1-adamantyl[1-(3-nitrophenyl)naphtho[2,1-b]furan-2-yl]methanone | 1437790-66-3

• 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: 1-adamantyl[1-(3-nitrophenyl)naphtho[2,1-b]furan-2-yl]methanone
• 英文别名: 1-Adamantyl-[1-(3-nitrophenyl)benzo[e][1]benzofuran-2-yl]methanone；1-adamantyl-[1-(3-nitrophenyl)benzo[e][1]benzofuran-2-yl]methanone
• CAS: 1437790-66-3
• 化学式: C₂₉H₂₅NO₄
• 分子量: 451.522
• InChiKey: QUGVONSFBCTEHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-金刚烷基溴甲酮 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三甲基镓 作用下， 以 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 11.0h， 生成 1-adamantyl[1-(3-nitrophenyl)naphtho[2,1-b]furan-2-yl]methanone
  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.