4,4-二甲基-2-(2,4,5-三氟-3-甲氧基苯基)-4,5-二氢-1,3-恶唑 | 865246-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4,4-二甲基-2-(2,4,5-三氟-3-甲氧基苯基)-4,5-二氢-1,3-恶唑
• 英文名称: 2-(2,4,5-trifluoro-3-methoxyphenyl)-4,4-dimethyl-oxazoline
• 英文别名: 2-(2,4,5-Trifluoro-3-methoxyphenyl)-4,5-dihydro-4,4-dimethyloxazole；4,4-dimethyl-2-(2,4,5-trifluoro-3-methoxyphenyl)-5H-1,3-oxazole
• CAS: 865246-09-9
• 化学式: C₁₂H₁₂F₃NO₂
• 分子量: 259.228
• InChiKey: JAAFPDWKUQBJFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  305.9±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4-二甲基-2-(2,4,5-三氟-3-甲氧基苯基)-4,5-二氢-1,3-恶唑 、 碘乙烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以65%的产率得到2-(6-ethyl-2,4,5-trifluoro-3-methoxy-phenyl)-4,4-dimethyl-oxazoline
  参考文献：
  名称：

  Synthesis of mono- and di-substituted 2,4,5-trifluorobenzoic acid synthons, key precursors for biologically active 6-fluoroquinolones

  摘要：

  In the search for new potent antiparasitical fluoroquinolones, a QSAR analysis by molecular connectivity led to the design of R-5 (Me or Et)/R-8 (MeO, Me or Et)-substituted analogs of the most powerful antibacterial or antiparasitical fluoroquinolones known so far. Unfortunately, the synthetic schemes that were elaborated in literature for 3- and 3,6-di-substiluted 2,4,5-trifluorobenzoic acids, the key precursors of the target R-5/R-8-substituted 6-fluoroquinolones, led in our hands to poor yields and/or to inextricable mixtures of derivatives. This led us to reinvestigate the key alkylation steps or the 2,4,5-trifluorophenyl-oxazoline synthons and the subsequent deprotection of their oxazoline into acid with the aim of optimising the syntheses of 3- and 3,6-di-Substituted 2.4,5-trifluorobenzoic acids, which constitute the entries to our target derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.078
• 作为产物：
  描述：

  3-甲氧基-2,4,5-三氟苯甲酸 在 sodium hydroxide 、 氯化亚砜 、 草酰氯 作用下， 以 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 4,4-二甲基-2-(2,4,5-三氟-3-甲氧基苯基)-4,5-二氢-1,3-恶唑
  参考文献：
  名称：

  Synthesis of mono- and di-substituted 2,4,5-trifluorobenzoic acid synthons, key precursors for biologically active 6-fluoroquinolones

  摘要：

  In the search for new potent antiparasitical fluoroquinolones, a QSAR analysis by molecular connectivity led to the design of R-5 (Me or Et)/R-8 (MeO, Me or Et)-substituted analogs of the most powerful antibacterial or antiparasitical fluoroquinolones known so far. Unfortunately, the synthetic schemes that were elaborated in literature for 3- and 3,6-di-substiluted 2,4,5-trifluorobenzoic acids, the key precursors of the target R-5/R-8-substituted 6-fluoroquinolones, led in our hands to poor yields and/or to inextricable mixtures of derivatives. This led us to reinvestigate the key alkylation steps or the 2,4,5-trifluorophenyl-oxazoline synthons and the subsequent deprotection of their oxazoline into acid with the aim of optimising the syntheses of 3- and 3,6-di-Substituted 2.4,5-trifluorobenzoic acids, which constitute the entries to our target derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.078

文献信息

• Synthesis of mono- and di-substituted 2,4,5-trifluorobenzoic acid synthons, key precursors for biologically active 6-fluoroquinolones
  作者：Guillaume Anquetin、Jacques Greiner、Pierre Vierling

  DOI：10.1016/j.tet.2005.06.078

  日期：2005.8

  In the search for new potent antiparasitical fluoroquinolones, a QSAR analysis by molecular connectivity led to the design of R-5 (Me or Et)/R-8 (MeO, Me or Et)-substituted analogs of the most powerful antibacterial or antiparasitical fluoroquinolones known so far. Unfortunately, the synthetic schemes that were elaborated in literature for 3- and 3,6-di-substiluted 2,4,5-trifluorobenzoic acids, the key precursors of the target R-5/R-8-substituted 6-fluoroquinolones, led in our hands to poor yields and/or to inextricable mixtures of derivatives. This led us to reinvestigate the key alkylation steps or the 2,4,5-trifluorophenyl-oxazoline synthons and the subsequent deprotection of their oxazoline into acid with the aim of optimising the syntheses of 3- and 3,6-di-Substituted 2.4,5-trifluorobenzoic acids, which constitute the entries to our target derivatives. (c) 2005 Elsevier Ltd. All rights reserved.