1-(morpholin-4-yl)-2-(4-nitrophenyl)ethanethione | 943333-28-6

• 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: 1-(morpholin-4-yl)-2-(4-nitrophenyl)ethanethione
• 英文别名: 1-Morpholino-2-(4-nitrophenyl)-1-ethanethione；1-morpholin-4-yl-2-(4-nitrophenyl)ethanethione
• CAS: 943333-28-6
• 化学式: C₁₂H₁₄N₂O₃S
• 分子量: 266.321
• InChiKey: VYEGLJHHKSRRDO-UHFFFAOYSA-N

物化性质

• 沸点：
  439.9±55.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  90.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吗啉 、 对硝基苯乙酮 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 反应 0.33h， 以85%的产率得到1-(morpholin-4-yl)-2-(4-nitrophenyl)ethanethione
  参考文献：
  名称：

  超声介导的 Willgerodt-Kindler 反应：硫代乙酰胺的非热合成

  摘要：

  摘要 几种芳基甲基酮与胺和元素硫的非热、无溶剂缩合可在短时间内使用超声波辐射有效地进行。因此，可以方便地合成各种硫代乙酰胺。在受控温度 (25 ± 1° C) 下进行的类似实验产生了可比的产率，显示了超声辐射在反应进程中的促进作用。图形概要

  DOI：

  10.1080/10426507.2010.550269

文献信息

• Rapid and efficient protocol for Willgerodt–Kindler’s thioacetamides catalyzed by sulfated polyborate
  作者：Deelip S. Rekunge、Chetan K. Khatri、Ganesh U. Chaturbhuj

  DOI：10.1007/s00706-017-2013-x

  日期：2017.12

  AbstractA simple and efficient method for the synthesis of one-pot, three-component thioacetamides via Willgerodt–Kindler reaction was developed using a sulfated polyborate catalyst. The method described the reaction of ketones, sulfur, and secondary amines with high yields under a solvent-free condition at 100 °C. The key advantages of the present method are short reaction time, high yields, solvent-free

  摘要通过使用硫酸化的多硼酸盐催化剂，开发了一种通过Willgerodt-Kindler反应合成一锅三组分硫代乙酰胺的简单有效的方法。该方法描述了酮，硫和仲胺在无溶剂条件下于100°C下高产率的反应。本方法的关键优点是反应时间短，产率高，无溶剂条件和催化剂的可回收性，这带来了经济和生态上的回报。 图形概要
• Sulfated tungstate: A green catalyst for synthesis of thiomorpholides via Willgerodt–Kindler reaction
  作者：Suresh D. Salim、Sagar P. Pathare、Krishnacharya G. Akamanchi

  DOI：10.1016/j.catcom.2011.06.022

  日期：2011.10

  Use of sulfated tungstate as an efficient, green and reusable catalyst for preparation of thiomorpholides via Willgerodt–Kindler reaction pathway is presented. The reaction proceeds under solvent free condition. The advantages of this method are high yields, short reaction times, ease of product isolation and recyclability of catalyst for a number of times without significant loss of activity.

  本文介绍了使用硫酸钨作为一种高效，绿色且可重复使用的催化剂，通过Willgerodt-Kindler反应途径制备硫吗啡内酯的方法。反应在无溶剂条件下进行。该方法的优点是产率高，反应时间短，产物分离容易和催化剂可循环使用多次，而活性没有明显损失。
• Silica-supported fluoroboric acid (HBF4–SiO2) catalyzed highly productive synthesis of thiomorpholides as activators of l-asparaginase as well as the antioxidant agent
  作者：Babasaheb P. Bandgar、Shrikant S. Gawande、Suchita C. Warangkar、Jalinder V. Totre

  DOI：10.1016/j.bmc.2010.03.033

  日期：2010.5

  An efficient solvent-free procedure for the synthesis of thiomorpholides in the presence of a catalytic amount of solid-supported fluoroboric acid (HBF4-SiO2) is described. The advantages of this method are high yields, short reaction times, ease of product isolation, low cost, and the catalyst can be recycled for a number of times without significant loss of activity. Three thiomorpholides possessing electron-donating group (4c, 4g, and 4h) were exhibiting excellent stimulatory activities against Erwinia carotovora L-asparaginase. The most potent activator, compound 4h displayed the following kinetic parameters, K-m = 75 mu M and V-max = 1000 mu mol mg(-1) min(-1) and K-A = 0.985 mu M. Furthermore, these compounds (4g, 4h, 4c, 4f, 4a, and 4d) have also shown promising 2,2'-diphenyl-1-picrylhydrazyl (DPPH) reducing antioxidant activity (21-36%) at 1 mM concentration as compared to standard butylated hydroxyl anisole (72% at 1 mM). (C) 2010 Published by Elsevier Ltd.