7-(trifluoromethyl)norkhellin | 76301-24-1

• 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: 7-(trifluoromethyl)norkhellin
• 英文别名: 4,9-dimethoxy-7-(trifluoromethyl)-5H-furo[3,2-g]chromen-5-one；4,9-dimethoxy-7-(trifluoromethyl)furo[3,2-g]chromen-5-one
• CAS: 76301-24-1
• 化学式: C₁₄H₉F₃O₅
• 分子量: 314.218
• InChiKey: NSYPJSPCYBZGJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-(trifluoromethyl)norkhellin 在 盐酸 、 sodium tetrahydroborate 、 四甲基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.25h， 生成 4,9-dimethoxy-7,7-bis(trifluoromethyl)-6,7-dihydro-5H-furo[3,2-g]chroman-5-ol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo034591y
• 作为产物：
  描述：

  凯林酮 在 盐酸 、 lithium hydride 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 0.08h， 生成 7-(trifluoromethyl)norkhellin
  参考文献：
  名称：

  7-Polyfluoroalkylnorkhellins: synthesis and reactions with alkyl mercaptoacetates

  摘要：

  New R-F-containing benzofuran derivatives of 2-oxa-7-thiabicyclo[3.2.1]octane and dihydrothienopsoralens were synthesized from 7-polyfluoroalkylnorkhellins and alkyl mercaptoacetates. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00252-7

文献信息

• Synthesis of 3-alkylamino-3-(2-hydroxyaryl)-1-polyfluoroalkylprop-2-en-1-ones and 2-polyfluoroalkyl-4H-chromen-4-imines
  作者：V. Ya. Sosnovskikh、B. I. Usachev

  DOI：10.1023/b:rucb.0000030815.40767.a1

  日期：2004.2

  Condensation of Schiff"s bases (prepared from 2-hydroxy- or 2-hydroxy-5-methylacetophenones and primary amines) with ethyl polyfluoroalkanoates in the presence of LiH in THF affords 3-alkylamino-3-(2-hydroxyaryl)-1-polyfluoroalkylprop-2-en-1-ones, which undergo cyclization in acidic media into 2-polyfluoroalkyl-4H-chromen-4-iminium salts. When neutralized with aqueous ammonia, the latter give 2-po

  席夫碱（由 2-羟基-或 2-羟基-5-甲基苯乙酮和伯胺制备）与多氟链烷酸乙酯在 THF 中在 LiH 存在下缩合得到 3-烷基氨基-3-(2-羟基芳基)-1-多氟烷基丙-2-烯-1-酮，在酸性介质中环化成2-多氟烷基-4H-chromen-4-亚胺盐。当用氨水中和时，后者得到2-多氟烷基-4H-chromen-4-亚胺高产。
• Synthesis and some properties of 2-(polyfluoroalkyl)chroman-4-ols and 2-(polyfluoroalkyl)chroman-4-ones
  作者：V. Ya. Sosnovskikh、R. A. Irgashev、B. I. Usachev

  DOI：10.1007/s11172-009-0345-3

  日期：2009.12

  Reduction of 2-(polyfluoroalkyl)chromones by sodium borohydride in methanol gives cis-2-(polyfluoroalkyl)chroman-4-ols in high yields, which are easily oxidized by chromic acid to 2-(polyfluoroalkyl)chroman-4-ones. The latter are of interest as the starting materials for the preparation of novel RF-containing chromane derivatives.

  用硼氢化钠在甲醇中还原 2-（多氟烷基）色满酮，以高产率得到顺式-2-（多氟烷基）色满-4-醇，它很容易被铬酸氧化为 2-（多氟烷基）色满-4-酮。后者作为制备新型含 RF 的色满衍生物的起始材料很受关注。
• GAMMILL, R. B.
  作者：GAMMILL, R. B.

  DOI：——

  日期：——
• Reactions of 7-polyfluoroalkylnorkhellins with alkyl mercaptoacetates: a simple synthesis of dihydrothienopsoralens and benzofuran derivatives of 2-oxa-7-thiabicyclo[3.2.1]octane
  作者：Vyacheslav Ya Sosnovskikh、Boris I Usachev

  DOI：10.1016/s0040-4039(01)00948-0

  日期：2001.7

  New fluoro-containing derivatives of khellin were synthesized from 7-polyfluoroalkylnorkhellins and alkyl mercaptoacetates. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.