2-[(1R,2R,5R)-5-Hydroxy-2-((E)-3-hydroxy-1-methyl-propenyl)-cyclohexyl]-5-pentyl-benzene-1,3-diol | 154783-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(1R,2R,5R)-5-Hydroxy-2-((E)-3-hydroxy-1-methyl-propenyl)-cyclohexyl]-5-pentyl-benzene-1,3-diol
• 英文别名: 2-[(1R,2R,5R)-5-hydroxy-2-[(E)-4-hydroxybut-2-en-2-yl]cyclohexyl]-5-pentylbenzene-1,3-diol
• CAS: 154783-07-0
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: UJAKEUYGLLGUEY-XEOYNYBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(1R,2R,5R)-5-Hydroxy-2-((E)-3-hydroxy-1-methyl-propenyl)-cyclohexyl]-5-pentyl-benzene-1,3-diol 在 sodium hydroxide 、 sodium tetrahydroborate 、 mercury(II) diacetate 作用下， 生成 6β-hydroxyethyl-9-nor-9β-hydroxyhexahydrocannabinol 、 6α-hydroxyethyl-9-nor-9β-hydroxyhexahydrocannabinol
  参考文献：
  名称：

  Conformationally restricted hybrids of CP-55,940 and HHC: Stereoselective synthesis and activity

  摘要：

  A stereoselective total synthesis of each of the two diastereomeric C6-hydroxyethyl analogs of (-)-9-nor-9 beta-hydroxyhexahydrocannabinol has been reported. Control of the stereochemistry at C6 during the key step is accomplished through an intramolecular oxymercuration reaction. The prediction that the analogs would exhibit different degrees of binding to the cannabinoid receptor was borne out. This observation sheds light on the stereochemical requirements of the receptor.

  DOI：

  10.1016/s0040-4020(01)86983-0
• 作为产物：
  描述：

  3-[4-pentyl-2,6-dihydroxyphenyl]-4-[3'-(1-hydroxy-3',4'-butenyl)]-cyclohexane-1-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以92%的产率得到2-[(1R,2R,5R)-5-Hydroxy-2-((E)-3-hydroxy-1-methyl-propenyl)-cyclohexyl]-5-pentyl-benzene-1,3-diol
  参考文献：
  名称：

  Conformationally restricted hybrids of CP-55,940 and HHC: Stereoselective synthesis and activity

  摘要：

  A stereoselective total synthesis of each of the two diastereomeric C6-hydroxyethyl analogs of (-)-9-nor-9 beta-hydroxyhexahydrocannabinol has been reported. Control of the stereochemistry at C6 during the key step is accomplished through an intramolecular oxymercuration reaction. The prediction that the analogs would exhibit different degrees of binding to the cannabinoid receptor was borne out. This observation sheds light on the stereochemical requirements of the receptor.

  DOI：

  10.1016/s0040-4020(01)86983-0