methyl 2-{(2-nitrophenyl)[(trifluoroacetyl)oxy]methyl}acrylate | 916526-79-9

• 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: methyl 2-{(2-nitrophenyl)[(trifluoroacetyl)oxy]methyl}acrylate
• 英文别名: Methyl 2-[(2-nitrophenyl)-(2,2,2-trifluoroacetyl)oxymethyl]prop-2-enoate；methyl 2-[(2-nitrophenyl)-(2,2,2-trifluoroacetyl)oxymethyl]prop-2-enoate
• CAS: 916526-79-9
• 化学式: C₁₃H₁₀F₃NO₆
• 分子量: 333.221
• InChiKey: SYKYHYQBYONRKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2-{(2-nitrophenyl)[(trifluoroacetyl)oxy]methyl}acrylate 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以62%的产率得到methyl 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
• 作为产物：
  描述：

  邻硝基苯甲醛 在 三乙烯二胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 生成 methyl 2-{(2-nitrophenyl)[(trifluoroacetyl)oxy]methyl}acrylate
  参考文献：
  名称：

  Formation of substituted N-oxide hydroxyquinolines from o-nitrophenyl Baylis–Hillman adduct: a new key intermediate intercepted by ESI-(+)-MS(/MS) monitoring

  摘要：

  A new mechanistic proposal on the formation of N-oxide hydroxyquinolines from BH adducts based on the interception by electrospray ionization mass spectrometry of a new key o-trifluoroacetylated intermediate. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.037

文献信息

• Formation of substituted N-oxide hydroxyquinolines from o-nitrophenyl Baylis–Hillman adduct: a new key intermediate intercepted by ESI-(+)-MS(/MS) monitoring
  作者：Giovanni W. Amarante、Mario Benassi、Adão A. Sabino、Pierre M. Esteves、Fernando Coelho、Marcos N. Eberlin

  DOI：10.1016/j.tetlet.2006.09.037

  日期：2006.11

  A new mechanistic proposal on the formation of N-oxide hydroxyquinolines from BH adducts based on the interception by electrospray ionization mass spectrometry of a new key o-trifluoroacetylated intermediate. (c) 2006 Elsevier Ltd. All rights reserved.
• Mechanism and synthesis of pharmacologically active quinolones from Morita–Baylis–Hillman adducts
  作者：Giovanni W. Amarante、Mario Benassi、Robert N. Pascoal、Marcos N. Eberlin、Fernando Coelho

  DOI：10.1016/j.tet.2010.04.018

  日期：2010.6

  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.