N¹,N¹-dimethyl-N³-phenylbenzene-1,3-diamine | 51488-26-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N¹,N¹-dimethyl-N³-phenylbenzene-1,3-diamine
• 英文别名: N,N-Dimethyl-N'-phenyl-m-phenylendiamin；3-Dimethylamino-diphenylamin；N,N-dimethyl-N'-phenyl-m-phenylenediamine；N1,N1-dimethyl-N3-phenylbenzene-1,3-diamine；3-N,3-N-dimethyl-1-N-phenylbenzene-1,3-diamine
• CAS: 51488-26-7
• 化学式: C₁₄H₁₆N₂
• 分子量: 212.294
• InChiKey: KRKCQGKWPXGWLP-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  357.5±25.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲酸 、 N¹,N¹-dimethyl-N³-phenylbenzene-1,3-diamine 在 盐酸 、 甘油 作用下， 生成 3-(dimethylamino)acridine
  参考文献：
  名称：

  242. 吖啶合成和反应。第四部分。甲酸和二芳胺合成氨基吖啶的新方法

  摘要：

  DOI：

  10.1039/jr9480001225
• 作为产物：
  描述：

  N-(3-dimethylamino-phenyl)-N-phenyl-acetamide 在 盐酸 作用下， 生成 N¹,N¹-dimethyl-N³-phenylbenzene-1,3-diamine
  参考文献：
  名称：

  242. 吖啶合成和反应。第四部分。甲酸和二芳胺合成氨基吖啶的新方法

  摘要：

  DOI：

  10.1039/jr9480001225

文献信息

• Nickel(II) complex incorporating methylene bridged tetradentate dicarbene ligand as an efficient catalyst toward CC and CN bond formation reactions
  作者：Muthukumaran Nirmala、Govindan Prakash、Rangasamy Ramachandran、Periasamy Viswanathamurthi、Jan Grzegorz Malecki、Wolfgang Linert

  DOI：10.1016/j.molcata.2014.10.031

  日期：2015.2

  Suzuki–Miyaura cross-coupling reaction between aryl halides and arylboronic acids under phosphine free conditions. The new complex also catalyzed the amination of aryl chlorides in the presence of KOtBu. Various aryl chlorides and amines can react smoothly to give the corresponding aminated products in moderate to high yields. Both secondary and primary amines are well tolerated under the optimal reaction conditions

  为了评估N-杂环卡宾（NHCs）及其络合物的结合和催化性质，已制备了一种新的亚甲基桥连双（芳氧基-NHC）配体。合成了带有新型NHC配体的新型空气稳定的Ni（II）络合物，并通过元素分析，NMR（1 H和13 C）以及ESI-质谱法对其进行了表征。通过单晶X射线衍射分析鉴定了配合物的分子结构，该分析表明Ni（II）配合物具有正方形的平面几何形状，且配体与双负四齿C 2 O 2配位。在不含膦的条件下，芳烃卤化物与芳基硼酸之间的Suzuki-Miyaura交叉偶联反应具有较高的催化活性。新的络合物还可以在KO t Bu存在的情况下催化芳基氯化物的胺化反应。各种芳基氯化物和胺可以平稳反应，以中等至高收率得到相应的胺化产物。在最佳反应条件下，仲胺和伯胺均具有良好的耐受性。
• Non-innocent electrophiles unlock exogenous base-free coupling reactions
  作者：Georgios Toupalas、Bill Morandi

  DOI：10.1038/s41929-022-00770-x

  日期：——

  metal-catalysed reactions rely on stoichiometric quantities of an exogenous base to enable catalytic turnover. Despite playing a fundamental role, the base poses major challenges, such as restricting the accessible chemical space or causing heterogeneous reaction mixtures. Here we introduce a unifying strategy that eliminates the need for an exogenous base through the use of non-innocent electrophiles (NIE)

