diethyl phenylaminothiocarbonylphosphonate | 110461-12-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl phenylaminothiocarbonylphosphonate
• 英文别名: diethoxyphosphorylthioformic acid anilide；diethyl anilinocarbonothioylphosphonate；diethyl phenylcarbamothioylphosphonate；diethyl phenylthiocarbamoylphosphonate；Phenylthiocarbamoylphosphonsaeure-diaethylester；1-diethoxyphosphoryl-N-phenylmethanethioamide
• CAS: 110461-12-6
• 化学式: C₁₁H₁₆NO₃PS
• 分子量: 273.293
• InChiKey: KYPMTRNVLXULFH-UHFFFAOYSA-N

物化性质

• 熔点：
  57.3-58 °C
• 沸点：
  120-128 °C(Press: 4 x 10)
• 密度：
  1.1758 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  79.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl phenylaminothiocarbonylphosphonate 、 苯乙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以74%的产率得到diethyl phenyl(2-phenylacetyl)carbamothioylphosphonate
  参考文献：
  名称：

  Reactivity of Phosphonothioamidates with Acid Chlorides and Primary Amines: Synthesis and Conformational Study of N-Acylated Phosphonothioamidates and Phosphonoamidines

  摘要：

  Various N-acyl phosphonothioamidate derivatives, 2, were obtained from N-acylation of phosphonothioamidates, 1, with different acid chlorides. Phosphonoamidines, 3, were prepared in high yields by reacting phosphonothioamidates, 1, with primary amines at room temperature, to short reaction periods. All compounds were characterized on the basis of IR and NMR spectroscopy (H-1, C-13, F-19, and P-31) and in some cases by elemental analysis and calculations using Density Functional Theory (DFT)-B3LYP// 3-21G+** and evolution study by P-31-NMR and F-19-NMR spectroscopy using an external lock with D2O.

  DOI：

  10.1080/10426507.2015.1071372
• 作为产物：
  描述：

  亚磷酸,1,1-二甲基乙基二乙基酯 、 硫代异氰酸苯酯 反应 10.0h， 以82%的产率得到diethyl phenylaminothiocarbonylphosphonate
  参考文献：
  名称：

  Gazizov, T. Kh.; Chugunov, Yu. V.; Sal'keeva, L. K., Journal of general chemistry of the USSR, 1990, vol. 60, # 3, p. 491 - 493

  摘要：

  DOI：

文献信息

• An efficient method for the phosphonation of C=X compounds
  作者：A. O. Kolodyazhnaya、O. O. Kolodyazhnaya、O. I. Kolodyazhnyi

  DOI：10.1134/s1070363210040055

  日期：2010.4

  (aldehydes, ketones, ketophosphonates, aldimines, ketimines, isocyanates, isothiocyanates, and activated olefins) in the presence of amines and anilines hydrohalides was studied. We found that pyridine hydrohalides effectively activate the reaction of tralkyl phosphites with various C=X electrophiles: aldehydes, ketones, ketophosphonates, aldimines, ketimines, isocyanates, isothiocyanates, and activated

  在胺和苯胺​​氢卤化物存在下，研究了亚磷酸三烷基酯与C = X亲电试剂（醛，酮，酮膦酸酯，醛亚胺，酮亚胺，异氰酸酯，异硫氰酸酯和活化烯烃）的反应。我们发现吡啶氢卤化物有效地激活了亚磷酸三烷基酯与各种C = X亲电试剂的反应：醛，酮，酮膦酸酯，醛亚胺，酮亚胺，异氰酸酯，异硫氰酸酯和活化的烯烃。特别高的活性显示出吡啶氢碘化物。该反应是合成羟基膦酸酯，氨基膦酸酯，氨基甲酰基膦酸酯，氨基甲酰基硫代膦酸酯和亚甲基双膦酸酯的便利方法。
• A novel and convenient method for synthesis of carbamoyl and thiocarbamoyl phosphonates
  作者：Babak Kaboudin、Hazegh Zahedi

  DOI：10.1002/hc.20538

  日期：——

  A simple, efficient, and general method has been developed for the synthesis of carbamoyl and thiocarbamoyl phosphonic esters using CaCl2 as an efficient Lewis base catalyst. Carbamoyl and thiocarbamoyl phosphonic esters were obtained in good yield (37%–65%) and purity under mild conditions by the reaction of diethyl phosphite with isocyanates and isothiocyanates in the presence of CaCl2. This method

