ethyl 3-ethyl-4-(3-hydroxyphenyl)-3-<(triethylsilyl)oxy>butanoate | 160721-50-6

• 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-ethyl-4-(3-hydroxyphenyl)-3-<(triethylsilyl)oxy>butanoate
• 英文别名: Ethyl 3-[(3-hydroxyphenyl)methyl]-3-triethylsilyloxypentanoate
• CAS: 160721-50-6
• 化学式: C₂₀H₃₄O₄Si
• 分子量: 366.573
• InChiKey: DGSXPWLMJNWIQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-ethyl-4-(3-hydroxyphenyl)-3-<(triethylsilyl)oxy>butanoate 在 吡啶 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 3-ethyl-1,8-<(isopropylidene)dioxy>-3-<(triethylsilyl)oxy>-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：

  1-<3-(benzyloxy)phenyl>butan-2-one 在 palladium on activated charcoal 2,6-二甲基吡啶 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 ethyl 3-ethyl-4-(3-hydroxyphenyl)-3-<(triethylsilyl)oxy>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

文献信息

• Regioselective synthesis of 1,8-dihydroxytetralins through a tandem reduction/intramolecular hydroxyalkylation of 4-(3-hydroxyphenyl)alkanoates
  作者：Giuseppe Guanti、Luca Banfi、Renata Riva

  DOI：10.1016/s0040-4020(01)89307-8

  日期：1994.1

  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.