1-(5-acetyl-2-hydroxyphenyl)-N,N,N-trimethylmethanaminium iodide | 1437790-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-acetyl-2-hydroxyphenyl)-N,N,N-trimethylmethanaminium iodide
• CAS: 1437790-78-7
• 化学式: C₁₂H₁₈NO₂*I
• 分子量: 335.185
• InChiKey: UPWODWCEOVRWSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.19
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(5-acetyl-2-hydroxyphenyl)-N,N,N-trimethylmethanaminium iodide 、 N-氯化乙酮吡啶 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以69%的产率得到2,5-diacetyl-2,3-dihydro-1-benzofuran
  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

• Potassium Trinitromethanide as a 1,1-Ambiphilic Synthon Equivalent: Access to 2-Nitroarenofurans
  作者：Vitaly A. Osyanin、Dmitry V. Osipov、Maxim R. Demidov、Yuri N. Klimochkin

  DOI：10.1021/jo402543s

  日期：2014.2.7

  The first example of the use of potassium trinitromethanide as a 1,1-ambiphilic synthon equivalent for the construction of a benzofuran moiety mediated by triethylamine has been developed. The method tolerates a variety of functional groups on the starting quaternary ammonium salt and has been successfully extended to polysubstituted benzofurans. Formation of an o-quinone methide intermediate is postulated as a key to the mechanism of this cascade process.