6α-hydroxyethyl-9-nor-9β-hydroxyhexahydrocannabinol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6α-hydroxyethyl-9-nor-9β-hydroxyhexahydrocannabinol
• 英文别名: 14α-hydroxymethyl-9-nor-9β-hydroxyhexahydrocannabinol；(6R,6aR,9R,10aR)-6-(2-hydroxyethyl)-6-methyl-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromene-1,9-diol
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: SIPOTUCBLSHXHD-BZLDKRAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-[4-pentyl-2,6-dihydroxyphenyl]-4-[3'-(1-hydroxy-3',4'-butenyl)]-cyclohexane-1-ol 在 sodium hydroxide 、 sodium tetrahydroborate 、 mercury(II) diacetate 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 生成 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

文献信息

• Classical/non-classical cannabinoid hybrids; Stereochemical requirements for the southern hydroxyalkyl chain
  作者：M.A. Tius、W.A.G. Hill、X.L. Zou、J. Busch-Petersen、J.K. Kawakami、M.C. Fernandez-Garcia、D.J. Drake、V. Abadji、A. Makriyannis

  DOI：10.1016/0024-3205(95)00182-6

  日期：1995.5

  We have synthesized a range of hybrid classical/non-classical cannabinoids (CC/NCCs) combining the hexahydrocannabinol dibenzopyran structure with the hydroxyalkyl chain found in CP-55940, in order to investigate the role of the hydroxyalkyl pharmacophore in cannabimimetic activity. This was achieved by synthesizing CC analogs in which the 6 alpha- and 6 beta-methyl groups were modified to the corresponding

  我们已经合成了一系列杂合的经典/非经典大麻素（CC / NCC），它们结合了六氢大麻酚二苯并吡喃结构与CP-55940中的羟烷基链，以研究羟烷基药效团在大麻模拟活性中的作用。这是通过合成CC类似物实现的，其中6个α-和6个β-甲基被修饰为相应的羟乙基。我们的结合数据表明，β位置是羟烷基部分的首选方向，对CB1受体的亲和力对于6β-羟乙基比对应的6α-类似物大20倍。使用6个β-羟烷基二苯并吡喃类似物进行的进一步研究表明，南部脂肪链的长度从6个β-羟甲基变为6个β-羟乙基，再到6个β-羟丙基，随着链长的变化，效价变化很小。因此，我们得出结论，尽管羟烷基药效团相对于二苯并吡喃环的构型受到强烈影响，但是羟烷基部分的链长（直至n = 3同源物）并不关键。
• Conformationally restricted hybrids of CP-55,940 and HHC: Stereoselective synthesis and activity
  作者：Marcus A. Tius、Alexandros Makriyannis、Xiang Long Zoua、V. Abadji

  DOI：10.1016/s0040-4020(01)86983-0

  日期：1994.2

  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.