(7S,7aS)-7-[tert-butyl(diphenyl)silyl]oxy-7a-methyl-2,5,6,7-tetrahydro-1H-inden-4-one | 184481-09-2

• 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: (7S,7aS)-7-[tert-butyl(diphenyl)silyl]oxy-7a-methyl-2,5,6,7-tetrahydro-1H-inden-4-one
• CAS: 184481-09-2
• 化学式: C₂₆H₃₂O₂Si
• 分子量: 404.624
• InChiKey: WPFMWECDVSPOHG-AHWVRZQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (7S,7aS)-7-[tert-butyl(diphenyl)silyl]oxy-7a-methyl-2,5,6,7-tetrahydro-1H-inden-4-one 在 ammonium hydroxide 、 三甲基溴硅烷 、 氯化铵 作用下， 以 乙醚 为溶剂， 反应 7.0h， 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 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 (7S,7aS)-7-[tert-butyl(diphenyl)silyl]oxy-7a-methyl-2,5,6,7-tetrahydro-1H-inden-4-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.