2-Ethenyl-3-isopropoxy-4-n-butyl-4-hydroxy-2-cyclobutenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Ethenyl-3-isopropoxy-4-n-butyl-4-hydroxy-2-cyclobutenone
• 英文别名: 4-Butyl-2-ethenyl-4-hydroxy-3-propan-2-yloxycyclobut-2-en-1-one
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: XVWHBRDJFRYJNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Ethenyl-3-isopropoxy-4-n-butyl-4-hydroxy-2-cyclobutenone 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-4-Ethylidene-3-isopropoxy-2-n-butyl-2-cyclobutenone 、 (Z)-4-Ethylidene-3-isopropoxy-2-n-butyl-2-cyclobutenone
  参考文献：
  名称：

  Regioselective Synthesis of Highly Substituted Naphthols

  摘要：

  2,3,4-Trisubstituted 4-hydroxy-2-cyclobutenones, prepared by regiospecific synthesis of substituted cyclobutenediones, undergo Lewis acid facilitated ionization to cyclobutenyl cations, which are trapped by trialkylsilanes in a regioselective sense. Thermolysis of the resulting cyclobutenones affords phenols in high yields.

  DOI：

  10.1021/jo00108a029
• 作为产物：
  描述：

  正丁基锂 、 3-Ethenyl-4-propan-2-yloxycyclobut-3-ene-1,2-dione 以 四氢呋喃 为溶剂， 以60%的产率得到2-Ethenyl-3-isopropoxy-4-n-butyl-4-hydroxy-2-cyclobutenone
  参考文献：
  名称：

  Regioselective Synthesis of Highly Substituted Naphthols

  摘要：

  2,3,4-Trisubstituted 4-hydroxy-2-cyclobutenones, prepared by regiospecific synthesis of substituted cyclobutenediones, undergo Lewis acid facilitated ionization to cyclobutenyl cations, which are trapped by trialkylsilanes in a regioselective sense. Thermolysis of the resulting cyclobutenones affords phenols in high yields.

  DOI：

  10.1021/jo00108a029

文献信息

• Regioselective Synthesis of Highly Substituted Naphthols
  作者：Philip Turnbull、Harold W. Moore

  DOI：10.1021/jo00108a029

  日期：1995.2

  2,3,4-Trisubstituted 4-hydroxy-2-cyclobutenones, prepared by regiospecific synthesis of substituted cyclobutenediones, undergo Lewis acid facilitated ionization to cyclobutenyl cations, which are trapped by trialkylsilanes in a regioselective sense. Thermolysis of the resulting cyclobutenones affords phenols in high yields.