(1S,8R,4aR)-1-[(4-methoxyphenyl)methoxy]-8,4a-dimethyl-4,7-dimethylene-8-[2-(tert-butyldimethylsilanyloxy)ethyl]-1,2,3,5,6,8,4a,8a-octahydronaphthalene | 1018479-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,8R,4aR)-1-[(4-methoxyphenyl)methoxy]-8,4a-dimethyl-4,7-dimethylene-8-[2-(tert-butyldimethylsilanyloxy)ethyl]-1,2,3,5,6,8,4a,8a-octahydronaphthalene
• 英文别名: 2-[(1R,4aR,8S,8aS)-8-[(4-methoxyphenyl)methoxy]-1,4a-dimethyl-2,5-dimethylidene-3,4,6,7,8,8a-hexahydronaphthalen-1-yl]ethoxy-tert-butyl-dimethylsilane
• CAS: 1018479-86-1
• 化学式: C₃₀H₄₈O₃Si
• 分子量: 484.795
• InChiKey: IOZHXGUDCOHYON-ZHTHUIBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.32
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,8R,4aR)-1-[(4-methoxyphenyl)methoxy]-8,4a-dimethyl-4,7-dimethylene-8-[2-(tert-butyldimethylsilanyloxy)ethyl]-1,2,3,5,6,8,4a,8a-octahydronaphthalene 在 硼烷四氢呋喃络合物 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以78 mg的产率得到{(1S,8S,4aS)-5-(hydroxymethyl)-8-[(4-methoxyphenyl)methoxy]-1,4a-dimethyl-1-[2-(tert-butyldimethylsilanyloxy)ethyl]perhydronaphth-2-yl}methan-1-ol
  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：

  (1S,8R,4aR)-8,4a-dimethyl-4,7-dimethylene-8-[2-(tert-butyldimethylsilanyloxy)ethyl]-1,2,3,5,6,8,4a,8a-octahydronaphthol 、 4-甲氧基氯苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.42h， 以94%的产率得到(1S,8R,4aR)-1-[(4-methoxyphenyl)methoxy]-8,4a-dimethyl-4,7-dimethylene-8-[2-(tert-butyldimethylsilanyloxy)ethyl]-1,2,3,5,6,8,4a,8a-octahydronaphthalene
  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.