(E)-2'-hydroxy-4'-methoxy-2-nitrochalcone | 52790-86-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-2'-hydroxy-4'-methoxy-2-nitrochalcone
• 英文别名: 2'-hydroxy-4'-methoxy-2-nitrochalcone；(E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one
• CAS: 52790-86-0
• 化学式: C₁₆H₁₃NO₅
• 分子量: 299.283
• InChiKey: QLVJPXFHAISYKS-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-2'-hydroxy-4'-methoxy-2-nitrochalcone 在 盐酸 、 tin(ll) chloride 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以66%的产率得到2-(2-hydroxy-4-methoxyphenyl)quinoline
  参考文献：
  名称：

  一锅法合成2-（2-羟基芳基）喹啉：2'-羟基-2-硝基查耳酮的还原偶联反应

  摘要：

  通过在酸性介质（HCl / AcOH）中由氯化亚锡诱导的2'-羟基-2-硝基查耳酮的分子内还原偶联反应，已经开发出了一锅合成新型2-（2-羟基芳基）喹啉的方法。在某些情况下，可以用甲酸铵/钯-碳在甲醇中进行这些转化。

  DOI：

  10.1016/s0040-4039(03)01374-1
• 作为产物：
  描述：

  丹皮酚 、 邻硝基苯甲醛 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以40%的产率得到(E)-2'-hydroxy-4'-methoxy-2-nitrochalcone
  参考文献：
  名称：

  Synthesis, experimental and theoretical NMR study of 2′-hydroxychalcones bearing a nitro substituent on their B ring

  摘要：

  The synthesis of several 2'-hydroxynitrochalcones has been accomplished by an aldol reaction of equimolar amounts of the appropriate 2'-hydroxyacetophenones with nitrobenzaldehydes in alkaline medium. The reaction of 2'-hydroxyacetophenones bearing a 6'-methoxy with 2- or 4-nitrobenzaldehydes gave the expected 2'-hydroxynitrochalcones and also 4-methoxynitroaurones, being the latter ones the unique reaction products when using 2 molar equiv of nitrobenzaldehydes. The reaction mechanisms for the formation of both products are discussed. The C-13 NMR chemical shifts have been discussed first by means of an empirical additive model and then by comparison with GIAO/B3LYP calculated absolute shieldings. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.005

文献信息

• Efficient Synthesis of Nitroflavones by Cyclodehydrogenation of 2′-Hydroxychalcones and by the Baker-Venkataraman Method
  作者：Ana I. R. N. A. Barros、Artur M. S. Silva

  DOI：10.1007/s00706-006-0550-9

  日期：2006.12

  Several nitroflavone derivatives were synthesized by cyclodehydrogenation of 2'-hydroxychalcones and by the Baker-Venkataraman approach, starting from 2'-hydroxyacetophenones and benzoic acid derivatives. Nitroflavones synthesised by the first synthetic approach were obtained in better global yields than those obtained by the later method. The structures of all new compounds were elucidated by microanalyses, 1D and 2D NMR, IR, and mass spectroscopic measurements.
• Reductive Coupling Reactions of 2-Nitrochalcones and their β-Hydroxy-analogues: New Syntheses of 2-Arylquinoline and 2-Aryl-4-hydroxyquinoline Derivatives
  作者：Ana I. R. N. A. Barros、André F. R. Dias、Artur M. S. Silva

  DOI：10.1007/s00706-007-0647-9

  日期：2007.6

  A one-pot synthesis of novel 2-arylquinolines and 2-aryl-4-hydroxyquinolines was developed from the intramolecular reductive coupling reactions of 2-nitrochalcones and 3-hydroxy-1-phenyl-3-(2-nitrophenyl)-2-propen-1-ones. Depending on the reduction method and on the presence of electron donating substituents on the A ring of 2-nitrochalcones one can modulate the formation of 2-arylquinolines, their N-oxides, and of 2-aminochalcones. The reduction of 3-hydroxy-1-(2-hydroxyphenyl)-3-(2-nitrophenyl)-2-propen-1-ones with stannous chloride in hydrochloric acid gave 2 '-aminoflavones and with ammonium formate and Pd/C yielded 2-(2-hydroxyaryl)-4-hydroxyquinolines.
• One-pot synthesis of 2-(2-hydroxyaryl)quinolines: reductive coupling reactions of 2′-hydroxy-2-nitrochalcones
  作者：Ana I.R.N.A Barros、Artur M.S Silva

  DOI：10.1016/s0040-4039(03)01374-1

  日期：2003.7

  A one-pot synthesis of novel 2-(2-hydroxyaryl)quinolines have been developed from the intramolecular reductive coupling reactions of 2′-hydroxy-2-nitrochalcones, induced by stannous chloride in acidic medium (HCl/AcOH). In some cases these transformations can be performed with ammonium formate/Pd–C in methanol.

  通过在酸性介质（HCl / AcOH）中由氯化亚锡诱导的2'-羟基-2-硝基查耳酮的分子内还原偶联反应，已经开发出了一锅合成新型2-（2-羟基芳基）喹啉的方法。在某些情况下，可以用甲酸铵/钯-碳在甲醇中进行这些转化。
• Synthesis, experimental and theoretical NMR study of 2′-hydroxychalcones bearing a nitro substituent on their B ring
  作者：Ana I.R.N.A. Barros、Artur M.S. Silva、Ibon Alkorta、José Elguero

  DOI：10.1016/j.tet.2004.06.005

  日期：2004.7

  The synthesis of several 2'-hydroxynitrochalcones has been accomplished by an aldol reaction of equimolar amounts of the appropriate 2'-hydroxyacetophenones with nitrobenzaldehydes in alkaline medium. The reaction of 2'-hydroxyacetophenones bearing a 6'-methoxy with 2- or 4-nitrobenzaldehydes gave the expected 2'-hydroxynitrochalcones and also 4-methoxynitroaurones, being the latter ones the unique reaction products when using 2 molar equiv of nitrobenzaldehydes. The reaction mechanisms for the formation of both products are discussed. The C-13 NMR chemical shifts have been discussed first by means of an empirical additive model and then by comparison with GIAO/B3LYP calculated absolute shieldings. (C) 2004 Elsevier Ltd. All rights reserved.