furan-2-yl N,N,N',N'-dicyclohexylamidophosphate | 1315635-18-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: furan-2-yl N,N,N',N'-dicyclohexylamidophosphate
• 英文别名: N-[(cyclohexylamino)-(furan-2-yloxy)phosphoryl]cyclohexanamine
• CAS: 1315635-18-7
• 化学式: C₁₆H₂₇N₂O₃P
• 分子量: 326.376
• InChiKey: UDIGKOWRAWBTHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  呋喃基磷二氯化酸酯 、 环己胺 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以10%的产率得到furan-2-yl N,N,N',N'-dicyclohexylamidophosphate
  参考文献：
  名称：

  Spectroscopic and dynamic NMR study, X-ray crystallography and DFT calculations of two phosphoramidates: (C4H3O2)P(O)(Cl)C6H14N and (C4H3O2)P(O)(C6H11NH)2

  摘要：

  In recent years, research in organophosphorus compounds, particularly phosphoramidates, has attracted attention because of their many applications. In this work, we report a combined experimental and theoretical study on the molecular structure and NMR spectra of two phosphoramidates (furan-2-yl N,N-diisopro-pylamidochlorophosphate (1) and furan-2-yl N,N,N',N'-dicyclohexylamidophosphate (2)). In the NMR time scale a free rotation of the C-N/P N single bonds was observed at room temperature (298 K) while the rotation freezes below 195 K for compound 1. From dynamic NMR analysis, the activation free energy (AG(#)) for rotation of the C-N/P N bonds was calculated as 9.9 +/- 0.3 kcal mol(-1). The experimental data were reinforced by theoretical calculation using the density functional theory method B3LYP and the 6-31G(d) basis set which provided activation energy (AE(double dagger)) of 9.2 kcal mol(-1). The structures of compounds 1 and 2 were determined by single crystal X-ray diffraction method. Compound 1 is formed by a racemic mixture, whose presence was evidenced only in the structure determination by X-ray. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.04.059

文献信息

• Spectroscopic and dynamic NMR study, X-ray crystallography and DFT calculations of two phosphoramidates: (C4H3O2)P(O)(Cl)C6H14N and (C4H3O2)P(O)(C6H11NH)2
  作者：F.M. Oliveira、L.C.A. Barbosa、A.J. Demuner、C.R.A. Maltha、S.A. Fernandes、J.W.de M. Carneiro、R.S. Corrêa、A.C. Doriguetto

  DOI：10.1016/j.molstruc.2013.04.059

  日期：2013.8

  In recent years, research in organophosphorus compounds, particularly phosphoramidates, has attracted attention because of their many applications. In this work, we report a combined experimental and theoretical study on the molecular structure and NMR spectra of two phosphoramidates (furan-2-yl N,N-diisopro-pylamidochlorophosphate (1) and furan-2-yl N,N,N',N'-dicyclohexylamidophosphate (2)). In the NMR time scale a free rotation of the C-N/P N single bonds was observed at room temperature (298 K) while the rotation freezes below 195 K for compound 1. From dynamic NMR analysis, the activation free energy (AG(#)) for rotation of the C-N/P N bonds was calculated as 9.9 +/- 0.3 kcal mol(-1). The experimental data were reinforced by theoretical calculation using the density functional theory method B3LYP and the 6-31G(d) basis set which provided activation energy (AE(double dagger)) of 9.2 kcal mol(-1). The structures of compounds 1 and 2 were determined by single crystal X-ray diffraction method. Compound 1 is formed by a racemic mixture, whose presence was evidenced only in the structure determination by X-ray. (C) 2013 Elsevier B.V. All rights reserved.