1-methylethyl 2-amino-5-(2-methylpropanamido)benzoate

• 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: 1-methylethyl 2-amino-5-(2-methylpropanamido)benzoate
• 英文别名: Propan-2-yl 2-amino-5-(2-methylpropanoylamino)benzoate；propan-2-yl 2-amino-5-(2-methylpropanoylamino)benzoate
• 化学式: C₁₄H₂₀N₂O₃
• 分子量: 264.324
• InChiKey: HNHBESHLBPORAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氟他胺 在 氯化铵 、 锌 作用下， 以 甲醇 为溶剂， 反应 1.03h， 生成 1-methylethyl 2-amino-5-(2-methylpropanamido)benzoate
  参考文献：
  名称：

  Comparison of photoreactions of flutamide in acetonitrile and 2-propanol solvents in the absence of cage-forming compounds

  摘要：

  Flutamide(2-methyl-N-[4-nitro-3-(trifluoromethylphenyl)]propanamide) is a widely used anti-cancer drug. It has been reported that photodermatosis is occasionally induced when an individual taking flutamide is exposed to sunlight. In this study, we found that flutamide undergoes different photoreactions in two different solvents: acetonitrile and 2-propanol. The photo-induced nitro-nitrite rearrangement was the predominant reaction when a flutamide solution in acetonitrile was irradiated with UV light, and phenoxy radicals and nitrogen monoxide were generated. The nitrogen monoxide recombined with the phenoxy radical at the ortho position and was oxidized by the oxygen dissolved in the acetonitrile. The final product was o-nitrophenol derivative. However, the photoreduction of the nitro group followed by solvolysis of the trifluoromethyl group was observed when a flutamide solution in 2-propanol was irradiated with UV light. The three fluorine atoms in the trifluoromethyl group were eliminated by being nucleophilically attacked by a solvent molecule, resulting in an ester bond with 2-propanol being formed. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2014.10.009

文献信息

• Comparison of photoreactions of flutamide in acetonitrile and 2-propanol solvents in the absence of cage-forming compounds
  作者：Yurie Watanabe、Shuichi Fukuyoshi、Akifumi Oda

  DOI：10.1016/j.jphotochem.2014.10.009

  日期：2015.2

  Flutamide(2-methyl-N-[4-nitro-3-(trifluoromethylphenyl)]propanamide) is a widely used anti-cancer drug. It has been reported that photodermatosis is occasionally induced when an individual taking flutamide is exposed to sunlight. In this study, we found that flutamide undergoes different photoreactions in two different solvents: acetonitrile and 2-propanol. The photo-induced nitro-nitrite rearrangement was the predominant reaction when a flutamide solution in acetonitrile was irradiated with UV light, and phenoxy radicals and nitrogen monoxide were generated. The nitrogen monoxide recombined with the phenoxy radical at the ortho position and was oxidized by the oxygen dissolved in the acetonitrile. The final product was o-nitrophenol derivative. However, the photoreduction of the nitro group followed by solvolysis of the trifluoromethyl group was observed when a flutamide solution in 2-propanol was irradiated with UV light. The three fluorine atoms in the trifluoromethyl group were eliminated by being nucleophilically attacked by a solvent molecule, resulting in an ester bond with 2-propanol being formed. (C) 2014 Elsevier B.V. All rights reserved.