3,3'-dibromo-5,5'-dimethyl-1,1'-biphenyl | 13974-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3'-dibromo-5,5'-dimethyl-1,1'-biphenyl
• 英文别名: 1-bromo-3-(3-bromo-5-methylphenyl)-5-methylbenzene
• CAS: 13974-84-0
• 化学式: C₁₄H₁₂Br₂
• 分子量: 340.057
• InChiKey: GRMLGYULZHLWRH-UHFFFAOYSA-N

物化性质

• 沸点：
  356.1±37.0 °C(predicted)
• 密度：
  1.548±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  3,3'-dibromo-5,5'-dimethyl-1,1'-biphenyl 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 氢气 、 magnesium 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、350.0 kPa 条件下， 反应 80.0h， 生成 diethyl 5,5'-bis<(4-tolylsulfonylamino)methyl>biphenyl-3,3'-dicarboxylate
  参考文献：
  名称：

  Broad Molecular Ribbons of Nanometer Size Composed of Biphenyl Units

  摘要：

  The new tetrafunctionalized biphenyl key building blocks 16 and 39 led, for the first time, to the hitherto broadest molecular ribbons that contain biphenyl units in a transverse arrangement by iterative synthetic methods. The length and breadth of the molecular ribbons, as single chemical entities, are diversified. They can be used as cyclization precursors in the synthesis of long molecular tubes of type 2 with a large diameter. The solubility and the host-guest behavior (clathrate formation with benzene, dimethylformamide, and dichloromethane) of these nanometer-size molecular ribbons were optimized by the introduction of various side chains (benzenesulfonamide, 4-toluenesulfonamide, and 4-terf-butylbenzenesulfonamide groups) into the skeleton of the ribbons. New 14-, 15-, and 16-membered model ring systems (compounds 20a, 22a, and 24 respectively) were synthesized in order to examine the constitution of the 16-membered diaza[3.3]-phane 18a. Nanometer-size tube-shaped molecules 7a, 7b and 8 were obtained by cyclization of tetrafunctionalized molecular ribbons with the biphenyl building block. The constitution and conformation of the molecular ribbons and belts were proven by NOE experiments and X-ray analyses.

  DOI：

  10.1002/(sici)1521-3765(19990104)5:1<345::aid-chem345>3.0.co;2-t
• 作为产物：
  描述：

  2-(3-bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 1,10-菲罗啉 、 copper diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以0.145 g的产率得到3,3'-dibromo-5,5'-dimethyl-1,1'-biphenyl
  参考文献：
  名称：

  经由CH硼化的芳烃立体控制CH / CH均偶联。

  摘要：

  描述了一种温和的一锅法方案，该方案通过顺序的Ir催化的CH硼酸酯化和Cu催化的芳烃均偶联合成对称的联芳基。所形成的联芳基的区域化学空间上受CH硼酸酯化步骤的控制。该方法还成功地扩展到了杂芳烃。通过这种方法获得的某些产品无法通过Ullmann或Suzuki耦合协议获得。最后，我们显示了一锅序列描述了CH硼化/ Cu催化的均偶联/ Pd催化的Suzuki偶联以获得π扩展的芳烃骨架。

  DOI：

  10.1039/c9ob00995g

文献信息

• Palladium (II)‐Catalyzed Decarboxylative Cross‐Dehydrogenative Coupling: Direct Synthesis of <i>meta</i> ‐Substituted Biaryls from Aromatic Acids
  作者：Fan Pu、Lin‐Yan Zhang、Zhong‐Wen Liu、Xian‐Ying Shi

  DOI：10.1002/adsc.201800333

  日期：2018.7.16

  afford meta‐substituted biaryls in moderate to good yields. The reaction proceeds via carboxyl‐directed intermolecular cross‐dehydrogenative coupling and subsequent decarboxylation. The new C−C bonds in this transformation are formed in the ortho position of carboxyl and the reaction tolerates electron‐rich acids. Both symmetrical and unsymmetrical meta‐substituted biaryls can be directly synthesized

  已经实现了钯催化的简单芳族酸串联工艺，以中等到良好的产率提供了间位取代的联芳基。该反应通过羧基定向的分子间交叉脱氢偶联和随后的脱羧反应进行。在这种转变中，新的CC键在羧基的邻位形成，反应可耐受富电子酸。对称和不对称的间取代联芳基都可以通过这种方法直接合成。
• Phosphorescent OLED and hole transporting materials for phosphorescent OLEDs
  申请人：Novaled AG

  公开号：EP2722908A1

  公开（公告）日：2014-04-23

  The present invention relates to phosphorescent organic light-emitting diodes (OLEDs) comprising a hole-transporting or a hole-transporting and an electron-blocking layer comprising an N,N,N',N'-tetraaryl-phenylene-3,5-diamine or an N,N,N',N'-tetraaryl-1,1'-biphenyl-3,3'-diamine matrix compound and to new N,N,N',N'-tetraarylsubstituted m-arylene diamine compounds useful as hole-transporting and electron-blocking layer matrices in phosphorescent OLEDs.

