ethyl 2-[(1'R,4'aR,8'S,8'aR)-8'-hydroxy-1',4'a-dimethyl-2'-oxospiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydronaphthalene]-1'-yl]acetate | 1018479-81-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-[(1'R,4'aR,8'S,8'aR)-8'-hydroxy-1',4'a-dimethyl-2'-oxospiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydronaphthalene]-1'-yl]acetate
• CAS: 1018479-81-6
• 化学式: C₁₈H₂₈O₆
• 分子量: 340.417
• InChiKey: AXWDTSAYTZGIRY-NKKGCODLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(1'R,4'aR,8'S,8'aR)-8'-hydroxy-1',4'a-dimethyl-2'-oxospiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydronaphthalene]-1'-yl]acetate 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以100%的产率得到ethyl 2-((10S,2R,6R)-10-hydroxy-2,6-dimethyl-3,7-dioxobicyclo[4.4.0]dec-2-yl)acetate
  参考文献：
  名称：

  Total Synthesis of the Hallucinogenic Neoclerodane Diterpenoid Salvinorin A

  摘要：

  Total synthesis of salvinorin A (1), a neoclerodane diterpenoid having the most potent hallucinogenic activity and a selective K-opioid agonist, was completed in 20 steps starting from enantiomerically pure hydroxy-Wieland-Miescher ketone 5.

  DOI：

  10.1021/ol800101v
• 作为产物：
  描述：

  (4’S,8a’R) 4’-hydroxy-5’,8a’-dimethyl-3’,4’,8’,8a’-tetrahydro-2’Hspiro[[1,3]dioxolane-2,1’-naphthalen]-6’(7’H)-one 、 碘代醋酸乙酯 在 氨 、 lithium 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以51%的产率得到ethyl 2-[(1'R,4'aR,8'S,8'aR)-8'-hydroxy-1',4'a-dimethyl-2'-oxospiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydronaphthalene]-1'-yl]acetate
  参考文献：
  名称：

  Total Synthesis of the Hallucinogenic Neoclerodane Diterpenoid Salvinorin A

  摘要：

  Total synthesis of salvinorin A (1), a neoclerodane diterpenoid having the most potent hallucinogenic activity and a selective K-opioid agonist, was completed in 20 steps starting from enantiomerically pure hydroxy-Wieland-Miescher ketone 5.

  DOI：

  10.1021/ol800101v

文献信息

• Total Synthesis of the Hallucinogenic Neoclerodane Diterpenoid Salvinorin A
  作者：Masato Nozawa、Yuhki Suka、Takashi Hoshi、Toshio Suzuki、Hisahiro Hagiwara

  DOI：10.1021/ol800101v

  日期：2008.4.1

  Total synthesis of salvinorin A (1), a neoclerodane diterpenoid having the most potent hallucinogenic activity and a selective K-opioid agonist, was completed in 20 steps starting from enantiomerically pure hydroxy-Wieland-Miescher ketone 5.