2-Methyl-5-oxo-3,4-dihydropyrano[3,2-c]chromene-2-carbaldehyde | 161634-44-2

• 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: 2-Methyl-5-oxo-3,4-dihydropyrano[3,2-c]chromene-2-carbaldehyde
• CAS: 161634-44-2
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: CFQMFQZMECDSBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Diethylgeranylphosphonate 、 2-Methyl-5-oxo-3,4-dihydropyrano[3,2-c]chromene-2-carbaldehyde 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以25%的产率得到(3'RS)-(4'E)-Isoferprenin
  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
• 作为产物：
  描述：

  (2RS)-3,4-Dihydro-2-(hydroxymethyl)-2-methyl-2H,5H-pyrano<3,2-c><1>benzopyran-5-one 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到2-Methyl-5-oxo-3,4-dihydropyrano[3,2-c]chromene-2-carbaldehyde
  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.