2-[3-amino-2-(trifluoromethoxy)phenyl]-4,5-dihydro-4,4-dimethyloxazole | 561304-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[3-amino-2-(trifluoromethoxy)phenyl]-4,5-dihydro-4,4-dimethyloxazole
• 英文别名: 3-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-2-(trifluoromethoxy)aniline
• CAS: 561304-55-0
• 化学式: C₁₂H₁₃F₃N₂O₂
• 分子量: 274.243
• InChiKey: ORTPUXFLCBPMIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 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：
  56.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[3-amino-2-(trifluoromethoxy)phenyl]-4,5-dihydro-4,4-dimethyloxazole 在 盐酸 作用下， 反应 12.0h， 以56%的产率得到3-amino-2-(trifluoromethoxy)benzoic acid
  参考文献：
  名称：

  Trifluoromethoxy Substituted Anilines: Metalation as the Key Step for Structural Elaboration

  摘要：

  Trifluoromethoxy-substituted anilines undergo hydrogen/lithium permutation (''metalation'') with optional site selectivity depending on the N-protective group employed. N-tert-Butoxycarbonyl-2- and -4-(trifluoromethoxy)aniline react with tert-butyllithium. at the nitrogen-adjacent 6- and 2-position affording, after electrophilic trapping, products 1-6. In contrast, deprotonation of the para isomer occurs at the oxygen-neighboring 3-position, giving rise to the acid 12, when the amino group is carrying two trimethylsilyl groups. sec-Butyllithium attacks 3-trifluoromethoxy-N-mono-(trimethylsilyl)aniline at the 2-position, but 3-trifluoromethoxy-N,N-bis(trimethylsilyl)aniline at the 4-position to provide respectively the acids 10 and 11 after carboxylation. The synthesis of two new benzodiazepines illustrates (19 and 22) the preparative potential of the aniline functionalization mediated by organometallic reagents.

  DOI：

  10.1021/jo0267798
• 作为产物：
  描述：

  3-溴-2-三氟甲氧基苯甲酸 在 苯磺酰基叠氮化物 、 sodium tetrahydroborate 、 正丁基锂 、 氯化亚砜 作用下， 以 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 18.0h， 生成 2-[3-amino-2-(trifluoromethoxy)phenyl]-4,5-dihydro-4,4-dimethyloxazole
  参考文献：
  名称：

  Trifluoromethoxy Substituted Anilines: Metalation as the Key Step for Structural Elaboration

  摘要：

  Trifluoromethoxy-substituted anilines undergo hydrogen/lithium permutation (''metalation'') with optional site selectivity depending on the N-protective group employed. N-tert-Butoxycarbonyl-2- and -4-(trifluoromethoxy)aniline react with tert-butyllithium. at the nitrogen-adjacent 6- and 2-position affording, after electrophilic trapping, products 1-6. In contrast, deprotonation of the para isomer occurs at the oxygen-neighboring 3-position, giving rise to the acid 12, when the amino group is carrying two trimethylsilyl groups. sec-Butyllithium attacks 3-trifluoromethoxy-N-mono-(trimethylsilyl)aniline at the 2-position, but 3-trifluoromethoxy-N,N-bis(trimethylsilyl)aniline at the 4-position to provide respectively the acids 10 and 11 after carboxylation. The synthesis of two new benzodiazepines illustrates (19 and 22) the preparative potential of the aniline functionalization mediated by organometallic reagents.

  DOI：

  10.1021/jo0267798

文献信息

• Trifluoromethoxy Substituted Anilines: Metalation as the Key Step for Structural Elaboration
  作者：Frédéric Leroux、Eva Castagnetti、Manfred Schlosser

  DOI：10.1021/jo0267798

  日期：2003.6.1

  Trifluoromethoxy-substituted anilines undergo hydrogen/lithium permutation (''metalation'') with optional site selectivity depending on the N-protective group employed. N-tert-Butoxycarbonyl-2- and -4-(trifluoromethoxy)aniline react with tert-butyllithium. at the nitrogen-adjacent 6- and 2-position affording, after electrophilic trapping, products 1-6. In contrast, deprotonation of the para isomer occurs at the oxygen-neighboring 3-position, giving rise to the acid 12, when the amino group is carrying two trimethylsilyl groups. sec-Butyllithium attacks 3-trifluoromethoxy-N-mono-(trimethylsilyl)aniline at the 2-position, but 3-trifluoromethoxy-N,N-bis(trimethylsilyl)aniline at the 4-position to provide respectively the acids 10 and 11 after carboxylation. The synthesis of two new benzodiazepines illustrates (19 and 22) the preparative potential of the aniline functionalization mediated by organometallic reagents.