2,2'-oxybis(N,N-bis(2-hydroxyethyl)acetamide) | 144084-73-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2'-oxybis(N,N-bis(2-hydroxyethyl)acetamide)
• 英文别名: 2-[2-[bis(2-hydroxyethyl)amino]-2-oxoethoxy]-N,N-bis(2-hydroxyethyl)acetamide
• CAS: 144084-73-1
• 化学式: C₁₂H₂₄N₂O₇
• 分子量: 308.332
• InChiKey: CSISHMLKKCQESR-UHFFFAOYSA-N

物化性质

• 沸点：
  596.1±50.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2'-oxybis(N,N-bis(2-hydroxyethyl)acetamide) 在 lithium aluminium tetrahydride 、 lithium hydride 、 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 98.0h， 生成 4,12,18,26,31-Pentaoxa-1,15,34,35-tetraazatetracyclo<13.13.5^1,15.1^6,10.1^20,24>pentatriaconta-6(34),7,9,20(35),21,23-hexaene
  参考文献：
  名称：

  Synthesis and complexation properties of new unsymmetrical cryptands

  摘要：

  Twelve novel unsymmetrical cryptands (1-12) containing various units (methylene, 2-methylenylpropylene, pyridine-2,6-diyldimethylene, o- and m-xylylene) each in two bridges have been synthesized by a one-step cyclization procedure. These cryptands were obtained by treating tetraalcohols 15-17, obtained from diethanolamine and diglycolyl dichloride followed by reduction or from diethanolamine and the appropriate oligoethylene glycol dichloride or ditosylate, with methylene chloride, 3-chloro-2-(chloromethyl)-l-propene, alpha,alpha'-dibromo-o-xylene, alpha,alpha'-dibromo-m-xylene, and 2,6-pyridinediyldimethyl ditosylate. Cryptancls 7 and 11, containing two acetal functions, were obtained in yields of 59 and 40%, respectively. Bis(2-methylenepropylene)-bridged cryptand 4 was independently synthesized by another method. Complexation properties of nearly all of these cryptands with the alkali metal cations were studied by an NMR technique. Some of the results were verified by a calorimetric titration technique. Cryptands 5 and 9, containing a 2,6-pyridinediyldimethylene unit in two bridges, and 11, containing a methylene unit in two bridges, showed high selectivity for potassium over sodium ions by factors ranging from 40 to 200. Bisacetal-containing cryptand 7 exhibited high selectivity for sodium over potassium ions with a selectivity factor of over 1000.

  DOI：

  10.1021/jo00049a013
• 作为产物：
  描述：

  2,2'-氧化二乙酰氯 、 二乙醇胺 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以67%的产率得到2,2'-oxybis(N,N-bis(2-hydroxyethyl)acetamide)
  参考文献：
  名称：

  Synthesis and evaluation of novel water-soluble ligands for the complexation of metals during the partitioning of actinides

  摘要：

  合成了不同类型的水溶性配体，并通过溶剂萃取研究评估了它们络合三价锕系元素的能力，并通过强亲脂配体（例如 TODGA）抑制其萃取。具有不同数量乙二醇基团或酰胺氮上含有乙酸钠部分的亲水性二甘醇酰胺 (DGA) 衍生物的反萃取效率表明，随着不同温度下酰胺氮上乙二醇单元数量的增加，反萃取效率会降低。水相的pH值。在 PS 供体配体中，只有具有丙二酰胺主链的配体表现出高反萃取效率，但对镅没有选择性。在水溶性三足配体（即带有 N,N-二甲基和 N,N-双（羟乙基）部分的次氮基三酸的酰胺衍生物）中，第一个配体对 Am(III) 表现出比 Eu(III) 显着的选择性，其中最大分离因子为 11.1，而后者更有效地络合水相中的放射性核素，最大分离因子为 5。通过一系列选定的配体络合 Eu(III) 的等温微量热实验证实了观察到的趋势反萃取特性。

