(+/-)-6,6a,7,8-tetrahydro-1-hydroxy-6,6-[2H6]dimethyl-3-pentyl-9H-dibenzo[b,d]pyran-9-one | 137530-65-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (+/-)-6,6a,7,8-tetrahydro-1-hydroxy-6,6-[2H6]dimethyl-3-pentyl-9H-dibenzo[b,d]pyran-9-one
• CAS: 137530-65-5
• 化学式: C₂₀H₂₆O₃
• 分子量: 320.377
• InChiKey: KWVVHJXZVFZYPC-XERRXZQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+/-)-6,6a,7,8-tetrahydro-1-hydroxy-6,6-[2H6]dimethyl-3-pentyl-9H-dibenzo[b,d]pyran-9-one 在 正丁基锂 、 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.05h， 生成 (+/-)-6,6-[2H6]dimethyl-11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol
  参考文献：
  名称：

  Synthesis of [2H6]-labelled metabolites of cannabinoids

  摘要：

  Four [H-2(6)]-labelled metabolites of cannabinoids were synthesized for use as internal standards for GC/MS analysis. The hexadeutero-ketone 3, prepared from ketal 1, undergoes a Shapiro reaction to give (+/-)-6,6-[H-2(6)]dimethyl-11-nor-9-carboxy-Delta(9)-THC (4a) as the major product. The minor product, (+/-)-6,6-[H-2(6)] dimethyl-11-nor-9-carboxy-Delta(8)-THC (4b), was obtained after hydrolysis of its acetate methyl ester which was isolated using preparative HPLC. Reduction of 4a gave (+/-)-6,6-[H-2(6)]dimethyl-11-hydroxy-Delta(9)-THC (6). (+/-)-6,6-[H-2(6)]dimethyl-8 beta,11-dihydroxy-Delta(9)-THC (10), was also prepared from 3 using a reported procedure for the non-labelled analog.

  DOI：

  10.1002/1099-1344(200006)43:7<655::aid-jlcr350>3.0.co;2-t
• 作为产物：
  描述：

  1-hydroxy-3-pentyl-7,8-dihydrospiropyran-9,2'-<1,3>-dioxolan>-6(10H)-one 、 (Methyl-d3)magnesium iodide 在 盐酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 49.5h， 以88%的产率得到(+/-)-6,6a,7,8-tetrahydro-1-hydroxy-6,6-[2H6]dimethyl-3-pentyl-9H-dibenzo[b,d]pyran-9-one
  参考文献：
  名称：

  Synthesis of [2H6]-labelled metabolites of cannabinoids

  摘要：

  Four [H-2(6)]-labelled metabolites of cannabinoids were synthesized for use as internal standards for GC/MS analysis. The hexadeutero-ketone 3, prepared from ketal 1, undergoes a Shapiro reaction to give (+/-)-6,6-[H-2(6)]dimethyl-11-nor-9-carboxy-Delta(9)-THC (4a) as the major product. The minor product, (+/-)-6,6-[H-2(6)] dimethyl-11-nor-9-carboxy-Delta(8)-THC (4b), was obtained after hydrolysis of its acetate methyl ester which was isolated using preparative HPLC. Reduction of 4a gave (+/-)-6,6-[H-2(6)]dimethyl-11-hydroxy-Delta(9)-THC (6). (+/-)-6,6-[H-2(6)]dimethyl-8 beta,11-dihydroxy-Delta(9)-THC (10), was also prepared from 3 using a reported procedure for the non-labelled analog.

  DOI：

  10.1002/1099-1344(200006)43:7<655::aid-jlcr350>3.0.co;2-t