研究论文

高效合成含P—O—P键化合物: 焦膦酸酯、四烷基焦膦酸酯和焦膦酰胺的方法

  • 张子璇 ,
  • 高润利 ,
  • 胡慧娟 ,
  • 卢晓刚 ,
  • 王瑾陈霄 ,
  • 王红梅
展开
  • 国民核生化灾害防护国家重点实验室 北京 102205

收稿日期: 2022-02-07

  修回日期: 2022-03-05

  网络出版日期: 2022-03-30

基金资助

国民核生化灾害防护国家重点实验室(SKLNBC2021-09)

Development of an Efficient Method for the Synthesis of Compounds Containing P—O—P Bonds: Pyrophosphonates, Tetraalkyl Pyrophosphates and Pyrophosphonamidates

  • Zixuan Zhang ,
  • Runli Gao ,
  • Huijuan Hu ,
  • Xiaogang Lu ,
  • Jin,Chen,Xiao Wang ,
  • Hongmei Wang
Expand
  • State Key Laboratory of NBC Protection for Civilian, Beijing 102205

Received date: 2022-02-07

  Revised date: 2022-03-05

  Online published: 2022-03-30

Supported by

State Key Laboratory of Nuclear Biological and Chemical Protection for Civilian(SKLNBC2021-09)

摘要

研究了焦膦酸酯、四烷基焦膦酸酯和焦膦酰胺的合成方法. 原料烷基氯膦酸酯、Et3N和水以1∶1.2∶0.5 (物质的量比)的比例, 丙酮为溶剂, 回流条件下, 反应15 min, 焦膦酸酯的产率最高可达95%. 以三乙胺为反应溶剂及缚酸剂的方法合成四烷基焦膦酸酯和焦膦酰胺的速率和产率较使用传统方法更加高效.

本文引用格式

张子璇 , 高润利 , 胡慧娟 , 卢晓刚 , 王瑾陈霄 , 王红梅 . 高效合成含P—O—P键化合物: 焦膦酸酯、四烷基焦膦酸酯和焦膦酰胺的方法[J]. 有机化学, 2022 , 42(7) : 2214 -2221 . DOI: 10.6023/cjoc202201050

Abstract

This work describes a method of synthesizing pyrophosphonates, tetraalkyl pyrophosphates and pyrophosphonamidates. Pyrophosphonates can be synthesized by the reaction of alkyl dichlorophosphonate, triethylamine (Et3N), and water, in a molar ratio of 1∶1.2∶0.5 (dichlorophosphonate∶Et3N∶water). When the reaction was allowed to proceed for 15 min in acetone, the maximum yield recorded for the pyrophosphonates was 95%. Et3N was the solvent, with an acid-binding agent. Following this method, the achieved rate of production of tetraalkyl pyrophosphate and pyrophosphonamidate was faster than the rate of production of the compounds reached using traditional methods.

