5-acetyloxy-8,8-dimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one | 31525-77-6

• 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: 5-acetyloxy-8,8-dimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one
• 英文别名: 5-acetoxyseselin；(8,8-dimethyl-2-oxopyrano[2,3-f]chromen-5-yl) acetate
• CAS: 31525-77-6
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: MPXGNKGXGBCOFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  471.0±45.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,7-二乙酰氧基-8-(3'-甲基-2'-丁烯基)香豆素 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 锌 作用下， 以 吡啶 、 甲醇 、 乙醚 为溶剂， 反应 49.33h， 生成 5-acetyloxy-8,8-dimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one
  参考文献：
  名称：

  Claisen rearrangements-XII

  摘要：

  DOI：

  10.1016/s0040-4020(01)82438-8

文献信息

• Natural and Synthetic 2,2-Dimethylpyranocoumarins with Antibacterial Activity
  作者：Eleni Melliou、Prokopios Magiatis、Sofia Mitaku、Alexios-Leandros Skaltsounis、Efrosini Chinou、Ioanna Chinou

  DOI：10.1021/np0497447

  日期：2005.1.1

  A new efficient synthetic approach to the natural coumarins 5-hydroxyseselin (5), 5-methoxyseselin (3), and (+/-) cis-grandmarin (9) is described as well as the synthesis of some new derivatives in the 5-methoxyseselin series (10-15). The natural coumarins 7-hydroxyalloxanthyletin (6), alloxanthoxyletin (8), and dipetalolactone (7) have also been obtained as secondary products. The type of fusion of the pyrano ring in all cases has been established by 2D NMR spectroscopy. The compounds have been studied for their in vitro antibacterial activity, which has been compared with that of some previously synthesized seselin derivatives. The most active compounds were 3, 7, 8, 11, and 14. Some structure-activity relationships are discussed.
• Zawadowski, Teodor; Mazur, Andrzej; Kleps, Jerzy, Polish Journal of Chemistry, 1985, vol. 59, # 5-6, p. 547 - 552
  作者：Zawadowski, Teodor、Mazur, Andrzej、Kleps, Jerzy

  DOI：——

  日期：——