(dibutylphosphoryl)methyl 4-methylbenzenesulfonate | 630065-13-3

• 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: (dibutylphosphoryl)methyl 4-methylbenzenesulfonate
• 英文别名: p-toluenesulfonic acid dibutylphosphorylmethyl ester；dibutylphosphinylmethyl tosylate；dibutylphosphonylmethanol tosylate；Bu2P(O)CH2OTs；Dibutylphosphorylmethyl 4-methylbenzenesulfonate
• CAS: 630065-13-3
• 化学式: C₁₆H₂₇O₄PS
• 分子量: 346.428
• InChiKey: QNIKBNWPXMIZFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (dibutylphosphoryl)methyl 4-methylbenzenesulfonate 、 4-叔丁基硫杂杯[4]芳烃 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 5,11,17,23-Tetratert-butyl-28-(dibutylphosphorylmethoxy)-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27-triol
  参考文献：
  名称：

  Phosphorylated Thiacalix[4]arenes

  摘要：

  Thiacalix[4]arenes bearing one, three, or four P=O containing groups at the upper or at the lower rim have been synthesized. Stereochemistry of the compounds was investigated by X-ray method.

  DOI：

  10.1080/10426507.2010.522636
• 作为产物：
  描述：

  dibutylphosphine oxide 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 48.0h， 生成 (dibutylphosphoryl)methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis and evaluation of ligands with mixed amide and phosphonate, phosphinoxide, and phosphonothioate sites for An(iii)/Ln(iii) extraction

  摘要：

  合成了各种具有不同供体位点组合的有机磷配体，并通过溶剂萃取研究评估了它们对铽(III)/铕(III)的络合能力。在具有甘油酰胺主链的配体中，采用混合酰胺和磷氧供体位点以及中央氧或氮原子的配体表现出了对铕(III)和铽(III)的合理萃取。中央氧原子的配体对铕(III)表现出选择性，而中央氮原子的配体则对铽(III)表现出选择性。具有磷硫供体位点和甘油酰胺主链的配体未表现出任何合理的萃取效果。在具有美克酰胺主链的配体中，带有富电子取代基的配体表现出较高的萃取效率，但对铽(III)和铕(III)几乎没有选择性。不同配体对铕(III)的萃取效率通过微量热法得到了证实。

  DOI：

  10.1039/c2nj40330g

文献信息

• Synthesis of Phosphorus-Containing Podands―Analogs of Diglycolamide Based on Diphenyl- and Dibutylphosphorylmethanol under Phase Transfer Catalysis Conditions
  作者：A. V. Kharlamov、S. K. Belus、O. I. Artyushin、N. A. Bondarenko

  DOI：10.1134/s107036321809013x

  日期：2018.9

  = Bu via OH-alkylation of phosphorylmethanols under the phase transfer conditions in the presence of Cs2CO3 was developed. Carbamoyl-substituted dimethyl ethers were synthesized via transformation of phosphorylmethanols to phosphorylmethoxyacetic acids, followed by amidation. Symmetrical bisphosphoryl substituted dimethyl ethers were obtained by reaction of phosphorylmethanols with tosyl chloride in

  一种方便的制备含磷豆荚的方法R 2 P（O）CH 2 OCH 2 X，其中X = C（O）NBu 2；P（O）R' 2，R = R'=苯基，卜，R =苯基，R'=卜经由铯的存在下，相转移条件下的phosphorylmethanols OH-烷基化2 CO 3被开发。氨基甲酰基取代的二甲醚是通过将磷酰基甲醇转化为磷酰基甲氧基乙酸，然后进行酰胺化反应而合成的。在Cs 2 CO 3存在下，使磷酰基甲醇与甲苯磺酰氯反应，得到对称的双磷酰基取代的二甲醚。在Cs 2 CO 3存在下不对称取代醚的合成由于甲苯磺酸磷酰基甲基酯的酯交换反应而复杂化，导致形成对称的副产物二甲醚。
• Calixarenes grafted with Bu2P(O)CH2O binding groups at the narrow rim: synthesis, structure and extraction of heterometallic Ru/Zn complexes
  作者：V. G. Torgov、G. A. Kostin、T. V. Us、T. M. Korda、O. V. Klimchuk、S. I. Miroshnichenko、K. Suwinska、A. A. Varnek、V. I. Kalchenko

  DOI：10.1007/s10847-010-9904-3

  日期：2011.10

  Calix[n]arenes (n = 4, 6) existing in the cone, 1,3-alternate or 1,3,5-alternate conformations and functionalized by two, four or six Bu2P(O)CH2O groups have been synthesized by the alkylation of hydroxycalix[4,6]arenes with tosylate of dibutylhydroxymethylphosphine oxide. Their molecular and crystal structures as well as binding properties towards of heterometallic Ru/Zn complexes were investigated. Due to the “calixarene effect” the phosphine oxides are effective extractants for the Ru/Zn complexes.

