(E)-(2R,5S,6R)-Methyl 6-(2,5-dimethoxyphenyl)-2,6-dimethoxy-5-methylhex-3-enoate | 143491-51-4

• 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)-(2R,5S,6R)-Methyl 6-(2,5-dimethoxyphenyl)-2,6-dimethoxy-5-methylhex-3-enoate
• 英文别名: methyl (E,2R,5S,6R)-6-(2,5-dimethoxyphenyl)-2,6-dimethoxy-5-methylhex-3-enoate
• CAS: 143491-51-4
• 化学式: C₁₈H₂₆O₆
• 分子量: 338.401
• InChiKey: JSBQWKXVHINAHG-SZTCHAPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 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：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

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

  甲氧基三甲基硅烷 、 2,5-二甲氧基苯甲醛 、 (2S,3R)-(E)-Methyl 2-methoxy-3-(dimethylphenylsilyl)hex-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 16.0h， 以93%的产率得到(E)-(2R,5S,6R)-Methyl 6-(2,5-dimethoxyphenyl)-2,6-dimethoxy-5-methylhex-3-enoate
  参考文献：
  名称：

  Diastereoselective additions of chiral (E)-crotylsilanes to in situ generated oxonium ions: a direct asymmetric synthesis of functionalized homoallylic ethers

  摘要：

  DOI：

  10.1021/jo00047a046

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
• 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.