Methyl [(pyrrolidin-1-ylcarbonothioyl)thio]acetate | 852399-75-8

• 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: Methyl [(pyrrolidin-1-ylcarbonothioyl)thio]acetate
• 英文别名: methyl 2-(pyrrolidine-1-carbothioylsulfanyl)acetate
• CAS: 852399-75-8
• 化学式: C₈H₁₃NO₂S₂
• mdl: MFCD06660533
• 分子量: 219.329
• InChiKey: BUWIQLRAMLHWNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  86.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl [(pyrrolidin-1-ylcarbonothioyl)thio]acetate 、 三氟甲烷磺酸甲酯 以 乙醚 为溶剂， 以91%的产率得到
  参考文献：
  名称：

  Design and synthesis of new family of ionic liquids based on 2-iminium-1,3-dithiolanes: A combined theoretical and experimental effort

  摘要：

  An efficient method for synthesis of 2-iminium-1,3-dithiolane as a new family of ionic liquids with reaction of dithiocarbamates with methyl triflouromethanesulfonate was described. Theoretical study on the synthesized ionic liquids was also performed by quantum chemistry calculation. Geometry optimization on the ion pairs was carried out with the B3LYP/6-311++G(d,p) level of theory. The interaction energies were calculated, and corrected by the basis set superposition error (BSSE) calculated by the counterpoise method. The results of natural bond orbital (NBO) and quantum theory of atoms in molecules (QTAIM) analyses indicate that the interactions occur via hydrogen bonding between oxygen atom lone pairs (lp(O)) of triflouromethanesulfonate anion and antibonding orbitals of sigma*C-H of 2-iminium-1,3-dithiolane cations. Also, the results of QTAIM analysis show that the hydrogen bonds are closed shell (electrostatic) in the nature. Finally, the H-1 and C-13 calculated chemical shifts at the B3LYP/6-311++G** level were in agreement with experimental chemical shifts for synthesized ionic liquids. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.10.017
• 作为产物：
  描述：

  四氢吡咯 、 二硫化碳 、 溴乙酸甲酯 以80%的产率得到Methyl [(pyrrolidin-1-ylcarbonothioyl)thio]acetate
  参考文献：
  名称：

  在无溶剂条件下直接高效地进行无催化剂的一锅法合成二硫代氨基甲酸酯。

  摘要：

  [结构：见正文]基于胺，CS2和烷基卤化物的一锅反应，在无溶剂条件下无需使用催化剂，即可高效且简单地合成二硫代氨基甲酸酯。温和的反应条件，高收率和广泛的反应范围说明了该方法的良好合成实用性。该反应是生产S-烷基硫代氨基甲酸酯的高度原子经济的方法，可成功地大量用于制药或农业化学工业。

  DOI：

  10.1021/ol0620141

文献信息

• 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
• Catalyst- and additive-free syntheses of rhodanine and <i>S</i>-alkyl dithiocarbamate derivatives from sulfoxonium ylides
  作者：Ajay Sharma、Satyendra Kumar Pandey

  DOI：10.1039/d2cc06092b

  日期：——

  An efficient catalyst- and additive-free facile access to rhodanine and S-alkyl dithiocarbamate derivatives via multi-component reaction of amines, CS2 and α-ester sulfoxonium ylides in methanol has been described. The new synthetic methods offer excellent synthetic prospects for several functionalized rhodanines and S-alkyl dithiocarbamates with simple operational procedures.

  已经描述了通过胺、CS 2和 α-酯氧化亚砜叶立德在甲醇中的多组分反应，一种无需催化剂和添加剂即可轻松获得绕丹宁和S-烷基二硫代氨基甲酸酯衍生物的方法。新的合成方法通过简单的操作程序为多种功能化的绕丹宁和S-烷基二硫代氨基甲酸酯提供了极好的合成前景。
• Versatile and Large-Scale Synthesis of Functional Dithiocarbamates in Water
  作者：Najmedin Azizi、Fezzeh Aryanasab、Laleh Tourkian、Mohammad R. Saidi

  DOI：10.1080/00397910903531847

  日期：2010.12.21

  Structural diversity is possible in direct access to functional dithiocarbamates based on a highly efficient and simple one-pot reaction of CS2, amines, and alkyl halides in nearly quantitative yields in water.