N,N-dimethyl-1H-pyrrole-2-carbothioamide | 30380-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N,N-dimethyl-1H-pyrrole-2-carbothioamide
• 英文别名: N,N-Dimethyl-2-pyrrolthiocarbamid；N,N-dimethylpyrrole-2-carbothioamide；pyrrole-2-carbothioic acid dimethylamide
• CAS: 30380-74-6
• 化学式: C₇H₁₀N₂S
• 分子量: 154.236
• InChiKey: KDSRNQOBKNORCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-1H-pyrrole-2-carbothioamide 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Palladium(II) complexes of N,N-dimethylpyrrole-1- and 2-carbothioamides

  摘要：

  The reaction of the sodium salt of pyrrole with N,N-dimethylthiocarbamoyl chloride in N,N-dimethylformamide gave N,N-dimethylpyrrole-1-carbothioamide (Hnpt), while the reaction of pyrrole with N,N-dimethylthiocarbamoyl chloride under phase transfer conditions afforded N,N-dimethylpyrrole-2-carbothioamide (Hapt), together with a very small amount of N,N,N',N'-tetramethylpyrrole-1,2-dicarbothioamide. Hnpt and Hapt were metallated with lithium tetrachloropalladate in methanol to yield PdCl(npt) and PdCl(apt), respectively. Both complexes reacted with tri-n-butylphosphine (PBu3) and 4-tert-butyl-pyridine (tbp), forming PdCl(npt)(PBu3), PdCl(npt)(tbp), PdCl(apt)(PBu3) and PdCl(apt)(tbp). These and some additional complexes were characterized spectroscopically. In the npt complexes, the ligand was cyclopalladated at C(2) of the pyrrole ring, forming a five-membered, organometallic chelate ring accompanied by thioamide sulphur coordination. In the apt complexes, the ligand acted as a bidentate N-S chelate, the ring N-H proton being deprotonated. The X-ray analysis of PdCl(npt)(PBu3) and PdCl(apt)(PBu3) confirmed the coordination modes.

  DOI：

  10.1016/s0277-5387(00)83456-7
• 作为产物：
  描述：

  2-吡咯甲醛 、 二甲胺 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 四氢呋喃 、 水 为溶剂， 以60%的产率得到N,N-dimethyl-1H-pyrrole-2-carbothioamide
  参考文献：
  名称：

  室温下水介导的醛直接硫酰胺化

  摘要：

  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。

  DOI：

  10.1021/acs.joc.1c02307

文献信息

• Nonoyama, M.; Nonoyama, K., Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1995, vol. 25, p. 569 - 574
  作者：Nonoyama, M.、Nonoyama, K.

  DOI：——

  日期：——
• Efficient Synthesis of Esters by Cleavage of C–S and C–N Bonds via Alkylation and Activation of Thioamides
  作者：Guddeangadi N. Gururaja、Jigarkumar K. Vankar、Jaydeepbhai P. Jadav

  DOI：10.1055/s-0043-1774910

  日期：2024.9

  A 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.