Synthesis and conformational analysis of 6-[N,N-bis(dihydroxyphosphorylmethyl)amino]methyl-2-hydroxy-2-oxido-1,4,2-oxazaphosphorinane-4-methylphosphonic acid by NMR spectroscopy

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• 作者：Ya. V. Bolt ; S. K. Belus’ ; N. V. Tsirul’nikova
• 关键词：Kabachnik—Fields reaction ; phosphonic acids ; thermal dehydration ; 1H ; 13C ; and 31P NMR spectra ; homo ; and heteronuclear correlation spectra (J ; resolved ; HSQC ; HMBC) ; 1 ; 4 ; 2 ; oxazaphosphorinanes ; conformation
• 刊名：Russian Chemical Bulletin
• 出版年：2016
• 出版时间：January 2016
• 年：2016
• 卷：65
• 期：1
• 页码：291-294
• 全文大小：248 KB
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Chemistry
  Organic Chemistry
  Inorganic Chemistry
  Russian Library of Science
  
• 出版者：Springer New York
• ISSN：1573-9171
• 卷排序：65

文摘

The Kabachnik—Fields methylphosphorylation of 1,3-diaminopropan-2-ol affords a mixture of 1,3-diamino-2-hydroxypropane-N,N,N′,N′-tetrakismethylphosphonic acid and its intramolecular cyclic ester. Subsequent heating of this mixture led to the thermal dehydration of the acid with the 1,4,2-oxazaphosphorinane ring closure and the formation of 6-[N,N-bis(dihydroxyphosphorylmethyl)amino]methyl-2-hydroxy-2-oxido-1,4,2-oxazaphosphorinane4-methylphosphonic acid. A predominant chair conformation of the formed six-membered heterocycle was inferred from the data of 2D homonuclear (1H, 1H; J-resolved) and heteronuclear (1H, 13C; HSQC, HMBC) NMR correlation spectra.