methyl 4-{4'-[4''-(tetrahydropyran-2'''-yloxy)butyl]phenoxy}butanoate | 912338-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 4-{4'-[4''-(tetrahydropyran-2'''-yloxy)butyl]phenoxy}butanoate
• 英文别名: Methyl 4-[4-[4-(oxan-2-yloxy)butyl]phenoxy]butanoate
• CAS: 912338-86-4
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: KJMWHDCZEDSFAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-{4'-[4''-(tetrahydropyran-2'''-yloxy)butyl]phenoxy}butanoate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以84%的产率得到Butanoic acid, 4-[4-(4-hydroxybutyl)phenoxy]-, methyl ester
  参考文献：
  名称：

  Highly Chemoselective Formation of Aldehyde Enamines under Very Mild Reaction Conditions

  摘要：

  Although ketone enamines are widely used in organic synthesis, aldehyde enamines are rarely employed due to the limitations of their preparation using known methods (need for acid or base, excess of amine, and/or elevated temperature). We have successfully developed rapid and particularly mild condensation conditions (1 h, 0 degrees C, 1.2 equiv of amine) leading to di- and trisubstituted enamines with excellent conversion (84-100%). Remarkably high chemoselectivity was observed with complete discrimination between aldehyde and ketone, among other functional groups positively tested.

  DOI：

  10.1021/jo0611061
• 作为产物：
  描述：

  4-羟基苯丁酸甲酯 在 sodium chlorite 、 sodium dihydrogenphosphate 、 lithium aluminium tetrahydride 、 2-甲基-2-丁烯 、 草酰氯 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 30.5h， 生成 methyl 4-{4'-[4''-(tetrahydropyran-2'''-yloxy)butyl]phenoxy}butanoate
  参考文献：
  名称：

  Highly Chemoselective Formation of Aldehyde Enamines under Very Mild Reaction Conditions

  摘要：

  Although ketone enamines are widely used in organic synthesis, aldehyde enamines are rarely employed due to the limitations of their preparation using known methods (need for acid or base, excess of amine, and/or elevated temperature). We have successfully developed rapid and particularly mild condensation conditions (1 h, 0 degrees C, 1.2 equiv of amine) leading to di- and trisubstituted enamines with excellent conversion (84-100%). Remarkably high chemoselectivity was observed with complete discrimination between aldehyde and ketone, among other functional groups positively tested.

  DOI：

  10.1021/jo0611061