2-((10S,2R,3R,6R,7R)-3,7-di(1,3-dioxolan-2-yl)-10-[(4-methoxyphenyl)methoxy]-2,6-dimethylbicyclo[4.4.0]dec-2-yl)ethanal | 1018479-89-4

• 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: 2-((10S,2R,3R,6R,7R)-3,7-di(1,3-dioxolan-2-yl)-10-[(4-methoxyphenyl)methoxy]-2,6-dimethylbicyclo[4.4.0]dec-2-yl)ethanal
• 英文别名: 2-[(1R,2R,4aR,5R,8S,8aS)-2,5-bis(1,3-dioxolan-2-yl)-8-[(4-methoxyphenyl)methoxy]-1,4a-dimethyl-2,3,4,5,6,7,8,8a-octahydronaphthalen-1-yl]acetaldehyde
• CAS: 1018479-89-4
• 化学式: C₂₈H₄₀O₇
• 分子量: 488.621
• InChiKey: YLENXODOSMLWMK-YPZLOKHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-溴呋喃 、 2-((10S,2R,3R,6R,7R)-3,7-di(1,3-dioxolan-2-yl)-10-[(4-methoxyphenyl)methoxy]-2,6-dimethylbicyclo[4.4.0]dec-2-yl)ethanal 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.92h， 以27%的产率得到(1S)-2-((10S,2R,3R,6R,7R)-3,7-di(1,3-dioxolan-2-yl)-10-[(4-methoxyphenyl)methoxy]-2,6-dimethylbicyclo[4.4.0]dec-2-yl)-1-(3-furyl)ethan-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：

  2-((10S,2R,3R,6R,7R)-3,7-di(1,3-dioxolan-2-yl)-10-[(4-methoxyphenyl)methoxy]-2,6-dimethylbicyclo[4.4.0]dec-2-yl)ethan-1-ol 在 重铬酸吡啶 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以78%的产率得到2-((10S,2R,3R,6R,7R)-3,7-di(1,3-dioxolan-2-yl)-10-[(4-methoxyphenyl)methoxy]-2,6-dimethylbicyclo[4.4.0]dec-2-yl)ethanal
  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.