2,7-bis(2-methylphenyl)fluorene | 96069-60-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,7-bis(2-methylphenyl)fluorene
• 英文别名: 2,7-bis(2-methylphenyl)-9H-fluorene
• CAS: 96069-60-2
• 化学式: C₂₇H₂₂
• 分子量: 346.472
• InChiKey: NXIHJBPHFNCOBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-丙-2-亚基茚 、 2,7-bis(2-methylphenyl)fluorene 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 以60%的产率得到9-[1-(inden-3-yl)-1-methylethyl]-2,7-bis-(2-tolyl)fluorene
  参考文献：
  名称：

  Novel C1 symmetric zirconocenes containing substituted fluorenyl moieties for the polymerization of olefins

  摘要：

  The synthesis and polymerization behavior of four new asymmetric ansa-metallocenes containing a 2,7-disubstituted fluorenyl moiety and an indenyl moiety is reported. Three of the four catalysts, dichloro[eta(5)-1-indenyl(1-methylethylidene)-[2,7-bis-(2,4,6-trimethylphenyl)-eta(5)-9-fluorenyl]zirconium (11), dichloro[eta(5)-1-indenyl(I-methylethylidene)-[2,7-bis-(2,6-dimethylphenyl)-eta(5)-9-fluorenyl]zirconium (12), and dichloro[eta(5)-1-indenyl(l-methylethylidene)-[2,7-bis-(2-methylphenyl)-eta(5)-9-fluorenyl] zirconium (13) were highly active for the polymerization of both ethylene and propylene when activated with excess methylaluminoxane (MAO). Dichloro[eta(5)-1-indenyl(1-methylethylidene)-[2,7-dibenzyl-eta(5)-9-fluorenyl]zirconium (14) was poorly active for the polymerization of ethylene and was therefore not evaluated as a propylene catalyst. The activities for propylene polymerizations with catalysts 11 - 13 increased as the size of the substituents around the ligand framework increased, following the trend 11 > 12 > 13. Molecular weights of the polypropylenes decreased as the temperature was increased. The molecular weight data follows the same trend (11 > 12 > 13) as the activity data, wherein the largest substituents gave rise to the highest molecular weights. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00239-0
• 作为产物：
  描述：

  2-溴甲苯 、 2,7-二碘芴 以81%的产率得到2,7-bis(2-methylphenyl)fluorene
  参考文献：
  名称：

  Novel C1 symmetric zirconocenes containing substituted fluorenyl moieties for the polymerization of olefins

  摘要：

  The synthesis and polymerization behavior of four new asymmetric ansa-metallocenes containing a 2,7-disubstituted fluorenyl moiety and an indenyl moiety is reported. Three of the four catalysts, dichloro[eta(5)-1-indenyl(1-methylethylidene)-[2,7-bis-(2,4,6-trimethylphenyl)-eta(5)-9-fluorenyl]zirconium (11), dichloro[eta(5)-1-indenyl(I-methylethylidene)-[2,7-bis-(2,6-dimethylphenyl)-eta(5)-9-fluorenyl]zirconium (12), and dichloro[eta(5)-1-indenyl(l-methylethylidene)-[2,7-bis-(2-methylphenyl)-eta(5)-9-fluorenyl] zirconium (13) were highly active for the polymerization of both ethylene and propylene when activated with excess methylaluminoxane (MAO). Dichloro[eta(5)-1-indenyl(1-methylethylidene)-[2,7-dibenzyl-eta(5)-9-fluorenyl]zirconium (14) was poorly active for the polymerization of ethylene and was therefore not evaluated as a propylene catalyst. The activities for propylene polymerizations with catalysts 11 - 13 increased as the size of the substituents around the ligand framework increased, following the trend 11 > 12 > 13. Molecular weights of the polypropylenes decreased as the temperature was increased. The molecular weight data follows the same trend (11 > 12 > 13) as the activity data, wherein the largest substituents gave rise to the highest molecular weights. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00239-0

文献信息

• Green, Efficient and Reusable Bis(imidazolium) Ionic Liquids Promoted Pd-Catalyzed Aqueous Suzuki Reaction for Organic Functional Materials
  作者：Zhonggao Zhou、Yangyang Yuan、Yongrong Xie、Mei Li

  DOI：10.1007/s10562-018-2452-y

  日期：2018.9

  bis(imidazolium) ionic liquids were used to promote environmentally friendly, efficient and reusable Pd-catalyzed Suzuki reaction between arylboronic acids and 2-bromofluorene, 2,7-dibromo-9,9′-dialkylfluorene. Over 30 carbazole-based fluorene core potential organic functional materials were synthesized. In addition, recyclability of catalyst system was inspected on the Suzuki reaction observing nearly

  摘要 吡喃葡萄糖苷取代的不对称双（咪唑鎓）离子液体用于促进环保、高效和可重复使用的 Pd 催化芳基硼酸与 2-溴芴、2,7-二溴-9,9'-二烷基芴之间的 Suzuki 反应。合成了 30 多种咔唑基芴核电位有机功能材料。此外，在 Suzuki 反应中检查了催化剂体系的可回收性，观察到在五个循环内催化活性几乎没有损失。图形摘要绿色、高效和可循环的吡喃葡萄糖苷取代的双（咪唑鎓）离子液体的开发促进了 Pd 催化的 OFM 的 Suzuki 水溶液反应。
• Glucopyranoside-Functionalized NHCs-Pd(II)-PEPPSI Complexes: Anomeric Isomerism Controlled and Catalytic Activity in Aqueous Suzuki Reaction
  作者：Zhonggao Zhou、Qian Xie、Jing Li、Yangyang Yuan、Yong Liu、Yulong Liu、Dongliang Lu、Yongrong Xie

