diethyl 7-N,N-diethylamino-2-oxo-2H-1-benzopyran-3-phosphonate | 112901-46-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: diethyl 7-N,N-diethylamino-2-oxo-2H-1-benzopyran-3-phosphonate
• 英文别名: 3-Diethoxyphosphoryl-7-(diethylamino)chromen-2-one
• CAS: 112901-46-9
• 化学式: C₁₇H₂₄NO₅P
• 分子量: 353.355
• InChiKey: SEJCVNSKMXCUMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 4-(二乙氨基)水杨醛 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 diethyl 7-N,N-diethylamino-2-oxo-2H-1-benzopyran-3-phosphonate
  参考文献：
  名称：

  Substituted Esters of Coumarin-3-phosphonic Acid—Linear-Polarized IR-Spectroscopic Elucidation

  摘要：

  Correlation between the structure and IR-spectroscopic properties of two halogen and one amino substituted esters of coumarin-3-phosphonic acid has been studied by means of linear-polarized IR-spectroscopy of oriented colloid suspensions in nematic host. The influence of the ester group on the peak positions of the IR-characteristic bands of these derivatives and in particular, on phosphorus group is investigated by a comparison with the data for corresponding coumarin-3-phosphonic acids. Theoretical quantum chemical DFT calculations (B3LYP/6-311++G**) are carried out, thus supporting the experimental assignment of the IR-bands and predicting the electronic structure of all of the compounds studied.

  DOI：

  10.1080/10426500802049837

文献信息

• A comparative study of the interaction of salicylaldehydes with phosphonoacetates under Knoevenagel reaction conditions. Synthesis of 1,2-benzoxaphosphorines and their dimers
  作者：Anka Bojilova、R. Nikolova、Christo Ivanov、Nestor A. Rodios、A. Terzis、C.P. Raptopoulou

  DOI：10.1016/0040-4020(96)00748-x

  日期：1996.9

  The reaction of salicylaldehydes 5 with phosphonoacetates 6 gives the coumarin-3-phosphonates 7 and the 1,2-benzoxaphosphorine-3-carboxylates 8 in yields and 7:8 ratios depending on the reaction conditions. A mechanistic explanation is given for the stereoselectivity of these reactions. Irradiation of compounds 8 or direct exposure to sunlight causes their head-to-tail dimerization, giving the dimers

  水杨醛5与膦酰基乙酸酯6的反应产生香豆素3-膦酸酯7和1,2-苯并氧杂膦基-3-羧酸酯8，其产率和反应比取决于反应条件为7：8。对这些反应的立体选择性给出了机械的解释。化合物8的照射或直接暴露在阳光下会导致它们的头到尾二聚化，从而得到二聚体11，在一种情况下，得到其磷差向异构体12。通过X射线晶体学分析证实了它们的结构。对化合物7、8、11和还讨论了图12。
• Chen, Chin H.; Fox, John L.; Lippert, Joseph L., Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 931 - 932
  作者：Chen, Chin H.、Fox, John L.、Lippert, Joseph L.

  DOI：——

  日期：——
• Substituted Esters of Coumarin-3-phosphonic Acid—Linear-Polarized IR-Spectroscopic Elucidation
  作者：Rositca D. Nikolova、Sonya Zareva、Anka G. Bojilova、Tsonko Kolev、Bojidarka Koleva

  DOI：10.1080/10426500802049837

  日期：2008.11.7

  Correlation between the structure and IR-spectroscopic properties of two halogen and one amino substituted esters of coumarin-3-phosphonic acid has been studied by means of linear-polarized IR-spectroscopy of oriented colloid suspensions in nematic host. The influence of the ester group on the peak positions of the IR-characteristic bands of these derivatives and in particular, on phosphorus group is investigated by a comparison with the data for corresponding coumarin-3-phosphonic acids. Theoretical quantum chemical DFT calculations (B3LYP/6-311++G**) are carried out, thus supporting the experimental assignment of the IR-bands and predicting the electronic structure of all of the compounds studied.