  已经开发了一种简单、有效和通用的方法，用于使用 CaCl2 作为有效的路易斯碱催化剂合成氨基甲酰基和硫代氨基甲酰基膦酸酯。通过亚磷酸二乙酯与异氰酸酯和异硫氰酸酯在 存在下的反应，在温和条件下以良好的产率 (37%–65%) 和纯度获得氨基甲酰基和硫代氨基甲酰基膦酸酯。该方法反应简单、快速、产率好，用于合成氨基甲酰基和硫代氨基甲酰基膦酸酯。© 2009 Wiley Periodicals, Inc. 杂原子化学 20:250–253, 2009; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20538
• Synthesis, Design, and Biological Evaluation of Novel Diethylphenylcarbamothioylphosphonate
  作者：Ridha Ben Ali、Rania Omrani、Amal Ben Othman、Anis Raddaoui、Azaiez Ben Akacha、Michèle Véronique El May

  DOI：10.1134/s1068162021010192

  日期：2021.1

  Abstract The aim of this work was to synthesize a diethyl phenylcarbamothioyl phosphonate (EThmP) and evaluate its biological activities. ThmP has been prepared with high yields and its conformation was determined. This phosphonothioamidate derivative was characterized by IR, and NMR Spectroscopy (1H, 13C, and 31P). On the component of EThmP, the Hirshfeld surface analysis indicates that the major

  摘要 这项工作的目的是合成苯基乙基氨基甲硫酰基膦酸二乙酯（EThmP）并评估其生物学活性。已经以高产率制备了ThmP，并确定了其构象。通过IR和NMR光谱（1 H，13 C和31P）。关于EThmP的成分，Hirshfeld表面分析表明，对晶体堆积的主要贡献是H···H（53.3％），H···O（12.9％）H···S（14.5％）和C···H（17.6％）相互作用。抗伤害感受试验（福尔马林试验）表明，EThmP可以在早期和晚期阶段调节疼痛，这是通过大鼠行为表现出来的，该行为的特征是没有受到感染的爪子的舔，咬和摇动。EThmP对疼痛的调节可能是由于其抗炎作用。热板测试表明，用EThmP进行的预处理未调节将大鼠保持在48°C的固定温度下所引起的疼痛伤害感受。被治疗的大鼠的行为表现为抬高，舔爪，跳跃和逃跑。EThmP不会影响记忆能力和乙酰胆碱酯酶活性。大鼠的发病率是正常的，没有死亡或毒性迹象。
• Thermolyses of α-phosphorylmethyl tetrazolyl sulfoxides in the presence of 2,3-dimethyl-1,3-butadiene and their reactions with several amines
  作者：Hiroyuki Morita、Shintaro Tashiro、Masahiro Takeda、Ken Fujimori、Nobuhiko Yamada、Md. Chanmiya Sheikh、Hiroyuki Kawaguchi

  DOI：10.1016/j.tet.2008.01.082

  日期：2008.4

  We have synthesized alpha-(phosphoryl)methyl tetrazolyl sulfoxides and examined the reactivities in the thermolyses and in the presence of several amines, such as aniline, benzylamine, piperidine, pyrrolidine, and morpholine. Thermolyses of the derivatives in the presence of 2,3-dimethyl-1,3-butadiene afforded 2-phosphoryl substituted 4,5-dimethyl-3,6-dihydro-2H-thiopyran S-oxide. In addition, novel phosphinecar-bothioamides were obtained in the reaction of the derivatives with amines. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and structural Studies of phosphonothioamidates
  作者：R. Omrani、F. Ben Amor、M. Bahri、M. L. Efrit、A. Ben Akacha

  DOI：10.1080/10426507.2015.1024783

  日期：2015.10.3

  The reaction of isothiocyanates with dialkylphosphites in the presence of strong base yielded the phosphonothioamides 2. Treatment of 2 with methyl iodide afforded the corresponding thioimidates 3 with high yields. All compounds were characterized on the basis of their IR, NMR Spectroscopy (H-1, C-13, F-19, and P-31) and in some cases by elemental analysis, HRMS data, and calculations using Density Functional Theory (DFT)-B3LYP//6-311G** and evolution study by P-31-NMR in an external lock with D2O. The conformational molecular structure of compounds 2d and 2f were determined by single-crystal X-ray diffraction analysis.