2-methyl-3-((4-nitrophenyl)thio)tetrahydrofuran

• 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-3-((4-nitrophenyl)thio)tetrahydrofuran
• 英文别名: 2-Methyl-3-(4-nitrophenyl)sulfanyloxolane；2-methyl-3-(4-nitrophenyl)sulfanyloxolane
• 化学式: C₁₁H₁₃NO₃S
• 分子量: 239.295
• InChiKey: YXRSFDXZMCCLAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  80.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对二硝基苯 、 2-甲基-3-四氢呋喃硫醇 在 potassium phosphate 、 18-冠醚-6 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以69%的产率得到2-methyl-3-((4-nitrophenyl)thio)tetrahydrofuran
  参考文献：
  名称：

  C-S coupling with nitro group as leaving group via simple inorganic salt catalysis

  摘要：

  An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition elimination mechanism. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.07.012

文献信息

• Nucleobase Having Perfluoroalkyl Group and Process for Producing the Same
  申请人：Yamakawa Tetsu

  公开号：US20090124796A1

  公开（公告）日：2009-05-14

  Provided is a simple and efficient production process of a nucleobase having a perfluoroalkyl group. A nucleobase (for example, uracils, cytosines, adenines, guanines, hypoxanthines, xanthines, or the like) is reacted with a perfluoroalkyl halide in the presence of a sulfoxide, a peroxide and an iron compound to produce a perfluoroalkyl-substituted nucleobase, which is useful as an intermediate for medical drugs, economically.

  提供一种具有全氟烷基的核碱的简单高效的生产工艺。将核碱（例如尿嘧啶、胞嘧啶、腺嘌呤、鸟嘌呤、次黄嘌呤、黄嘌呤等）与全氟烷基卤化物在亚砜、过氧化物和铁化合物的存在下反应，制得全氟烷基取代的核碱，该中间体在医药制剂中具有经济价值。
• US7884202B2
  申请人：——

  公开号：US7884202B2

  公开（公告）日：2011-02-08
• C-S coupling with nitro group as leaving group via simple inorganic salt catalysis
  作者：Maojie Xuan、Chunlei Lu、Bo-Lin Lin

  DOI：10.1016/j.cclet.2019.07.012

  日期：2020.1

  An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition elimination mechanism. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.