(-)-(trans)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-yl trifluoromethanesulfonate | 128660-94-6

• 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: (-)-(trans)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-yl trifluoromethanesulfonate
• 英文别名: (-)-(trans)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-yl trifluoromethanesulfonate；[(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-9-yl] trifluoromethanesulfonate
• CAS: 128660-94-6
• 化学式: C₂₁H₂₇F₃O₅S
• 分子量: 448.504
• InChiKey: ZLTFKJRKBYVTNJ-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (-)-(trans)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-yl trifluoromethanesulfonate 在 四(三苯基膦)钯 碘 、 六甲基二锡 、 lithium carbonate 、 lithium chloride 作用下， 生成 1-hydroxy-6a,7,10,10a-tetrahydro-6,6-dimethyl-9-iodo-6H-dibenzopyran
  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：

  3,5-二羟基戊苯 在 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (-)-(trans)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of 11-nor-.DELTA.8-tetrahydrocannabinol-9-carboxylic acid methyl ester

  摘要：

  DOI：

  10.1021/jo00309a014

文献信息

• TIUS, MARCUS A.;KANNANGARA, G. S. KAMALI, J. ORG. CHEM., 55,(1990) N2, C. 5711-5714
  作者：TIUS, MARCUS A.、KANNANGARA, G. S. KAMALI

  DOI：——

  日期：——
• Halogenated cannabinoid synthesis
  作者：Marcus A. Tius、G.S.Kamali Kannangara、Michael A. Kerr、Krista J.S. Grace

  DOI：10.1016/s0040-4020(01)90158-9

  日期：1993.4

  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.
• Synthesis of 11-nor-.DELTA.8-tetrahydrocannabinol-9-carboxylic acid methyl ester
  作者：Marcus A. Tius、G. S. Kamali Kannangara

  DOI：10.1021/jo00309a014

  日期：1990.10