参考文献

[1]
(a) Barpanda, P.; Nishimura, S.-I.; Yamada, A. Adv. Energy Mater. 2012, 2, 841.
[1]
(b) Ikotun, O. F.; Marino, N.; Kruger, P. E.; Julve, M.; Doyle, R. P. Coord. Chem. Rev. 2010, 254, 890.
[1]
(c) Jordan, F. Nat. Prod. Rep. 2003, 20, 184.
[1]
(d) Kim, S. K.; Lee, D. H.; Hong, J.-I.; Yoon, J. Acc. Chem. Res. 2009, 42, 23.
[1]
(e) Orriss, I. R.; Arnett, T. R.; Russell, R. G. G. Curr. Opin. Pharmacol. 2016, 28, 57.
[2]
(a) Lin, H. Org. Biomol. Chem. 2007, 5, 2541.
[2]
(b) Pehar, M.; Harlan, B. A.; Killoy, K. M.; Vargas, M. R. Antioxid. Redox Signaling 2018, 28, 1652.
[2]
(c) Davila, A.; Liu, L.; Chellappa, K.; Redpath, P.; Nakamaru-Ogiso, E.; Paolella, L. M.; Zhang, Z.; Migaud, M. E.; Rabinowitz, J. D.; Baur, J. A. Elife 2018, 7, 1.
[3]
(a) McPhillips, J. J.; Coon, J. M. Toxicol. Appl. Pharmacol. 1966, 8, 66.
[3]
(b) Rider, J. A.; Ellinwood, L. E.; Coon, J. M. Proc. Soc. Exp. Biol. Med. 1952, 81, 455.
[3]
(c) Rider, J. A.; Schulman, S.; Richter, R. B.; Moeller, H. C.; DuBois, K. P. J. Am. Med. Assoc. 1951, 145, 967.
[4]
(a) Kimmerle, G.; Klimmer, O. R. Arch. Toxicol. 1974, 33, 1.
[4]
(b) Wood, S. J.; Osborne, R. H. Pestic. Sci. 1991, 32, 485.
[5]
(a) Wolf, R. Ind. Eng. Chem. Prod. Res. Dev. 1981, 20, 413.
[5]
(b) Wolf, R. Kunststoffe 1986, 76, 943.
[6]
(a) D'Agostino, P. A.; Provost, L. R. J. Chromatogr. 1992, 589, 287.
[6]
(b) D'Agostino, P. A.; Hancock, J. R.; Chenier, C. L. Eur. J. Mass Spectrom. 2003, 9, 609.
[6]
(c) Terent'ev, A. G.; Morozik, Y. I.; Ivanova, M. V.; Dudkin, A. V. J. Anal. Chem. 2020, 75, 208
[7]
(a) Ahmadibeni, Y.; Parang, K. J. Org. Chem. 2006, 71, 5837.
[7]
(b) Dash, C.; Ahmadibeni, Y.; Hanley, M. J.; Pandhare, J.; Gotte, M.; Le Grice, S. F. J.; Parang, K. Bioorg. Med. Chem. Lett. 2011, 21, 3519.
[7]
(c) Gaines, J. C.; Ivy, E. E.; Dean, H. A.; Scales, A. L. J. Econ. Entomol. 1950, 43, 614.
[7]
(d) Kiran, Y. B.; Reddy, C. D.; Gunasekar, D.; Raju, C. N.; Barbosa, L. C. A.; Marney, D. C. O.; Russell, L. J. J. Fire Sci. 2007, 25, 193.
[7]
(e) Davidson, A.; Foley, D. A.; Frericks-Schmidt, H.; Ruggeri, S. G.; Herman, M.; LaCasse, S.; Liu, Y.; McInturff, E. L.; Morris, R.; Mugheirbi, N.; Samas, B.; Sarkar, A.; Singer, R. A.; Witkos, F.; Yu, S. Org. Process Res. Dev. 2021, 25, 621.
[8]
(a) Parakin, O. V.; Romakhin, A. S.; Nikitin, E. V.; Ignat'ev, Y. A.; Romanov, G. V.; Mironov, B. S.; Kargin, Y. M.; Pudovik, A. N. Zh. Obshch. Khim. 1985, 55, 2621.
[8]
(b) Pavlichenko, V. F.; Presnov, A. E.; Tomilov, A. P. Zh. Obshch. Khim. 1995, 65, 1347.
[9]
(a) Kumar, R.; Pardasani, D.; Mazumder, A.; Dubey, D. K.; Gupta, A. K. Aust. J. Chem. 2008, 61, 476.
[9]
(b) Kumar, R.; Gupta, A. K.; Kaushik, M. P. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 765.
[10]
(a) Toy, A. D. F. J. Am. Chem. Soc. 1948, 70, 3882.
[10]
(b) Toy, A. D. F. J. Am. Chem. Soc. 1950, 72, 2065.
[11]
Zhou, Y.; Yin, S.; Gao, Y.; Zhao, Y.; Goto, M.; Han, L.-B. Angew. Chem., Int. Ed. 2010, 49, 6852.
[12]
Huang, J.; He, W.; Wang, B. Phosphorus, Sulfur Silicon Relat. Elem. 2012, 187, 1125.
[13]
Kins, C. F.; Brunklaus, G.; Spiess, H. W. Macromolecules 2013, 46, 2067.
[14]
Dunning, T. H. J. Chem. Phys. 1989, 90, 1007.
文章导航

/