9,9-dioctyl-N,N,N’,N’-tetraphenyl-9H-fluorene-2,7-diamine | 1159100-85-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 9,9-dioctyl-N,N,N’,N’-tetraphenyl-9H-fluorene-2,7-diamine
• 英文别名: 9,9-dioctyl-2-N,2-N,7-N,7-N-tetraphenylfluorene-2,7-diamine
• CAS: 1159100-85-2
• 化学式: C₅₃H₆₀N₂
• 分子量: 725.073
• InChiKey: XEDBSDCOXUZANB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.5
• 重原子数：
  55
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,1,1-三甲基-N,N-二苯基-硅烷胺 、 9,9-二辛基-2,7-二溴代芴 在 cesium fluoride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 反应 8.0h， 以93%的产率得到9,9-dioctyl-N,N,N’,N’-tetraphenyl-9H-fluorene-2,7-diamine
  参考文献：
  名称：

  Silicon-based C–N Cross-coupling Reaction

  摘要：

  研究发现，在 1,3-二甲基-2-咪唑烷酮（DMI）中存在氟活化剂的情况下，N-三甲基硅胺与芳基溴化物和氯化物的钯催化 C-N 键形成交叉偶联反应可以进行，并以极高的产率得到三芳基胺。在该反应中使用芳基溴和双(硅烷基)胺时，可获得高产率的双 C-N 键形成产物。本反应被成功应用于 C-N 键形成聚合反应。

  DOI：

  10.1246/cl.131075

文献信息

• Catalytic Carbon–Nitrogen Bond-Forming Cross-Coupling Using <i>N</i>-Trimethylsilylamines
  作者：Yasunori Minami、Takeshi Komiyama、Kenta Shimizu、Tamejiro Hiyama、Osamu Goto、Hideyuki Ikehira

  DOI：10.1246/bcsj.20150179

  日期：2015.10.15

  Carbon–nitrogen bond-forming cross-coupling reaction of haloarenes with N-trimethylsilyl (TMS)-substituted secondary and primary arylamines proceeded with the aid of a palladium catalyst and a fluoride activator. Various TMS-N(aryl)2, TMS-NH(aryl), and TMS-N(alkyl)2 reacted to give the corresponding coupled products in high yields. Multi-TMS-amine nucleophiles such as N,N-(TMS)2-aniline and N,N′-Ph2-N,N′-(TMS)2-p-phenylenediamine also participated in this C–N coupling to give multiply C–N coupled products in high yields. The novel C–N cross-coupling reaction was successfully applied to C–N bond-forming polymerization. Relative rates of the cross-coupling of p-bromotoluene with N-TMS-substituted primary and secondary amines showed that N-TMS-diphenylamine reacted faster than N-TMS-N-methylaniline or N-TMS-aniline, and N-TMS-morpholine was the least reactive, indicating that the low basicity of the nitrogen nucleophile is the key for the smooth coupling.

  在钯催化剂和氟化物活化剂的帮助下，卤代烯烃与 N-三甲基硅烷基（TMS）取代的仲芳基和伯芳基胺发生了碳-氮键形成交叉偶联反应。各种 TMS-N（芳基）2、TMS-NH（芳基）和 TMS-N（烷基）2 在高产率下反应生成相应的偶联产物。N,N-(TMS)2-苯胺和 N,N′-Ph2-N,N′-(TMS)2-对苯二胺等多重 TMS-amine 亲核物也参与了这种 C-N 偶联反应，从而以高产率得到多重 C-N 偶联产物。新型 C-N 交叉偶联反应被成功应用于 C-N 键形成的聚合反应。对溴甲苯与 N-TMS 取代的伯胺和仲胺发生交叉偶联的相对速率表明，N-TMS-二苯胺的反应速度快于 N-TMS-N-methylaniline 或 N-TMS-aniline，而 N-TMS-morpholine 的反应速度最低，这表明氮亲核体的低碱性是顺利偶联的关键。
• AMINE COMPOUND HAVING FLUORENE GROUP AS FRAMEWORK, PROCESS FOR PRODUCING THE AMINE COMPOUND, AND USE OF THE AMINE COMPOUND
  申请人：TOSOH CORPORATION

