9-nor-9α-fluoro-hexahydrocannabinol acetate | 148638-86-2

• 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: 9-nor-9α-fluoro-hexahydrocannabinol acetate
• CAS: 148638-86-2
• 化学式: C₂₂H₃₁FO₃
• 分子量: 362.485
• InChiKey: YCHIDVUYEOGUHV-RCCFBDPRSA-N

物化性质

• 沸点：
  419.6±45.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  9-nor-9α-fluoro-hexahydrocannabinol acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 9-nor-9α-fluoro-hexahydrocannabinol
  参考文献：
  名称：

  Halogenated cannabinoid synthesis

  摘要：

  A convenient synthesis of several tricyclic and bicyclic fluoro- and iodo analogs of cannabinoids has been reported. A new, mild methodology for the synthesis of vinyl fluorides from vinylstannanes has also been demonstrated. These C9 halo-functionalized cannabinoid analogs, along with (-) and (+)-DELTA9-THC carboxylic acids, were screened for anti-inflammatory activity in the mouse ear edema assay. It was interesting Lo find that both enantiomers of DELTA9-THC carboxylic acid were moderately active as anti-inflammatories. The bicyclic vinyl iodide (18C) also showed appreciable anti-inflammatory activity.

  DOI：

  10.1016/s0040-4020(01)90158-9
• 作为产物：
  描述：

  dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 二甲氨基三氟化硫 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 为溶剂， 反应 4.17h， 生成 9-nor-9α-fluoro-hexahydrocannabinol acetate
  参考文献：
  名称：

  Halogenated cannabinoid synthesis

  摘要：

  A convenient synthesis of several tricyclic and bicyclic fluoro- and iodo analogs of cannabinoids has been reported. A new, mild methodology for the synthesis of vinyl fluorides from vinylstannanes has also been demonstrated. These C9 halo-functionalized cannabinoid analogs, along with (-) and (+)-DELTA9-THC carboxylic acids, were screened for anti-inflammatory activity in the mouse ear edema assay. It was interesting Lo find that both enantiomers of DELTA9-THC carboxylic acid were moderately active as anti-inflammatories. The bicyclic vinyl iodide (18C) also showed appreciable anti-inflammatory activity.

  DOI：

  10.1016/s0040-4020(01)90158-9