ethyl 4-<3-(benzyloxy)phenyl>-3-ethyl-3-hydroxybutanoate | 160721-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 4-<3-(benzyloxy)phenyl>-3-ethyl-3-hydroxybutanoate
• 英文别名: ethyl 3-hydroxy-3-[(3-phenylmethoxyphenyl)methyl]pentanoate
• CAS: 160721-48-2
• 化学式: C₂₁H₂₆O₄
• 分子量: 342.435
• InChiKey: PZNRXTQGFLULGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-<3-(benzyloxy)phenyl>-3-ethyl-3-hydroxybutanoate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以90%的产率得到ethyl 3-ethyl-3-hydroxy-4-<3-(hydroxy)phenyl>butanoate
  参考文献：
  名称：

  Regioselective synthesis of 1,8-dihydroxytetralins through a tandem reduction/intramolecular hydroxyalkylation of 4-(3-hydroxyphenyl)alkanoates

  摘要：

  A series of 4-(3-hydroxyphenyl)butanoates 3 has been prepared and transformed into 1,8-dihydroxytetralins of general formula 2 by treatment with 2 equivalents of DIBALH followed by quenching with aqueous NH4Cl. A possible mechanism for this novel totally regioselective intramolecular hydroxyalkylation is suggested and the factors affecting the stability of 1,8-dihydroxytetralins 2 are also discussed.

  DOI：

  10.1016/s0040-4020(01)89307-8
• 作为产物：
  描述：

  3-羟基苯乙酸 在 氢氧化钾 、 硫酸 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.5h， 生成 ethyl 4-<3-(benzyloxy)phenyl>-3-ethyl-3-hydroxybutanoate
  参考文献：
  名称：

  Regioselective synthesis of 1,8-dihydroxytetralins through a tandem reduction/intramolecular hydroxyalkylation of 4-(3-hydroxyphenyl)alkanoates

  摘要：

  A series of 4-(3-hydroxyphenyl)butanoates 3 has been prepared and transformed into 1,8-dihydroxytetralins of general formula 2 by treatment with 2 equivalents of DIBALH followed by quenching with aqueous NH4Cl. A possible mechanism for this novel totally regioselective intramolecular hydroxyalkylation is suggested and the factors affecting the stability of 1,8-dihydroxytetralins 2 are also discussed.

  DOI：

  10.1016/s0040-4020(01)89307-8