3β,7β-dihydroxy-5β-<(tert-butyldimethylsilyl)oxy>-4α,6α-dimethoxycyclohept-1-ene | 142458-31-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3β,7β-dihydroxy-5β-<(tert-butyldimethylsilyl)oxy>-4α,6α-dimethoxycyclohept-1-ene
• CAS: 142458-31-9
• 化学式: C₁₅H₃₀O₅Si
• 分子量: 318.486
• InChiKey: BJGIKETXDBEPSJ-SIMOQEFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3β,7β-dihydroxy-5β-<(tert-butyldimethylsilyl)oxy>-4α,6α-dimethoxycyclohept-1-ene 在 四氧化锇 、 四丁基碘化铵 、 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 17.0h， 生成 1β,5β-bis(benzyloxy)-3β-<(tert-butyldimethylsilyl)oxy>-6α,7α-dihydroxy-2α,4α-dimethoxycycloheptane
  参考文献：
  名称：

  Approaches to the synthesis of heptitol derivatives via iron-mediated stereocontrolled functionalization of cycloheptatrienone

  摘要：

  Stereocontrolled reduction of tropone-Fe(CO)3 (9) followed by alcohol protection gives the [(trialkylsilyl)oxy]cycloheptatriene complex 11. Osmylation of 11 proceeds with complete stereoselectivity to give the protected trihydroxycycloheptadiene complex 12, treatment of which with acid in the presence of methanol (generated in situ) gives the symmetrically trioxygenated diene complex 15. Decomplexation of these complexes, followed by stereocontrolled diene oxygenation and ring cleavage, provides methodology for the construction of heptitol derivatives. Conversion of complex 15 to ether-substituted dienyl-Fe(CO)3 cationic complexes was studied. These complexes react with nucleophiles to give diene-, dienyl-, or enediyl-Fe(CO)2L complexes, depending on the nature of the nucleophile and the spectator ligand.

  DOI：

  10.1021/jo00040a043
• 作为产物：
  描述：

  5β-<(tert-butyldimethylsilyl)oxy>-3β,7β-endoperoxy-4α,6α-dimethoxycyclohept-1-ene 在 硫脲 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以83 mg的产率得到3β,7β-dihydroxy-5β-<(tert-butyldimethylsilyl)oxy>-4α,6α-dimethoxycyclohept-1-ene
  参考文献：
  名称：

  Approaches to the synthesis of heptitol derivatives via iron-mediated stereocontrolled functionalization of cycloheptatrienone

  摘要：

  Stereocontrolled reduction of tropone-Fe(CO)3 (9) followed by alcohol protection gives the [(trialkylsilyl)oxy]cycloheptatriene complex 11. Osmylation of 11 proceeds with complete stereoselectivity to give the protected trihydroxycycloheptadiene complex 12, treatment of which with acid in the presence of methanol (generated in situ) gives the symmetrically trioxygenated diene complex 15. Decomplexation of these complexes, followed by stereocontrolled diene oxygenation and ring cleavage, provides methodology for the construction of heptitol derivatives. Conversion of complex 15 to ether-substituted dienyl-Fe(CO)3 cationic complexes was studied. These complexes react with nucleophiles to give diene-, dienyl-, or enediyl-Fe(CO)2L complexes, depending on the nature of the nucleophile and the spectator ligand.

  DOI：

  10.1021/jo00040a043