(3R,1'S,4'R,7'R)-5'Methyl-7'-(1-methylethyl)-spiro<2H,4H-<1>benzopyran-3,2'-bicyclo<2.2.2>oct-5'-ene>-2,4-dione

• 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: (3R,1'S,4'R,7'R)-5'Methyl-7'-(1-methylethyl)-spiro<2H,4H-<1>benzopyran-3,2'-bicyclo<2.2.2>oct-5'-ene>-2,4-dione
• 英文别名: (1R,4R,5R,8R)-2-methyl-8-propan-2-ylspiro[bicyclo[2.2.2]oct-2-ene-5,3'-chromene]-2',4'-dione
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: AFIWQMOSDUYIFT-BCEDRHLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 4-羟基香豆素 、 水芹烯 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以32%的产率得到(7aR,9R,11aS)-11a-Methyl-9-(1-methylethyl)-7,7a,8,9-tetrahydro-6H,11aH-<1>benzopyrano<4,3-b><1>benzopyran-6-one
  参考文献：
  名称：

  The Chemistry of Coumarin Derivatives. Part VI. Diels-Alder Trapping of 3-Methylene-2,4-chromandione. A New Entry to Substituted Pyrano[3,2-c]coumarins

  摘要：

  3-Methylene-2,4-chromandione (1) can be generated from dicumarol or from paraformaldehyde and 4-hydroxycoumarin. 1 is a versatile substrate for cycloaddition reactions. Depending on the reaction partner, 1 can behave as an ambident heterodiene or as a dienophile. The reaction was investigated with a series of olefins and dienes, including several isoprenoids. Some generalizations could be drawn and rationalized in terms of HOMO-LUMO interactions. The reaction of 1 and certain asymmetrically substituted olefins gives pyrano[3,2-c]coumarins in a highly regio- and chemoselective way. As an application of this reaction to natural products chemistry, a concise (three steps) synthesis of the prenylated coumarin (+/-)-isoferprenin (35a) is reported.

  DOI：

  10.1021/jo00098a013

文献信息

• The Chemistry of Coumarin Derivatives. Part VI. Diels-Alder Trapping of 3-Methylene-2,4-chromandione. A New Entry to Substituted Pyrano[3,2-c]coumarins
  作者：Giovanni Appendino、Giancarlo Cravotto、Lucio Toma、Rita Annunziata、Giovanni Palmisano

  DOI：10.1021/jo00098a013

  日期：1994.9

  3-Methylene-2,4-chromandione (1) can be generated from dicumarol or from paraformaldehyde and 4-hydroxycoumarin. 1 is a versatile substrate for cycloaddition reactions. Depending on the reaction partner, 1 can behave as an ambident heterodiene or as a dienophile. The reaction was investigated with a series of olefins and dienes, including several isoprenoids. Some generalizations could be drawn and rationalized in terms of HOMO-LUMO interactions. The reaction of 1 and certain asymmetrically substituted olefins gives pyrano[3,2-c]coumarins in a highly regio- and chemoselective way. As an application of this reaction to natural products chemistry, a concise (three steps) synthesis of the prenylated coumarin (+/-)-isoferprenin (35a) is reported.
• Annunziata, Rita; Raimondi, Laura; Appendino, Giovanni, Gazzetta Chimica Italiana, 1995, vol. 125, # 10, p. 465 - 478
  作者：Annunziata, Rita、Raimondi, Laura、Appendino, Giovanni、Cravotto, Giancarlo、Palmisano, Giovanni

  DOI：——

  日期：——