(2R,1'S,5'S)-3,4-Dihydro-6,6'-dimethylspiro<2H,5H-pyrano<3,2-c><1>benzopyran-2,2'-bicyclo<3.1.1>heptane>-5-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,1'S,5'S)-3,4-Dihydro-6,6'-dimethylspiro<2H,5H-pyrano<3,2-c><1>benzopyran-2,2'-bicyclo<3.1.1>heptane>-5-one
• 英文别名: (2R,1'S,5'S)-3,4-Dihydro-6,6'-dimethylspiro(2H,5H-pyrano[3,2-c][1]benzopyran-2,2'-bicyclo[3.1.1]heptane)-5-one；(1'R,2R,5'S)-6',6'-dimethylspiro[3,4-dihydropyrano[3,2-c]chromene-2,2'-bicyclo[3.1.1]heptane]-5-one
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: WMXBEPYSAJXFMI-BXJCWQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  35.5
• 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 、 beta-pinene 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以48%的产率得到(2R,1'S,5'S)-3,4-Dihydro-6,6'-dimethylspiro<2H,5H-pyrano<3,2-c><1>benzopyran-2,2'-bicyclo<3.1.1>heptane>-5-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

• 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：——
• 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.