2-(4-nitrophenyl)-1,2-dihydronaphtho[2,1-b]furan | 1437790-61-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(4-nitrophenyl)-1,2-dihydronaphtho[2,1-b]furan
• 英文别名: 2-(4-Nitrophenyl)-1,2-dihydrobenzo[e][1]benzofuran；2-(4-nitrophenyl)-1,2-dihydrobenzo[e][1]benzofuran
• CAS: 1437790-61-8
• 化学式: C₁₈H₁₃NO₃
• 分子量: 291.306
• InChiKey: WRDQTDCPJLGIHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(二甲基胺甲基)萘酚 、 N-(4-nitrobenzyl)pyridinium bromide 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以45%的产率得到2-(4-nitrophenyl)-1,2-dihydronaphtho[2,1-b]furan
  参考文献：
  名称：

  Reactions of o-Quinone Methides with Pyridinium Methylides: A Diastereoselective Synthesis of 1,2-Dihydronaphtho[2,1-b]furans and 2,3-Dihydrobenzofurans

  摘要：

  A simple, general route to the 1,2-dihydronaphtho[2,1-b]furans and 2,3-dihydrobenzofurans substituted at C-2 by an acyl or aryl group, starting from phenolic Mannich bases and pyridinium ylides, has been developed. The mechanism of the reaction is believed to involve the formation of the o-quinone methide intermediate, Michael-type addition of the ylide to the o-quinone methide, followed by intramolecular nucleophilic substitution.

  DOI：

  10.1021/jo400621r

文献信息

• Reactions of <i>o</i>-Quinone Methides with Pyridinium Methylides: A Diastereoselective Synthesis of 1,2-Dihydronaphtho[2,1-<i>b</i>]furans and 2,3-Dihydrobenzofurans
  作者：Vitaly A. Osyanin、Dmitry V. Osipov、Yuri N. Klimochkin

  DOI：10.1021/jo400621r

  日期：2013.6.7

  A simple, general route to the 1,2-dihydronaphtho[2,1-b]furans and 2,3-dihydrobenzofurans substituted at C-2 by an acyl or aryl group, starting from phenolic Mannich bases and pyridinium ylides, has been developed. The mechanism of the reaction is believed to involve the formation of the o-quinone methide intermediate, Michael-type addition of the ylide to the o-quinone methide, followed by intramolecular nucleophilic substitution.