8-hydroxy-1-(2-naphthyl)naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-hydroxy-1-(2-naphthyl)naphthalene
• 英文别名: [1,2′-binaphthalen]-8-ol；8-Naphthalen-2-ylnaphthalen-1-ol
• 化学式: C₂₀H₁₄O
• 分子量: 270.331
• InChiKey: ABSJWWWVPNUEMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-hydroxy-1-(2-naphthyl)naphthalene 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 1-金刚烷甲酸 、 三乙胺 作用下， 以 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 反应 28.0h， 生成 苯并[k]荧蒽 、 苯并[j]荧蒽
  参考文献：
  名称：

  通过Pd催化的分子间和分子内CH芳基化三步合成芴酮

  摘要：

  已经开发了一种三步合成的荧光素合成方法，涉及Miura的分子间C–H芳基化，非消融和分子内C–H芳基化。各种1-萘酚和卤代芳烃已成功用作底物。已经为分子内CH芳基化步骤开发了具有高位点选择性的反应条件。

  DOI：

  10.1021/acs.joc.6b00553
• 作为产物：
  描述：

  1-甲氧基萘 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 8-hydroxy-1-(2-naphthyl)naphthalene
  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

• Three-Step Synthesis of Fluoranthenes through Pd-Catalyzed Inter- and Intramolecular C–H Arylation
  作者：Miyuki Yamaguchi、Mayu Higuchi、Kanae Tazawa、Kei Manabe

  DOI：10.1021/acs.joc.6b00553

  日期：2016.5.6

  the preparation of fluoranthenes, involving Miura’s intermolecular C–H arylation, nonaflation, and intramolecular C–H arylation, has been developed. Various 1-naphthols and haloarenes were successfully used as substrates. Reaction conditions that afford high site selectivity have been developed for the intramolecular C–H arylation step.

  已经开发了一种三步合成的荧光素合成方法，涉及Miura的分子间C–H芳基化，非消融和分子内C–H芳基化。各种1-萘酚和卤代芳烃已成功用作底物。已经为分子内CH芳基化步骤开发了具有高位点选择性的反应条件。
• An intramolecular arene-triflate coupling reaction for the regiospecific synthesis of substituted benzofluoranthenes
  作者：Joseph E. Rice、Zhen Wei Cai

  DOI：10.1021/jo00058a023

  日期：1993.3

  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.