methyl 3-((phenylcarbamothioyl)thio)propanoate | 56624-42-1

• 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: methyl 3-((phenylcarbamothioyl)thio)propanoate
• 英文别名: methyl 3-(phenylcarbamothioylthio)propanoate；Methyl 3-(phenylcarbamothioylsulfanyl)propanoate
• CAS: 56624-42-1
• 化学式: C₁₁H₁₃NO₂S₂
• 分子量: 255.362
• InChiKey: WATRHIHDTGHIKH-UHFFFAOYSA-N

物化性质

• 熔点：
  50 °C
• 沸点：
  370.0±44.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-((phenylcarbamothioyl)thio)propanoate 、 2-氨基苯甲酰胺 在 三乙胺 作用下， 以 乙醇 为溶剂， 以85%的产率得到3-苯基-2-硫代-2,3-二氢-4(1H)-喹唑啉酮
  参考文献：
  名称：

  通过二硫代氨基甲酸酯-邻氨基苯甲酸反应制备2-thioxo-2,3-dihydroquinazolin-4（1H）-one的实用方法

  摘要：

  已经开发了一种实用而直接的方案，用于从二硫代氨基甲酸酯化学中制备2-硫代-2-3，3-二氢喹唑啉-4（1H）-一衍生物。该方法包括使用乙醇作为溶剂，使邻氨基苯甲酸衍生物（2-氨基苯甲酸，2-氨基苯甲酰胺和异丙酸酐）与各种二硫代氨基甲酸酯衍生物反应。该方案的主要优点包括实用的简便性，良好的高收率，以及易于产品分离，纯化和溶剂便宜。

  DOI：

  10.1016/j.cclet.2016.06.012
• 作为产物：
  描述：

  3-Phenyl-4-oxo-2-thioxo-tetrahydro-1,3-thiazin 、 sodium methylate 以 甲醇 为溶剂， 生成 methyl 3-((phenylcarbamothioyl)thio)propanoate
  参考文献：
  名称：

  1,3-噻嗪的研究，IV 关于 2-thioxo-4-oxo- 和 2,4-dioxo-tetrahydro-1,3-thiazines 与醇化物的反应产物的构成

  摘要：

  当醇化物作用于 2-thioxo-4-oxo-tetrahydro-1,3-thiazines 1a-d 时，不会形成旧文献中给出的 C = S 键的加成产物，但 β-（氨基-硫代羰基巯基）丙酸酯 4a – e，其结构由红外光谱和反合成证实。2,4-二氧代化合物 5a 和 5b 在相同条件下进一步裂解，得到氨基甲酸酯 7a 和 7b 以及 β-巯基丙酸酯 (8)。

  DOI：

  10.1002/ardp.19753080610

文献信息

• The thiocarbonyl ‘S’ is softer than thiolate ‘S’: A catalyst-free one-pot synthesis of isothiocyanates in water
  作者：Latonglila Jamir、Abdur Rezzak Ali、Harisadhan Ghosh、Francis A. S. Chipem、Bhisma K. Patel

  DOI：10.1039/b923336a

  日期：——

  Treatment of the preformed or the in situ generated aryl/alkyl dithiocarbamates triethylammonium salt (ArNHCSS−.Et3NH+) with methyl acrylate in an aqueous medium gave solely arylisothiocyanate (ArNCS), whereas the in situ generated aryl dithiocarbamic acid (ArNHCSS−.H+) yielded exclusively the thia-Michael adduct (ArNHCSSCH2CH2COOMe). This differential reactivity can be explained by two alternative mechanisms which is dependent both on the nature of the counter cation and on the pH of the reaction medium. Irrespective of the counter cations, the thiocarbonyl sulfur (=S) atom, having large orbital-coefficient, is softer compared to the thiol/thiolate sulfur (-SH/S−) in a dithiocarbamate salt and the former adds to the Michael acceptor by a 1,4-addition.

  在水中介质中，用甲基丙烯酸处理预制的或原位生成的芳基/烷基二硫代氨基甲酸盐三乙基铵盐（ArNHCSS−.Et3NH+）仅得到芳基异硫氰酸酯（ArNCS），而原位生成的芳基二硫代氨基甲酸（ArNHCSS−.H+）仅生成硫代迈克尔加合物（ArNHCSSCH2CH2COOMe）。这种差异性反应活性可以通过两种替代机制来解释，这取决于反荷离子的性质和反应介质的pH值。不管反荷离子如何，与二硫代氨基甲酸盐中的硫醇/硫醇盐硫（−SH/S−）相比，硫羰基硫（=S）原子具有较大的轨道系数，更为柔软，前者通过1,4-加成与迈克尔受体加合。
• Expeditious one-pot three component synthesis of N-aryl dithiocarbamate derivatives using mesoporous Cu-materials
  作者：Soumen Payra、Arijit Saha、Rui Peng、Chia-Ming Wu、Ranjit T. Koodali、Subhash Banerjee

  DOI：10.1016/j.tetlet.2015.01.158

  日期：2015.3

  In this study, a facile one-pot three component protocol has been demonstrated for the preparation of synthetically challenging N-aryl dithiocarbamate derivatives using mesoporous Cu-materials as catalyst at room temperature. The mesoporous Cu-catalysts namely Cu-MCM-41, Cu-MCM-48, and Cu-SBA-15 were prepared by impregnation of Cu-salts on the synthesized mesoporous materials and were characterized by powder X-ray diffraction, N-2 adsorption-desorption, and transmission electron microscopic studies. Significant improvement of yields was obtained using mesoporous Cu-catalysts under milder reaction conditions compared to the earlier reported catalysts. All the three mesoporous Cu-catalysts showed comparative reactivity however a little higher yield was obtained using Cu-MCM-48. (C) 2015 Elsevier Ltd. All rights reserved.
• 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.
• OH⁻/Silica-Mediated One-Pot Synthesis of Dithiocarbamates Under Solvent-Free Conditions
  作者：Ghasem Rezanejade Bardajee、Hamid Samareh Afsari、Seyediraj Sadraei、Seyedehmaryamdokht Taimoory

  DOI：10.1080/10426507.2011.582593

  日期：2012.7

  An efficient, versatile, and environmentally benign method for the synthesis of dithiocarbamates under solvent-free conditions is reported. The Michael addition of electron-deficient alkenes with alkyl or aryl amines and CS2 in the presence of OH-/silica in a one-pot three-component reaction protocol gave the corresponding dithiocarbamates in good to excellent yields. This method is suitable for a wide range of amines and a variety of Michael acceptors in solvent-free conditions. The results of the present work show the desired products in excellent yields.
• HANEFELD W., ARCH. PHARM. <APBD-AJ>, 1975, 308, NO 6, 450-454
  作者：HANEFELD W.

  DOI：——

  日期：——