6,6-diethoxy-(5R)-hydroxy-8-methyl-1-triethylsilanylnon-8-en-1-yn-3-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6-diethoxy-(5R)-hydroxy-8-methyl-1-triethylsilanylnon-8-en-1-yn-3-one
• 英文别名: (5R)-6,6-diethoxy-5-hydroxy-8-methyl-1-triethylsilylnon-8-en-1-yn-3-one
• 化学式: C₂₀H₃₆O₄Si
• 分子量: 368.589
• InChiKey: IDXUKROGXACIST-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三乙基矽乙炔 在 正丁基锂 、 4 A molecular sieve 、 diethylzinc 、 (S,S)-(+)-2,6-双[2-(羟基二苯甲基)-1-吡咯烷基-甲基]-4-甲基苯酚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 23.17h， 生成 6,6-diethoxy-(5R)-hydroxy-8-methyl-1-triethylsilanylnon-8-en-1-yn-3-one
  参考文献：
  名称：

  Direct Catalytic Asymmetric Aldol Additions of Methyl Ynones. Spontaneous Reversal in the Sense of Enantioinduction

  摘要：

  In this Communication, we report the direct, catalytic, asymmetric aldol addition of methyl ynones using our dinuclear zinc catalyst. A spontaneous reversal in the sense of enantioinduction was observed for these reactions; formation of the (S)-enantiomer is favored in the early stages (69% ee after 5 min), whereas the (R)-enantiomer is isolated as the major product after prolonged reaction times (97% ee after 22 h). It could be shown that this reversal in enantioselectivity is due to formation of a new catalytic species which incorporates the aldol product.

  DOI：

  10.1021/ja038666r

文献信息

• Direct Catalytic Asymmetric Aldol Additions of Methyl Ynones. Spontaneous Reversal in the Sense of Enantioinduction
  作者：Barry M. Trost、Alec Fettes、Brock T. Shireman

  DOI：10.1021/ja038666r

  日期：2004.3.1

  In this Communication, we report the direct, catalytic, asymmetric aldol addition of methyl ynones using our dinuclear zinc catalyst. A spontaneous reversal in the sense of enantioinduction was observed for these reactions; formation of the (S)-enantiomer is favored in the early stages (69% ee after 5 min), whereas the (R)-enantiomer is isolated as the major product after prolonged reaction times (97% ee after 22 h). It could be shown that this reversal in enantioselectivity is due to formation of a new catalytic species which incorporates the aldol product.