(2S,5S,6R)-(E)-methyl 6-(2,5-dimethoxy-3-nitrophenyl)-2,6-dimethoxy-5-methylhex-3-enoate | 134333-56-5

• 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: (2S,5S,6R)-(E)-methyl 6-(2,5-dimethoxy-3-nitrophenyl)-2,6-dimethoxy-5-methylhex-3-enoate
• 英文别名: (E)-(2S,5S,6R)-Methyl 6-(2,5-dimethoxy-3-nitrophenyl)-2,6-dimethoxy-4-methylhex-3-enoate；methyl (E,2S,5S,6R)-6-(2,5-dimethoxy-3-nitrophenyl)-2,6-dimethoxy-5-methylhex-3-enoate
• CAS: 134333-56-5
• 化学式: C₁₈H₂₅NO₈
• 分子量: 383.398
• InChiKey: KBLRWBRRAZNLHS-QJVHFLHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,5S,6R)-(E)-methyl 6-(2,5-dimethoxy-3-nitrophenyl)-2,6-dimethoxy-5-methylhex-3-enoate 在 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 作用下， 生成 (2R,3S,5S,6R)-6-(2,5-Dimethoxy-3-nitro-phenyl)-2,6-dimethoxy-5-methyl-hexane-1,3-diol 、 (2R,3R,5S,6R)-6-(2,5-Dimethoxy-3-nitro-phenyl)-2,6-dimethoxy-5-methyl-hexane-1,3-diol
  参考文献：
  名称：

  Diastereoselectivity in the borane methyl sulfide promoted hydroboration of .alpha.-alkoxy-.beta.,.gamma.-unsaturated esters. Documentation of an alkoxy-directed hydroboration reaction

  摘要：

  Alpha-Alkoxy-beta,gamma-unsaturated methyl esters of structural type 1 undergo an alkoxy-directed hydroboration with the mild hydroborating reagent borane-methyl sulfide complex (BH3-SMe2) in THF from 0-degrees-C to room temperature, and after standard alkaline hydrogen peroxide oxidation the 1,3-diol product 2 is produced with useful levels of selectivity favoring the anti diastereomer.

  DOI：

  10.1021/jo00046a006
• 作为产物：
  描述：

  2,5-dimethoxy-3-nitrobenzaldehyde dimethyl acetal 、 (E)-(2R,3R)-methyl 3-(dimethylphenylsilyl)-2-methoxyhex-4-enoate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以95%的产率得到(2S,5S,6R)-(E)-methyl 6-(2,5-dimethoxy-3-nitrophenyl)-2,6-dimethoxy-5-methylhex-3-enoate
  参考文献：
  名称：

  Panek, James S.; Yang, Michael, Journal of the American Chemical Society, 1991, vol. 113, # 17, p. 6594 - 6600

  摘要：

  DOI：

文献信息

• Diastereoselective additions of chiral (E)-crotylsilanes to in situ generated oxonium ions: a direct asymmetric synthesis of functionalized homoallylic ethers
  作者：James S. Panek、Michael Yang、Feng Xu

  DOI：10.1021/jo00047a046

  日期：1992.10
• Panek, James S.; Yang, Michael, Journal of the American Chemical Society, 1991, vol. 113, # 17, p. 6594 - 6600
  作者：Panek, James S.、Yang, Michael

  DOI：——

  日期：——
• Diastereoselectivity in the borane methyl sulfide promoted hydroboration of .alpha.-alkoxy-.beta.,.gamma.-unsaturated esters. Documentation of an alkoxy-directed hydroboration reaction
  作者：James S. Panek、Feng Xu

  DOI：10.1021/jo00046a006

  日期：1992.9

  Alpha-Alkoxy-beta,gamma-unsaturated methyl esters of structural type 1 undergo an alkoxy-directed hydroboration with the mild hydroborating reagent borane-methyl sulfide complex (BH3-SMe2) in THF from 0-degrees-C to room temperature, and after standard alkaline hydrogen peroxide oxidation the 1,3-diol product 2 is produced with useful levels of selectivity favoring the anti diastereomer.