ethyl 3,3-ethylenedithio-4-(3-hydroxyphenyl)butanoate | 160721-43-7

• 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-ethylenedithio-4-(3-hydroxyphenyl)butanoate
• 英文别名: Ethyl 2-[2-[(3-hydroxyphenyl)methyl]-1,3-dithiolan-2-yl]acetate
• CAS: 160721-43-7
• 化学式: C₁₄H₁₈O₃S₂
• 分子量: 298.427
• InChiKey: IRYWCTBDJOEARD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3,3-ethylenedithio-4-(3-hydroxyphenyl)butanoate 在 二异丁基氢化铝 、 氯化铵 作用下， 生成 3,3-ethylenedithio-1,8-dihydroxy-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Tandem reduction / intramolecular hydroxyalkylation of (3-hydroxyphenyl)alkanoates: a new regioselective approach to 1,8-dihydroxytetralins

  摘要：

  4-(3-hydroxyphenyl)-butanoates 4, on treatment with DIBALH, followed by hydrolytic work-up, undergo a novel completely regioselective intramolecular hydroxyalkylation reaction to give 1,8-dihydroxytetralins. The yield of the reaction depends heavily on the structure of starting material, best results being achieved with 3,3-disubstituted butanoates.

  DOI：

  10.1016/s0040-4039(00)74819-2
• 作为产物：
  描述：

  3-羟基苯乙酸 在 氢氧化钾 、 三氟化硼乙醚 、 碘 、 magnesium 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 7.5h， 生成 ethyl 3,3-ethylenedithio-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

文献信息

• Tandem reduction / intramolecular hydroxyalkylation of (3-hydroxyphenyl)alkanoates: a new regioselective approach to 1,8-dihydroxytetralins
  作者：Giuseppe Guanti、Luca Banfi、Enrica Narisano、Renata Riva、Sergio Thea

  DOI：10.1016/s0040-4039(00)74819-2

  日期：1992.6

  4-(3-hydroxyphenyl)-butanoates 4, on treatment with DIBALH, followed by hydrolytic work-up, undergo a novel completely regioselective intramolecular hydroxyalkylation reaction to give 1,8-dihydroxytetralins. The yield of the reaction depends heavily on the structure of starting material, best results being achieved with 3,3-disubstituted butanoates.
• 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.