3-chloro-2-(trifluoromethyl)chromone | 125647-92-9

• 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: 3-chloro-2-(trifluoromethyl)chromone
• 英文别名: 3-chloro-2-(trifluoromethyl)chromen-4-one
• CAS: 125647-92-9
• 化学式: C₁₀H₄ClF₃O₂
• 分子量: 248.589
• InChiKey: JUHJUJQOMPOMRF-UHFFFAOYSA-N

物化性质

• 沸点：
  218.2±40.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 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：

  3-chloro-2-(trifluoromethyl)chromone 在 硫酸 、 硝酸 作用下， 以 水 为溶剂， 反应 1.5h， 生成 萘莫胺
  参考文献：
  名称：

  摘要：

  3-Chloro-2-polyfluoroalkyl- and 3-chloro-6-nitro-2-polyfluoroalkylchromones were synthesized. These compounds react with N(2)H(4)(.)2HCl on boiling in ethanol to form 4-chloro-3(5)-(2-hydroxyaryl)-5(3)-polyfluoroalkylpyrazoles.

  DOI：

  10.1023/a:1023408327104
• 作为产物：
  描述：

  2-三氟甲基-4H-色烯-4-酮 在 氯 作用下， 以 四氯化碳 、 乙醇 为溶剂， 反应 0.75h， 生成 3-chloro-2-(trifluoromethyl)chromone
  参考文献：
  名称：

  摘要：

  3-Chloro-2-polyfluoroalkyl- and 3-chloro-6-nitro-2-polyfluoroalkylchromones were synthesized. These compounds react with N(2)H(4)(.)2HCl on boiling in ethanol to form 4-chloro-3(5)-(2-hydroxyaryl)-5(3)-polyfluoroalkylpyrazoles.

  DOI：

  10.1023/a:1023408327104

文献信息

• Synthesis and reactivity of 2-polyfluoroalkylchromene-4(4H)-thiones
  作者：B. I. Usachev、M. A. Shafeev、V. Ya. Sosnovskikh

  DOI：10.1007/s11172-005-0115-9

  日期：2004.10

  2-Polyfluoroalkylchromene-4(4H)-thiones, synthesized from 2-polyfluoroalkylchromones and P2S5, react with aniline, phenylhydrazines, and hydroxylamine at the C(4) atom and afford corresponding anils, phenylhydrazones, and oximes of chromones. On heating in alcohol in the presence of concentrated HCl, chromone phenylhydrazones and oximes undergo ring closure to form 3-(2-hydroxyaryl)-1-phenyl-5-polyfluoroalkylpyrazoles and 5-hydroxy-3-(2-hydroxyaryl)-5-polyfluoroalkyl-Δ2-isoxazolines.

  由 2-多氟烷基铬和 P2S5 合成的 2-多氟烷基铬-4(4H)-亚硫酰，与苯胺、苯肼和羟胺在 C(4)原子上发生反应，生成相应的苯胺、苯肼和铬酮的肟。在有浓盐酸存在的酒精中加热时，铬酮苯肼和肟会发生闭环反应，生成 3-（2-羟基芳基）-1-苯基-5-聚氟烷基吡唑和 5-羟基-3-（2-羟基芳基）-5-聚氟烷基-Δ2-异恶唑。
• Regioselective Nucleophilic 1,4-Trifluoromethylation of 2-Polyfluoroalkylchromones with (Trifluoromethyl)trimethylsilane. Synthesis of Fluorinated Analogs of Natural 2,2-Dimethylchroman-4-ones and 2,2-Dimethylchromenes
  作者：Vyacheslav Ya. Sosnovskikh、Boris I. Usachev、Dmitri V. Sevenard、Gerd-Volker Röschenthaler

  DOI：10.1021/jo034591y

  日期：2003.10.1

  Reactions of 2-polyfluoroalkylchromones with (perfluoroalkyl)trimethylsilanes proceed as a 1,4-nucleophilic perfluoroalkylation to give 2,2-bis(polyfluoroalkyl)chroman-4-ones with high regioselectivity and good yields after acid hydrolysis. Oxidation of 6-methyl-2,2-bis(trifluoromethyl)chroman-4-one with a mixture of K2S2O8 and CuSO4 in aqueous acetonitrile leads to fluorinated analogues of natural lactarochromal and the corresponding acid. Reduction of substituted 2,2-bis(trifluoromethyl)chroman-4-one with sodium borohydride in methanol and subsequent dehydration of chromanols in refluxing xylene in the presence of p-toluene sulfonic acid gives 2,2-bis(trifluoromethyl)chromenes, which are fluorinated analogues of natural precocenes.
• ——
  作者：V. Ya. Sosnovskikh、B. I. Usachev

  DOI：10.1023/a:1009544630187

  日期：——

  Electrophilic nitration of 2-trifluoromethylchromone and its 6- and 7-methoxy derivatives affords 6-, 5-, and 8-nitro derivatives, respectively, while 5,7-dimethyl-2-trifluoromethylchromone yields a 6,8-dinitro derivative. Radical chlorination results in 3-chloro derivatives.
• ——
  作者：V. Ya. Sosnovskikh、B. I. Usachev、A. Yu. Sizov

  DOI：10.1023/a:1024425131436

  日期：——

  The reactions of 3-chloro-2-(polyfluoroalkyl)chrom ones with hydroxylamine in the presence of sodium acetate proceed with ring contraction to form benzofuran derivatives.
• ——
  作者：V. Ya. Sosnovskikh

  DOI：10.1023/a:1023408327104

  日期：——

  3-Chloro-2-polyfluoroalkyl- and 3-chloro-6-nitro-2-polyfluoroalkylchromones were synthesized. These compounds react with N(2)H(4)(.)2HCl on boiling in ethanol to form 4-chloro-3(5)-(2-hydroxyaryl)-5(3)-polyfluoroalkylpyrazoles.