(5S,6R)-7-(Benzyloxy)-5,6-epoxy-5-methyl-3-hepten-2-one | 132409-33-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5S,6R)-7-(Benzyloxy)-5,6-epoxy-5-methyl-3-hepten-2-one
• 英文别名: (E)-4-[(2S,3R)-2-methyl-3-(phenylmethoxymethyl)oxiran-2-yl]but-3-en-2-one
• CAS: 132409-33-7
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: ZSPVDJRKVGUZPN-PQAPVRDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S,6R)-7-(Benzyloxy)-5,6-epoxy-5-methyl-3-hepten-2-one 在 咪唑 、 lithium aluminium tetrahydride 、 (2R,3R)-4-dimethylamino-3-methyl-1,2-diphenyl-butan-2-ol 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 [(E)-3-((2S,3R)-3-Benzyloxymethyl-2-methyl-oxiranyl)-1-methyl-allyloxy]-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  Diastereodifferentiation in SN2' additions of methylcuprates to nonracemic acyclic vinyloxiranes

  摘要：

  S(N)2' additions of Me2CuLi, MeCu(CN)Li, and Me2Cu(CN)Li2 to the 2S and 2R alkoxy cis-(Z)- and -(E)- vinyloxiranes 8, 9, 13, and 14 were examined as possible routes to acrylic subunits of polypropionate natural products. Highest antisyn ratios were found for the (2S)- and (2R)-hydroxy-(E)-vinyloxiranes 13a and 14a followed by the (2R)-MTM ether analogue 14c. In both cases Me2CuLi gave higher ratios than either of the cyanocuprates (> 99:1 vs 14:1 for 13a/13b and > 40:1 vs approximately 24:1 for 14c).

  DOI：

  10.1021/jo00006a049
• 作为产物：
  描述：

  (2S,3R)-4-(benzyloxy)-2,3-epoxy-2-methylbutan-1-ol 在 草酰氯 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 (5S,6R)-7-(Benzyloxy)-5,6-epoxy-5-methyl-3-hepten-2-one
  参考文献：
  名称：

  Diastereodifferentiation in SN2' additions of methylcuprates to nonracemic acyclic vinyloxiranes

  摘要：

  S(N)2' additions of Me2CuLi, MeCu(CN)Li, and Me2Cu(CN)Li2 to the 2S and 2R alkoxy cis-(Z)- and -(E)- vinyloxiranes 8, 9, 13, and 14 were examined as possible routes to acrylic subunits of polypropionate natural products. Highest antisyn ratios were found for the (2S)- and (2R)-hydroxy-(E)-vinyloxiranes 13a and 14a followed by the (2R)-MTM ether analogue 14c. In both cases Me2CuLi gave higher ratios than either of the cyanocuprates (> 99:1 vs 14:1 for 13a/13b and > 40:1 vs approximately 24:1 for 14c).

  DOI：

  10.1021/jo00006a049

文献信息

• Diastereodifferentiation in SN2' additions of methylcuprates to nonracemic acyclic vinyloxiranes
  作者：James A. Marshall、Bruce E. Blough

  DOI：10.1021/jo00006a049

  日期：1991.3

  S(N)2' additions of Me2CuLi, MeCu(CN)Li, and Me2Cu(CN)Li2 to the 2S and 2R alkoxy cis-(Z)- and -(E)- vinyloxiranes 8, 9, 13, and 14 were examined as possible routes to acrylic subunits of polypropionate natural products. Highest antisyn ratios were found for the (2S)- and (2R)-hydroxy-(E)-vinyloxiranes 13a and 14a followed by the (2R)-MTM ether analogue 14c. In both cases Me2CuLi gave higher ratios than either of the cyanocuprates (> 99:1 vs 14:1 for 13a/13b and > 40:1 vs approximately 24:1 for 14c).