(E)-3-{(1R,2R)-2-[2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-pentyl-phenyl]-4-oxo-cyclohexyl}-but-2-enal | 154783-05-8

• 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: (E)-3-{(1R,2R)-2-[2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-pentyl-phenyl]-4-oxo-cyclohexyl}-but-2-enal
• CAS: 154783-05-8
• 化学式: C₃₃H₅₆O₄Si₂
• 分子量: 572.976
• InChiKey: XNZXQTLCDYRJJT-WEETWJIHSA-N

物化性质

• 沸点：
  574.9±50.0 °C(predicted)
• 密度：
  0.967±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  (E)-3-{(1R,2R)-2-[2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-pentyl-phenyl]-4-oxo-cyclohexyl}-but-2-enal 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 0.5h， 以72%的产率得到(E)-3-{(1R,2R,4R)-2-[2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-pentyl-phenyl]-4-hydroxy-cyclohexyl}-but-2-enal
  参考文献：
  名称：

  Conformationally restricted hybrids of CP-55,940 and HHC: Stereoselective synthesis and activity

  摘要：

  A stereoselective total synthesis of each of the two diastereomeric C6-hydroxyethyl analogs of (-)-9-nor-9 beta-hydroxyhexahydrocannabinol has been reported. Control of the stereochemistry at C6 during the key step is accomplished through an intramolecular oxymercuration reaction. The prediction that the analogs would exhibit different degrees of binding to the cannabinoid receptor was borne out. This observation sheds light on the stereochemical requirements of the receptor.

  DOI：

  10.1016/s0040-4020(01)86983-0
• 作为产物：
  描述：

  3-<4-pentyl-2,6-bis(tert-butyldimethylsilyloxy)phenyl>-4-<3'-(1'-hydroxy-3',4'-butenyl)>cyclohexane-1-one 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到(E)-3-{(1R,2R)-2-[2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-pentyl-phenyl]-4-oxo-cyclohexyl}-but-2-enal
  参考文献：
  名称：

  Conformationally restricted hybrids of CP-55,940 and HHC: Stereoselective synthesis and activity

  摘要：

  A stereoselective total synthesis of each of the two diastereomeric C6-hydroxyethyl analogs of (-)-9-nor-9 beta-hydroxyhexahydrocannabinol has been reported. Control of the stereochemistry at C6 during the key step is accomplished through an intramolecular oxymercuration reaction. The prediction that the analogs would exhibit different degrees of binding to the cannabinoid receptor was borne out. This observation sheds light on the stereochemical requirements of the receptor.

  DOI：

  10.1016/s0040-4020(01)86983-0