1-adamantyl-5-nitro-2,3-dihydrobenzo[b]furan-2-ylmethanone | 1437790-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 1-adamantyl-5-nitro-2,3-dihydrobenzo[b]furan-2-ylmethanone
• 英文别名: 1-Adamantyl-(5-nitro-2,3-dihydro-1-benzofuran-2-yl)methanone；1-adamantyl-(5-nitro-2,3-dihydro-1-benzofuran-2-yl)methanone
• CAS: 1437790-72-1
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: RHLKPBVPPVROHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  72.1
• 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 三甲基镓 作用下， 以 乙醚 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 1-adamantyl-5-nitro-2,3-dihydrobenzo[b]furan-2-ylmethanone
  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.