(2-diethylaminoethyl)diphenylphosphine oxide | 25284-53-1

• 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: (2-diethylaminoethyl)diphenylphosphine oxide
• 英文别名: N-[2-(diphenylphosphinyl)ethyl]diethylamine；2-(diphenylphosphoryl)-N,N-diethylethanamine；2-diphenylphosphoryl-N,N-diethylethanamine
• CAS: 25284-53-1
• 化学式: C₁₈H₂₄NOP
• 分子量: 301.368
• InChiKey: DRWZABOPWAFOBK-UHFFFAOYSA-N

物化性质

• 熔点：
  111.5-112.5 °C
• 沸点：
  396.2±25.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-diethylaminoethyl)diphenylphosphine oxide 在 高氯酸 作用下， 以 乙腈 为溶剂， 生成 diethyl(2-diphenylphosphorylethyl)ammonium perchlorate
  参考文献：
  名称：

  Hydrogen bonds and the structure of perchlorates of phosphorylated diazacycloalkanes

  摘要：

  Mono- and diperchlorates of phosphorylated diazacycloalkanes (PDAC), viz. 1,5-bis(2-diphenylphosphorylethyl)-1,5-diazacyclooctanes (1a, 1b), 1,4-bis(2-diphenylphosphorylethyl)1,4-piperazine (2a), and 1-methyl-4-(2-diphenylphosphorylethyl)-1,4-piperazines (3a, 3b), were prepared. The formation of inter- and intramolecular hydrogen bonds in PDAC perchlorates and some model compounds in the solid state and in solution was investigated by IR spectroscopy. The dependence between the effect of the hydrogen bond formation and association of the ions in solution was analyzed. Conformational analysis of the cations of PDAC was carried out.

  DOI：

  10.1007/bf00696325
• 作为产物：
  描述：

  2-(diphenylphosphinyl)ethanol 在 三乙胺 、 三氯化磷 作用下， 以 水 为溶剂， 反应 0.5h， 生成 (2-diethylaminoethyl)diphenylphosphine oxide
  参考文献：
  名称：

  A practical and efficient green synthesis of β-aminophosphoryl compounds via the aza-Michael reaction in water

  摘要：

  简述 室温咪唑离子液体（RTIL）/水双相体系或以水为溶剂可显著加快胺与乙烯基磷化合物的加成反应，从而在较短的反应时间内以优异的产率绿色、有效地合成β-氨基磷化合物。水是最廉价、最无毒的溶剂，不需要任何催化剂或助溶剂，因此使用水的好处更多，因为它提供了一个简单的分离程序，通过简单的冷冻干燥就能得到纯度很高（核磁共振数据显示大于 95%）的产品，而且不需要使用有机溶剂萃取。正如使用不溶于水的二苯基乙烯基氧化膦所证明的那样，起始磷底物在水中的溶解度在反应中并不起关键作用。与典型程序不同的是，使用 2:1 的反应物比例（乙烯基磷化合物：胺）很容易在水中实现伯胺（包括多胺）的双磷酸化。

  DOI：

  10.1016/j.crci.2010.03.005

文献信息

• New method for the syntheses of 2-aminoethyldiphenylphosphine oxides under the phase transfer conditions using cesium carbonate
  作者：Natalia A. Bondarenko、Kseniia V. Tcarkova、Svetlana K. Belus'、Oleg I. Artyushin

  DOI：10.1080/10426507.2021.2008923

  日期：2022.6.3
• Konstantinovskaya, M. A.; Sinyavskaya, E. I., Russian Journal of Inorganic Chemistry, 1980, vol. 25, p. 227 - 231
  作者：Konstantinovskaya, M. A.、Sinyavskaya, E. I.

  DOI：——

  日期：——
• Yatsimirskii, K. B.; Kabachnik, M. I.; Sinyavskaya, E. I., Russian Journal of Inorganic Chemistry, 1978, vol. 23, p. 551 - 556
  作者：Yatsimirskii, K. B.、Kabachnik, M. I.、Sinyavskaya, E. I.、Medved', T. Ya.、Polikarpov, Yu. T.、et al.

  DOI：——

  日期：——
• Hydrogen bonds and the structure of perchlorates of phosphorylated diazacycloalkanes
  作者：E. I. Matrosov、A. G. Matveeva、S. V. Matveev、Yu. M. Potikarpov、B. K. Shcherbakov、M. I. Kabachnik

  DOI：10.1007/bf00696325

  日期：1994.11

  Mono- and diperchlorates of phosphorylated diazacycloalkanes (PDAC), viz. 1,5-bis(2-diphenylphosphorylethyl)-1,5-diazacyclooctanes (1a, 1b), 1,4-bis(2-diphenylphosphorylethyl)1,4-piperazine (2a), and 1-methyl-4-(2-diphenylphosphorylethyl)-1,4-piperazines (3a, 3b), were prepared. The formation of inter- and intramolecular hydrogen bonds in PDAC perchlorates and some model compounds in the solid state and in solution was investigated by IR spectroscopy. The dependence between the effect of the hydrogen bond formation and association of the ions in solution was analyzed. Conformational analysis of the cations of PDAC was carried out.
• A practical and efficient green synthesis of β-aminophosphoryl compounds via the aza-Michael reaction in water
  作者：Ekaterina V. Matveeva、Pavel V. Petrovskii、Zinaida S. Klemenkova、Natalya A. Bondarenko、Irina L. Odinets

  DOI：10.1016/j.crci.2010.03.005

  日期：2010.8

  Résumé Biphasic systems room temperature imidazolium ionic liquid (RTIL)/water or water as a solvent significantly accelerate the addition of amines to vinylphosphoryl compounds hence opening green and effective synthesis of β-aminophosphoryl compounds in excellent yields over short reaction times. The application of water, being the cheapest and most non-toxic solvent, without any catalyst or co-solvent, is more advantageous as it provides a simple isolation procedure for products having high purity (> 95% according to the NMR data) via simple freeze-drying and does not require extraction with organic solvents. The solubility of the starting phosphorus substrate in water does not play crucial role in the reaction as it was demonstrated using water insoluble diphenylvinylphosphine oxide. In contrast to typical procedures, using a reactant ratio (vinylphosphoryl compound: amine) of 2:1 readily resulted in double phosphorylation of primary amines, including polyamines, in water.

  简述 室温咪唑离子液体（RTIL）/水双相体系或以水为溶剂可显著加快胺与乙烯基磷化合物的加成反应，从而在较短的反应时间内以优异的产率绿色、有效地合成β-氨基磷化合物。水是最廉价、最无毒的溶剂，不需要任何催化剂或助溶剂，因此使用水的好处更多，因为它提供了一个简单的分离程序，通过简单的冷冻干燥就能得到纯度很高（核磁共振数据显示大于 95%）的产品，而且不需要使用有机溶剂萃取。正如使用不溶于水的二苯基乙烯基氧化膦所证明的那样，起始磷底物在水中的溶解度在反应中并不起关键作用。与典型程序不同的是，使用 2:1 的反应物比例（乙烯基磷化合物：胺）很容易在水中实现伯胺（包括多胺）的双磷酸化。