9-nor-9,9-bisfluoro-hexahydrocannabinol acetate | 148638-83-9

• 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-9,9-bisfluoro-hexahydrocannabinol acetate
• CAS: 148638-83-9
• 化学式: C₂₂H₃₀F₂O₃
• 分子量: 380.475
• InChiKey: IHIGYSRBFIXJQB-IAGOWNOFSA-N

物化性质

• 沸点：
  416.8±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 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：
  0.68
• 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-9,9-bisfluoro-hexahydrocannabinol acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以80%的产率得到9-nor-9,9-bisfluoro-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 、 二甲氨基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 9-nor-9,9-bisfluoro-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