2-(4-chlorophenyl)-N,N-dimethylethanethioamide | 76579-51-6

• 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-chlorophenyl)-N,N-dimethylethanethioamide
• 英文别名: 2-(4-chlorophenyl)-N,N-dimethylthioacetamide
• CAS: 76579-51-6
• 化学式: C₁₀H₁₂ClNS
• mdl: MFCD00214709
• 分子量: 213.731
• InChiKey: YBWXXVZHRLCKFI-UHFFFAOYSA-N

物化性质

• 熔点：
  74 °C(Solv: methanol (67-56-1))
• 沸点：
  294.7±42.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：

  2-(4-chlorophenyl)-N,N-dimethylethanethioamide 在 碘 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以70%的产率得到3,5-bis(4-chlorophenyl)-2-N,2-N,4-N,4-N-tetramethylthiophene-2,4-diamine
  参考文献：
  名称：

  Novel Route to Thiophene-2,4-diamines

  摘要：

  A novel and simple procedure for the construction of fully substituted thiophene-2,4-diamines using tertiary thioamides was developed. Thus, thioacetomorpholides undergo self-condensation to the corresponding 3,5-diarylthiophene-2,4-diamine derivatives in the presence of iodine and potassium carbonate in a suitable solvent and under mild conditions.

  DOI：

  10.1055/s-0034-1378724
• 作为产物：
  描述：

  2-(p-Chlorphenyl)-1-methylsulfinyl-1-methylthio-ethylen 以 甲醇 为溶剂， 反应 5.0h， 生成 2-(4-chlorophenyl)-N,N-dimethylethanethioamide
  参考文献：
  名称：

  New Method for Preparation of Methyl Aryldithioacetates and Arylthioacetamides

  摘要：

  DOI：

  10.1055/s-1980-29194

文献信息

• Selective reduction of carbonyl groups in the presence of low-valent titanium reagents
  作者：Wei Lin、Ming-Hua Hu、Xian Feng、Lei Fu、Cheng-Pao Cao、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1016/j.tetlet.2014.02.072

  日期：2014.4

  The chemoselective reduction of several structurally diverse compounds containing carbonyl groups was achieved in the presence of low-valent titanium reagents. This novel synthetic method provides easy access to highly selective reduction of carbonyl groups, and possesses several advantages including one-step procedure, convenient manipulation, good to excellent yields, and short reaction times.

  在低价钛试剂的存在下，实现了几种含有羰基的结构多样的化合物的化学选择性还原。这种新颖的合成方法易于获得羰基的高选择性还原，并具有多个优点，包括一步法，方便的操作，良好或优异的收率以及较短的反应时间。
• 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。
• 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。
• Dimethylammonium-dimethylcarbamat (Dimcarb) - ein vorteilhaftes Reagens für die Willgerodt-Kindler-Reaktion
  作者：Werner Schroth、Jörg Andersch

  DOI：10.1055/s-1989-27197

  日期：——

  Dimethylammonium Dimethylcarbamate - A Useful Reagent for the Willgerodt-Kindler Reaction Dimethylammonium dimethylcarbamate (dimcarb), easily accessible from dimethylamine and carbon dioxide, is a useful reagent for the Willgerodt-Kindler synthesis of N,N-dimethylthiocarboxamides. Moreover, dimcarb displays some unusual properties, and generally behaves as a preparatively useful dimethylamine source.

  二甲基铵二甲基氨基甲酸酯 - Willgerodt-Kindler反应的有用试剂 二甲基铵二甲基氨基甲酸酯（dimcarb）可从二甲基胺和二氧化碳轻松获得，是Willgerodt-Kindler合成N,N-二甲基硫酸酰胺的有用试剂。此外，dimcarb展现出一些不寻常的属性，并且通常作为有用的二甲基胺来源。
• 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。