2-methyl-6-[2-(methylamino)-3-nitro-4H-4-chromenyl]phenol | 1338924-94-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 2-methyl-6-[2-(methylamino)-3-nitro-4H-4-chromenyl]phenol
• 英文别名: 2-methyl-6-[2-(methylamino)-3-nitro-4H-chromen-4-yl]phenol
• CAS: 1338924-94-9
• 化学式: C₁₇H₁₆N₂O₄
• 分子量: 312.325
• InChiKey: WKULVCQRYJEPNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  87.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-methyl-4-(methylthio)-3-nitro-4H-chromen-2-amine 、 邻甲酚 以 乙醇 为溶剂， 反应 16.0h， 以88%的产率得到2-methyl-6-[2-(methylamino)-3-nitro-4H-4-chromenyl]phenol
  参考文献：
  名称：

  Synthesis of 4-(2-hydroxyaryl)-3-nitro-4H-chromenes

  摘要：

  A combinatorial library of 4-(2-hydroxyaryl)-3-nitro-4H-chromenes was synthesized in high yield by C4-SMe substitution in N-alkyl/phenyl 4-(methylthio)-3-nitro-4H-chromen-2-amines with a variety of phenols. The reaction always provided C2 substitution in the phenol ring, dictated by hydrogen bond interactions between the phenolic hydroxyl group and the nitro group in 3-nitro-4H-chromenes. Reduction of the nitro group with concomitant hydrolysis of the enamine in 4-(2-hydroxyaryl)-3-nitro-4H-chromenes with Zn, Ac(2)O in AcOH furnished hybrid amino-acid lactone incorporating ortho-tyrosine and phenyl alanine moieties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.045

文献信息

• Synthesis of 4-(2-hydroxyaryl)-3-nitro-4H-chromenes
  作者：H. Surya Prakash Rao、K. Geetha、M. Kamalraj

  DOI：10.1016/j.tet.2011.08.045

  日期：2011.10

  A combinatorial library of 4-(2-hydroxyaryl)-3-nitro-4H-chromenes was synthesized in high yield by C4-SMe substitution in N-alkyl/phenyl 4-(methylthio)-3-nitro-4H-chromen-2-amines with a variety of phenols. The reaction always provided C2 substitution in the phenol ring, dictated by hydrogen bond interactions between the phenolic hydroxyl group and the nitro group in 3-nitro-4H-chromenes. Reduction of the nitro group with concomitant hydrolysis of the enamine in 4-(2-hydroxyaryl)-3-nitro-4H-chromenes with Zn, Ac(2)O in AcOH furnished hybrid amino-acid lactone incorporating ortho-tyrosine and phenyl alanine moieties. (C) 2011 Elsevier Ltd. All rights reserved.