(+/-)-3-Norpentyl-3-(1',1'-dimethylheptyl)-9-normethyl-9-(1,3-dithianyl)-Δ9-tetrahydrocannabiol tert-butyldimethylsilyl ether | 136984-73-1

• 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: (+/-)-3-Norpentyl-3-(1',1'-dimethylheptyl)-9-normethyl-9-(1,3-dithianyl)-Δ9-tetrahydrocannabiol tert-butyldimethylsilyl ether
• 英文别名: (+/-)-3-Norpentyl-3-(1',1'-dimethylheptyl)-9-normethyl-9-(1,3-dithianyl)-Δ⁹-tetrahydrocannabiol tert-butyldimethylsilyl ether
• CAS: 136984-73-1
• 化学式: C₃₄H₅₆O₂S₂Si
• 分子量: 589.035
• InChiKey: PUEGTKISPLWCAQ-KAYWLYCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.11
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+/-)-3-Norpentyl-3-(1',1'-dimethylheptyl)-9-normethyl-9-(1,3-dithianyl)-Δ9-tetrahydrocannabiol tert-butyldimethylsilyl ether 在 potassium carbonate 、 碘甲烷 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以82%的产率得到(+/-)-(6aR,10aR)-3-(1',1'-dimethylheptyl)-9-formyl-6a,7,8,10a-tetrahydro-6,6-dimethyl-6H-dibenzopyran-1-yl tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Synthesis of racemic and optically active .DELTA.9-tetrahydrocannabinol (THC) metabolites

  摘要：

  The preparation of racemic and optically active DELTA-9-THC metabolites is described from synthon 13. Racemic synthon 13 is prepared in four steps (46%) from Danishefsky's diene. Optically active synthon 13 is prepared from perillaldehyde via the enone 22 in six steps (23% yield). Alternatively, nopinone can be converted to 13 in three steps (50% yield) via a cyclobutane ring cleavage. The acid-catalyzed condensation of 13 with olivetol (6a) and subsequent conversion to 11-hydroxy and 9-carboxyl DELTA-9-THC metabolites 2a and 4a is described, as well as the preparation of 1',1'-dimethylheptyl THC analogues 2b, 3b, and 4b from 5-(1',1'-dimethylheptyl)resorcinol (6c).

  DOI：

  10.1021/jo00024a031
• 作为产物：
  描述：

  2-(2-methoxy-4-trimethylsilyloxycyclohex-3-en-1-yl)propan-2-ol 在 咪唑 、 正丁基锂 、 对甲苯磺酸 、 三氯乙酸 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 22.0h， 生成 (+/-)-3-Norpentyl-3-(1',1'-dimethylheptyl)-9-normethyl-9-(1,3-dithianyl)-Δ9-tetrahydrocannabiol tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Synthesis of racemic and optically active .DELTA.9-tetrahydrocannabinol (THC) metabolites

  摘要：

  The preparation of racemic and optically active DELTA-9-THC metabolites is described from synthon 13. Racemic synthon 13 is prepared in four steps (46%) from Danishefsky's diene. Optically active synthon 13 is prepared from perillaldehyde via the enone 22 in six steps (23% yield). Alternatively, nopinone can be converted to 13 in three steps (50% yield) via a cyclobutane ring cleavage. The acid-catalyzed condensation of 13 with olivetol (6a) and subsequent conversion to 11-hydroxy and 9-carboxyl DELTA-9-THC metabolites 2a and 4a is described, as well as the preparation of 1',1'-dimethylheptyl THC analogues 2b, 3b, and 4b from 5-(1',1'-dimethylheptyl)resorcinol (6c).

  DOI：

  10.1021/jo00024a031