8-methoxy-1-(1-naphthyl)naphthalene | 146746-39-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-methoxy-1-(1-naphthyl)naphthalene
• 英文别名: 8-methoxy-1,1'-binaphthalene；1-Methoxy-8-naphthalen-1-ylnaphthalene
• CAS: 146746-39-6
• 化学式: C₂₁H₁₆O
• 分子量: 284.357
• InChiKey: VESAJSUGTKRMSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-methoxy-1-(1-naphthyl)naphthalene 在 2,6-二甲基吡啶 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 8-hydroxy-1-(1-naphtyl)naphthalene triflate
  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-溴代萘 、 1-甲氧基萘 生成 8-methoxy-1-(1-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

• Compounds and the use thereof in metathesis reactions
  申请人：Verbio Vereinigte Bioenergie AG

  公开号：US11414446B1

  公开（公告）日：2022-08-16

  The disclosure provides Group 6 complexes, which, in some embodiments, are useful for catalyzing olefin metathesis reactions. In some embodiments, the compounds are compounds of the following formula: wherein: M is a Group 6 metal atom; X is an oxygen atom, ═N—R5, ═N—N(R5)(R5′) or ═N—O—R5, R5 and R5′ independently being various substituents, such as aryl or heteroaryl, each optionally substituted; n is 0 or 1; Rz is a neutral ligand; R1 is hydrogen or an organic substituent; R2 is an aryl or heteroaryl group, each optionally substituted; R3 is an anionic ligand; and R4 is an anionic ligand, such as a pyrrolide, a pyrazolide, an imidazolide, an indolide, an azaindolide, or an indazolide, each optionally substituted.

  本公开提供了第 6 族配合物，在某些实施方案中，它们可用于催化烯烃偏合成反应。在某些实施方案中，所述化合物为下式化合物： 其中 M 是第 6 族金属原子 X是氧原子、═N-R5、═N-N(R5)(R5′)或═N-O-R5，R5和R5′各自独立地是各种取代基，例如芳基或杂芳基，各自任选被取代； n 为 0 或 1； Rz 是中性配体； R1 是氢或有机取代基； R2 是芳基或杂芳基，每个都可选择被取代； R3 是阴离子配体；以及 R4 是阴离子配体，如吡咯内酯、吡唑内酯、咪唑内酯、吲哚内酯、氮杂吲哚内酯或吲唑内酯，各自可选被取代。
• Synthesis of novel 1-aryl-substituted 8-methoxynaphthalenes and their tendency for atropisomerization
  作者：Seiji Yoshikawa、Jun-ichi Odaira、Yuki Kitamura、Ashutosh V Bedekar、Takumi Furuta、Kiyoshi Tanaka

  DOI：10.1016/j.tet.2004.01.025

  日期：2004.3

  Novel 1-aryl-substituted 8-methoxynaphthalenes were conveniently prepared by using Suzuki-Miyaura cross-coupling as a key reaction. Chemical transformations of the coupled products gave a variety of biaryls bearing various functional groups. The optical behavior of the separated enantiomers of these derivatives was also investigated by HPLC analysis. The optical resolution and determination of absolute configuration of novel binaphtyl derivative were also described. These new compounds may have some potential as mono- or bidentate ligands for metal-catalyzed chemical transformations including asymmetric induction. (C) 2004 Elsevier Ltd. All rights reserved.
• COMPOUNDS AND THE USE THEREOF IN METATHESIS REACTIONS
  申请人：XiMo AG

  公开号：US20170037069A1

  公开（公告）日：2017-02-09

  The disclosure provides Group 6 complexes, which, in some embodiments, are useful for catalyzing olefin metathesis reactions. In some embodiments, the compounds are compounds of the following formula (I) wherein: M is a Group 6 metal atom; X is an oxygen atom, ═N—R 5 , ═N—N(R 5 )(R 5′ ) or ═N—O—R 5 , R 5 and R 5′ independently being various substituents, such as aryl or heteroaryl, each optionally substituted; n is 0 or 1; R z is a neutral ligand; R 1 is hydrogen or an organic substituent; R 2 is an aryl or heteroaryl group, each optionally substituted; R 3 is an anionic ligand; and R 4 is an anionic ligand, such as a pyrrolide, a pyrazolide, an imidazolide, an indolide, an azaindolide, or an indazolide, each optionally substituted.
• 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.