Butyric acid 8-(1-acetoxymethyl-2-methyl-allyl)-2-oxo-2H-chromen-7-yl ester | 139115-65-4

• 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: Butyric acid 8-(1-acetoxymethyl-2-methyl-allyl)-2-oxo-2H-chromen-7-yl ester
• 英文别名: [8-(1-acetyloxy-3-methylbut-3-en-2-yl)-2-oxochromen-7-yl] butanoate
• CAS: 139115-65-4
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: YTXFZGRFUUHEOY-UHFFFAOYSA-N

物化性质

• 沸点：
  500.2±50.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  82.81
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Butyric acid 8-(1-acetoxymethyl-2-methyl-allyl)-2-oxo-2H-chromen-7-yl ester 在 草酰氯 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 九里香醛
  参考文献：
  名称：

  Total syntheses of microminutin and other coumarins through the key intermediate isomurralonginol.

  摘要：

  A straightforward route to isomurralonginol (1) from umbelliferone (4 steps, 59% yield) is described. Isomurralonginol is used as the key intermediate in the preparation of isomurralonginol acetate (2) (1 step, 94% yield), murralongin (3) (1 step, 75% yield) and microminutin (2 steps and 38% yield). The synthesis of microminutin involves the selenolactonization of alpha, beta-substituted vinyl acetic acid (12) (50% yield) with spontaneous elimination of the selenyl moiety, without oxidation, to the unsaturated lactone.

  DOI：

  10.1016/s0040-4020(01)80713-4
• 作为产物：
  描述：

  7-羟基香豆素 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 Butyric acid 8-(1-acetoxymethyl-2-methyl-allyl)-2-oxo-2H-chromen-7-yl ester
  参考文献：
  名称：

  Total syntheses of microminutin and other coumarins through the key intermediate isomurralonginol.

  摘要：

  A straightforward route to isomurralonginol (1) from umbelliferone (4 steps, 59% yield) is described. Isomurralonginol is used as the key intermediate in the preparation of isomurralonginol acetate (2) (1 step, 94% yield), murralongin (3) (1 step, 75% yield) and microminutin (2 steps and 38% yield). The synthesis of microminutin involves the selenolactonization of alpha, beta-substituted vinyl acetic acid (12) (50% yield) with spontaneous elimination of the selenyl moiety, without oxidation, to the unsaturated lactone.

  DOI：

  10.1016/s0040-4020(01)80713-4