4-[(E)-5-(3,4-dichlorophenyl)-3-oxopent-4-enoyl]piperidine-1-carboxylic acid tert-butyl ester | 736150-30-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-[(E)-5-(3,4-dichlorophenyl)-3-oxopent-4-enoyl]piperidine-1-carboxylic acid tert-butyl ester
• CAS: 736150-30-4
• 化学式: C₂₁H₂₅Cl₂NO₄
• 分子量: 426.34
• InChiKey: HFUXXGZQGZVCPK-GQCTYLIASA-N

物化性质

• 沸点：
  556.3±50.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[(E)-5-(3,4-dichlorophenyl)-3-oxopent-4-enoyl]piperidine-1-carboxylic acid tert-butyl ester 在 sodium hydroxide 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4-[1-(3-chlorophenyl)-5-[(E)-2-(3,4-dichlorophenyl)ethenyl]pyrazol-3-yl]piperidine
  参考文献：
  名称：

  Synthesis and antibacterial activity of a novel series of DNA gyrase inhibitors: 5-[(E)-2-arylvinyl]pyrazoles

  摘要：

  The 2-arylvinyl moiety in 1-(3-chlorophenyl)-3-(4-piperidyl)-5-[(E)-2-(5-chloro-1H-indol-3-yl)vinyl]pyrazole 2, which has previously shown improved DNA gyrase inhibition and target-related antibacterial activity, was transformed to other groups and the in vitro antibacterial activity of the synthesized compounds was evaluated. Many of the 5-[(E)-2-arylvinyl]pyrazoles synthesized in this study exhibited potent antibacterial activity against quinolone-resistant clinical isolates of Gram-positive bacteria with minimal inhibitory concentration values equivalent to those against susceptible strains. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.103
• 作为产物：
  描述：

  4-(3,4-二氯苯基)丁-3-烯-2-酮 、 1-Boc-4-哌啶甲酸 在 lithium diisopropyl amide 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 以53%的产率得到4-[(E)-5-(3,4-dichlorophenyl)-3-oxopent-4-enoyl]piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of a Novel Series of Potent DNA Gyrase Inhibitors. Pyrazole Derivatives

  摘要：

  We have previously found that a pyrazole derivative 1 possesses antibacterial activity and inhibitory activity against DNA gyrase and topoisomerase TV. Here, we synthesized new pyrazole derivatives and found that 5-[(E)-2-(5-chloroindol-3-yl)vinyl]pyrazole 16 possesses potent antibacterial activity and selective inhibitory activity against bacterial topoisomerases. Many of the synthesized pyrazole derivatives were potent against clinically isolated quinolone- or coumarin-resistant Gram-positive strains and had minimal inhibitory concentration values against these strains equivalent to those against susceptible strains.

  DOI：

  10.1021/jm030394f