2-tert-butyl-3,4-dimethoxy-4-[5-(2-methylfuryl)]-2-cyclobutenone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-tert-butyl-3,4-dimethoxy-4-[5-(2-methylfuryl)]-2-cyclobutenone
• 英文别名: 2-Tert-butyl-3,4-dimethoxy-4-(5-methylfuran-2-yl)cyclobut-2-en-1-one
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: SKVUOULPRLWJEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-tert-butyl-3,4-dimethoxy-4-[5-(2-methylfuryl)]-2-cyclobutenone 在 4-二甲氨基吡啶 、 三正丁胺 作用下， 以 xylene 为溶剂， 反应 18.0h， 以81%的产率得到4-acetoxy-5-tert-butyl-6,7-dimethoxy-2-methylbenzofuran
  参考文献：
  名称：

  tert-Butyl Substituent as a Regiodirecting and Novel C−H Protecting Group in Cyclobutenedione-Based Benzannulation Chemistry

  摘要：

  2-Unsubstituted hydroquinone monoacetates, quinones, and 3-unsubstituted quinolizinones were synthesized in moderate to high yields via tert-butyl and trimethylsilyl substituted cyclobutenediones. The addition of unsaturated carbon nucleophiles proceeded regiospecifically at the carbonyl group most distant from the tert-butyl or trimethylsilyl substituent. Thermolysis of the adducts, followed by treatment under acidic conditions to remove the tert-butyl and trimethylsilyl groups in good overall yields, provided access to a variety of "less-substituted" hydroquinone monoacetates, quinones, and quinolizinones. Of the two systems, the tert-butyl-substituted cyclobutenediones proved the most useful.

  DOI：

  10.1021/jo971565p
• 作为产物：
  描述：

  2-甲基呋喃 、 3-tert-butyl-4-methoxycyclobutene-1,2-dione 、 三氟甲烷磺酸甲酯 在 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 、 正己烷 、 四氢呋喃 为溶剂， 反应 6.0h， 以81%的产率得到2-tert-butyl-3,4-dimethoxy-4-[5-(2-methylfuryl)]-2-cyclobutenone
  参考文献：
  名称：

  tert-Butyl Substituent as a Regiodirecting and Novel C−H Protecting Group in Cyclobutenedione-Based Benzannulation Chemistry

  摘要：

  2-Unsubstituted hydroquinone monoacetates, quinones, and 3-unsubstituted quinolizinones were synthesized in moderate to high yields via tert-butyl and trimethylsilyl substituted cyclobutenediones. The addition of unsaturated carbon nucleophiles proceeded regiospecifically at the carbonyl group most distant from the tert-butyl or trimethylsilyl substituent. Thermolysis of the adducts, followed by treatment under acidic conditions to remove the tert-butyl and trimethylsilyl groups in good overall yields, provided access to a variety of "less-substituted" hydroquinone monoacetates, quinones, and quinolizinones. Of the two systems, the tert-butyl-substituted cyclobutenediones proved the most useful.

  DOI：

  10.1021/jo971565p