2-(2'-furylmethyl)amino-4-nitrophenol | 890657-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2'-furylmethyl)amino-4-nitrophenol
• 英文别名: 2-(Furan-2-ylmethylamino)-4-nitrophenol
• CAS: 890657-56-4
• 化学式: C₁₁H₁₀N₂O₄
• 分子量: 234.211
• InChiKey: AWGCGWABSWLTGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  91.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2'-furylmethyl)amino-4-nitrophenol 、 2-溴丙酸乙酯 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以74%的产率得到3,4-dihydro-4-(2'-furylmethyl)-2-methyl-6-nitro-3-oxo-2H-1,4-benzoxazine
  参考文献：
  名称：

  One-pot regioselective annulation toward 3,4-dihydro-3-oxo-2H-1,4-benzoxazine scaffolds under controlled microwave heating

  摘要：

  An efficient and general synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazines under controlled microwave heating has been established. It consists of a microwave-assisted reductive N-arylmethylation of substituted 2-aminophenols with aromatic aldehydes followed by a one-pot base-mediated regioselective O-alkylation of the N-arylmethyl-2-aminophenois with 2-bromoalkanoates to give the acyclic intermediates, which cyclize spontaneously to furnish the benzoxazine scaffolds in good to excellent yields. It was found that microwave heating over 180 degrees C was necessary for ring closure of the acyclic intermediates possessing an electron-withdrawing group. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.059
• 作为产物：
  描述：

  糠醛 、 2-氨基-4-硝基苯酚 在 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到2-(2'-furylmethyl)amino-4-nitrophenol
  参考文献：
  名称：

  One-pot regioselective annulation toward 3,4-dihydro-3-oxo-2H-1,4-benzoxazine scaffolds under controlled microwave heating

  摘要：

  An efficient and general synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazines under controlled microwave heating has been established. It consists of a microwave-assisted reductive N-arylmethylation of substituted 2-aminophenols with aromatic aldehydes followed by a one-pot base-mediated regioselective O-alkylation of the N-arylmethyl-2-aminophenois with 2-bromoalkanoates to give the acyclic intermediates, which cyclize spontaneously to furnish the benzoxazine scaffolds in good to excellent yields. It was found that microwave heating over 180 degrees C was necessary for ring closure of the acyclic intermediates possessing an electron-withdrawing group. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.059

文献信息

• One-pot regioselective annulation toward 3,4-dihydro-3-oxo-2H-1,4-benzoxazine scaffolds under controlled microwave heating
  作者：Gaofeng Feng、Jinlong Wu、Wei-Min Dai

  DOI：10.1016/j.tet.2005.12.059

  日期：2006.5

  An efficient and general synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazines under controlled microwave heating has been established. It consists of a microwave-assisted reductive N-arylmethylation of substituted 2-aminophenols with aromatic aldehydes followed by a one-pot base-mediated regioselective O-alkylation of the N-arylmethyl-2-aminophenois with 2-bromoalkanoates to give the acyclic intermediates, which cyclize spontaneously to furnish the benzoxazine scaffolds in good to excellent yields. It was found that microwave heating over 180 degrees C was necessary for ring closure of the acyclic intermediates possessing an electron-withdrawing group. (c) 2006 Elsevier Ltd. All rights reserved.