methylene-bis(diethyldithiocarbamate) | 28535-08-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: methylene-bis(diethyldithiocarbamate)
• 英文别名: methylene bis-(di-ethylamino-dithioformate)；methylene bis(diethylcarbamodithioate)；methylene bis(N,N-diethyldithiocarbamate)；Methylenebis(N,N-diethyldithiocarbamate)；diethylcarbamothioylsulfanylmethyl N,N-diethylcarbamodithioate
• CAS: 28535-08-2
• 化学式: C₁₁H₂₂N₂S₄
• 分子量: 310.573
• InChiKey: GEKMQLNEANPVFN-UHFFFAOYSA-N

物化性质

• 熔点：
  73-74 °C
• 沸点：
  378.1±52.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methylene-bis(diethyldithiocarbamate) 、 对硝基氯苯 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以55%的产率得到5-Chloro-2-nitrobenzyl diethyldithiocarbamate
  参考文献：
  名称：

  Vicarious substitution of hydrogen with carbanions of dithioacetals

  摘要：

  DOI：

  10.1021/jo00200a059
• 作为产物：
  描述：

  三乙胺 以 乙腈 为溶剂， 反应 28.0h， 生成 methylene-bis(diethyldithiocarbamate)
  参考文献：
  名称：

  Development of disulfide-derived fructose-1,6-bisphosphatase (FBPase) covalent inhibitors for the treatment of type 2 diabetes

  摘要：

  Fructose-1,6-bisphosphatase (FBPase), as a key rate-limiting enzyme in the gluconeogenesis (GNG) pathway, represents a practical therapeutic strategy for type 2 diabetes (T2D). Our previous work first identified cysteine residue 128 (C128) was an important allosteric site in the structure of FBPase, while pharmacologically targeting C128 attenuated the catalytic ability of FBPase. Herein, ten approved cysteine covalent drugs were selected for exploring FBPase inhibitory activities, and the alcohol deterrent disulfiram displayed superior inhibitory efficacy among those drugs. Based on the structure of lead compound disulfiram, 58 disulfide-derived compounds were designed and synthesized for investigating FBPase inhibitory activities. Optimal compound 3a exhibited significant FBPase inhibition and glucose-lowering efficacy in vitro and in vivo. Furthermore, 3a covalently modified the C128 site, and then regulated the N125-S124-S123 allosteric pathway of FBPase in mechanism. In summary, 3a has the potential to be a novel FBPase inhibitor for T2D therapy. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112500

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。
• C-16 Artemisinin Derivatives and Their Antimalarial and Cytotoxic Activities:  Syntheses of Artemisinin Monomers, Dimers, Trimers, and Tetramers by Nucleophilic Additions to Artemisitene
  作者：Sanchai Ekthawatchai、Sumalee Kamchonwongpaisan、Palangpon Kongsaeree、Bongkoch Tarnchompoo、Yodhathai Thebtaranonth、Yongyuth Yuthavong

  DOI：10.1021/jm0103007

  日期：2001.12.1

  Nucleophilic additions of lithium keto and ester enolates and mono- and bifunctional Grignard reagents to artemisitene provided C-16-derived artemisinin monomers, dimers, trimers, and tetramers whose antimalarial and cytotoxic activities have been evaluated.

  锂酮和酯烯醇化物以及单和双功能格氏试剂向青蒿素的亲核加成提供了 C-16 衍生的青蒿素单体、二聚体、三聚体和四聚体，其抗疟和细胞毒活性已得到评估。
• Metal complexes of sulphur ligands. Part III. Reaction of platinum(<scp>II</scp>)NN-dialkyldithiocarbamates, O-ethyl dithiocarbonate (xanthate), and OO′-diethyl dithiophosphate with tertiary phosphines
  作者：J. M. C. Alison、T. A. Stephenson

