6,8-dibromo-2-(trifluoromethyl)chromone | 497147-45-2

• 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: 6,8-dibromo-2-(trifluoromethyl)chromone
• 英文别名: 6,8-Dibromo-2-trifluoromethylchromone；6,8-dibromo-2-(trifluoromethyl)chromen-4-one
• CAS: 497147-45-2
• 化学式: C₁₀H₃Br₂F₃O₂
• 分子量: 371.936
• InChiKey: VBXHNSVCHYCFIF-UHFFFAOYSA-N

物化性质

• 熔点：
  115-116 °C
• 沸点：
  320.0±42.0 °C(Predicted)
• 密度：
  2.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,8-dibromo-2-(trifluoromethyl)chromone 在 硫酸 、 硝酸 作用下， 反应 0.17h， 以75%的产率得到6,8-dibromo-5-nitro-2-(trifluoromethyl)chromone
  参考文献：
  名称：

  摘要：

  The nitration of 6,8-dibromo-2-trifluoromethylchromone depends on the reaction conditions and affords 6,8-dibromo-5-nitro- or 3,6,8-tribromo-5-nitro-2-trifluoromethylchromones. The structures of these compounds were determined from the H-1 and C-13 NMR spectroscopic data.

  DOI：

  10.1023/a:1021385409506
• 作为产物：
  描述：

  3',5'-二溴-2'-羟基苯乙酮 在 盐酸 、 lithium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 6,8-dibromo-2-(trifluoromethyl)chromone
  参考文献：
  名称：

  摘要：

  The nitration of 6,8-dibromo-2-trifluoromethylchromone depends on the reaction conditions and affords 6,8-dibromo-5-nitro- or 3,6,8-tribromo-5-nitro-2-trifluoromethylchromones. The structures of these compounds were determined from the H-1 and C-13 NMR spectroscopic data.

  DOI：

  10.1023/a:1021385409506

文献信息

• Synthesis of 2-(trifluoromethyl)-1,2-dihydro-4H-thieno[2,3-c]chromen-4-ones and 2-(trifluoromethyl)-4H-thieno[2,3-c]chromen-4-ones from 2-trifluoromethylchromones and ethyl mercaptoacetate
  作者：Vyacheslav Ya Sosnovskikh、Boris I Usachev、Dmitri V Sevenard、Gerd-Volker Röschenthaler

  DOI：10.1016/s0040-4020(03)00329-6

  日期：2003.4

  mercaptoacetate in the presence of triethylamine results in the formation of 1,2-dihydrothieno[2,3-c]chromen-4-ones and diethyl 3,4-dithiadipate in high yields. Oxidation of the first compounds with nitrogen dioxide gave 1,2-dihydrothieno[2,3-c]chromen-3,4-diones which were converted into thieno[2,3-c]chromen-4-ones.

  在三乙胺的存在下，2-三氟甲基色酮与巯基乙酸乙酯的氧化还原反应可高产率地形成1,2-二氢噻吩并[2,3 - c ]铬-4-酮和3,4-二硫代二乙酯二乙酯。用二氧化氮氧化第一化合物，得到1,2-二氢噻吩并[2,3- c ] chromen-3,4-二酮，将其转化为噻吩并[2,3 - c ] chromen-4-ones。
• Synthesis of isomerically pure 3-(5-trifluoromethyl-1,2,3-triazol-4-yl)cinnamic acid derivatives via the reaction of 4-aryl-6-trifluoromethyl-2-pyrones with sodium azide
  作者：Sergey A. Usachev、Boris I. Usachev、Oleg S. Eltsov、Vyacheslav Y. Sosnovskikh

  DOI：10.1016/j.tet.2014.09.093

  日期：2014.11

  afforded the corresponding (Z)-3-(5-trifluoromethyl-1,2,3-triazol-4-yl)cinnamic acids in good yields. Similarly, 4-aryl-3-carbethoxy-6-trifluoromethyl-2-pyrones smoothly reacted with sodium azide in acetonitrile to produce (E)-2-ethoxycarbonyl-3-(5-trifluoromethyl-1,2,3-triazol-4-yl)cinnamic acids in high yields, whereas their reactions in ethanol, accompanied by a configurational change, gave the thermodynamically

  在DMSO中用叠氮化钠处理4-芳基-6-三氟甲基-2-吡喃酮，以良好的收率得到相应的（Z）-3-（5-三氟甲基-1，2，3-三唑-4-基）肉桂酸。类似地，4-芳基-3-碳乙氧基-6-三氟甲基-2-吡喃酮与叠氮化钠在乙腈中平稳反应，生成（E）-2-乙氧基羰基-3-（5-三氟甲基-1,2,3-三唑-4 -基）肉桂酸的收率高，而它们在乙醇中的反应伴随构型变化，使热力学上更稳定的（Z）-2-乙氧基羰基-3-（5-三氟甲基-1,2,3-三唑-4 -基）肉桂酸。
• One-pot synthesis of functionalized benzo[c]coumarins and their precursors via the reaction of 2-(polyfluoroalkyl)chromones with 4-alkyl-3-cyanocoumarins
  作者：Vyacheslav Ya. Sosnovskikh、Vladislav Yu. Korotaev、Igor B. Kutyashev、Alexey Yu. Barkov、Alexander V. Safrygin

  DOI：10.1039/c6ra12492e

  日期：——

  dichloromethane in the presence of triethylamine to give a wide variety of functionalized benzo[c]coumarin derivatives in good yields. This new annulation reaction presumably proceeds by a tandem intermolecular Michael addition and subsequent intramolecular condensation between an intermediate enolate anion and cyano group. In the case of 3-cyano-4-methylcoumarin and 2-(trifluoromethyl)chromones activated

  2-（多氟烷基）色酮与4-烷基-3-氰基香豆素在二氯甲烷中，在三乙胺的存在下反应，以高收率得到各种官能化的苯并[ c ]香豆素衍生物。这种新的环化反应大概是通过串联分子间迈克尔加成反应以及随后的中间烯醇式阴离子和氰基之间的分子内缩合而进行的。在3-氰基-4-甲基香豆素和2-（三氟甲基）色酮被两个吸电子取代基激活的情况下，分离出三个无环中间体，并提出了可能的反应机理。
• 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。
• A convenient synthesis of 4(5)-(2-hydroxyaroyl)-5(4)-trifluoromethyl-1,2,3-triazoles from 2-trifluoromethylchromones and chromen-4-imines
  作者：Vyacheslav Ya. Sosnovskikh、Boris I. Usachev

  DOI：10.1070/mc2002v012n02abeh001562

  日期：——

  The reactions of 2-trifluoromethylchromones and 2-trifluoromethyl-4H-chromen-4-inlines with sodium azide in the presence of acetic acid give the ketone and imine derivatives of 5(4)-trifluoromethyl-1,2,3-triazole in high yields.