trifluoromethyl)(2-pyridyl) phenyl ketone
• 英文别名: 2-Benzoyl-3-chloro-5-(trifluoromethyl)pyridine；[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-phenylmethanone
• CAS: 339010-42-3
• 化学式: C₁₃H₇ClF₃NO
• 分子量: 285.653
• InChiKey: BMGWEDZKCXRPNQ-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C
• 沸点：
  341.0±42.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-二氟苯硼酸 、 3-chloro-5-(trifluoromethyl)(2-pyridyl) phenyl ketone 在 dihydrogen dichloro-bis(di-tert-butylphosphinito-κP)palladium(2-) caesium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 以79%的产率得到[3-(3,5-Difluoro-phenyl)-5-trifluoromethyl-pyridin-2-yl]-phenyl-methanone
  参考文献：
  名称：

  Use of highly reactive, versatile and air-stable palladium–phosphinous acid complex [(t-Bu)2P(OH)]2PdCl2 (POPd) as a catalyst for the optimized Suzuki–Miyaura cross-coupling of less reactive heteroaryl chlorides and arylboronic acids

  摘要：

  Using highly reactive air-stable palladium-phosphinous acid complex [(t-Bu)(2)P(OH)](2)PdCl2 (POPd) as a catalyst, synthesis of heteroaryl-aryl cross-coupled products via palladium-catalyzed Suzuki-Miyaura coupling of less reactive substituted 3-chloropyridines with arylboronic acids was achieved in high yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.010
• 作为产物：
  描述：

  2-[3-chloro-5-(trifluoromethyl)(2-pyridyl)]-2-phenylethanenitrile 在 双(三甲基硅烷基)氨基钾 、 air 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 以98%的产率得到3-chloro-5-(trifluoromethyl)(2-pyridyl) phenyl ketone
  参考文献：
  名称：

  3-[4-(Methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) Phenyl Ketone as a Potent and Orally Active Cyclooxygenase-2 Selective Inhibitor:  Synthesis and Biological Evaluation

  摘要：

  Incorporation of a spacer group between the central scaffold and the aryl ring resulted in a new cyclooxygenase-2 (COX-2) selective inhibitor core structure, 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) phenyl ketone (20), with COX-2 IC50 = 0.25 mu M and COX-1 IC50 = 14 mu M (human whole blood assay). Compound 20 was orally active in the rat air pouch model of inflammation, inhibiting white blood cell infiltration and COX-2-derived PG production. Our data support the identification of a novel COX-2 selective inhibitor core structure exemplified by 20.

  DOI：

  10.1021/jm0582064

文献信息

• Use of highly reactive, versatile and air-stable palladium–phosphinous acid complex [(t-Bu)2P(OH)]2PdCl2 (POPd) as a catalyst for the optimized Suzuki–Miyaura cross-coupling of less reactive heteroaryl chlorides and arylboronic acids
  作者：Subhash P. Khanapure、David S. Garvey

  DOI：10.1016/j.tetlet.2004.05.010

  日期：2004.6

  Using highly reactive air-stable palladium-phosphinous acid complex [(t-Bu)(2)P(OH)](2)PdCl2 (POPd) as a catalyst, synthesis of heteroaryl-aryl cross-coupled products via palladium-catalyzed Suzuki-Miyaura coupling of less reactive substituted 3-chloropyridines with arylboronic acids was achieved in high yields. (C) 2004 Elsevier Ltd. All rights reserved.
• 3-[4-(Methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) Phenyl Ketone as a Potent and Orally Active Cyclooxygenase-2 Selective Inhibitor:  Synthesis and Biological Evaluation
  作者：Subhash P. Khanapure、Michael E. Augustyniak、Richard A. Earl、David S. Garvey、L. Gordon Letts、Allison M. Martino、Madhavi G. Murty、David J. Schwalb、Matthew J. Shumway、Andrzej M. Trocha、Delano V. Young、Irina S. Zemtseva、David R. Janero

  DOI：10.1021/jm0582064

  日期：2005.6.1

  Incorporation of a spacer group between the central scaffold and the aryl ring resulted in a new cyclooxygenase-2 (COX-2) selective inhibitor core structure, 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) phenyl ketone (20), with COX-2 IC50 = 0.25 mu M and COX-1 IC50 = 14 mu M (human whole blood assay). Compound 20 was orally active in the rat air pouch model of inflammation, inhibiting white blood cell infiltration and COX-2-derived PG production. Our data support the identification of a novel COX-2 selective inhibitor core structure exemplified by 20.