  DOI：

  10.1039/c1nj20523d

文献信息

• Synthesis and complexation properties of new unsymmetrical cryptands
  作者：Jerald S. Bradshaw、Haoyun An、Krzysztof E. Krakowiak、Tingmin Wang、Chengyue Zhu、Reed M. Izatt

  DOI：10.1021/jo00049a013

  日期：1992.11

  Twelve novel unsymmetrical cryptands (1-12) containing various units (methylene, 2-methylenylpropylene, pyridine-2,6-diyldimethylene, o- and m-xylylene) each in two bridges have been synthesized by a one-step cyclization procedure. These cryptands were obtained by treating tetraalcohols 15-17, obtained from diethanolamine and diglycolyl dichloride followed by reduction or from diethanolamine and the appropriate oligoethylene glycol dichloride or ditosylate, with methylene chloride, 3-chloro-2-(chloromethyl)-l-propene, alpha,alpha'-dibromo-o-xylene, alpha,alpha'-dibromo-m-xylene, and 2,6-pyridinediyldimethyl ditosylate. Cryptancls 7 and 11, containing two acetal functions, were obtained in yields of 59 and 40%, respectively. Bis(2-methylenepropylene)-bridged cryptand 4 was independently synthesized by another method. Complexation properties of nearly all of these cryptands with the alkali metal cations were studied by an NMR technique. Some of the results were verified by a calorimetric titration technique. Cryptands 5 and 9, containing a 2,6-pyridinediyldimethylene unit in two bridges, and 11, containing a methylene unit in two bridges, showed high selectivity for potassium over sodium ions by factors ranging from 40 to 200. Bisacetal-containing cryptand 7 exhibited high selectivity for sodium over potassium ions with a selectivity factor of over 1000.
• Synthesis and evaluation of novel water-soluble ligands for the complexation of metals during the partitioning of actinides
  作者：Mudassir Iqbal、Jurriaan Huskens、Michal Sypula、Giuseppe Modolo、Willem Verboom

  DOI：10.1039/c1nj20523d

  日期：——

  Different types of water-soluble ligands were synthesized and their capability was evaluated by solvent extraction studies to complex trivalent actinides and suppress their extraction by a strong lipophilic ligand, such as TODGA. The back extraction efficiency of hydrophilic diglycolamide (DGA) derivatives with a varying number of ethylene glycol groups, or containing sodium acetate moieties on the amidic nitrogen shows a decrease in back-extraction efficiency with increasing number of ethylene glycol units on the amidic nitrogen at various pH values of the aqueous phase. Among the PS donating ligands only the ligand with a malonamide backbone exhibits a high reverse extraction efficiency, although, with no selectivity for americium. Within the water-soluble tripodal ligands, i.e. the amide derivatives of nitrilotriacid with N,N-dimethyl and N,N-bis(hydroxyethyl) moieties, the first one shows a pronounced selectivity for Am(III) over Eu(III), with a maximum separation factor of 11.1, while the latter one more efficiently complexes the radionuclides in the aqueous phase with a maximum separation factor of 5. Isothermal microcalorimetry experiments of the complexation of Eu(III) by a selected series of ligands confirm the observed trend in the back extraction properties.

  合成了不同类型的水溶性配体，并通过溶剂萃取研究评估了它们络合三价锕系元素的能力，并通过强亲脂配体（例如 TODGA）抑制其萃取。具有不同数量乙二醇基团或酰胺氮上含有乙酸钠部分的亲水性二甘醇酰胺 (DGA) 衍生物的反萃取效率表明，随着不同温度下酰胺氮上乙二醇单元数量的增加，反萃取效率会降低。水相的pH值。在 PS 供体配体中，只有具有丙二酰胺主链的配体表现出高反萃取效率，但对镅没有选择性。在水溶性三足配体（即带有 N,N-二甲基和 N,N-双（羟乙基）部分的次氮基三酸的酰胺衍生物）中，第一个配体对 Am(III) 表现出比 Eu(III) 显着的选择性，其中最大分离因子为 11.1，而后者更有效地络合水相中的放射性核素，最大分离因子为 5。通过一系列选定的配体络合 Eu(III) 的等温微量热实验证实了观察到的趋势反萃取特性。