5,7-dimethyl-6,8-dinitro-2-(1,1,2,2,3,3,4,4-octafluorobutyl)-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5,7-dimethyl-6,8-dinitro-2-(1,1,2,2,3,3,4,4-octafluorobutyl)-4H-chromen-4-one
• 英文别名: 5,7-dimethyl-6,8-dinitro-2-(1,1,2,2,3,3,4,4-octafluorobutyl)chromen-4-one
• 化学式: C₁₅H₈F₈N₂O₆
• mdl: MFCD02626244
• 分子量: 464.226
• InChiKey: PUYSEWGYYDLEKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2-(1-苯基亚乙基)丙二腈 、 5,7-dimethyl-6,8-dinitro-2-(1,1,2,2,3,3,4,4-octafluorobutyl)-4H-chromen-4-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以27%的产率得到3-amino-4-(2-hydroxy-4,6-dimethyl-3,5-dinitrobenzoyl)-5-(1,1,2,2,3,3,4,4-octafluorobutyl)-[1,1'-biphenyl]-2-carbonitrile
  参考文献：
  名称：

  来自 2-(多氟烷基)色酮的多官能化二苯甲酮、二氢氧杂蒽酮和间三联苯的一锅多米诺合成

  摘要：

  而由苯环中的吸电子取代基活化的 2-（多氟烷基）色酮与 2-（1-苯基亚烷基）丙二腈在二氯甲烷中的三乙胺存在下反应生成多种多官能化二苯甲酮和二氢氧杂蒽酮，它们与乙基 α -氰基-β-甲基肉桂酸酯在相同条件下采取完全不同的过程，主要产生间三联苯衍生物。丙二腈的亚芳基衍生物与氰基乙酸乙酯的亚芳基衍生物之间的行为差​​异是显着的。

  DOI：

  10.1002/ejoc.201403585
• 作为产物：
  描述：

  1-(2-羟基-4,6-二甲基苯基)乙酮 在 盐酸 、 硫酸 、 硝酸 、 lithium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 5,7-dimethyl-6,8-dinitro-2-(1,1,2,2,3,3,4,4-octafluorobutyl)-4H-chromen-4-one
  参考文献：
  名称：

  摘要：

  The nitration of 5,7-dimethyl-2-polyhaloalkylchromones affords either 5,7-dimethyl-6-nitro- or 5,7-dimethyl-6,8-dinitro-2-polyhaloalkylchromones, depending on the reaction conditions. Signals in the H-1 and C-13 NMR spectra of the sterically hindered chromones were completely assigned using the 2D NOESY, HETCOR, and COLOC spectra. The influence of nonplanar nitro groups on chemical shifts of carbon atoms was studied. Some spectral peculiarities of the peri-methyl group were revealed. The H-1-H-1 and C-13-H-1 spin-spin coupling constants, including the extreme six-bond long-range coupling between the protons of the Me(5) group and H(8), were determined.

  DOI：

  10.1023/a:1021340132279

文献信息

• ——
  作者：V. Ya. Sosnovskikh、B. I. Usachev、M. I. Kodess

  DOI：10.1023/a:1021340132279

  日期：——

  The nitration of 5,7-dimethyl-2-polyhaloalkylchromones affords either 5,7-dimethyl-6-nitro- or 5,7-dimethyl-6,8-dinitro-2-polyhaloalkylchromones, depending on the reaction conditions. Signals in the H-1 and C-13 NMR spectra of the sterically hindered chromones were completely assigned using the 2D NOESY, HETCOR, and COLOC spectra. The influence of nonplanar nitro groups on chemical shifts of carbon atoms was studied. Some spectral peculiarities of the peri-methyl group were revealed. The H-1-H-1 and C-13-H-1 spin-spin coupling constants, including the extreme six-bond long-range coupling between the protons of the Me(5) group and H(8), were determined.
• One-Pot Domino Synthesis of Polyfunctionalized Benzophenones, Dihydroxanthones, and<i>m</i>-Terphenyls from 2-(Polyfluoroalkyl)chromones
  作者：Vyacheslav Ya. Sosnovskikh、Vladislav Yu. Korotaev、Alexey Yu. Barkov、Igor B. Kutyashev、Alexander V. Safrygin

  DOI：10.1002/ejoc.201403585

  日期：2015.3

  Whereas 2-(polyfluoroalkyl)chromones activated by electron-withdrawing substituents in the benzene ring react with 2-(1-phenylalkylidene)malononitriles in the presence of triethylamine in dichloromethane to produce a wide range of polyfunctionalized benzophenones and dihydroxanthones, their reactions with ethyl α-cyano-β-methylcinnamate under the same conditions took an entirely different course and

  而由苯环中的吸电子取代基活化的 2-（多氟烷基）色酮与 2-（1-苯基亚烷基）丙二腈在二氯甲烷中的三乙胺存在下反应生成多种多官能化二苯甲酮和二氢氧杂蒽酮，它们与乙基 α -氰基-β-甲基肉桂酸酯在相同条件下采取完全不同的过程，主要产生间三联苯衍生物。丙二腈的亚芳基衍生物与氰基乙酸乙酯的亚芳基衍生物之间的行为差​​异是显着的。