(3S,4S)-4-[tert-butyl(diphenyl)silyl]oxy-3-[2-(1,3-dioxan-2-yl)ethyl]-3-methylcyclohexan-1-one | 184481-12-7

• 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: (3S,4S)-4-[tert-butyl(diphenyl)silyl]oxy-3-[2-(1,3-dioxan-2-yl)ethyl]-3-methylcyclohexan-1-one
• CAS: 184481-12-7
• 化学式: C₂₉H₄₀O₄Si
• 分子量: 480.72
• InChiKey: LVIMRQJDQMMXQH-WNJJXGMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-[tert-butyl(diphenyl)silyl]oxy-3-[2-(1,3-dioxan-2-yl)ethyl]-3-methylcyclohexan-1-one 在 ammonium hydroxide 、 三甲基溴硅烷 、 sodium methylate 、 氯化铵 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 水 为溶剂， 反应 42.5h， 生成 (3S,3aS,4R,7S,7aS)-7-[tert-butyl(diphenyl)silyl]oxy-4,7a-dimethyl-3-(2-methylprop-2-enyl)-2,3,3a,5,6,7-hexahydro-1H-inden-4-ol
  参考文献：
  名称：

  Concise Total Syntheses of the Sesquiterpenoids (−)-Homalomenol A and (−)-Homalomenol B

  摘要：

  The conjugate additions of the organocopper(I) reagents 22 and 27 to the enantiomerically homogeneous bicyclic enone 4 provided, after epimerization (NaOMe, MeOH) of the resultant product mixtures and appropriate chromatographic separations, the bicyclo[4.3.0]nonan-2-ones 24 and 28. Compounds 24 and 28 were readily converted, via two synthetic steps in each case, into,the sesquiterpenoids (-)-homalomenols B (2) and A (1), respectively.

  DOI：

  10.1021/jo961605+
• 作为产物：
  描述：

  (S)-4-hydroxy-3-methyl-cyclohex-2-en-1-one 在 咪唑 、 六甲基磷酰三胺 、 ammonium hydroxide 、 三甲基氯硅烷 、 copper(I) bromide dimethylsulfide complex 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 (3S,4S)-4-[tert-butyl(diphenyl)silyl]oxy-3-[2-(1,3-dioxan-2-yl)ethyl]-3-methylcyclohexan-1-one
  参考文献：
  名称：

  Concise Total Syntheses of the Sesquiterpenoids (−)-Homalomenol A and (−)-Homalomenol B

  摘要：

  The conjugate additions of the organocopper(I) reagents 22 and 27 to the enantiomerically homogeneous bicyclic enone 4 provided, after epimerization (NaOMe, MeOH) of the resultant product mixtures and appropriate chromatographic separations, the bicyclo[4.3.0]nonan-2-ones 24 and 28. Compounds 24 and 28 were readily converted, via two synthetic steps in each case, into,the sesquiterpenoids (-)-homalomenols B (2) and A (1), respectively.

  DOI：

  10.1021/jo961605+

文献信息

• Concise Total Syntheses of the Sesquiterpenoids (−)-Homalomenol A and (−)-Homalomenol B
  作者：Edward Piers、Renata M. Oballa

  DOI：10.1021/jo961605+

  日期：1996.1.1

  The conjugate additions of the organocopper(I) reagents 22 and 27 to the enantiomerically homogeneous bicyclic enone 4 provided, after epimerization (NaOMe, MeOH) of the resultant product mixtures and appropriate chromatographic separations, the bicyclo[4.3.0]nonan-2-ones 24 and 28. Compounds 24 and 28 were readily converted, via two synthetic steps in each case, into,the sesquiterpenoids (-)-homalomenols B (2) and A (1), respectively.