2-(4-bromophenyl)-N,N-dimethylethanethioamide | 909387-04-8

• 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-(4-bromophenyl)-N,N-dimethylethanethioamide
• CAS: 909387-04-8
• 化学式: C₁₀H₁₂BrNS
• 分子量: 258.182
• InChiKey: SPNYEFNSGMMMLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C(Solvent: Methanol)
• 沸点：
  320.4±44.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  乙酸烯丙酯 、 2-(4-bromophenyl)-N,N-dimethylethanethioamide 在 bis(η3-allyl-μ-chloropalladium(II)) 、 1,4-双(二苯基膦)丁烷 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以79%的产率得到2-(4-bromophenyl)-N,N-dimethylpent-4-enethioamide
  参考文献：
  名称：

  Pd-catalyzed allylic alkylation of thioamides

  摘要：

  This work describes the first Pd-catalyzed allylic alkylation of thioamides. Various thioamides were efficiently alpha-allylated in high yields and with excellent selectivity for monoallylation under mild reaction conditions. The process not only provides a facile method for the synthesis of functionalized thioamides, but also presents a useful transformation for synthetically important thioamides. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.081
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 1,1-二溴-2-(4-溴苯基)乙烯 在 sodiumsulfide nonahydrate 作用下， 反应 1.0h， 以87%的产率得到2-(4-bromophenyl)-N,N-dimethylethanethioamide
  参考文献：
  名称：

  由宝石-二溴代烯烃和硫化钠合成取代的硫代酰胺

  摘要：

  据报道，在催化剂或无添加剂条件下，由双二溴代烯烃，硫化钠和甲酰胺合成了硫代酰胺。对照实验和机理研究表明，硫化钠在这种整体转化过程中具有必要的作用。

  DOI：

  10.1002/ejoc.201901411

文献信息

• The thioamidation of <i>gem</i>-dibromoalkenes in an aqueous medium
  作者：Jigarkumar K. Vankar、Ankush Gupta、Jaydeepbhai P. Jadav、Shankara H. Nanjegowda、Guddeangadi N. Gururaja

  DOI：10.1039/d0ob02319a

  日期：——

  1-dibromoalkenes for thioamide synthesis has been achieved in an aqueous medium. The presented green protocol emphasizes the suitability of aqueous media for the thioamidation reaction and enables greater selectivity with synthetic utility. A wide range of thioamides in moderate to excellent yields has been achieved using readily available starting materials, with the use of no organic solvents, catalysts

  已经在水性介质中实现了硫和胺基与1，1-二溴代烯烃的直接结合以用于硫酰胺的合成。提出的绿色方案强调了水性介质对硫酰胺化反应的适用性，并具有更高的选择性和合成效用。使用容易获得的起始原料，不使用有机溶剂，催化剂或添加剂，已经获得了各种中等至优异收率的硫酰胺。
• Thio-Michael addition of thioamides and allenes for the selective construction of polysubstituted 2-arylthiophenes <i>via</i> TBAI/H₂O₂ promoted tandem oxidative annulation and 1,2-sulfur migration
  作者：Teng Han、Xiaoyan Luo

  DOI：10.1039/c8ob01835a

  日期：——

  addition/oxidative annulation of allenes and thioamides for the construction of polysubstituted 2-arylthiophenes under a sulfur migration transformation protocol has been developed. The transition-metal-free protocol achieves the oxidative cyclization reaction of thioamides containing electron-rich substituents with allenes to construct polysubstituted thiophenes selectively by controlling oxidation conditions

  开发了一种新颖的TBAI催化的串联结构，用于在硫迁移转化规程下构建多取代的2-芳基噻吩的丙二烯和硫代酰胺的串联硫代-Michael加成/氧化环化反应。不含过渡金属的方案可通过控制氧化条件，实现含有富电子取代基的硫代酰胺与烯丙基的氧化环化反应，从而选择性地构建多取代的噻吩。
• New method for the preparation of N,N-dimethyl-(thioacetamides) from 4-substituted 1,2,3-thiadiazoles
  作者：D. A. Androsov、M. L. Petrov、A. A. Shchipalkin

  DOI：10.1134/s1070428007120226

  日期：2007.12
• Synthesis of Substituted Thioamides from <i>gem</i> -Dibromoalkenes and Sodiumsulfide
  作者：Ashok K. Morri、Yadagiri Thummala、Ramesh Adepu、Gangavaram V. M. Sharma、Subhash Ghosh、Venkata Ramana Doddi

  DOI：10.1002/ejoc.201901411

  日期：2019.11.14

  Synthesis of thioamides from geminal dibromoalkenes, sodium sulfide and formamide have been reported under catalyst or additive free conditions. Control experiment and mechanistic studies revealed that necessary role of sodium sulfide in this overall transformation.

  据报道，在催化剂或无添加剂条件下，由双二溴代烯烃，硫化钠和甲酰胺合成了硫代酰胺。对照实验和机理研究表明，硫化钠在这种整体转化过程中具有必要的作用。
• Pd-catalyzed allylic alkylation of thioamides
  作者：Bin Rong、Lei Ding、Hailei Yu、Qin Yang、Xuliang Liu、Dongfang Xu、Guisheng Li、Baoguo Zhao

  DOI：10.1016/j.tetlet.2013.09.081

  日期：2013.11

  This work describes the first Pd-catalyzed allylic alkylation of thioamides. Various thioamides were efficiently alpha-allylated in high yields and with excellent selectivity for monoallylation under mild reaction conditions. The process not only provides a facile method for the synthesis of functionalized thioamides, but also presents a useful transformation for synthetically important thioamides. (C) 2013 Elsevier Ltd. All rights reserved.