N,N-dimethyl-[1,1ʹ-biphenyl]-4-carbothioamide

• 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: N,N-dimethyl-[1,1ʹ-biphenyl]-4-carbothioamide
• 英文别名: N,N-dimethyl-[1,1′-biphenyl]-4-carbothioamide；N,N-dimethyl-4-phenylbenzenecarbothioamide
• 化学式: C₁₅H₁₅NS
• 分子量: 241.357
• InChiKey: HWJQCPPDEIFIGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  正丁醇 、 N,N-dimethyl-[1,1ʹ-biphenyl]-4-carbothioamide 在 碘甲烷 、 silver fluoride 作用下， 以 乙腈 为溶剂， 以65 %的产率得到butyl [1,1′-biphenyl]-4-carboxylate
  参考文献：
  名称：

  10.1055/s-0043-1774910

  摘要：

  AbstractA mild and efficient reaction for synthesizing esters from thioamide precursors has been established. This method is accomplished in one pot under mild conditions. The process involves the alkylation and activation of inert thioamides, which leads to the cleavage of stable C–N and C–S bonds, eventually resulting in valuable esters with a broad range of substrates. The transformation can be easily carried out at room temperature using thioamide substrates, reactants, and activating agents. This protocol has been demonstrated by synthesizing important esters with applications.

  DOI：

  10.1055/s-0043-1774910
• 作为产物：
  描述：

  4-联苯乙酸 、 N,N-二甲基甲酰胺 在 potassium carbonate 、 sulfur 作用下， 反应 24.0h， 以59%的产率得到N,N-dimethyl-[1,1ʹ-biphenyl]-4-carbothioamide
  参考文献：
  名称：

  使用甲酰胺作为胺代用品，硫促进了羧酸的脱羧硫酰胺化反应

  摘要：

  已经开发了一种有效的脱甲磺酸和肉桂酸的脱羧硫酰胺化反应，采用甲酰胺作为胺替代物，而硫作为促进剂。在温和的反应条件下，无需使用过渡金属催化剂和氧化剂即可获得具有可变结构特征的硫酰胺。

  DOI：

  10.1016/j.tet.2016.02.070

文献信息

• Water Mediated Direct Thioamidation of Aldehydes at Room Temperature
  作者：Ankush Gupta、Jigarkumar K. Vankar、Jaydeepbhai P. Jadav、Guddeangadi N. Gururaja

  DOI：10.1021/acs.joc.1c02307

  日期：2022.3.4

  A mild, greener approach toward thioamide synthesis has been developed. Its unique features include water-mediated reaction with no input energy, additives, or catalysts as well. The presented protocol is attractive with readily available starting materials and the use of different array amines, along with a scaled-up method. Biologically active molecules such as thionicotinamide and thioisonicotinamide

  已开发出一种温和、更环保的硫代酰胺合成方法。它的独特之处包括无需输入能量、添加剂或催化剂的水介导反应。所提出的协议具有现成的起始材料和不同阵列胺的使用以及按比例放大的方法的吸引力。生物活性分子，如硫代烟酰胺和硫代异烟酰胺，可以从这个过程中合成。
• 10.1021/acs.orglett.4c00691
  作者：Lv, Jianxing、Liang, Yixuan、Ouyang, Yepeng、Zhang, Hua

  DOI：10.1021/acs.orglett.4c00691

  日期：——

  A BBr3-mediated S-directed ortho C–H borylation of thiobenzamides was developed. A variety of ortho-borylated thiobenzamides were obtained in moderate to good yields with a wide functional group tolerance under simple and metal-free conditions. This transformation provided a convenient and practical route to important functionalized thiobenzamides.

  开发了 BBr 3介导的硫代苯甲酰胺的 S定向邻位C-H 硼基化。在简单和无金属的条件下，以中等至良好的收率获得了多种邻硼基化硫代苯甲酰胺，并且具有广泛的官能团耐受性。这种转化为重要的官能化硫代苯甲酰胺提供了一条方便实用的途径。
• Sulfur promoted decarboxylative thioamidation of carboxylic acids using formamides as amine proxy
  作者：Saurabh Kumar、Rajeshwer Vanjari、Tirumaleswararao Guntreddi、Krishna Nand Singh

  DOI：10.1016/j.tet.2016.02.070

  日期：2016.4

  An efficient decarboxylative thioamidation of arylacetic and cinnamic acids has been developed employing formamides as amine surrogate and sulfur as promoter. Thioamides with variant structural features are obtained under mild reaction conditions without the use of transition metal catalysts and oxidants.

  已经开发了一种有效的脱甲磺酸和肉桂酸的脱羧硫酰胺化反应，采用甲酰胺作为胺替代物，而硫作为促进剂。在温和的反应条件下，无需使用过渡金属催化剂和氧化剂即可获得具有可变结构特征的硫酰胺。
• 10.1055/s-0043-1774910
  作者：Vankar, Jigarkumar K.、Jadav, Jaydeepbhai P.、Gururaja, Guddeangadi N.

  DOI：10.1055/s-0043-1774910

  日期：——

  AbstractA mild and efficient reaction for synthesizing esters from thioamide precursors has been established. This method is accomplished in one pot under mild conditions. The process involves the alkylation and activation of inert thioamides, which leads to the cleavage of stable C–N and C–S bonds, eventually resulting in valuable esters with a broad range of substrates. The transformation can be easily carried out at room temperature using thioamide substrates, reactants, and activating agents. This protocol has been demonstrated by synthesizing important esters with applications.