8-羟基-1-(1-萘基)萘 | 146746-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 8-羟基-1-(1-萘基)萘
• 英文名称: 8-hydroxy-1-(1-naphthyl)naphthalene
• 英文别名: [1,1'-Binaphthalen]-8-ol；8-naphthalen-1-ylnaphthalen-1-ol
• CAS: 146746-40-9
• 化学式: C₂₀H₁₄O
• 分子量: 270.331
• InChiKey: QYVLFKNPUCXXQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  457.8±14.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)
• 溶解度：
  溶于二氯甲烷

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-羟基-1-(1-萘基)萘 在 bis(triphenylphosphine)palladium(II)-chloride 2,6-二甲基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 苯并[j]荧蒽
  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
• 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-羟基-1-(1-萘基)萘
  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

• METATHESIS CATALYSTS AND REACTIONS USING THE CATALYSTS
  申请人：XiMo AG

  公开号：US20140309466A1

  公开（公告）日：2014-10-16

  The invention relates to a method of forming an olefin from a first olefin and a second olefin in a metathesis reaction, comprising step (i): (i) reacting the first olefin with the second olefin in the presence of a compound that catalyzes said metathesis reaction such that the molar ratio of said compound to the first or the second olefin is from 1:500 or less, and the conversion of the first or the second olefin to said olefin is at least 50%, characterized in that as compound that catalyzes said metathesis reaction a compound of the following formula is used: wherein M is Mo or W; R 1 is aryl, heteroaryl, alkyl, or heteroalkyl; optionally substituted; R 2 and R 3 can be the same or different and are hydrogen, alkyl, alkenyl, heteroalkyl, heteroalkenyl, aryl, or heteroaryl; optionally substituted; R 5 is alkyl, alkoxy, heteroalkyl, aryl, heteroaryl, silylalkyl, silyloxy, optionally substituted; and R 4 is a residue R 6 —X—, wherein X═O and R 6 is aryl, optionally substituted; or X═S and R 6 is aryl, optionally substituted; or X═O and R 6 is (R 7 , R 8 , R 9 )Si; wherein R 7 , R 8 , R 9 are alkyl or phenyl, optionally substituted; or X═O and R 6 is (R 10 , R 11 , R 12 )C, wherein R 10 , R 11 , R 12 are independently selected from phenyl, alkyl; optionally substituted; and to the catalysts used in the method.

  本发明涉及一种从第一烯烃和第二烯烃在交换反应中形成烯烃的方法，包括步骤(i)：(i)在催化所述交换反应的化合物存在下，将第一烯烃与第二烯烃反应，使所述化合物与第一或第二烯烃的摩尔比为1:500或更低，并且第一或第二烯烃转化为所述烯烃至少为50％，其中作为催化所述交换反应的化合物使用以下公式的化合物：其中M为Mo或W；R1为芳基、杂环烷基、烷基或杂烷基；可选择地取代；R2和R3可以相同也可以不同，为氢、烷基、烯基、杂烷基、杂烯基、芳基或杂环烷基；可选择地取代；R5为烷基、烷氧基、杂烷基、芳基、杂环烷基、硅烷基、硅氧基，可选择地取代；R4为残基R6—X—，其中X=O且R6为芳基，可选择地取代；或X=S且R6为芳基，可选择地取代；或X=O且R6为(R7, R8, R9)Si；其中R7、R8、R9为烷基或苯基，可选择地取代；或X=O且R6为(R10, R11, R12)C，其中R10、R11、R12独立地选自苯基、烷基；可选择地取代；以及所述方法中使用的催化剂。
• Metathesis catalysts and reactions using the catalysts
  申请人：XiMo AG

  公开号：US10343153B2

  公开（公告）日：2019-07-09

  A method is provided of forming an olefin from a first olefin and a second olefin in a metathesis reaction, comprising reacting the first olefin with the second olefin in the presence of a compound that catalyzes the metathesis reaction such that the molar ratio of the compound to the first or the second olefin is from 1:500 or less, and the conversion of the first or the second olefin to the olefin is at least 30%.

  提供了一种在偏析反应中由第一烯烃和第二烯烃生成烯烃的方法，包括在催化偏析反应的化合物存在下，使第一烯烃与第二烯烃反应，从而使化合物与第一或第二烯烃的摩尔比为 1:500 或更低，且第一或第二烯烃转化为烯烃的转化率至少为 30%。
• MOLYBDENUM AND TUNGSTEN COMPLEXES AS OLEFIN METATHESIS CATALYSTS AND REACTIONS USING THE CATALYSTS
  申请人：XiMo AG

  公开号：EP2969204A2

  公开（公告）日：2016-01-20
• US9919299B2
  申请人：——

  公开号：US9919299B2

  公开（公告）日：2018-03-20
• [EN] METATHESIS CATALYSTS AND REACTIONS USING THE CATALYSTS<br/>[FR] CATALYSEURS DE MÉTATHÈSE ET RÉACTIONS UTILISANT LES CATALYSEURS
  申请人：XIMO AG

  公开号：WO2014139679A2

  公开（公告）日：2014-09-18

  The invention relates to a method of forming an olefin from a first olefin and a second olefin in a metathesis reaction, comprising step (i): (i) reacting the first olefin with the second olefin in the presence of a compound that catalyzes said metathesis reaction such that the molar ratio of said compound to the first or the second olefin is from 1 : 500 or less, and the conversion of the first or the second olefin to said olefin is at least 50 %, characterized in that as compound that catalyzes said metathesis reaction a compound of formula (A) is used: wherein M is Mo or W; R1 is aryl, heteroaryl, alkyl, or heteroalkyl; optionally substituted; R2 and R3 can be the same or different and are hydrogen, alkyl, alkenyl, heteroalkyl, heteroalkenyl, aryl, or heteroaryl; optionally substituted; R5 is alkyl, alkoxy, heteroalkyl, aryl, heteroaryl, silylalkyl, silyloxy, optionally substituted; and R4 is a residue R6-X-, wherein X = O and R6 is aryl, optionally substituted; or X = S and R6 is aryl, optionally substituted; or X = O and R6 is (R7, R8, R9)Si; wherein R7, R8, R9 are alkyl or phenyl, optionally substituted; or X = O and R6 is (R10, R11, R12)C, wherein R10, R11, R12 are independently selected from phenyl, alkyl; optionally substituted; and to the catalysts used in the method.