2-苯基-1-(1-吡咯烷基)乙硫酮 | 18732-58-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-苯基-1-(1-吡咯烷基)乙硫酮
• 中文别名: 乙硫酮,2-苯基-1-(1-吡咯烷基)-
• 英文名称: 2-phenyl-1-(pyrrolidin-1-yl)ethanethione
• 英文别名: 2-phenyl-1-pyrrolidin-1-ylethanethione
• CAS: 18732-58-6
• 化学式: C₁₂H₁₅NS
• 分子量: 205.324
• InChiKey: KWDQKASMLNFOEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 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：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-苯基-1-(1-吡咯烷基)乙硫酮 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 1-(2-苯基乙基)吡咯烷
  参考文献：
  名称：

  Borohydride and cyanoborohydride reduction of thioimonium salts. A convenient route for transformation of amides to amines

  摘要：

  DOI：

  10.1021/jo00331a032
• 作为产物：
  描述：

  phenylacetylpyrrolidine 在 alumina-supported P₂S₅ 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以92%的产率得到2-苯基-1-(1-吡咯烷基)乙硫酮
  参考文献：
  名称：

  Thionation of amides using a solid-supported P2S5 reagent under microwave irradiation

  摘要：

  In this Letter, we describe an improved method for the thionation of amides. Using a solid-supported P2S5 reagent, heating under microwave irradiation furnished thioamides in good to excellent yields, with a significantly reduced reaction time compared with that achieved under conventional heating. Furthermore, a change of solvent from that described in the literature enabled a simplified work-up and purification of the products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.104

文献信息

• Synthesis of thioamides via one-pot A³-coupling of alkynyl bromides, amines, and sodium sulfide
  作者：Yadong Sun、Huanfeng Jiang、Wanqing Wu、Wei Zeng、Jianxiao Li

  DOI：10.1039/c3ob42275e

  日期：——

  We herein describe a novel method for the synthesis of thioamides by a three component condensation of alkynyl bromides, amines, and Na₂S·9H₂O.

  我们在此描述了一种新颖的方法，通过炔基溴化物、胺和Na₂S·9H₂O的三组分缩合合成硫代酰胺。
• Three-Component Reaction between Alkynes, Elemental Sulfur, and Aliphatic Amines: A General, Straightforward, and Atom Economical Approach to Thioamides
  作者：Thanh Binh Nguyen、Minh Quan Tran、Ludmila Ermolenko、Ali Al-Mourabit

  DOI：10.1021/ol403345e

  日期：2014.1.3

  A general, straightforward, and atom-economical three-component synthesis of thioamides from alkynes, elemental sulfur, and aliphatic amines has been developed.

  已经开发了从炔烃，元素硫和脂族胺合成硫酰胺的常规，直接且原子经济的三组分方法。
• Decarboxylative Thioamidation of Arylacetic and Cinnamic Acids: A New Approach to Thioamides
  作者：Tirumaleswararao Guntreddi、Rajeshwer Vanjari、Krishna Nand Singh

  DOI：10.1021/ol501482g

  日期：2014.7.18

  A new decarboxylative strategy has been developed for the synthesis of thioamides via a three-component reaction involving arylacetic or cinnamic acids, amines and elemental sulfur powder, without the need of a transition metal and an external oxidant.

  已经开发了一种新的脱羧策略，用于通过三组分反应合成硫代酰胺，该反应涉及芳酸或肉桂酸，胺和元素硫粉，而无需过渡金属和外部氧化剂。
• 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
• Ultrasound-Mediated Willgerodt–Kindler Reactions: Non-thermal Synthesis of Thioacetamides
  作者：Mohammad M. Mojtahedi、Tooba Alishiri、M. Saeed Abaee

  DOI：10.1080/10426507.2010.550269

  日期：2011.9.1

  are conveniently synthesized. Similar experiments at controlled temperature (25 ± 1° C) resulted in comparable yields, showing the promotional role of ultrasound irradiation in the progress of the reaction. GRAPHICAL ABSTRACT

  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