  DOI：10.1039/dt9730000254

  日期：——

  Evidence is presented to show that the reaction of all M(S–S)2 compounds [M = Pt, Pd; (S–S)–=–S2CNR2(R = Me, Et), –S2COR (R = Et, PhCH2), –S2P(OEt)2, and –S2PR2(R = Me, Et, Ph)] with tertiary phosphines occurs by stepwise cleavage of metal–sulphur bonds to generate four-co-ordinate compounds of formulae [M(S–S)2PR′3] and [M(S–S)(PR′3)2](S–S) with unidentate/bidentate (III) and ionic/bidentate (IV)

  证据表明所有M（S–S）2化合物的反应[M = Pt，Pd; （S-S）- = -小号2 CNR 2（R =甲基，乙基），-小号2 COR（R =的Et，物理信道2），- š 2 P（OET）2，和-小号2 PR 2（R = ME等中，Ph）]与叔膦发生通过金属-硫键逐步切割，以产生式[M（S-S）的四坐标化合物2 PR' 3 ]和[M（S-S） （PR' 3）2]（S–S）分别具有不完全/完全（III）和离子/完全（IV）的配位。所有的离子化合物容易地恢复到[M（S-S）2 PR' 3 ]中的非极性溶剂的存在下复合体通过亲核攻击由（S-S）-对金属。此外，对于（S-S）- = -小号2 COR，-小号2 P（OET）2，亲核攻击也可以在协调的烷氧基发生，得到新化合物〔（R' 3 P）2 MS 2 CO]（I）和[（R' 3 P）2个MS 2P（O）OEt]（II）。
• PROCESS FOR PREPARING METHYLENE BIS-(DIALKYLAMINO-DITHIOFORMATE) IN ONE STEP
  申请人：CHINA PETROLEUM & CHEMICAL CORPORATION

  公开号：US20140371483A1

  公开（公告）日：2014-12-18

  A process for preparing methylene bis-(dialkylamino-dithioformate) in one step includes: simultaneously feeding all or part of four raw materials: dialkylamine, an aqueous solution of sodium hydroxide, dichloromethane and carbon disulfide through a constant-flow pump into a continuous flow reactor; performing the reactions in the continuous flow reactor under a temperature of 10 to 100° C. and with a residence time of 10 to 100 s; simply separating of the obtained reaction products to give the final product. The process synthesizes the product in one step by using the continuous flow reactor. The rapid mass transfer and heat transfer in the continuous flow reactor promote the main reaction, reduce side reactions, improve the product color, and shorten the operation time. Moreover, the yield is relatively high and the quality of the final product meets the requirements.

  一种制备亚甲基双-(二烷基氨基-二硫代甲酸酯)的方法包括：同时将四种原料之一或全部：二烷基胺、氢氧化钠水溶液、二氯甲烷和二硫化碳通过恒流泵输入连续流反应器；在连续流反应器中在10至100°C的温度下进行反应，并在10至100秒的停留时间内进行反应；简单地分离获得的反应产物以得到最终产物。该方法通过使用连续流反应器在一步中合成产品。连续流反应器中的快速质量传递和热传递促进主反应，减少副反应，改善产品颜色，并缩短操作时间。此外，产率相对较高，最终产品的质量符合要求。
• Bis(dialkylaminethiocarbonyl)disulfides as Potent and Selective Monoglyceride Lipase Inhibitors
  作者：Coco N. Kapanda、Giulio G. Muccioli、Geoffray Labar、Jacques H. Poupaert、Didier M. Lambert

  DOI：10.1021/jm901323s

  日期：2009.11.26

  Monoglyceride lipase (MGL) inhibition may offer an approach in treating diseases in which higher 2-arachidonoyglycerol activity would be beneficial. We report here the synthesis and pharmacological evaluation of bis(dialkylaminethiocarbonyl)disulfide derivatives as irreversible MGL inhibitors. Inhibition occurs through interactions with MGL C208 and C242 residues, and these derivatives exhibit high inhibition selectivity over fatty acid amide hydrolase, another endocannabinoid-hydrolyzing enzyme.