7-acetylamino-5-hydroxy-2-methylquinolin-8-yl diethyl phosphate | 1269811-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-acetylamino-5-hydroxy-2-methylquinolin-8-yl diethyl phosphate
• CAS: 1269811-29-1
• 化学式: C₁₆H₂₁N₂O₆P
• 分子量: 368.326
• InChiKey: XKRTZSXXWBQKHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  106.98
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  亚磷酸二乙酯 、 乙酰胺,N-(5,8-二氢-2-甲基-5,8-二羰基-7-喹啉基)- 以 四氢呋喃 为溶剂， 反应 16.0h， 以57%的产率得到7-acetylamino-5-hydroxy-2-methylquinolin-8-yl diethyl phosphate
  参考文献：
  名称：

  Synthesis, spectroscopy and computational studies of some novel phosphorylated derivatives of quinoline-5,8-diones

  摘要：

  The neutral phosphorus nucleophiles such as R2P(=Y)M [1a-f, Y=O or lone pair; R = Ph, tBu, OCH2C(CH3)(2) CH2O, (PrO)-O-i, EtO or MeO: M = H or SiMe3] allowed the radical addition to 2-methyl-5,8-dioxo-5,8-dihydroquinoline-7-amine (2a) and N-(2-methyl-5,8-dioxo-5,8-dihydroquinolin-7-yl)acetamide (2b) giving exclusively O-phosphorylated products, i.e.: 7-acetylamino-5-hydroxy-2-methylquinolin-8-yl diphenylphosphinate (3a), 7-acetylamino-5-hydroxy-2-methylquinolin-8-yl-tbutylphenylphosphinate (3b), 7-acetylamino-5-hydroxy-2-methylquinolin-8-yl diisopropyl phosphate (3c), 7-acetylamino-5-hydroxy-2-methylquinolin-8-yl diethyl phosphate (3d), N-(8-[(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2yl)oxy]-5-hydroxy-2-methylquinolin-7-yl)acetamide (3e), 7-amino-5-hydroxy-2-methylquinolin-8-yl dimethyl phosphate (3f) and 7-amino-5-hydroxy-2-methylquinolin-8-yl-tbutylphenylphosphinate (3g), respectively, with high yield. All products were quantitatively prepared and characterized by microanalysis, and multinuclear NMR spectroscopy. Seven of them, i.e.: 2a, 2b, 3a, 3b, 3d, 3e and 3g have been characterized by single crystal X-ray diffraction method. The geometries of the studied compounds were optimized in singlet states using the density functional theory (DFT) method with B3LYP functional. The redox properties of 2a and 2b have been studied using cyclic voltammetry. The reduction corresponds to the electrochemical behaviour of naturally occurring quinones. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2010.11.032