methyl 7-chloro-6-fluoro-4-hydroxyquinoline-3-carboxylate-1-oxide | 1234704-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl 7-chloro-6-fluoro-4-hydroxyquinoline-3-carboxylate-1-oxide
• CAS: 1234704-31-4
• 化学式: C₁₁H₇ClFNO₄
• 分子量: 271.63
• InChiKey: HZUHTFUOUZOCSO-UHFFFAOYSA-N

物化性质

• 熔点：
  252-253 °C
• 沸点：
  434.8±55.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  73.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 7-chloro-6-fluoro-4-hydroxyquinoline-3-carboxylate-1-oxide 生成 7-氯-6-氟-4-氧代-1,4-二氢喹啉-3-羧酸乙酯
  参考文献：
  名称：

  Compounds having antibacterial activity, process for their preparation and pharmaceutical compositions containing them

  摘要：

  公开号：

  EP0155006B1
• 作为产物：
  描述：

  (+/-)-methyl 2-[(4-chloro-5-fluoro-2-nitrophenyl)hydroxymethyl]acrylate 在 三氟乙酸 作用下， 反应 48.0h， 以60%的产率得到methyl 7-chloro-6-fluoro-4-hydroxyquinoline-3-carboxylate-1-oxide
  参考文献：
  名称：

  Mechanism and synthesis of pharmacologically active quinolones from Morita–Baylis–Hillman adducts

  摘要：

  The synthesis of quinolones from Morita-Baylis-Hillman (MBH) adducts is reported. The quinolone skeleton is formed via a TFA-mediated cyclization of the MBH adduct, and a mechanism study using ESI (+)-MS(/MS) has indicated the role played by TFA in this key reaction step. The total syntheses of Norfloxacin and a benzyl quinolone carboxylic acid (BQCA) derivative are described. Norfloxacin is a fluoroquinolonic antibacterial drug whereas BQCA is M-1 receptor positive allosteric modulator and seem to provide access to new potential drugs for Alzheimer disease, pain, and sleep disorders. The syntheses of these two important quinolones exemplify the versatility and potentiality of the approach. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.018

文献信息

• Tetrahedron 2010, 66, 4370-4376
  作者：

  DOI：——

  日期：——