3-<4-pentyl-2,6-(tert-butyldimethylsilyloxy)phenyl>-4-<3'-(1-hydroxy-3',4'-butenyl)>cyclohexane-1-ol | 154783-03-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-<4-pentyl-2,6-(tert-butyldimethylsilyloxy)phenyl>-4-<3'-(1-hydroxy-3',4'-butenyl)>cyclohexane-1-ol
• CAS: 154783-03-6
• 化学式: C₃₃H₆₀O₄Si₂
• 分子量: 577.008
• InChiKey: ZXAJCUZJQKEJIJ-OZNIXHKMSA-N

反应信息

• 作为反应物：
  描述：

  3-<4-pentyl-2,6-(tert-butyldimethylsilyloxy)phenyl>-4-<3'-(1-hydroxy-3',4'-butenyl)>cyclohexane-1-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以96%的产率得到3-[4-pentyl-2,6-dihydroxyphenyl]-4-[3'-(1-hydroxy-3',4'-butenyl)]-cyclohexane-1-ol
  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 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 0.5h， 以88%的产率得到3-<4-pentyl-2,6-(tert-butyldimethylsilyloxy)phenyl>-4-<3'-(1-hydroxy-3',4'-butenyl)>cyclohexane-1-ol
  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