N-(diethoxyphosphoryl)toluene-p-sulphonamide | 51956-75-3

• 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: N-(diethoxyphosphoryl)toluene-p-sulphonamide
• 英文别名: o,o-diethyl p-tolylsulfonylamidophosphate；(toluene-4-sulfonyl)-amidophosphoric acid diethyl ester；(Toluol-4-sulfonyl)-amidophosphorsaeure-diaethylester；Diethyl-N-p-toluolsulfonylphosphoramidat；N-diethoxyphosphoryl-4-methylbenzenesulfonamide
• CAS: 51956-75-3
• 化学式: C₁₁H₁₈NO₅PS
• 分子量: 307.307
• InChiKey: OGFXMRSHYYZRIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(diethoxyphosphoryl)toluene-p-sulphonamide 在 potassium tert-butylate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Organophosphorus ligands with XPNSO skeleton (X = O, S) and their Pd(II) complexes. Crystal and molecular structure of [{XP(OEt)2}(O2SR)]NH (X = O, R = Me, Ph; X = S, R = C6H4Cl-4) and Pd[{SP(OEt)2}(O2SC6H4Cl-4)N]2

  摘要：

  Several organophosphorus acids of type [{XP(OEt)(2))(O2SR)]NH [X= O, R= Me (1), Ph (2), C6H4CH3-4 (3); X = S, R = C6H4Cl-4 (4)] were obtained by a method based on the reaction between (EtO)(2)P(X)NHLi and the corresponding organosulfonyl chloride. They were subsequently deprotonated with KOBut. Salt metathesis reactions between PdCl2 and the corresponding potassium salts K[{XP(OEt)(2))(O2SR)N] [X = O, R = Me (5), Ph (6), C6H4CH3-4 (7); X = S. R = C6H4Cl-4 (8)] in a 1:2 molar ratio resulted in palladium(II) complexes of type Pd[{XP(OEt)(2))(O2SR)N](2) [X = O, R = Me (9), Ph (10), C6H4CH3-4 (11); X = S, R = C6H4Cl-4 (12)]. In a similar way was obtained the palladium(II) complex Pd[(SPPh2)(O2SPh)N](2) (13), using the appropriate reagents. All compounds were characterized by multinuclear NMR (H-1, C-13, P-31) and infrared spectroscopy. The potassium salts and the palladium complexes were investigated also by mass spectrometry. Single-crystal X-ray diffraction studies revealed a layered supramolecular assembly in case of acid 1, a monomeric structure for compound 4, while in case of compound 2 dimeric associations are formed in the solid state by NH center dot center dot center dot OP hydrogen bonding. A trans-S,N-coordination pattern of the organophosphorus ligand was found in the palladium complex 12. Moreover, short Cl center dot center dot center dot H contacts result in a polymeric [Pd[{SP(OEt)(2)}(O2SC6H4Cl-4)N](2)](n) chain. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.01.023
• 作为产物：
  描述：

  氯磷酸二乙酯 、 sodium p-toluenesulfonamide 生成 N-(diethoxyphosphoryl)toluene-p-sulphonamide
  参考文献：
  名称：

  Diethyl N-Arylsulfonylphosphoramidates

  摘要：

  DOI：

  10.1021/jo01355a006

文献信息

• Removal of toluene-p-sulphonyl groups from sulphonamides. Part 4. Synthesis of phenylglyoxal imine monomers
  作者：William R. McKay、George R. Proctor

  DOI：10.1039/p19810002435

  日期：——

  with bases have been systematically examined. Monomeric C-methoxy-imines are available from some of these reactions. C-methoxyphenacylarylamines, made by two routes, were converted into monomeric imines on treatment with noble-metal catalysts. The boron trifluoridecatalysed reactions of aryl aldehydes with sulphonamides provide a new and convenient route to N-sulphonylarylimines.

  已经系统地检查了N-甲苯磺酰基苯甲胺与碱的合成和反应。单体C-甲氧基亚胺可从这些反应中的一些获得。在贵金属催化剂处理下，通过两种途径制得的C-甲氧基苯甲酰基芳基胺被转化为单体亚胺。芳基醛与磺酰胺的三氟化硼催化反应为制备N-磺酰基芳烃提供了新的便捷途径。
• Organocatalytic Asymmetric Synthesis of 1,2,4-Trisubstituted Azetidines by Reductive Cyclization of Aza-Michael Adducts of Enones
  作者：Lal Yadav、Ritu Kapoor、Ruchi Chawla、Santosh Singh

  DOI：10.1055/s-0031-1290954

  日期：2012.6

  aza-Michael addition of N-substituted phosphoramidates to enones generates aza-Michael adducts which undergo intramolecular reductive cyclization with (R)-alpine borane to afford 1,2,4-trisubstituted azetidines in a one-pot procedure. These optically active products are obtained in good to high yields (67–93%) with excellent stereocontrol (78–96% ee) from a vast variety of enones.

  N-取代的氨基磷酸酯与烯酮的高效和高度对映选择性有机催化氮杂-迈克尔加成生成氮杂-迈克尔加合物，该加合物与 (R)-高山硼烷进行分子内还原环化，在一锅法中提供 1,2,4-三取代氮杂环丁烷. 这些光学活性产物以良好到高产率 (67–93%) 获得，具有出色的立体控制 (78–96% ee)，来自种类繁多的烯酮。
• Strategic applications of Baylis–Hillman adducts to general syntheses of 3-nitroazetidines
  作者：Ankita Rai、Lal Dhar S. Yadav

  DOI：10.1039/c1ob06274c

  日期：——

  A novel one-pot highly diastereoselective synthesis of substituted 3-nitroazetidines via an anionic domino process is described. The synthesis involves a high yielding annulation of Baylis–Hillman alcohols and their aldehydes with either N-aryl/tosylphosphoramidates or N-aryl/tosylphosphoramidates in combination with a task-specific ionic liquid [bmim][X–Y] to afford the corresponding 1,2,3-tri- and

  描述了一种经由阴离子多米诺法的新颖的一锅式高度非对映选择性合成取代的3-硝基氮杂环丁烷。合成涉及将Baylis-Hillman醇及其醛与N-芳基/甲苯磺酰基膦酸酯或N-芳基/甲苯磺酰基膦酸酯与特定任务的离子液体[bmim] [X-Y]结合使用，以高收率环化得到相应的1 1,2,3-三-和1,2,3,4-四取代的氮杂环丁烷。已经提出了形成各种3-硝基氮杂环丁烷的合理机理。
• Kirsanow; Schewtschenko, Zhurnal Obshchei Khimii, 1954, vol. 24, p. 474,482,882,883;engl.Ausg.S.483,490,879,880
  作者：Kirsanow、Schewtschenko

  DOI：——

  日期：——
• Kremlev, M. M.; Kharchenko, A. V.; Shaposhnikov, S. I., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 7, p. 1452 - 1453
  作者：Kremlev, M. M.、Kharchenko, A. V.、Shaposhnikov, S. I.

  DOI：——

  日期：——