(4S,1R,5R,6R,8aR)-4-[(4-methoxyphenyl)methoxy]-5,8a-dimethyl-5-[2-(tert-butyldimethylsilanyloxy)ethyl]perhydronaphthalene-1,6-dicarbaldehyde | 1018479-87-2

• 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: (4S,1R,5R,6R,8aR)-4-[(4-methoxyphenyl)methoxy]-5,8a-dimethyl-5-[2-(tert-butyldimethylsilanyloxy)ethyl]perhydronaphthalene-1,6-dicarbaldehyde
• 英文别名: (1R,4S,4aS,5R,6R,8aR)-5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(4-methoxyphenyl)methoxy]-5,8a-dimethyl-1,2,3,4,4a,6,7,8-octahydronaphthalene-1,6-dicarbaldehyde
• CAS: 1018479-87-2
• 化学式: C₃₀H₄₈O₅Si
• 分子量: 516.794
• InChiKey: CXIQSJREYRPSLR-OPQYXRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-乙基-2-甲基-1,3-二氧杂烷 、 (4S,1R,5R,6R,8aR)-4-[(4-methoxyphenyl)methoxy]-5,8a-dimethyl-5-[2-(tert-butyldimethylsilanyloxy)ethyl]perhydronaphthalene-1,6-dicarbaldehyde 在 对甲苯磺酸 作用下， 以 乙二醇 为溶剂， 反应 7.5h， 以99%的产率得到(8S,1R,2R,5R,4aR)-2,5-di(1,3-dioxolan-2-yl)-8-[(4-methoxyphenyl)methoxy]-1,4a-dimethyl-1-[2-(tert-butyldimethylsilanyloxy)ethyl]perhydronaphthalene
  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,8S,4aS)-5-(hydroxymethyl)-8-[(4-methoxyphenyl)methoxy]-1,4a-dimethyl-1-[2-(tert-butyldimethylsilanyloxy)ethyl]perhydronaphth-2-yl}methan-1-ol 在 重铬酸吡啶 、 sodium acetate 、 sodium methylate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 2.0h， 以68 mg的产率得到(4S,1R,5R,6R,8aR)-4-[(4-methoxyphenyl)methoxy]-5,8a-dimethyl-5-[2-(tert-butyldimethylsilanyloxy)ethyl]perhydronaphthalene-1,6-dicarbaldehyde
  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.