2'-hydroxy-4'-methoxyphenyl-4-nitrostyrylketone | 111599-77-0

• 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: 2'-hydroxy-4'-methoxyphenyl-4-nitrostyrylketone
• 英文别名: (E)-2'-hydroxy-4'-methoxy-4-nitrochalcone；2'-hydroxy-4'-methoxy-4-nitrochalcone；2'-hydroxy-4'-methoxy-4-nitro-trans-chalcone；2'-Hydroxy-4'-methoxy-4-nitro-trans-chalkon；(E)-1-(2-hydroxy-4-methoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one
• CAS: 111599-77-0
• 化学式: C₁₆H₁₃NO₅
• 分子量: 299.283
• InChiKey: JIEARLLHXIVDHC-RUDMXATFSA-N

物化性质

• 沸点：
  502.3±50.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：

  2'-hydroxy-4'-methoxyphenyl-4-nitrostyrylketone 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以68%的产率得到4-amino-2'-hydroxy-4'-methoxychalcone
  参考文献：
  名称：

  Reductive Coupling Reactions of 2-Nitrochalcones and their β-Hydroxy-analogues: New Syntheses of 2-Arylquinoline and 2-Aryl-4-hydroxyquinoline Derivatives

  摘要：

  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.

  DOI：

  10.1007/s00706-007-0647-9
• 作为产物：
  描述：

  丹皮酚 、 对硝基苯甲醛 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到2'-hydroxy-4'-methoxyphenyl-4-nitrostyrylketone
  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

• Regioselective synthesis of 2-arylidene coumaran-3-ones by dye-sensitized photooxygenation of 2-hydroxyphenyl-styrylketones in the presence of sodium dodecyl sulphate
  作者：H. Mohindra Chawla、S. Kumar Sharma

  DOI：10.1016/s0040-4020(01)81970-0

  日期：1990.1

  2'-Hydroxyphenylstyrylketones when subjected to dye- sensitized photooxygenation in the presence of sodium dodecylsulphate (8× x 10-3M) in methanol, yielded the corresponding oxidatively cyclized products, i.e., 2-aryl idenecoumaran 3-ones and 2-phenyl-3-hydroxy-4H-benzopyran-4- ones. It has been observed that the nature of the substituents on the styryl moiety plays an important role in determining

  2'-羟基苯基苯乙烯基酮在甲醇中的十二烷基硫酸钠（8×x 10 -3 M）存在下进行染料敏化的光氧合时，会生成相应的氧化环化产物，即2-芳基亚烷基香豆素3-ones和2-phenyl- 3-羟基-4H-苯并吡喃-4-基。已经观察到，苯乙烯基部分上的取代基的性质在确定2-亚芳基香豆素-3-酮相对于2-芳基-3-羟基-4H-苯并吡喃-4-酮的优势中起重要作用。已经观察到该反应受阴离子胶束产生的疏水环境的影响。描述了反应的合理机制。
• 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.
• Chawla, H. Mohindra; Sharma, S. Kumar, Heterocycles, 1987, vol. 26, # 6, p. 1527 - 1534
  作者：Chawla, H. Mohindra、Sharma, S. Kumar

  DOI：——

  日期：——
• Matsuoka, Nippon Kagaku Zasshi, 1959, vol. 80, p. 64
  作者：Matsuoka

  DOI：——

  日期：——
• CHAWLA, H. MOHINDRA;SHARMA, S. KUMAR, TETRAHEDRON, 46,(1990) N, C. 1611-1624
  作者：CHAWLA, H. MOHINDRA、SHARMA, S. KUMAR

  DOI：——

  日期：——