(6aR,10aR)-1-Hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-4-carboxylic acid methyl ester | 63976-49-8

• 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: (6aR,10aR)-1-Hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-4-carboxylic acid methyl ester
• 英文别名: methyl (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-4-carboxylate
• CAS: 63976-49-8
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: LKLZAPSGDVLPGH-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (6aR,10aR)-1-Hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-4-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 生成 4-methyl-Δ⁸-tetrahydrocannabinol
  参考文献：
  名称：

  2-Methyl- and 4-Methyl-D8-tetrahydrocaniiabinol: Correlation of Spatial Distinction with Cannabinoid Receptor Binding

  摘要：

  A high level of binding to the brain cannabinoid receptor was found for 2-methyl-Delta(8)-tetrahydrocannabinol (THC) while no binding was observed for 4-methyl-Delta(8)-THC. Four energy minima were found by molecular mechanics for ethyl side-chain models of Delta(8)-THC [syn- and antiperiplanar and (+/-)-orthogonal values for torsion angle C(4)-C(3)-C(alpha)-C(beta)]. The active Delta(8)-THC and 2-methyl-Delta(8)-THC molecules share a common structural feature [a relatively low energy synperiplanar value C(4)-C(3)-C(alpha)-C(beta) torsion angle conformation for the n-pentyl side chain] that is not exhibited by the inactive 4-methyl-Delta(8)-THC analogue. This spatial distinction may represent the basis for the difference in biological activity between the tn two isomers examined.

  DOI：

  10.3987/com-94-s(b)86
• 作为产物：
  描述：

  大麻二酚 在 silica gel 、 对甲苯磺酸 作用下， 生成 (6aR,10aR)-1-Hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-4-carboxylic acid methyl ester
  参考文献：
  名称：

  2-Methyl- and 4-Methyl-D8-tetrahydrocaniiabinol: Correlation of Spatial Distinction with Cannabinoid Receptor Binding

  摘要：

  A high level of binding to the brain cannabinoid receptor was found for 2-methyl-Delta(8)-tetrahydrocannabinol (THC) while no binding was observed for 4-methyl-Delta(8)-THC. Four energy minima were found by molecular mechanics for ethyl side-chain models of Delta(8)-THC [syn- and antiperiplanar and (+/-)-orthogonal values for torsion angle C(4)-C(3)-C(alpha)-C(beta)]. The active Delta(8)-THC and 2-methyl-Delta(8)-THC molecules share a common structural feature [a relatively low energy synperiplanar value C(4)-C(3)-C(alpha)-C(beta) torsion angle conformation for the n-pentyl side chain] that is not exhibited by the inactive 4-methyl-Delta(8)-THC analogue. This spatial distinction may represent the basis for the difference in biological activity between the tn two isomers examined.

  DOI：

  10.3987/com-94-s(b)86

文献信息

• 2-Methyl- and 4-Methyl-D8-tetrahydrocaniiabinol: Correlation of Spatial Distinction with Cannabinoid Receptor Binding
  作者：Robert Glaser、Itay Adin、Raphael Machoulam、Lumir Hanus

  DOI：10.3987/com-94-s(b)86

  日期：——

  A high level of binding to the brain cannabinoid receptor was found for 2-methyl-Delta(8)-tetrahydrocannabinol (THC) while no binding was observed for 4-methyl-Delta(8)-THC. Four energy minima were found by molecular mechanics for ethyl side-chain models of Delta(8)-THC [syn- and antiperiplanar and (+/-)-orthogonal values for torsion angle C(4)-C(3)-C(alpha)-C(beta)]. The active Delta(8)-THC and 2-methyl-Delta(8)-THC molecules share a common structural feature [a relatively low energy synperiplanar value C(4)-C(3)-C(alpha)-C(beta) torsion angle conformation for the n-pentyl side chain] that is not exhibited by the inactive 4-methyl-Delta(8)-THC analogue. This spatial distinction may represent the basis for the difference in biological activity between the tn two isomers examined.