rac-3-(3-benzoylphenyl)-2-oxo-1-chlorobutane | 41652-44-2

• 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: rac-3-(3-benzoylphenyl)-2-oxo-1-chlorobutane
• 英文别名: 3-(1'-methyl-2'-oxo-3'-chloropropyl)-benzophenone；3-(3-Benzoylphenyl)-1-chlorobutan-2-one
• CAS: 41652-44-2
• 化学式: C₁₇H₁₅ClO₂
• 分子量: 286.758
• InChiKey: NFVGDXQOHOVFRU-UHFFFAOYSA-N

物化性质

• 沸点：
  419.7±30.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  rac-3-(3-benzoylphenyl)-2-oxo-1-chlorobutane 、 coenzyme A disodium salt 在 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis and Biological Testing of Acyl-CoA–Ketoprofen Conjugates as Selective Irreversible Inhibitors of COX-2

  摘要：

  Ketoprofenoyl-CoA thioester 3 was synthesized by coupling ketoprofen to coenzyme A using the mixed anhydride method. Diastereoisomeric compounds 3a and 3b corresponding to the enantiomers of ketoprofen, were obtained in optically pure form by preparative HPLC. A non-acylating analogue, rac-3-(3-benzoylphenyl)-2-oxo-butanoyl-CoA (7) was also prepared. The biological evaluation suggested that 3a and 3b are reversible inhibitors of COX-1 and irreversible inhibitors of COX-2. Compound 7 appears to be a poor but selective inhibitor of COX-1. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00330-3
• 作为产物：
  描述：

  酮基布洛芬 在 盐酸 、 草酰氯 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 rac-3-(3-benzoylphenyl)-2-oxo-1-chlorobutane
  参考文献：
  名称：

  Synthesis and Biological Testing of Acyl-CoA–Ketoprofen Conjugates as Selective Irreversible Inhibitors of COX-2

  摘要：

  Ketoprofenoyl-CoA thioester 3 was synthesized by coupling ketoprofen to coenzyme A using the mixed anhydride method. Diastereoisomeric compounds 3a and 3b corresponding to the enantiomers of ketoprofen, were obtained in optically pure form by preparative HPLC. A non-acylating analogue, rac-3-(3-benzoylphenyl)-2-oxo-butanoyl-CoA (7) was also prepared. The biological evaluation suggested that 3a and 3b are reversible inhibitors of COX-1 and irreversible inhibitors of COX-2. Compound 7 appears to be a poor but selective inhibitor of COX-1. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00330-3

文献信息

• US3931302A
  申请人：——

  公开号：US3931302A

  公开（公告）日：1976-01-06
• US3995056A
  申请人：——

  公开号：US3995056A

  公开（公告）日：1976-11-30