N,N-dimethyl-4-[tris(methylsulfanyl)methyl]aniline | 116538-58-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethyl-4-[tris(methylsulfanyl)methyl]aniline
• CAS: 116538-58-0
• 化学式: C₁₂H₁₉NS₃
• 分子量: 273.488
• InChiKey: MHTOSQKJJBRNSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-4-[tris(methylsulfanyl)methyl]aniline 在 tetrafluoroboric acid 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以95%的产率得到S-methyl 4-(dimethylamino)benzothioate
  参考文献：
  名称：

  Simple Procedures for the Hydrolysis of Trimethyl Trithioorthocarboxylates to Methyl Thiolcarboxylates. A Convenient Route to Electron-Rich Aromatic and Heteroaromatic Methyl Thiolcarboxylates

  摘要：

  N,N-二烷基芳基胺、吡咯和吲哚的三甲基三硫代羧酸酯可以通过与DMSO/水（4:1）在130°C下部分水解5-100小时，或与DMSO/35%氟硼酸水溶液（4:1）在80-130°C下反应20分钟至4小时，轻松转化为相应的甲基硫醇羧酸酯，产率优秀（分别为86-98%和82-99%）。

  DOI：

  10.1055/s-1988-27548
• 作为产物：
  描述：

  N,N-二甲基苯胺 、 Tris(methylthio)carbenium-tetrafluoroborat 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以60%的产率得到N,N-dimethyl-4-[tris(methylsulfanyl)methyl]aniline
  参考文献：
  名称：

  Synthetic Application of Tris(methylthio)methyl Salts. An Efficient Route to Trithioorthocarboxylic Esters from Strongly Activated Aromatic and Heteroaromatic Systems

  摘要：

  通过三(甲硫基)甲基硫酸盐或四氟硼酸盐与富含电子的芳香族和杂芳香族化合物（即 N,N-二烷基芳胺、吡咯和吲哚）反应，合成了九种三硫代正羧酸酯。新方法简单易行，具有以下优点：试剂易于制备；反应条件温和；可在同一环中引入两个三（甲硫基）甲基；收率高至极佳。

  DOI：

  10.1055/s-1988-27455

文献信息

• FLUORINATING AGENT
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：US20160332877A1

  公开（公告）日：2016-11-17

  An object of the present invention is to provide a novel substance that has a high reactivity as a fluorinating agent, is effectively used in various fluorination reactions, and is safely handled even in air. As the solution for achieving this object, the present invention provides a complex obtained by reacting bromine trifluoride with at least one metal halide selected from the group consisting of halogenated metals and halogenated hydrogen metals in a nonpolar solvent. This complex serves as a fluorinating agent that provides excellent fluorination performance and that is stable in air.

  本发明的一个目的是提供一种新型物质，作为氟化剂具有高反应性，在各种氟化反应中有效地使用，并且即使在空气中也可以安全处理。为了实现这一目的，本发明提供了一种通过在非极性溶剂中将三氟化溴与来自卤化金属和卤化氢金属组成的金属卤化物中至少一种反应而获得的复合物。这种复合物作为氟化剂具有出色的氟化性能，并且在空气中是稳定的。
• Fluorinating agent
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：US10233080B2

  公开（公告）日：2019-03-19

  An object of the present invention is to provide a novel substance that has a high reactivity as a fluorinating agent, is effectively used in various fluorination reactions, and is safely handled even in air. As the solution for achieving this object, the present invention provides a complex obtained by reacting bromine trifluoride with at least one metal halide selected from the group consisting of halogenated metals and halogenated hydrogen metals in a nonpolar solvent. This complex serves as a fluorinating agent that provides excellent fluorination performance and that is stable in air.

  本发明的目的是提供一种新型物质，它作为氟化剂具有高反应活性，可有效地用于各种氟化反应，即使在空气中也可安全地处理。作为实现这一目标的解决方案，本发明提供了一种复合物，该复合物是由三氟化溴与至少一种金属卤化物在非极性溶剂中反应得到的，该金属卤化物选自由卤代金属和卤代氢金属组成的组。这种络合物可用作氟化剂，具有优异的氟化性能，并且在空气中稳定。
• Synthetic Application of Tris(methylthio)methyl Salts. An Efficient Route to Trithioorthocarboxylic Esters from Strongly Activated Aromatic and Heteroaromatic Systems
  作者：Margherita Barbero、Silvano Cadamuro、Iacopo Degani、Rita Fochi、Antonella Gatti、Valeria Regondi

  DOI：10.1055/s-1988-27455

  日期：——

  Nine trithioorthocarboxylic esters were synthesized by reaction of tris(methylthio)methyl methyl sulfate or tetrafluoroborate with electron-rich aromatic and heteroaromatic compounds, i.e. N,N-dialkylarylamines, pyrroles, and indoles. The new procedure is simple and offers the following advantages: easy preparation of reagents; mild reaction conditions; possibility to introduce two tris(methylthio)methyl groups into the same ring, good to excellent yields.

  通过三(甲硫基)甲基硫酸盐或四氟硼酸盐与富含电子的芳香族和杂芳香族化合物（即 N,N-二烷基芳胺、吡咯和吲哚）反应，合成了九种三硫代正羧酸酯。新方法简单易行，具有以下优点：试剂易于制备；反应条件温和；可在同一环中引入两个三（甲硫基）甲基；收率高至极佳。
• Simple Procedures for the Hydrolysis of Trimethyl Trithioorthocarboxylates to Methyl Thiolcarboxylates. A Convenient Route to Electron-Rich Aromatic and Heteroaromatic Methyl Thiolcarboxylates
  作者：Margherita Barbero、Silvano Cadamuro、Iacopo Degani、Rita Fochi、Antonella Gatti、Valeria Regondi

  DOI：10.1055/s-1988-27548

  日期：——

  Trimethyl trithioorthocarboxylates of N,N-dialkylarylamines, pyrroles and indoles were easily converted into the corresponding methyl thiolcarboxylates by partial hydrolysis with DMSO/water (4:1), at 130°C for 5-100 h or with DMSO/35% aqueous tetrafluoroboric acid (4: 1), at 80-130°C for 20 min - 4 h in excellent yields (86-98% and 82-99%, respectively).

  N,N-二烷基芳基胺、吡咯和吲哚的三甲基三硫代羧酸酯可以通过与DMSO/水（4:1）在130°C下部分水解5-100小时，或与DMSO/35%氟硼酸水溶液（4:1）在80-130°C下反应20分钟至4小时，轻松转化为相应的甲基硫醇羧酸酯，产率优秀（分别为86-98%和82-99%）。