[3,5-diacetyloxy-4-[(1R,2R,5R)-6,6-dimethyl-4-oxo-2-bicyclo[3.1.1]heptanyl]phenyl] acetate | 1236197-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: [3,5-diacetyloxy-4-[(1R,2R,5R)-6,6-dimethyl-4-oxo-2-bicyclo[3.1.1]heptanyl]phenyl] acetate
• CAS: 1236197-83-3
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: DVPNSDZFCKCTAO-OAGGEKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [3,5-diacetyloxy-4-[(1R,2R,5R)-6,6-dimethyl-4-oxo-2-bicyclo[3.1.1]heptanyl]phenyl] acetate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (1R,4R,5R)-6,6-dimethyl-4-(2,4,6-trihydroxyphenyl)bicyclo[3.1.1]heptan-2-one
  参考文献：
  名称：

  Heteroadamantyl Cannabinoids

  摘要：

  The aliphatic side chain plays a pivotal role in determining the cannabinergic potency of tricyclic classical cannabinoids. We have synthesized a series of analogues in which the C3 position is substituted either directly or through a one-carbon atom linker with an adamantylamine or with an oxa- or an oxazaadamantane. The oxaadamantane pharmacophore in analogue 16 showed the best binding profile for both receptors.

  DOI：

  10.1021/jm100390h
• 作为产物：
  描述：

  (1R,4R,5R)-6,6-dimethyl-4-(2,4,6-trihydroxyphenyl)bicyclo[3.1.1]heptan-2-one 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以4.9 g的产率得到[3,5-diacetyloxy-4-[(1R,2R,5R)-6,6-dimethyl-4-oxo-2-bicyclo[3.1.1]heptanyl]phenyl] acetate
  参考文献：
  名称：

  Heteroadamantyl Cannabinoids

  摘要：

  The aliphatic side chain plays a pivotal role in determining the cannabinergic potency of tricyclic classical cannabinoids. We have synthesized a series of analogues in which the C3 position is substituted either directly or through a one-carbon atom linker with an adamantylamine or with an oxa- or an oxazaadamantane. The oxaadamantane pharmacophore in analogue 16 showed the best binding profile for both receptors.

  DOI：

  10.1021/jm100390h