dimethyl 3-(tert-butylamino)-2-acetyl-5-oxacyclopenta[a]naphthalen-4(2H)-one-1,2-dicarboxylate | 1422506-73-7

• 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: dimethyl 3-(tert-butylamino)-2-acetyl-5-oxacyclopenta[a]naphthalen-4(2H)-one-1,2-dicarboxylate
• 英文别名: Dimethyl 2-acetyl-3-(tert-butylamino)-4-oxocyclopenta[c]chromene-1,2-dicarboxylate
• CAS: 1422506-73-7
• 化学式: C₂₂H₂₃NO₇
• 分子量: 413.427
• InChiKey: HNBNFNHLGPUSMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-乙酰基香豆素 、 异氰酸叔丁酯 、 丁炔二酸二甲酯 以 甲苯 为溶剂， 反应 5.0h， 生成 dimethyl 3-(tert-butylamino)-2-acetyl-5-oxacyclopenta[a]naphthalen-4(2H)-one-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis of Cyclopentadiene-Fused Chromanones via One-Pot Multicomponent Reactions

  摘要：

  We have developed one-pot method for the synthesis of functionalized novel cyclopentadiene-fused chromanone scaffolds. A variety of 4-oxo-2,4-dihydro-cyclopenta[c]chromene-1,2-dicarboxylates were obtained in moderate to good yields via condensation of 2-hydroxybenzaldehydes and ethyl acetoacetate with 1:1 acetylenecarboxylate-isocyanides in toluene. These reactions presumably proceed via reaction of the in situ generated 3-acetyl-2H-chromen-2-ones with acetylenecarboxylate-isocyanide zwitterionic intermediates through Michael addition/intramolecular cyclization and double [1,5] acyl shift rearrangement cascade.

  DOI：

  10.1021/jo302790y