  许多重要的过渡金属催化反应依赖于化学计量数量的外源碱来实现催化周转。尽管发挥了基础性作用，但碱基也带来了重大挑战，例如限制可接近的化学空间或导致多相反应混合物。在这里，我们介绍了一种统一策略，该策略通过使用非无辜亲电试剂 (NIE) 消除了对外源碱基的需求，NIE 配备了在反应过程中以受控方式释放的掩蔽碱基。通过将多个传统上依赖碱基的催化反应转变为外源无碱基均相过程，证明了这一概念的普遍适用性。此外，NIE 的优势特性在多个应用中得到了证明，例如在基于微摩尔级荧光的测定中。这导致发现了使用异丙醇作为良性还原剂的氨基甲酸芳基酯的镍催化脱氧反应。在更广泛的背景下，这项工作为 NIE 在催化中的战略利用提供了概念蓝图。
• New <i>m</i>-MTDATA skeleton-based hole transporting materials for multi-resonant TADF OLEDs
  作者：A. Bucinskas、O. Bezvikonnyi、R. Durgaryan、D. Volyniuk、A. Tomkeviciene、J. V. Grazulevicius

  DOI：10.1039/d2cp03811k

  日期：——

  synthesized by introducing different electron donating groups, such as methoxy, ethoxy and dimethylamino groups. To achieve the target compounds simple two-step synthesis was used by employing the Buchwald–Hartwig reaction. New derivatives were investigated experimentally and their thermal, optical, photoelectrical, and charge transporting properties were compared with the respective results of their commercial

  通过引入不同的给电子基团，如甲氧基、乙氧基和二甲氨基，合成了六种基于商用m -MTDATA 核的新型空穴传输材料。为了实现目标化合物，通过采用 Buchwald-Hartwig 反应使用简单的两步合成。对新衍生物进行了实验研究，并将它们的热学、光学、光电和电荷传输特性与其商业对应物 ( m -MTDATA) 的各自结果进行了比较。在固态和 DCM 溶液中，目标化合物和商业m -MTDATA 显示出相当的电离电位值。间位带有甲氧基的化合物的空穴迁移率为 1.06 × 10−3 cm 2 V −1 s −1在 4.62 × 10 5 V cm −1的电场下。这些值超过了为m -MTDATA 报告的值。合成的衍生物用于制备多共振 TADF OLED 中的空穴传输层。使用合成的空穴传输材料和深蓝色 MR-TADF 发射体t -DABNA的 OLED 实现了出色的色纯度和高达 13.8% 的最高外部量子效率。
• Copper Mediated Formation of Carbon-Heteroatom Bonds Using Organoboron Reagents and Ultrasound
  作者：George W. Kabalka、Bryan J. Musolino

  DOI：10.3987/com-14-s(k)18

  日期：——

  This report summarizes research efforts focused on copper acetate mediated reactions to form new carbon-heteroatom bonds using organoboron reagents under ultrasound irradiation. The method involves the application of ultrasound irradiation to the Chan-Evans-Lam reaction to achieve O-arylation of phenols, N-arylation of anilines and indoles, and S-arylation of thiols. Ultrasound irradiation was found to decrease reaction times from 72 hours to 4 hours while improving the product yields an average of 20%(1) Representative C-O, C-N, and C-S coupling reactions were successfully scaled-up from the milligram to gram levels while maintaining good product yields offering potential applications in industrial processes.
• N-Heterocyclic Carbene–Palladium(II)–4,5-Dihydrooxazole Complexes: Synthesis and Catalytic Activity toward Amination of Aryl Chlorides
  作者：Pei Huang、Yi-Xiang Wang、Hong-Fei Yu、Jian-Mei Lu

  DOI：10.1021/om401028d

  日期：2014.4.14

  A series of novel N-heterocyclic carbene-palladium(II)-4,5-dihydrooxazole (NHC-Pd-II-Ox) complexes 3 were successfully synthesized from commercially available imidazolium salts 1, PdCl2, and 4,5-dihydrooxazoles 2 in a one-step process, and these complexes showed efficient catalytic activity toward the amination of aryl chlorides. Both secondary and primary amines were tolerated under the same reaction conditions. Under the optimal reaction conditions, the expected coupling products were obtained in moderate to high yields.