diethyl 5-(1,3-dioxoisoindolin-2-yl)-2-fluoropentylphosphonate | 1454660-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: diethyl 5-(1,3-dioxoisoindolin-2-yl)-2-fluoropentylphosphonate
• 英文别名: 2-(5-Diethoxyphosphoryl-4-fluoropentyl)isoindole-1,3-dione；2-(5-diethoxyphosphoryl-4-fluoropentyl)isoindole-1,3-dione
• CAS: 1454660-97-9
• 化学式: C₁₇H₂₃FNO₅P
• 分子量: 371.345
• InChiKey: ITNGZGSGCGWRGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-戊-4-烯基异吲哚-1,3-二酮 、 亚磷酸二乙酯 在 silver nitrate 、 溶剂黄146 、 Selectfluor 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 以90%的产率得到diethyl 5-(1,3-dioxoisoindolin-2-yl)-2-fluoropentylphosphonate
  参考文献：
  名称：

  Silver-Catalyzed Radical Phosphonofluorination of Unactivated Alkenes

  摘要：

  We report herein a mild and catalytic phosphonofluorination of unactivated alkenes. With catalysis by AgNO3, the condensation of various unactivated alkenes with diethyl phosphite and Selectfluor reagent in CH2Cl2/H2O/HOAc at 40 degrees C led to the efficient synthesis of beta-fluorinated alkylphosphonates with good stereoselectivity and wide functional group compatibility. A mechanism involving silver-catalyzed oxidative generation of phosphonyl radicals and silver-assisted fluorine atom transfer is proposed.

  DOI：

  10.1021/ja408031s

文献信息

• Silver-Catalyzed Radical Phosphonofluorination of Unactivated Alkenes
  作者：Chengwei Zhang、Zhaodong Li、Lin Zhu、Limei Yu、Zhentao Wang、Chaozhong Li

  DOI：10.1021/ja408031s

  日期：2013.9.25

  We report herein a mild and catalytic phosphonofluorination of unactivated alkenes. With catalysis by AgNO3, the condensation of various unactivated alkenes with diethyl phosphite and Selectfluor reagent in CH2Cl2/H2O/HOAc at 40 degrees C led to the efficient synthesis of beta-fluorinated alkylphosphonates with good stereoselectivity and wide functional group compatibility. A mechanism involving silver-catalyzed oxidative generation of phosphonyl radicals and silver-assisted fluorine atom transfer is proposed.