  本发明涉及包括一个孔传输层或一个孔传输层和一个电子阻挡层的磷光有机发光二极管（OLEDs），其中所述层包括N，N，N'，N'-四芳基-苯基-3,5-二胺或N，N，N'，N'-四芳基-1,1'-联苯-3,3'-二胺基质化合物，并且涉及新的N，N，N'，N'-四芳基取代的m-芳撑二胺化合物，用作磷光OLEDs中的孔传输和电子阻挡层基质。
• Phosphorescent OLED and hole transporting materials for phosphorescent OLEDS
  申请人：Novaled GmbH

  公开号：US10868254B2

  公开（公告）日：2020-12-15

  The present invention relates to phosphorescent organic light-emitting diodes (OLEDs) including a hole-transporting or a hole-transporting and an electron-blocking layer including an N,N,N′,N′-tetraaryl-phenylene-3,5-diamine or an N,N,N′,N′-tetraaryl-1,1′-biphenyl-3,3′-diamine matrix compound and to new N,N,N′,N′-tetraarylsubstituted m-arylene diamine compounds useful as hole-transporting and electron-blocking layer matrices in phosphorescent OLEDs.

  本发明涉及包括一个空穴传输层或一个空穴传输和电子阻挡层的磷光有机发光二极管（OLED），其中包括一种N，N，N′，N′-四芳基苯基-3,5-二胺或一种N，N，N′，N′-四芳基-1,1′-联苯-3,3′-二胺基基质化合物，并且涉及新的N，N，N′，N′-四芳基取代的m-芳香族二胺化合物，可用作磷光OLED中的空穴传输和电子阻挡层基质。
• Phosphorescent OLED and Hole Transporting Materials for Phosphorescent OLEDS
  申请人：NOVALED GMBH

  公开号：US20150287930A1

  公开（公告）日：2015-10-08

  The present invention relates to phosphorescent organic light-emitting diodes (OLEDs) comprising a hole-transporting or a hole-transporting and an electron-blocking layer comprising an N,N,N′,N′-tetraaryl-phenylene-3,5-diamine or an N,N,N′,N′-tetraaryl-1,1′-biphenyl-3,3′-diamine matrix compound and to new N,N,N′,N′-tetraarylsubstituted m-arylene diamine compounds useful as hole-transporting and electron-blocking layer matrices in phosphorescent OLEDs.

  本发明涉及磷光有机发光二极管（OLED），其包括一个空穴传输层或空穴传输层和电子阻挡层，其中包括N，N，N'，N'-四芳基苯基-3,5-二胺或N，N，N'，N'-四芳基-1,1'-联苯-3,3'-二胺基基质化合物，并且涉及新的N，N，N'，N'-四芳基取代的m-芳烃二胺化合物，用作磷光OLED中的空穴传输和电子阻挡层基质。
• Synthesis of a Negatively Curved Nanocarbon Molecule with an Octagonal Omphalos via Design‐of‐Experiments Optimizations Supplemented by Machine Learning
  作者：Koki Ikemoto、Misato Akiyoshi、Tatsuru Mio、Kaito Nishioka、Sota Sato、Hiroyuki Isobe

  DOI：10.1002/anie.202204035

  日期：2022.7.25

  A 192π-nanocarbon molecule was contorted by installation of an octagonal omphalos to form a 3-nm saddle. The omphalos was synthesized via dimerization with the aid of Design-of-Experiments optimizations supplemented by machine-learning predictions. The saddle was stacked in a dimer by matching contorted surfaces with a negative Gauss curvature.

  一个 192π-纳米碳分子通过安装一个八角形的 omphalos 来扭曲，形成一个 3-nm 的鞍形。借助实验设计优化并辅以机器学习预测，通过二聚化合成 omphalos。通过匹配具有负高斯曲率的扭曲表面，将鞍座堆叠成二聚体。