3-(6-methoxy-2,3,3-trimethyl-2,3-dihydrofurano[b]phenyl-6)-1-(4-hydroxyphenyl)prop-2-enon-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(6-methoxy-2,3,3-trimethyl-2,3-dihydrofurano[b]phenyl-6)-1-(4-hydroxyphenyl)prop-2-enon-1
• 英文别名: (E)-1-(4-hydroxyphenyl)-3-(6-methoxy-2,3,3-trimethyl-2H-1-benzofuran-5-yl)prop-2-en-1-one
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: NURHHZJJUCVZOM-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(6-methoxy-2,3,3-trimethyl-2,3-dihydrofurano[b]phenyl-6)-1-(4-hydroxyphenyl)prop-2-enon-1 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以94.7%的产率得到3-(6-methoxy-2,2,3-trimethyl-2,3-dihydrofurano[b]phenyl-6)-1-(4-hydroxyphenyl)prop-2-enon-1
  参考文献：
  名称：

  Lewis or brønsted acid provoked rearrangements in ortho-(1,1-dimethylpropenyl)phenols

  摘要：

  Treatment of the o-(1,1-dimethylpropenyl)phenol, dihydrolicochalcone A, with a Bronsted acid affords two isomeric 2,2-dimethyl-4H-dihydropyrano[b]benzenes. The rearrangement probably involves a [3,5] charge-accelerated rearrangement. Attempts to provoke the same reaction in licochalcone A only afforded poorly defined degradation products. Treatment of dihydrolicochalcone A as well as licochalcone A with Lewis acids afforded 2,3,3-trimethyldihydro-furano[b] benzenes and 2,2,3-trimethyldihydrofurano[b]benzenes. Proper use of solvents and Lewis acid enables preferential formation of the kinetically favoured product or the thermodynamically more stable product. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00212-3
• 作为产物：
  描述：

  甘草查耳酮A 在 四氯化钛 作用下， 以 硝基苯 为溶剂， 反应 0.5h， 以91%的产率得到3-(6-methoxy-2,3,3-trimethyl-2,3-dihydrofurano[b]phenyl-6)-1-(4-hydroxyphenyl)prop-2-enon-1
  参考文献：
  名称：

  Lewis or brønsted acid provoked rearrangements in ortho-(1,1-dimethylpropenyl)phenols

  摘要：

  Treatment of the o-(1,1-dimethylpropenyl)phenol, dihydrolicochalcone A, with a Bronsted acid affords two isomeric 2,2-dimethyl-4H-dihydropyrano[b]benzenes. The rearrangement probably involves a [3,5] charge-accelerated rearrangement. Attempts to provoke the same reaction in licochalcone A only afforded poorly defined degradation products. Treatment of dihydrolicochalcone A as well as licochalcone A with Lewis acids afforded 2,3,3-trimethyldihydro-furano[b] benzenes and 2,2,3-trimethyldihydrofurano[b]benzenes. Proper use of solvents and Lewis acid enables preferential formation of the kinetically favoured product or the thermodynamically more stable product. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00212-3

文献信息

• Lewis or brønsted acid provoked rearrangements in ortho-(1,1-dimethylpropenyl)phenols
  作者：Simon Feldbæk Nielsen、Carl Erik Olsen、Søren Brøgger Christensen

  DOI：10.1016/s0040-4020(97)00212-3

  日期：1997.4

  Treatment of the o-(1,1-dimethylpropenyl)phenol, dihydrolicochalcone A, with a Bronsted acid affords two isomeric 2,2-dimethyl-4H-dihydropyrano[b]benzenes. The rearrangement probably involves a [3,5] charge-accelerated rearrangement. Attempts to provoke the same reaction in licochalcone A only afforded poorly defined degradation products. Treatment of dihydrolicochalcone A as well as licochalcone A with Lewis acids afforded 2,3,3-trimethyldihydro-furano[b] benzenes and 2,2,3-trimethyldihydrofurano[b]benzenes. Proper use of solvents and Lewis acid enables preferential formation of the kinetically favoured product or the thermodynamically more stable product. (C) 1997 Elsevier Science Ltd.