6-acetyl-7-O-farnesylesculetine | 636574-82-8

• 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: 6-acetyl-7-O-farnesylesculetine
• CAS: 636574-82-8
• 化学式: C₂₆H₃₂O₅
• 分子量: 424.537
• InChiKey: ZZQOWNHLSQCCQL-GNUCVDFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.74
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-acetyl-7-O-farnesylesculetine 在 过氧化脲素 、 甲基三氧化铼(VII) 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 Acetic acid 7-[(2E,6E)-9-(3,3-dimethyl-oxiranyl)-3,7-dimethyl-nona-2,6-dienyloxy]-2-oxo-2H-chromen-6-yl ester
  参考文献：
  名称：

  Farnesyloxycoumarins, a new class of squalene-hopene cyclase inhibitors

  摘要：

  A few naturally occurring prenyl- and renyloxycoumarins and several new related synthetic derivatives were evaluated as inhibitors of squalene-hopene cyclase (SHC), a useful model enzyme, to predict their interactions with oxidosqualene cyclase (OSC). Umbelliprenin-10',11'-monoepoxide (IC50 2.5 muM) and the corresponding 6',7'-10', 11' diepoxide (IC50 1.5 muM) were the most active enzyme inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.085
• 作为产物：
  描述：

  反式,反式-金合欢醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 0.75h， 生成 6-acetyl-7-O-farnesylesculetine
  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