jaeschkeanadiol p-hydroxybenzyl ether

• 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: jaeschkeanadiol p-hydroxybenzyl ether
• 英文别名: (1R,3aR,8S,8aS)-8-[(4-hydroxyphenyl)methoxy]-3a,6-dimethyl-1-propan-2-yl-2,3,4,7,8,8a-hexahydroazulen-1-ol
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: BNWXYCISZYQGKN-LNRXMEIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(羟基甲基)苯基特戊酸酯 在 N-溴代丁二酰亚胺(NBS) 、 焦磷酸硫胺素 、 sodium hydride 、 二甲基亚砜 、 乙二胺 作用下， 以 二氯甲烷 为溶剂， 反应 60.08h， 生成 jaeschkeanadiol p-hydroxybenzyl ether
  参考文献：
  名称：

  Structure−Activity Relationships of the Estrogenic Sesquiterpene Ester Ferutinin. Modification of the Terpenoid Core

  摘要：

  Esterification of p-hydroxybenzoic acid, a very weak estrogenic compound, with the daucane alcohol jaeschkeanadiol (1b) leads to a spectacular magnification of the estrogenic activity. To identify the structural elements responsible for this effect, the terpenoid core of jaeschkeanadiol p-hydroxybenzoate (ferutinin, 1a) was modified, capitalizing on the presence of two functionalities, the monoacylated, hydrogen-bonded 1,3-diol system and the double bond. The hydrogen bonding, while possibly useful, was not critical for activity, while hydrogenation and cyclopropanation of the double bond were tolerated. Conversely, oxidative modifications of the double bond that placed a hydroxyl on the a-face of the molecule proved detrimental. Taken together, these observations identified the substitution at C-8/C-9 as critical for activity.

  DOI：

  10.1021/np049796w

文献信息

• Structure−Activity Relationships of the Estrogenic Sesquiterpene Ester Ferutinin. Modification of the Terpenoid Core
  作者：Giovanni Appendino、Paola Spagliardi、Olov Sterner、Stuart Milligan

  DOI：10.1021/np049796w

  日期：2004.9.1

  Esterification of p-hydroxybenzoic acid, a very weak estrogenic compound, with the daucane alcohol jaeschkeanadiol (1b) leads to a spectacular magnification of the estrogenic activity. To identify the structural elements responsible for this effect, the terpenoid core of jaeschkeanadiol p-hydroxybenzoate (ferutinin, 1a) was modified, capitalizing on the presence of two functionalities, the monoacylated, hydrogen-bonded 1,3-diol system and the double bond. The hydrogen bonding, while possibly useful, was not critical for activity, while hydrogenation and cyclopropanation of the double bond were tolerated. Conversely, oxidative modifications of the double bond that placed a hydroxyl on the a-face of the molecule proved detrimental. Taken together, these observations identified the substitution at C-8/C-9 as critical for activity.