5-tert-butyl-4-hydroxy-6,7-dimethoxy-2-methylbenzofuran | 202201-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5-tert-butyl-4-hydroxy-6,7-dimethoxy-2-methylbenzofuran
• 英文别名: 5-Tert-butyl-6,7-dimethoxy-2-methyl-1-benzofuran-4-ol
• CAS: 202201-94-3
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: FLWKQXXKCARFEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-tert-butyl-4-hydroxy-6,7-dimethoxy-2-methylbenzofuran 在 ammonium cerium(IV) nitrate 、 zinc diacetate 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 10.17h， 生成 黑木金合欢素
  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：

  4-acetoxy-5-tert-butyl-6,7-dimethoxy-2-methylbenzofuran 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以95%的产率得到5-tert-butyl-4-hydroxy-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

文献信息

• <i>tert</i>-Butyl Substituent as a Regiodirecting and Novel C−H Protecting Group in Cyclobutenedione-Based Benzannulation Chemistry
  作者：Fuqiang Liu、Lanny S. Liebeskind

  DOI：10.1021/jo971565p

  日期：1998.5.1

  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.