3-Phenyl-1-(4-nitro-phenyl)-4-nitro-butan-1-on | 13620-59-2

• 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: 3-Phenyl-1-(4-nitro-phenyl)-4-nitro-butan-1-on
• 英文别名: 4-nitro-1-(4-nitrophenyl)-3-phenylbutan-1-one
• CAS: 13620-59-2
• 化学式: C₁₆H₁₄N₂O₅
• 分子量: 314.298
• InChiKey: GJSCOQOPLPKQGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  103.35
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  硝基甲烷 、 (2E)-1-(4-硝基苯基)-3-苯基-2-丙烯-1-酮 在 aluminum oxide 、 potassium carbonate 作用下， 反应 0.08h， 以72%的产率得到3-Phenyl-1-(4-nitro-phenyl)-4-nitro-butan-1-on
  参考文献：
  名称：

  1,3-二芳基-4-硝基-1-丁酮在无溶剂微波促进下硝基甲烷与查耳酮的迈克尔加成新合成

  摘要：

  通过无溶剂微波辐射促进硝基甲烷与查耳酮的迈克尔加成反应，以良好的收率得到 1,3-二芳基-4-硝基-1-丁酮。产物通过IR、1H NMR和元素分析表征。

  DOI：

  10.3184/030823407x266199

文献信息

• Sequential Michael addition/retro-Claisen condensation of 1,3-diarylpropan-1,3-diones with nitrostyrenes: one-step synthesis of 4-nitro-1,3-diarylbutan-1-ones
  作者：ZHENG LI、HAO LU、ZHENRONG LIU、XIAOLONG MA

  DOI：10.1007/s12039-019-1603-z

  日期：2019.4

  Abstract The sequential Michael addition/retro-Claisen condensation of 1,3-diarylpropan-1,3-diones with nitrostyrenes is described. 4-Nitro-1,3-diarylbutan-1-ones were efficiently synthesized in good to high yield under mild, transition-metal-free condition. This one-step method involving sequential carbon-carbon bond formation and cleavage provides a good alternative to the synthesis of various \(\gamma

  摘要 描述了1，3-二芳基丙烷-1，3-二酮与硝基苯乙烯的顺序迈克尔加成/复古-克莱森缩合。在温和，无过渡金属的条件下，以高至高收率高效合成了4-Nitro-1,3-diarylbutan-1-one。涉及顺序碳-碳键形成和裂解的这一一步方法为合成各种（γ）-硝基酮提供了一个很好的选择。 图形概要描述了1，3-二芳基丙烷-1，3-二酮与硝基苯乙烯的顺序迈克尔加成/复古-克莱森缩合。在温和且无过渡金属的条件下，以高至高收率高效合成了4-Nitro-1,3-diarylbutan-1-one。
• MICHAEL ADDITIONS CATALYZED BY NICKEL(II) OR COBALT(II)ACETATE-2,2′-BIPYRIDINE COMPLEXES
  作者：Kazuo Irie、Ken-ichi Miyazu、Ken-ichi Watanabe

  DOI：10.1246/cl.1980.353

  日期：1980.3.5

  In the presence of nickel(II) or cobalt(II)acetate-2,2′-bipyridine complexes, α,β-unsaturated ketones, methyl acrylate, and acrylonitrile were found to react with nitromethane, malononitrile, and aniline at room temperature under neutral condition to afford addition products in good yields.

  在镍 (II) 或乙酸钴 (II)-2,2'-联吡啶配合物的存在下，发现 α,β-不饱和酮、丙烯酸甲酯和丙烯腈在室温下与硝基甲烷、丙二腈和苯胺反应中性条件以提供高产率的附加产品。
• Michael Additions Catalyzed by Metal(II) Complexes
  作者：Ken-ichi Watanabe、Ken-ichi Miyazu、Kazuo Irie

  DOI：10.1246/bcsj.55.3212

  日期：1982.10

  Michael-addition reactions have been found to proceed in the presence of the Ni(OAc)2 or Co(OAc)2-2,2′-bipyridine complex in DMF under neutral conditions at room temperature without any by-product. The reactions of chalcone and its derivatives with nitromethane generally gave good results. The effects of metal(II) ions, ligands, counter ions, and solvents on the catalysis were examined, and the features of the

  已发现迈克尔加成反应在 NMF 中的 Ni(OAc)2 或 Co(OAc)2-2,2'-联吡啶络合物存在下在中性条件下在室温下进行，没有任何副产物。查耳酮及其衍生物与硝基甲烷的反应通常产生良好的结果。研究了金属（II）离子、配体、反离子和溶剂对催化的影响，研究了金属配合物催化迈克尔反应的特征，并对催化机理进行了一些考虑。
• Enantioselective addition of aryl ketones and acetone to nitroalkenes organocatalyzed by carbamate-monoprotected cyclohexa-1,2-diamines
  作者：Jesús Flores-Ferrándiz、Alexander Stiven、Lia Sotorríos、Enrique Gómez-Bengoa、Rafael Chinchilla

  DOI：10.1016/j.tetasy.2015.07.011

  日期：2015.9

  Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as chiral organocatalysts for the addition of aryl ketones and acetone to nitroalkenes to give enantioenriched beta-substituted gamma-nitroketones. The reaction was performed in the presence of 3,4-dimethoxybenzoic acid as an additive, in chloroform as the solvent at room temperature, achieving enantioselectivities up to 96%. Theoretical calculations are used to justify the observed sense of the stereoinduction. (C) 2015 Elsevier Ltd. All rights reserved.
• Seter (Strumza),J., Israel Journal of Chemistry, 1966, vol. 4, p. 1 - 5
  作者：Seter (Strumza),J.

  DOI：——

  日期：——