7-[(3,7-dimethyl-2-octenyl)oxy]-8-hydroxy-2H-1-benzopyran-2-one

• 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: 7-[(3,7-dimethyl-2-octenyl)oxy]-8-hydroxy-2H-1-benzopyran-2-one
• 英文别名: isoferujol；7-[(E)-3,7-dimethyloct-2-enoxy]-8-hydroxychromen-2-one
• 化学式: C₁₉H₂₄O₄
• 分子量: 316.397
• InChiKey: MGBAZDUGSSQFKC-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6,7-dihydrogeraniol 、 瑞香素 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到7-[(3,7-dimethyl-2-octenyl)oxy]-8-hydroxy-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Monoalkylation of dihydroxycoumarins via Mitsunobu dehydroalkylation under high intensity ultrasound. The synthesis of ferujol

  摘要：

  Monoalkylation of natural dihydroxycoumarins was carried out by Mitsunobu dehydroalkylation under sonochemical conditions. Aesculetin (6,7-dihydroxycoumarin) was selectively alkylated in good yield with prenyl alcohols at position 7, as clearly shown by NOESY experiments; though less selectively, position 7 was also the most reactive in daphnetin (7,8-dihydroxycoumarin). The synthesis of the phytoestrogen ferujol is also reported for the first time. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.114

文献信息

• Monoalkylation of dihydroxycoumarins via Mitsunobu dehydroalkylation under high intensity ultrasound. The synthesis of ferujol
  作者：Giancarlo Cravotto、Stefano Chimichi、Bruna Robaldo、Marco Boccalini

  DOI：10.1016/j.tetlet.2003.09.114

  日期：2003.11

  Monoalkylation of natural dihydroxycoumarins was carried out by Mitsunobu dehydroalkylation under sonochemical conditions. Aesculetin (6,7-dihydroxycoumarin) was selectively alkylated in good yield with prenyl alcohols at position 7, as clearly shown by NOESY experiments; though less selectively, position 7 was also the most reactive in daphnetin (7,8-dihydroxycoumarin). The synthesis of the phytoestrogen ferujol is also reported for the first time. (C) 2003 Elsevier Ltd. All rights reserved.