ethyl 3,3-ethylenedioxy-4-(3-hydroxyphenyl)butanoate | 160721-46-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3,3-ethylenedioxy-4-(3-hydroxyphenyl)butanoate
• 英文别名: ethyl 2-[2-[(3-hydroxyphenyl)methyl]-1,3-dioxolan-2-yl]acetate
• CAS: 160721-46-0
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: MUTIURCJPOKRQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 3,3-ethylenedioxy-4-(3-hydroxyphenyl)butanoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以47%的产率得到3,3-ethylenedioxy-1,8-dihydroxy-1,2,3,4-tetrahydronaphthalene
  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 ethandithiol 、 氢氧化钾 、 BF₅O 、 camphor-10-sulfonic acid 、 碘 、 对甲苯磺酸 、 magnesium 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 、 苯 为溶剂， 反应 35.58h， 生成 ethyl 3,3-ethylenedioxy-4-(3-hydroxyphenyl)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