diethyl (4-hydroxy-6-chloro-2-(pentafluorethyl)-4H-chromen-3-yl)phosphonate | 1258945-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: diethyl (4-hydroxy-6-chloro-2-(pentafluorethyl)-4H-chromen-3-yl)phosphonate
• 英文别名: 6-chloro-3-diethoxyphosphoryl-2-(1,1,2,2,2-pentafluoroethyl)-4H-chromen-4-ol
• CAS: 1258945-05-9
• 化学式: C₁₅H₁₅ClF₅O₅P
• 分子量: 436.7
• InChiKey: AXUKXICVGPJCEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5-氯代水杨醛 、 diethyl 3,3,4,4,4-pentafluorobut-1-ynylphosphonate 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 11.0h， 以50%的产率得到diethyl (4-hydroxy-6-chloro-2-(pentafluorethyl)-4H-chromen-3-yl)phosphonate
  参考文献：
  名称：

  Synthesis of 2-Perfluoroalkyl 4H- and 2H-Chromenylphosphonates Mediated by Amines and Phosphines

  摘要：

  An efficient synthesis of 2-perfluoroalkyl 4H-chromen-3-ylphosphonates 4a-i (R-F = CF3) and 5a-i (R-F = C2F5) has been accomplished via regioselective cycloaddition of 2-hydroxybenzaldehydes to diethyl 3,3,3-trifluoropropyn-1-yl- and diethyl 3,3,4,4,4-pentafluorobutyn-1-ylphosphonate, using trialkyl amines or phosphines as mediators. 2H-Chromen-3-ylphosphonates 6a-i were regioselectively obtained in the presence of triphenylphosphine. A convenient method for the isomerization of 4H-chromen-3-ylphosphonates into 2H-chromen-3-ylphosphonates 6a-i (R-F = CF3) and 7a-i (R-F = C2F5) was established.

  DOI：

  10.1021/jo101913u

文献信息

• Synthesis of 2-Perfluoroalkyl 4<i>H</i>- and 2<i>H</i>-Chromenylphosphonates Mediated by Amines and Phosphines
  作者：Blazej Duda、Sergey N. Tverdomed、Gerd-Volker Röschenthaler

  DOI：10.1021/jo101913u

  日期：2011.1.7

  An efficient synthesis of 2-perfluoroalkyl 4H-chromen-3-ylphosphonates 4a-i (R-F = CF3) and 5a-i (R-F = C2F5) has been accomplished via regioselective cycloaddition of 2-hydroxybenzaldehydes to diethyl 3,3,3-trifluoropropyn-1-yl- and diethyl 3,3,4,4,4-pentafluorobutyn-1-ylphosphonate, using trialkyl amines or phosphines as mediators. 2H-Chromen-3-ylphosphonates 6a-i were regioselectively obtained in the presence of triphenylphosphine. A convenient method for the isomerization of 4H-chromen-3-ylphosphonates into 2H-chromen-3-ylphosphonates 6a-i (R-F = CF3) and 7a-i (R-F = C2F5) was established.