9-[(dimethylamino)methyl]-2-isopropyl-7-oxo-7H-furo[3,2-g]chromen-3-yl trifluoromethanesulfonate | 1430731-92-2

• 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: 9-[(dimethylamino)methyl]-2-isopropyl-7-oxo-7H-furo[3,2-g]chromen-3-yl trifluoromethanesulfonate
• CAS: 1430731-92-2
• 化学式: C₁₈H₁₈F₃NO₆S
• 分子量: 433.405
• InChiKey: PONZGXIMEHGHSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  89.96
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  9-[(dimethylamino)methyl]-2-isopropyl-7-oxo-7H-furo[3,2-g]chromen-3-yl trifluoromethanesulfonate 、 2-甲基苯硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.5h， 以76%的产率得到9-[(dimethylamino)methyl]-2-isopropyl-3-(2-methylphenyl)-7H-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  Plant coumarins: XIII. Synthesis of 2,3,9-trisubstituted furocoumarins

  摘要：

  Peucedanin reacted with methylideneiminium salt generated in situ from N,N,N',N'-tetramethylmethanediamine and acetyl chloride to give 2-(dimethylaminomethyl)oreoselone. Reactions of peucedanin with aminomethylating agents generated in situ from formaldehyde and dimethylamine, N-methylpiperazine, or N-Boc-piperazine in boiling methanol smoothly afforded the corresponding 9-aminomethyl derivatives whose hydrolysis produced 9-aminomethyl-substituted oreoselones. 2,3,9-Trisubstituted linearly fused furocoumarins were synthesized by reactions of 9-substituted oreoselone trifluoromethanesulfonates with arylboronic acids.

  DOI：

  10.1134/s1070428013030159
• 作为产物：
  描述：

  3-甲氧基-2-丙-2-基呋喃并[3,2-g]苯并吡喃-7-酮 在 吡啶 、 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 47.5h， 生成 9-[(dimethylamino)methyl]-2-isopropyl-7-oxo-7H-furo[3,2-g]chromen-3-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Plant coumarins: XIII. Synthesis of 2,3,9-trisubstituted furocoumarins

  摘要：

  Peucedanin reacted with methylideneiminium salt generated in situ from N,N,N',N'-tetramethylmethanediamine and acetyl chloride to give 2-(dimethylaminomethyl)oreoselone. Reactions of peucedanin with aminomethylating agents generated in situ from formaldehyde and dimethylamine, N-methylpiperazine, or N-Boc-piperazine in boiling methanol smoothly afforded the corresponding 9-aminomethyl derivatives whose hydrolysis produced 9-aminomethyl-substituted oreoselones. 2,3,9-Trisubstituted linearly fused furocoumarins were synthesized by reactions of 9-substituted oreoselone trifluoromethanesulfonates with arylboronic acids.

  DOI：

  10.1134/s1070428013030159