[(E,2S,5S,6R)-3,5-dimethyl-2,6-bis(phenylmethoxy)hept-3-enoxy]methylbenzene | 132488-22-3

• 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: [(E,2S,5S,6R)-3,5-dimethyl-2,6-bis(phenylmethoxy)hept-3-enoxy]methylbenzene
• CAS: 132488-22-3
• 化学式: C₃₀H₃₆O₃
• 分子量: 444.614
• InChiKey: ZSICFJOFUIJHEE-QSQATZJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(E,2S,5S,6R)-3,5-dimethyl-2,6-bis(phenylmethoxy)hept-3-enoxy]methylbenzene 在 lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride 、 二甲基硫 、 臭氧 作用下， 生成 (R)-3,4-bis(benzyloxy)butan-2-one 、 (S)-3-Benzyloxy-2-methyl-butan-1-ol
  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：

  溴甲苯 、 (E)-(2S,5S)-1-Benzyloxy-3,5-dimethyl-hept-3-ene-2,6-diol 在 氢氧化钾 作用下， 反应 72.0h， 以28%的产率得到[(E,2S,5S,6R)-3,5-dimethyl-2,6-bis(phenylmethoxy)hept-3-enoxy]methylbenzene
  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).