  公开号：EP1752440A1

  公开（公告）日：2007-02-14

  Novel amine compounds that can be utilized as hole transport materials, hole injection materials or the like of organic electroluminescence devices, electrophotographic receptors or the like, and their production processes are provided. The novel amine compound is represented by the following general formula (1). In the formula, R1 and R2 each independently represents hydrogen atom, a linear, branched or cyclic alkyl group or alkoxy group, an aryl group, an aryloxy group or a halogen atom; Ar1 and Ar2 each independently represents a substituted or unsubstituted aryl group or heteroaryl group, and may form a nitrogen-containing heterocyclic ring together with the nitrogen atom bonded thereto; and Ar3 each independently represents a substituted or unsubstituted phenyl group, naphthyl group, biphenylyl group, terphenylyl group, anthryl group, fluorenyl group or pyridyl group (except for amino-substituted groups); and M represents a single bond, an arylene group or a heteroarylene group.

  本发明提供了可用作有机电致发光器件、电致发光受体或类似器件的空穴传输材料、空穴注入材料或类似材料的新型胺化合物及其生产工艺。 新型胺化合物由以下通式（1）表示。 式中，R1 和 R2 各自独立地代表氢原子、直链、支链或环状烷基或烷氧基、芳基、芳氧基或卤原子；Ar1 和 Ar2 各自独立地代表取代或未取代的芳基或杂芳基，并可与其键合的氮原子一起形成含氮杂环；和 Ar3 各自独立地代表取代或未取代的苯基、萘基、联苯基、三苯基、蒽基、芴基或吡啶基（氨基取代的基团除外）；以及 M 代表单键、芳烯基或杂芳烯基。
• Amine Compound Having Fluorene Group as Framework, Process for Producing the Amine Compound, and Use of the Amine Compound
  申请人：Nishiyama Masakazu

  公开号：US20080194878A1

  公开（公告）日：2008-08-14

  Novel amine compounds that can be utilized as hole transport materials, hole injection materials or the like of organic electroluminescence devices, electrophotographic receptors or the like, and their production processes are provided. The novel amine compound is represented by the following general formula (1). In the formula, R 1 and R 2 each independently represents hydrogen atom, a linear, branched or cyclic alkyl group or alkoxy group, an aryl group, an aryloxy group or a halogen atom; Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group or heteroaryl group, and may form a nitrogen-containing heterocyclic ring together with the nitrogen atom bonded thereto; and Ar 3 each independently represents a substituted or unsubstituted phenyl group, naphthyl group, biphenylyl group, terphenylyl group, anthryl group, fluorenyl group or pyridyl group (except for amino-substituted groups); and M represents a single bond, an arylene group or a heteroarylene group.
• ORDINARY-TEMPERATURE-PHOSPHORESCENT ORGANIC MATERIAL, REVERSIBLY THERMOSENSITIVE RECORDING MATERIAL, REVERSIBLY THERMOSENSITIVE RECORDING MEDIUM, AND METHOD OF RECORDING IN REVERSIBLY THERMOSENSITIVE RECORDING MEDIUM
  申请人：Watanabe Toshiyuki

  公开号：US20100328412A1

  公开（公告）日：2010-12-30

  The present invention provides an organic material that is characterized by including a rigid matrix and a dye having a phosphorescence lifetime of 0.1 seconds or more in a rigid medium at 77 K and that exhibits such a strong and long-lived phosphorescence as to be recognizable with the naked eyes even at ordinary temperature: namely, an ordinary-temperature-phosphorescent organic material.
• US7482490B2
  申请人：——

  公开号：US7482490B2

  公开（公告）日：2009-01-27