N-benzylfuran-2-carbothioamide | 117070-04-9

• 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-benzylfuran-2-carbothioamide
• 英文别名: furan-2-carbothioic acid benzylamide；Furan-2-thiocarbonsaeure-benzylamid
• CAS: 117070-04-9
• 化学式: C₁₂H₁₁NOS
• mdl: MFCD09538346
• 分子量: 217.291
• InChiKey: DDEBIBBITVSOEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-苄基呋喃-2-甲酰胺 在 吡啶 、 phosphorous (V) sulfide 作用下， 生成 N-benzylfuran-2-carbothioamide
  参考文献：
  名称：

  Hahn et al., Croatica Chemica Acta, 1957, vol. 29, p. 319,322

  摘要：

  DOI：

文献信息

• Direct Transamidation of Thioamides with Amines via Acetophenone-Promoted Enamine Catalysis under Metal-Free Conditions
  作者：Yuxing Tan、Penghui Ni、Wu-jiu Jiang、Yang Fu、Qiuping Ding

  DOI：10.1021/acs.joc.3c02352

  日期：2024.3.1

  selective, efficient, and simple method for direct transamidation of thioamides with amines, promoted by commercially available acetophenone under metal-/solvent-free conditions. The reaction tolerated a wide range of functional groups and substrates, including single- or double-thioamides, benzylamines, or alkyl/cycloalkyl-substituted aliphatic amines. The present protocol can be applied to gram-scale in

  在此，我们开发了一种高选择性、高效且简单的方法，用于在无金属/溶剂的条件下通过市售苯乙酮促进硫代酰胺与胺的直接转酰胺基化。该反应可耐受多种官能团和底物，包括单硫代酰胺或双硫代酰胺、苄胺或烷基/环烷基取代的脂肪胺。本协议可以以良好的产量应用于克级。此外，双转酰胺基产物的 Pt-/Ni-配合物的产率也很高。光物理性质的研究表明，Pt配合物的荧光光谱显示出以550-750 nm为中心的发射带，并在紫外灯（365 nm）照射下呈现红色荧光。
• Antitubercular Substances. IV. Thioamides
  作者：Robert I. Meltzer、Arnold D. Lewis、John A. King

  DOI：10.1021/ja01620a029

  日期：1955.8
• Aminolysis of aryl dithio-2-thiophenates and dithio-2-furoates in acetonitrile
  作者：Hyuck Keun Oh、So Young Woo、Chul Ho Shin、Ikchoon Lee

  DOI：10.1002/(sici)1097-4601(1998)30:11<849::aid-kin7>3.0.co;2-v

  日期：——

  The aminolyses of the title substrates with anilines and benzylamines are investigated in acetonitrile. A clean second-order kinetics is obtained with a first-order rate law in the amine concentration, which is uncomplicated by the fast proton transfer step. The large magnitude of rho(z) (rho(1g)) as well as rho(x) (rho(nuc)) together with relatively large positive p(xz) values is consistent with a stepwise mechanism in which thiophenolate ion expulsion from the intermediate is rate limiting. For the reactions of aryl dithio-2-thiophenates with benzylamines the magnitude of rho(x) and rho(z) values is relatively smaller suggesting that both the addition and expulsion of thiophenolate are partially rate determining. Relatively large secondary kinetic isotope effects, k(H)/k(D) greater than or equal to 1.7, with deuterated nucleophiles, support involvement a concurrent proton transfer to the departing thiophenolate ion in the transition state. (C) 1998 John Wiley & Sons, Inc.