2-methyl-N-[4-hydroxy-3-(trifluoromethyl)phenyl]propanamide | 141304-68-9

• 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: 2-methyl-N-[4-hydroxy-3-(trifluoromethyl)phenyl]propanamide
• 英文别名: Propanamide, N-[4-hydroxy-3-(trifluoromethyl)phenyl]-2-methyl-；N-[4-hydroxy-3-(trifluoromethyl)phenyl]-2-methylpropanamide
• CAS: 141304-68-9
• 化学式: C₁₁H₁₂F₃NO₂
• 分子量: 247.217
• InChiKey: QSEKMWKMVYYCSN-UHFFFAOYSA-N

物化性质

• 沸点：
  360.4±42.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氟他胺 以 phosphate buffer 为溶剂， 生成 2-methyl-N-[4-hydroxy-3-(trifluoromethyl)phenyl]propanamide
  参考文献：
  名称：

  氟他胺及其与β-环糊精的包合物的光化学。微环境对自然和光降解途径效率的显着影响¶

  摘要：

  摘要 抗癌药物氟他胺 (FM)、2-甲基-N-[4-硝基-3-(三氟甲基)苯基]丙酰胺在均相介质和 β-环糊精 (β-CD) 腔中的光化学具有被调查。基于分子内硝基到亚硝酸盐的重排，随后亚硝酸盐中间体的裂解，使游离分子的光反应性合理化。硝基相对于芳族平面的扭曲几何形状在触发这种光处理过程中起着关键作用。在 β-CD 腔中掺入 FM 会对客体分子的光化学失活途径的效率和性质产生显着影响。在大环的存在下观察到 FM 光分解量子产率增加了 20 倍，并且由于硝基基团的还原和酰胺键的断裂而产生光产物的形成。这种行为不能完全归因于 β-CD 的微极性和/或其作为反应物的作用。诱导的圆二色性光谱和在这些实验条件下形成的光产物的性质表明，β-CD 微环境中的光反应性可能是由复合后 FM 的结构变化介导的。

  DOI：

  10.1562/0031-8655(2001)073<0006:tpofai>2.0.co;2

文献信息

• Synergistic Photo-Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides with Molecular Oxygen
  作者：Xin Zhang、Ge Wu、Wenxia Gao、Jinchang Ding、Xiaobo Huang、Miaochang Liu、Huayue Wu

  DOI：10.1021/acs.orglett.7b03840

  日期：2018.2.2

  Photoredox-mediated copper-catalyzed hydroxylation of (hetero)aryl halides (including chlorides, bromides, and iodides) with O2 at room temperature has been developed. Preliminary mechanistic studies indicate no arylcopper intermediate and that aryl radicals are involved in this procedure. 18O-labeling experiments confirm the hydroxyl oxygen atom originated from molecular oxygen.

  在室温下用O 2光氧化还原介导的铜催化（杂）芳基卤化物（包括氯化物，溴化物和碘化物）的铜催化羟基化作用。初步的机理研究表明，没有芳基铜中间体，并且芳基自由基也参与了该程序。18个O标记实验证实了羟基氧原子起源于分子氧。
• Photochemistry of flutamide in various media: Investigation of the reaction mechanism as revealed by external magnetic field effects on product yields
  作者：Chikako Udagawa、Shuichi Fukuyoshi、Shotaro Morimoto、Yoshifumi Tanimoto、Ryoichi Nakagaki

  DOI：10.1016/j.jphotochem.2011.10.015

  日期：2011.12

  propanamide has been investigated in various media in the absence and presence of 0.1 T magnetic field. On photoexcitation flutamide gives rise to a phenol derivative through nitro-to-nitrite rearrangement in homogeneous as well as in inhomogeneous solutions. Magnetic field effects on the product yields revealed that a radical pair is involved in the photoreduction, where the excited triplet state of flutamide

  在不存在和存在0.1 T磁场的情况下，已经在各种介质中研究了抗癌药物氟他胺2-甲基-N- [4-硝基-3-（三氟甲基）苯基]丙酰胺的光化学性质。在光激发下，氟他胺在均相和非均相溶液中通过硝基至亚硝酸盐的重排生成苯酚衍生物。磁场对产物收率的影响表明，自由基对参与了光还原，其中氟他胺的激发三重态是该对的前体。它在不均匀溶液中进行夺氢反应，在该溶液中溶剂分子不仅充当溶剂笼的成分，而且充当氢供体。
• 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.
• The Photochemistry of Flutamide and its Inclusion Complex with β-Cyclodextrin. Dramatic Effect of the Microenvironment on the Nature and on the Efficiency of the Photodegradation Pathways¶
  作者：S. Sortino、S. Giuffrida、G. De Guidi、R. Chillemi、S. Petralia、G. Marconi、G. Condorelli、S. Sciuto

  DOI：10.1562/0031-8655(2001)073<0006:tpofai>2.0.co;2

  日期：——

  media and in the β-cyclodextrin (β-CD) cavity has been investigated. The photoreactivity of the free molecule has been rationalized on the basis of an intramolecular nitro to nitrite rearrangement followed by cleavage of the nitrite intermediate. The twisted geometry of the nitro group with respect to the aromatic plane plays a key role in triggering such a photoprocess. Incorporation of FM in the β-CD

  摘要 抗癌药物氟他胺 (FM)、2-甲基-N-[4-硝基-3-(三氟甲基)苯基]丙酰胺在均相介质和 β-环糊精 (β-CD) 腔中的光化学具有被调查。基于分子内硝基到亚硝酸盐的重排，随后亚硝酸盐中间体的裂解，使游离分子的光反应性合理化。硝基相对于芳族平面的扭曲几何形状在触发这种光处理过程中起着关键作用。在 β-CD 腔中掺入 FM 会对客体分子的光化学失活途径的效率和性质产生显着影响。在大环的存在下观察到 FM 光分解量子产率增加了 20 倍，并且由于硝基基团的还原和酰胺键的断裂而产生光产物的形成。这种行为不能完全归因于 β-CD 的微极性和/或其作为反应物的作用。诱导的圆二色性光谱和在这些实验条件下形成的光产物的性质表明，β-CD 微环境中的光反应性可能是由复合后 FM 的结构变化介导的。