3-(pyrrolidine-1-carbothioylsulfanyl)-propionic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-(pyrrolidine-1-carbothioylsulfanyl)-propionic acid methyl ester
• 英文别名: methyl 3-(pyrrolidine-1-carbothioylthio)propanoate；Methyl 3-(pyrrolidine-1-carbothioylsulfanyl)propanoate
• 化学式: C₉H₁₅NO₂S₂
• 分子量: 233.356
• InChiKey: LFOSNSMZKYSQKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  86.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 二硫化碳 、 丙烯酸甲酯（MA） 以97%的产率得到3-(pyrrolidine-1-carbothioylsulfanyl)-propionic acid methyl ester
  参考文献：
  名称：

  在无溶剂条件下无废物和环境友好地非催化合成二硫代氨基甲酸酯

  摘要：

  一种温和、方便且实用的直接合成二硫代氨基甲酸酯的一锅法已通过胺、CS 2 和迈克尔受体在室温下的无溶剂条件下缩合而成，收率良好至极好。

  DOI：

  10.1055/s-2007-991085

文献信息

• Catalysis by Ionic Liquids: Significant Rate Acceleration with the Use of [pmIm]Br in the Three-Component Synthesis of Dithio­carbamates
  作者：Brindaban C. Ranu、Amit Saha、Subhash Banerjee

  DOI：10.1002/ejoc.200700842

  日期：2008.1

  An easily accessible neutral ionic liquid, 1-methyl-3-pentylimidazolium bromide, promoted a one-pot three-component condensation of an amine, carbon disulfide, and an activated alkene/dichloromethane/epoxide to produce the corresponding dithiocarbamates in high yields at room temperature. The reactions are very fast in ionic liquids relative to those in other reaction media. These reactions do not

  一种易于获得的中性离子液体，1-甲基-3-戊基咪唑溴化物，促进了胺、二硫化碳和活性烯烃/二氯甲烷/环氧化物的一锅三组分缩合反应，在室温下以高产率制备相应的二硫代氨基甲酸酯温度。与在其他反应介质中的反应相比，离子液体中的反应速度非常快。这些反应不需要任何额外的催化剂或溶剂。离子液体可回收再循环用于后续反应。提出了一个合理的机制。
• Waste-Free and Environment-Friendly Uncatalyzed Synthesis of Dithiocarbamates under Solvent-Free Conditions
  作者：Najmedin Azizi、Mohammad Saidi、Forogh Ebrahimi、Elham Aakbari、Fezzeh Aryanasab

  DOI：10.1055/s-2007-991085

  日期：——

  A mild, convenient, and practical one-pot procedure for the direct synthesis of dithiocarbamates has been developed by condensation of amines, CS 2 , and a Michael acceptor, under solvent-free conditions at room temperature in good to excellent yields.

  一种温和、方便且实用的直接合成二硫代氨基甲酸酯的一锅法已通过胺、CS 2 和迈克尔受体在室温下的无溶剂条件下缩合而成，收率良好至极好。
• An efficient synthesis of dithiocarbamates under ultrasound irradiation in water
  作者：Najmadin Azizi、Elahm Gholibeglo、Sanaz Dehghan Nayeri

  DOI：10.1007/s00706-011-0687-z

  日期：2012.8

  economic, and green method for the synthesis of dithiocarbamate derivatives in water. The one-pot, three-component condensation of primary and secondary amines with carbon disulfide and unsaturated carbonyl compounds or alkyl halides under ultrasonic irradiation was developed as a green and fast protocol for the rapid high-yielding preparation of dithiocarbamates in water. Graphical abstract

  摘要具有超声活化的多组分反应已被用作简单，快速，原子经济且绿色的方法，用于在水中合成二硫代氨基甲酸酯衍生物。伯胺和仲胺与二硫化碳和不饱和羰基化合物或烷基卤化物在超声波辐射下的一锅，三组分缩合反应是一种绿色快速的方法，用于在水中快速高产率地制备二硫代氨基甲酸酯。 图形概要
• An efficient synthesis of aryldithiocarbamic acid esters from Michael addition of electron-deficient alkenes with arylamines and CS2 in solid media alkaline Al2O3
  作者：Shuai Xia、Xin Wang、Ze-mei Ge、Tie-ming Cheng、Run-tao Li

  DOI：10.1016/j.tet.2008.11.084

  日期：2009.1

  An efficient synthesis of dithiocarbamic acid esters from Michael addition of electron-deficient alkenes with arylamines and CS2 in solid media alkaline Al2O3 was presented. This method was suitable for a wide range of amines and a variety of Michael receptors. Specially, a series of aryldithiocarbamic acid esters was obtained from arylamines through this method. The protocol offers clean reactions and high yields with simple experimental procedures. Besides, the alkaline Al2O3 could be reused. (C) 2008 Elsevier Ltd. All rights reserved.
• Exploring the Structural Requirements for Inhibition of the Ubiquitin E3 Ligase Breast Cancer Associated Protein 2 (BCA2) as a Treatment for Breast Cancer
  作者：Ghali Brahemi、Fathima R. Kona、Annalisa Fiasella、Daniela Buac、Jitka Soukupová、Andrea Brancale、Angelika M. Burger、Andrew D. Westwell

  DOI：10.1021/jm901757t

  日期：2010.4.8

  The zinc-ejecting aldehyde dehydrogenase (A LDH) inhibitory drug disulfiram (DS F) was found to be a breast cancer-associated protein 2 (BCA2) inhibitor with potent antitumor activity. We herein describe our work in the synthesis and evaluation of new series of zinc-affinic molecules to explore the structural requirements for selective BCA2-inhibitory antitumor activity. An N(C=S)S-S motif was found to be required, based on selective activity in BCA2-expressing breast cancer cell lines and against recombinant BCA2 protein. Notably, the DSF analogs (3a and 3c) and dithio(peroxo)thioate compounds (5d and 5f) were found to have potent activity (submicromolar IC(50)) in BCA2 positive MCF-7 and T47D cells but were inactive (IC(50)> 10 mu M) in BCA2 negative M DA-MB-231 breast cancer cells and the normal breast epithelial cell line MCF10A. Testing in the isogenic BCA2 +ve M DA-MB-231/ER cell line restored antitumor activity for compounds that were inactive in the BCA2 -ve MDA-MB-231 cell line. In contrast, structurally related dithiocarbamates and benzisothiazolones (lacking the disulfide bond) were all inactive. Compounds 5d and 5f were additionally found to lack ALDH-inhibitory activity, suggestive of selective E3 ligase-inhibitory activity and worthy of further development.