2-[(4-trifluoromethyl-2-nitrophenyl)thio]aniline | 322-71-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[(4-trifluoromethyl-2-nitrophenyl)thio]aniline
• 英文别名: 2-(2-nitro-4-trifluoromethyl-phenylsulfanyl)-aniline；2-(2-Nitro-4-trifluormethyl-phenylmercapto)-anilin；2-[2-Nitro-4-(trifluoromethyl)phenyl]sulfanylaniline
• CAS: 322-71-4
• 化学式: C₁₃H₉F₃N₂O₂S
• 分子量: 314.288
• InChiKey: RWSBANZPGBSQRS-UHFFFAOYSA-N

物化性质

• 沸点：
  376.1±42.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)
• 溶解度：
  5.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(4-trifluoromethyl-2-nitrophenyl)thio]aniline 在 氢氧化钾 、 丙酮 作用下， 生成 3-(trifluoromethyl)-10H-phenothiazine
  参考文献：
  名称：

  Yale et al., Journal of the American Chemical Society, 1957, vol. 79, p. 4375,4377

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴-3-硝基三氟甲苯 、 2-氨基苯硫醇 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以90 %的产率得到2-[(4-trifluoromethyl-2-nitrophenyl)thio]aniline
  参考文献：
  名称：

  Dibenzo[b,f][1,4,5]chalcogenadiazepine Photoswitches：激发能量转化为环应变

  摘要：

  硫属元素桥接的七元环状偶氮苯二苯并[ b , f ][1,4,5]硫属二氮杂卓 (DBChD) 具有高能 E 构型的独特光开关特性，特别是对于具有高能 E 构型的硫桥接 DBTD在 445 nm 激光激活下，能量转换效率为 21% (η)。在 DBTD 上引入低聚噻吩 π-EDG 可以进一步提高吸收 λ max和系数 ϵ，达到 η=29 %。

  DOI：

  10.1002/anie.202209441

文献信息

• THE PREPARATION OF SOME FLUORO- AND TRIFLUOROMETHYL-PHENOTHIAZINES, AND SOME OBSERVATIONS REGARDING DETERMINATION OF THEIR STRUCTURE BY INFRARED SPECTROSCOPY¹
  作者：ARTHUR ROE、WILLIAM F. LITTLE

  DOI：10.1021/jo01128a018

  日期：1955.11
• Dibenzo[1,4,5]thiadiazepine: A hardly-known heterocyclic system with neuroprotective properties of potential usefulness in the treatment of neurodegenerative diseases
  作者：Gema C. González-Muñoz、Mariana P. Arce、Concepción Pérez、Alejandro Romero、Mercedes Villarroya、Manuela G. López、Santiago Conde、María Isabel Rodríguez-Franco

  DOI：10.1016/j.ejmech.2014.04.075

  日期：2014.6

  In this work we describe a new family of dibenzo[1,4,5]thiadiazepines (2-12) that showed an interesting in vitro biological profile, namely neuroprotective and antioxidant properties, as well as blockade of cytosolic calcium entry. They showed no cytotoxic effects and the majority were predicted as CNS-permeable compounds. In human neuroblastoma cells they displayed good neuroprotective properties against mitochondrial oxidative stress which, in many cases, almost reached the full protection (>90%) when compounds were incubated with cells 24 h before the addition of toxic stressors. In co-incubation conditions these figures were smaller, although some compounds maintained an interesting level of neuroprotection, higher than 50%. Four selected compounds (2, 5, 8, and 11) were found to be effective antioxidant agents by sequestering mitochondrial radical oxygen species (ROS). Moreover, compound 2 showed a remarkable calcium-channel modulating activity. The interest of these compounds is increased by the fact that dibenzo[1,4,5]thiadiazepine is a barely known structure that is not difficult to synthesize and presents very few described derivatives, opening a new and broad line of research in Medicinal Chemistry. (C) 2014 Elsevier Masson SAS. All rights reserved.