2-((3-fluorophenyl)thio)aniline | 1229514-09-3

• 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-((3-fluorophenyl)thio)aniline
• 英文别名: (3-fluorophenyl)-4-aminophenylsulfide；2-(3-Fluorophenyl)sulfanylaniline；2-(3-fluorophenyl)sulfanylaniline
• CAS: 1229514-09-3
• 化学式: C₁₂H₁₀FNS
• 分子量: 219.283
• InChiKey: OIBKCXXCHLTUHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((3-fluorophenyl)thio)aniline 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 4-bromo-N-(2-(3-fluorophenylsulfonimidoyl)phenyl)benzamide
  参考文献：
  名称：

  通过不对称有机催化形成苯并噻二嗪-1-氧化物动态拆分亚磺酰亚胺

  摘要：

  通过手性磷酸催化的分子内脱水环化，开发了亚砜亚胺的催化动力学拆分。使用该方法对带有邻酰胺苯基部分的多种外消旋亚砜亚胺进行不对称脱水环化，产生回收的亚砜亚胺和苯并噻二嗪-1-氧化物产物，具有良好至高的对映选择性（ s因子高达61）。手性产物多种衍生化为多种含S-立体中心的S,N-杂环，证明了该方法的价值。

  DOI：

  10.1021/acs.orglett.4c00266
• 作为产物：
  描述：

  苯并噻唑 、 间氟碘苯 在 四丁基氢氧化铵 、 水 、 copper(l) chloride 作用下， 反应 12.0h， 以89%的产率得到2-((3-fluorophenyl)thio)aniline
  参考文献：
  名称：

  Unexpectedly ligand-free copper-catalyzed C–S cross-coupling of benzothiazole with aryl iodides in aqueous solution

  摘要：

  A novel synthetic protocol for 2-aminophenyl sulfide derivatives via the reactions of benzothiazole with aryl iodides was reported for the first time. The reactions were catalyzed by CuCl with tetrabutylammonium hydroxide as the base and water as the solvent without ligand at 50 degrees C or room temperature. A variety of aryl iodides underwent the C-S cross-coupling reaction with benzothiazole to afford smoothly the corresponding products in excellent yield. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.004

文献信息

• A novel and efficient cross-coupling of tris(fluorinated phenyl)boroxins with disulfides catalyzed by CuI/1,10-phenanthroline
  作者：Chuanming Yu、Beibei Jin、Zhenyu Liu、Weihui Zhong

  DOI：10.1139/v10-025

  日期：2010.5

  Under an oxygen atmosphere, the cross-coupling of tris(fluorinated phenyl)boroxins and disulfides catalyzed by CuI/1,10-phenanthroline were smoothly achieved to produce the corresponding asymmetric fluorinated arylsulfides in good-to-excellent yields.

  在氧气氛下，CuI/1,10-菲罗啉催化的三(氟化苯基)硼氧烷与二硫化物的交叉偶联反应顺利实现，以良好到极佳的收率生成相应的不对称氟化芳基硫化物。
• Unexpectedly ligand-free copper-catalyzed C–S cross-coupling of benzothiazole with aryl iodides in aqueous solution
  作者：Yi-Si Feng、Hong-Xia Qi、Wei-Cheng Wang、Yu-Feng Liang、Hua-Jian Xu

  DOI：10.1016/j.tetlet.2012.04.004

  日期：2012.6

  A novel synthetic protocol for 2-aminophenyl sulfide derivatives via the reactions of benzothiazole with aryl iodides was reported for the first time. The reactions were catalyzed by CuCl with tetrabutylammonium hydroxide as the base and water as the solvent without ligand at 50 degrees C or room temperature. A variety of aryl iodides underwent the C-S cross-coupling reaction with benzothiazole to afford smoothly the corresponding products in excellent yield. (C) 2012 Elsevier Ltd. All rights reserved.
• Kinetic Resolution of Sulfoximines via Asymmetric Organocatalyzed Formation of Benzothiadiazine-1-oxides
  作者：Mengyao Tang、Mengyao Yuan、Shibin Hong、Qianwen Jiang、Huanchao Gu、Xiaoyu Yang

  DOI：10.1021/acs.orglett.4c00266

  日期：2024.3.8

  A catalytic kinetic resolution of sulfoximines has been developed through chiral phosphoric acid-catalyzed intramolecular dehydrative cyclizations. A variety of racemic sulfoximines bearing an ortho-amidophenyl moiety underwent asymmetric dehydrative cyclizations using this method, yielding both the recovered sulfoximines and benzothiadiazine-1-oxide products with good to high enantioselectivities

  通过手性磷酸催化的分子内脱水环化，开发了亚砜亚胺的催化动力学拆分。使用该方法对带有邻酰胺苯基部分的多种外消旋亚砜亚胺进行不对称脱水环化，产生回收的亚砜亚胺和苯并噻二嗪-1-氧化物产物，具有良好至高的对映选择性（ s因子高达61）。手性产物多种衍生化为多种含S-立体中心的S,N-杂环，证明了该方法的价值。