N-allylpropanethioamide | 343859-37-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代酰胺
• 英文名称: N-allylpropanethioamide
• 英文别名: N-allyl-thiopropionamide；Thiopropionsaeure-allylamid；N-Allyl-thiopropionamid；N-prop-2-enylpropanethioamide
• CAS: 343859-37-0
• 化学式: C₆H₁₁NS
• mdl: MFCD19218369
• 分子量: 129.226
• InChiKey: VOPUCLBQGDZVSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-allylpropanethioamide 在 溴 、 溶剂黄146 作用下， 生成 N-(2,3-dibromo-propyl)-thiopropionamide
  参考文献：
  名称：

  Sachs; Loevy, Chemische Berichte, 1904, vol. 37, p. 875

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基溴化镁 、 天然芥菜籽油 生成 N-allylpropanethioamide
  参考文献：
  名称：

  Sachs; Loevy, Chemische Berichte, 1904, vol. 37, p. 875

  摘要：

  DOI：

文献信息

• Sulfur‐ and Amine‐ Promoted Multielectron Autoredox Transformation of Nitromethane: Multicomponent Access to Thiourea Derivatives
  作者：Supasorn Phaenok、Le Anh Nguyen、Darunee Soorukram、Thi Thanh Tam Nguyen、Pascal Retailleau、Thanh Binh Nguyen

  DOI：10.1002/chem.202303703

  日期：2024.2

  Thiourea derivatives are in‐demand motifs in organic synthesis, medicinal chemistry and material science, yet redox methods for the synthesis that start from safe, simple, inexpensive and readily available feedstocks are scarce. In this article, we disclose the synthesis of these motifs using elemental sulfur and nitromethane as the starting materials. The method harnesses the multi‐electron auto‐redox property of nitromethane in the presence of sulfur and amines, delivering thiourea products without any added oxidant or reductant. Extension of this reaction to cyclizable amines and/or higher homologues of nitromethane led to a wide range of nitrogen heterocycles and thioamides. Operationally simple, the reactions are scalable, tolerate a wide range of functional groups, and can be employed for the direct functionalization of natural products. Mechanistically, the nitro group was found to act as an oxidant leaving group, being reduced to ammonia whereas sulfur, along with the role of a sulfur building block for the thiocarbonyl group, behaved as a complementary reductant, being oxidized to sulfate.

  摘要 硫脲衍生物是有机合成、药物化学和材料科学中炙手可热的基团，然而以安全、简单、廉价和易于获得的原料为起始原料的氧化还原合成方法却十分稀缺。本文披露了以元素硫和硝基甲烷为起始原料合成这些基团的方法。该方法利用了硝基甲烷在硫和胺存在下的多电子自动氧化还原特性，在不添加任何氧化剂或还原剂的情况下生成硫脲产品。将这一反应扩展到可环化胺和/或硝基甲烷的更高同系物，可得到多种氮杂环和硫代酰胺。该反应操作简单，可扩展性强，可容忍多种官能团，可用于天然产物的直接官能化。从机理上讲，硝基可作为氧化剂离去基团，被还原成氨，而硫作为硫代羰基的硫构件，可作为互补还原剂，被氧化成硫酸盐。
• Dmitrieva; Sarapulova; Klyba, Russian Journal of Organic Chemistry, 2000, vol. 36, # 8, p. 1110 - 1115
  作者：Dmitrieva、Sarapulova、Klyba、Albanov、Zinovyeva、Tolmachev、Nedolya、Brandsma

  DOI：——

  日期：——
• Sachs,F.; Loevy, Chemische Berichte, 1903, vol. 36, p. 585
  作者：Sachs,F.、Loevy

  DOI：——

  日期：——
• AUTOTAXIN INHIBITORS AND USES THEREOF
  申请人：NATIONAL AND KAPODISTRIAN UNIVERSITY OF ATHENS

  公开号：US20180141965A1

  公开（公告）日：2018-05-24

  Novel inhibitors of the enzyme autotaxin are described. The inhibitors contain one or two zinc-binding groups at the appropriate distance, Also described are uses thereof, such as for the inhibition of autotaxin activity and the treatment of various conditions (e.g., inflammatory conditions, cancer, obesity, autoimmune diseases).
• Sachs; Loevy, Chemische Berichte, 1904, vol. 37, p. 875
  作者：Sachs、Loevy

  DOI：——

  日期：——