  DOI：10.1007/s10562-021-03654-0

  日期：2022.3

  the imidazole heterocycle ring N through ethoxy bridged anomeric carbon. In addition, the catalytic activities revealed that Glu-NHCs-Pd(II)-PEPPSI complexes 2a-d are efficient catalysts for the aqueous Suzuki reaction. Under optimized conditions, a series of fluorene-cored functional materials with different aryl-substituents were synthesized through the Suzuki reaction with excellent yields. The

  制备了吡喃葡萄糖苷官能化的N-杂环卡宾基于吡啶的第一个系统控制的异头异构体，吡啶增强了预催化剂的制备，稳定化和引发型钯（II）配合物（Glu-NHCs-Pd（II）-PEPPSI，2a–d）并进行了充分表征。有趣的是，纯β得到了–anomer PEPPSI配合物2d，其中Glu取代基通过乙氧基桥接的异头碳连接到咪唑杂环N。此外，催化活性表明，Glu-NHCs-Pd（II）-PEPPSI配合物2a-d是水性Suzuki反应的有效催化剂。在最佳条件下，通过铃木反应以优异的收率合成了一系列具有不同芳基取代基的芴核功能材料。含有庞大且刚性的2,5-二甲基苯基的Glu-NHCs-Pd（II）-PEPPSI络合物在维持β构象和显着提高催化活性方面起着重要作用。 图形摘要
• Poly(ethylene glycol)- and glucopyranoside-substituted N-heterocyclic carbene precursors for the synthesis of arylfluorene derivatives using efficient palladium-catalyzed aqueous Suzuki reaction
  作者：Zhonggao Zhou、Yan Zhao、Hongyu Zhen、Zhenghuan Lin、Qidan Ling

  DOI：10.1002/aoc.3522

  日期：2016.11

  This paper reports an environmentally friendly and highly efficient synthesis of organic semiconductor materials via a Pd/N‐heterocyclic carbene (NHC)‐catalyzed Suzuki reaction in aqueous ethanol with high isolated yields (86–98%). Firstly, four glucopyranoside‐substituted NHC precursors with poly(ethylene glycol) (PEG) chains were synthesized and characterized. The NHC precursor with the longest PEG

  本文报告了在乙醇水溶液中通过Pd / N杂环卡宾（NHC）催化的Suzuki反应以环保的方式高效合成有机半导体材料的方法，其分离产率高（86-98％）。首先，合成并表征了四种具有聚（乙二醇）（PEG）链的吡喃葡萄糖苷取代的NHC前体。发现具有最长PEG链（n  = 16）的NHC前体是各种芳基卤化物和芳基硼​​酸反应中最有效的配体。在这项工作中获得的最佳催化剂体系可以循环使用五次而不会显着降低催化活性。l版权所有©2016 John Wiley＆Sons，Ltd.
• Synthesis of glucopyranoside benzimidazolium-based ionic liquids for Pd-catalyzed aqueous Suzuki reaction
  作者：Xiaoming Wen、Jian Wang、Luan He、Bisheng Wei、Ying Xie

  DOI：10.1080/07328303.2022.2141770

  日期：2022.7.24

  Abstract Several novel benzimidazolium-based ionic liquids (BzIm ILs) with free and acetyl protected glucopyranoside unit were synthesized and used as ligand for Pd-catalyzed environment-friendly Suzuki reaction. The BzIm ILs with the acetyl protection shows the highest activity, probably because the sugar has a large steric hindrance and acetyl groups can coordinate with Pd. The nuclear magnetic resonance

  摘要 合成了几种具有游离和乙酰基保护的吡喃葡萄糖苷单元的新型苯并咪唑鎓基离子液体 (BzIm ILs)，并将其用作 Pd 催化的环境友好型 Suzuki 反应的配体。具有乙酰基保护的 BzIm ILs 显示出最高的活性，可能是因为糖具有较大的空间位阻，乙酰基可以与 Pd 配位。Pd(OAc) 2 /Glc-BzIm ILs游离吡喃葡萄糖苷的核磁共振谱表明形成了Pd-C。尺寸为 5.3 (0.6) nm 的离子液体保护的 Pd 纳米粒子被认为是真正的活性物质。制备了一系列芴核芳基芴衍生物，分离收率均在90%以上。
• Unexpectedly superior efficiency of chloride-directed double Suzuki–Miyaura cross-coupling reactions to bromide-directed reactions for the synthesis of sterically hindered 2,7-diaryl fluorenes
  作者：Yu-Qing Peng、Yong-Qing Li、Miao-Miao Liu、Chen Ni、Yu-Cai Cao

  DOI：10.1039/d4nj00718b

  日期：——

  Sterically hindered 2,7-diaryl fluorenes have been efficiently synthesized via double Suzuki–Miyaura cross-coupling reactions of challenging 2,7-dichlorofluorene with a broad range of di-ortho-substituted arylboronic acids using the N-heterocyclic carbene Pd catalyst INPd. The efficiency of chloride-directed reactions is superior to that of bromide-directed reactions. Mechanistic studies revealed a

  使用 N-杂环卡宾 Pd 催化剂 INPd，通过具有挑战性的 2,7-二氯芴与多种二邻位取代的芳基硼酸的双 Suzuki-Miyaura 交叉偶联反应，有效合成了位阻 2,7-二芳基芴。氯化物直接反应的效率优于溴化物直接反应。机理研究揭示了铃木-宫浦双交叉偶联反应的串联过程。