2,6-dimethoxyphenyl 4-methylbenzoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2,6-dimethoxyphenyl 4-methylbenzoate
• 英文别名: (2,6-Dimethoxyphenyl) 4-methylbenzoate；(2,6-dimethoxyphenyl) 4-methylbenzoate
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: HPZWEKAXIYFLGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dimethoxyphenyl 4-methylbenzoate 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以65%的产率得到1-(4-allylhepta-1,6-dien-4-yl)-4-methylbenzene
  参考文献：
  名称：

  烯丙基硅烷对酯的第一次烯丙基化：一锅多米诺骨牌合成三烯丙基甲烷衍生物

  摘要：

  AbstractWe report the first successful allylation of aromatic esters by allyltrimethylsilane. The reaction is mediated by 0.3–1.0 equiv. of titanium tetrachloride (TiCl4) at room temperature and leads in a multi‐step, one‐pot reaction to quaternary triallylmethane derivatives 5. The most efficient ester possessed two ortho‐methoxy substituents on the phenol ring. Molecular modelling revealed the ability of this compound to form a bidentate titanium complex, thus improving the steric accessibility of the ester carbonyl to nucleophilic attack.magnified image

  DOI：

  10.1002/adsc.201400296
• 作为产物：
  描述：

  2,6-二甲氧基苯酚 、 对甲基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以88%的产率得到2,6-dimethoxyphenyl 4-methylbenzoate
  参考文献：
  名称：

  烯丙基硅烷对酯的第一次烯丙基化：一锅多米诺骨牌合成三烯丙基甲烷衍生物

  摘要：

  AbstractWe report the first successful allylation of aromatic esters by allyltrimethylsilane. The reaction is mediated by 0.3–1.0 equiv. of titanium tetrachloride (TiCl4) at room temperature and leads in a multi‐step, one‐pot reaction to quaternary triallylmethane derivatives 5. The most efficient ester possessed two ortho‐methoxy substituents on the phenol ring. Molecular modelling revealed the ability of this compound to form a bidentate titanium complex, thus improving the steric accessibility of the ester carbonyl to nucleophilic attack.magnified image

  DOI：

  10.1002/adsc.201400296

文献信息

• The First Allylation of Esters by an Allylsilane: One-Pot Domino Synthesis of Triallylmethane Derivatives
  作者：Chenna Kesava Reddy Bandi、Anatoly Belostotskii、Alfred Hassner

  DOI：10.1002/adsc.201400296

  日期：2014.8.11

  AbstractWe report the first successful allylation of aromatic esters by allyltrimethylsilane. The reaction is mediated by 0.3–1.0 equiv. of titanium tetrachloride (TiCl4) at room temperature and leads in a multi‐step, one‐pot reaction to quaternary triallylmethane derivatives 5. The most efficient ester possessed two ortho‐methoxy substituents on the phenol ring. Molecular modelling revealed the ability of this compound to form a bidentate titanium complex, thus improving the steric accessibility of the ester carbonyl to nucleophilic attack.magnified image