1,8-diacetoxy-3,3-dimethyl-1,2,3,4-tetrahydronaphthalene | 143536-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,8-diacetoxy-3,3-dimethyl-1,2,3,4-tetrahydronaphthalene
• 英文别名: (8-acetyloxy-3,3-dimethyl-2,4-dihydro-1H-naphthalen-1-yl) acetate
• CAS: 143536-36-1
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: BGHWLHWYNKPSCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲氧基丙烯 、 1,8-diacetoxy-3,3-dimethyl-1,2,3,4-tetrahydronaphthalene 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 3,3-dimethyl-1,8-<(isopropylidene)dioxy>-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：

  ethyl 3-<3-(benzyloxy)phenyl>-2,2-dimethylpropanoate 在 4-二甲氨基吡啶 、 锂硼氢 、 正丁基锂 、 草酰氯 、 三氟化硼乙醚 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 mercury dichloride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 乙硫醇 为溶剂， 反应 29.75h， 生成 1,8-diacetoxy-3,3-dimethyl-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

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.