  通过羟基钙[4,6]烯与二丁基羟甲基氧化膦的对甲苯磺酸盐的烷基化，合成了锥形、1,3-互变或 1,3,5-互变构象的钙[n]烯（n = 4, 6），并使其具有两个、四个或六个 Bu2P(O)CH2O 官能团。研究了它们的分子和晶体结构以及与异金属 Ru/Zn 配合物的结合特性。由于 "卡利沙林效应"，膦氧化物是 Ru/Zn 复合物的有效萃取剂。
• Supramolecular Chemistry of Phosphorus-Containing (Thia)Calixarenes
  作者：Sergiy O. Cherenok、Stanislav I. Miroshnichenko、Andriy B. Drapailo、Olga I. Kalchenko、Roman V. Rodik、Vyacheslav I. Boiko、Yury I. Matveev、Alexander V. Ruban、Vitaly I. Kalchenko

  DOI：10.1080/10426507.2010.525766

  日期：2011.3.31

  Molecular modeling, synthesis, and structural investigations of the phosphorus-containing (thia)calixarenes and their supramolecular complexes with biorelevant or ecologically hazardous molecules and ions are discussed within the context of cationic and molecular recognition, extraction properties, and bioactivity.
• Synthesis and evaluation of ligands with mixed amide and phosphonate, phosphinoxide, and phosphonothioate sites for An(iii)/Ln(iii) extraction
  作者：Mudassir Iqbal、Richard G. Struijk、Jurriaan Huskens、Michal Sypula、Andreas Wilden、Giuseppe Modolo、Willem Verboom

  DOI：10.1039/c2nj40330g

  日期：——

  Various organophosphorus ligands with a combination of different donor sites were synthesized and evaluated by solvent extraction studies for the complexation of Am(III)/Eu(III). Among the ligands with a glycolamide backbone, those with mixed amide and PO donor sites and a central oxygen or nitrogen atom showed a reasonable extraction of Am(III) and Eu(III). Ligands with a central oxygen atom exhibited selectivity towards Eu(III), and those with a central nitrogen atom towards Am(III). Ligands with PS donor sites and a glycolamide backbone did not show any reasonable extraction. Amongst the ligands with a malonamide backbone, high extraction efficiency was observed for the ligand with electron-rich substituents on phosphorus, however, with almost no discrimination between Am(III) and Eu(III). The extraction efficiency of different ligands towards Eu(III) was confirmed by microcalorimetry.

  合成了各种具有不同供体位点组合的有机磷配体，并通过溶剂萃取研究评估了它们对铽(III)/铕(III)的络合能力。在具有甘油酰胺主链的配体中，采用混合酰胺和磷氧供体位点以及中央氧或氮原子的配体表现出了对铕(III)和铽(III)的合理萃取。中央氧原子的配体对铕(III)表现出选择性，而中央氮原子的配体则对铽(III)表现出选择性。具有磷硫供体位点和甘油酰胺主链的配体未表现出任何合理的萃取效果。在具有美克酰胺主链的配体中，带有富电子取代基的配体表现出较高的萃取效率，但对铽(III)和铕(III)几乎没有选择性。不同配体对铕(III)的萃取效率通过微量热法得到了证实。
• Phosphorylated Thiacalix[4]arenes
  作者：Andriy B. Drapailo、Sergiy G. Kharchenko、Svitlana V. Shishkina、Oleg V. Shishkin、Vitaly I. Kalchenko

  DOI：10.1080/10426507.2010.522636

  日期：2011.3.31

  Thiacalix[4]arenes bearing one, three, or four P=O containing groups at the upper or at the lower rim have been synthesized. Stereochemistry of the compounds was investigated by X-ray method.