9-(2-羟基苯基)蒽三氟甲磺酸酯 | 146746-38-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 中文名称: 9-(2-羟基苯基)蒽三氟甲磺酸酯
• 英文名称: 9-(2-hydroxyphenyl)anthracene triflate
• 英文别名: 2-(anthracen-9-yl)phenyl trifluoromethanesulfonate；(2-Anthracen-9-ylphenyl) trifluoromethanesulfonate
• CAS: 146746-38-5
• 化学式: C₂₁H₁₃F₃O₃S
• 分子量: 402.394
• InChiKey: CBXTZZJUAGGWHI-UHFFFAOYSA-N

物化性质

• 沸点：
  497.1±45.0 °C(Predicted)
• 密度：
  1.414±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-(2-羟基苯基)蒽三氟甲磺酸酯 在 bis-triphenylphosphine-palladium(II) chloride 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以84%的产率得到苯并(A)荧蒽
  参考文献：
  名称：

  Rice, Joseph E.; Cai, Zhen-Wei, Tetrahedron Letters, 1992, vol. 33, # 13, p. 1663 - 1678

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(甲氧基甲氧基)苯 在 1,2-双(二苯基膦)乙烷氯化镍 2,6-二甲基吡啶 、 盐酸 、 正丁基锂 、 magnesium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 9-(2-羟基苯基)蒽三氟甲磺酸酯
  参考文献：
  名称：

  An intramolecular arene-triflate coupling reaction for the regiospecific synthesis of substituted benzofluoranthenes

  摘要：

  An intramolecular triflate-arene coupling reaction mediated by bis(triphenylphosphine)palladium(II) chloride has been developed for the synthesis of each of the isomeric benzofluoranthenes. This reaction, which results in formation of a new five-membered ring, proceeds in highest yield when performed using 0.1 equiv of the palladium catalyst, 3 equiv of lithium chloride, and 1.2 equiv of 1,8-diazabicyclo[5.4.0]undec-7-ene in N,N-dimethylformamide at 140-degrees-C. The biaryl precursors needed for the coupling reaction can be prepared by [1,2-bis(diphenylphosphino)ethane]nickel(II) chloride catalyzed coupling of an aryl bromide with an [o-(methoxymethoxy)aryl]magnesium bromide (prepared by ortho-lithiation of an aryl methoxymethyl ether followed by transmetalation with magnesium bromide). Using this procedure benzo[a]fluoranthene, benzo[b]fluoranthene, benzo[j]fluoranthene, and benzo[k]fluoranthene were prepared in yields of 84%, 85%, 93%, and 64%, respectively. The reaction to prepare benzo[j]fluoranthene was regiospecific and afforded none of the six-membered ring product, perylene. The method was extended to the preparation of benzo[b]fluoranthene (BbF) derivatives with fluoro or methoxy groups on the benzo ring. The cyclization of compounds possessing a methoxy group on the same ring as the triflate required the addition of 0.4 equiv of triphenylphosphine to the reaction mixture. Strategies are reported for the regiospecific preparation of 4-, 5-, 6-, and 7-substituted benzo[b]fluoranthenes. Evidence is presented which suggests the intermediacy of radicals in the oxidative-addition of aryl triflates to the palladium catalyst.

  DOI：

  10.1021/jo00058a023

文献信息

• CN116947580
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  公开号：——

  公开（公告）日：——