9-(4-methylpyridin-2-yl)-9H-carbazole | 1570075-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-(4-methylpyridin-2-yl)-9H-carbazole
• 英文别名: 9-(4-methylpyridin-2-yl)carbazole
• CAS: 1570075-58-9
• 化学式: C₁₈H₁₄N₂
• 分子量: 258.323
• InChiKey: CATUCBDMZZJFID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-(4-methylpyridin-2-yl)-9H-carbazole 、 二苯基碘酰氯 在 palladium diacetate 、 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 以84 %的产率得到9-(4-methylpyridin-2-yl)-1-phenyl-9H-carbazole
  参考文献：
  名称：

  Pd(II) catalyzed regioselective ortho arylation of 2-arylpyridines, 1-phenyl-1H-pyrazoles, and N-pyridinylcarbazoles with diaryliodonium salts

  摘要：

  DOI：

  10.1007/s00706-022-02990-0
• 作为产物：
  描述：

  2-溴-4-甲基吡啶 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium tert-butylate 、 silver(I) acetate 、 copper diacetate 、 palladium diacetate 、 双(2-二苯基磷苯基)醚 、 对苯醌 作用下， 以 1,4-二氧六环 、 甲苯 、 叔丁醇 为溶剂， 反应 6.0h， 生成 9-(4-methylpyridin-2-yl)-9H-carbazole
  参考文献：
  名称：

  Palladium(II)-Catalyzed Direct Ortho Arylation of 4-Methyl-N-phenylpyridin-2-amines via C–H Activation/C–C Coupling and Synthetic Applications

  摘要：

  The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C-H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of H-1 NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications.

  DOI：

  10.1021/om401195w

文献信息

• CYCLOMETALLATED TETRADENTATE PLATINUM COMPLEXES
  申请人：Universal Display Corporation

  公开号：US20130168656A1

  公开（公告）日：2013-07-04

  Novel phosphorescent platinum complexes containing tetradentate ligands are provided. The disclosed compounds have three 6-membered metallocycle units in each tertadentate ligand. The disclosed compounds have desirable electronic properties that make them useful when incorporated into a variety of OLED devices.

  本发明提供了含有四齿配体的新型磷光铂配合物。所揭示的化合物在每个四齿配体中具有三个六元金属环单元。所揭示的化合物具有理想的电子性质，使它们在被纳入各种OLED设备时非常有用。
• Trivalent Organostibines: Sb,N Ligands in Double N-Arylation of Primary Amines toward Functionalized Carbazoles
  作者：Lifen Peng、Yanting Zhao、Jiayi Chen、Hao Lu、Zilong Tang、Yi Chen、Shuang-Feng Yin、Nobuaki Kambe、Renhua Qiu

  DOI：10.1021/acs.joc.3c01863

  日期：2024.1.5

  A Sb,N ligand (L-Sb) for Pd-catalyzed double N-arylation of primary amines was developed. This trivalent ligand L-Sb, containing a 5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine skeleton and stable under air and moisture, could be synthesized facilely on a gram scale from chlorostibine (1) and cyclopentylmagnesium bromide. L-Sb showed excellent catalytic performance in Pd2(dba)3-catalyzed double

  开发了一种用于 Pd 催化伯胺双 N-芳基化的 Sb,N 配体 ( L-Sb )。这种三价配体L-Sb含有 5,6,7,12-四氢二苯并[ c , f ][1,5]氮杂替博辛骨架，在空气和湿气下稳定，可以从氯锑碱轻松合成克级 ( 1 )和环戊基溴化镁。 L-Sb在 Pd 2 (dba) 3催化的 2,2'-二溴-1,1'-联苯 ( 2 ) 与伯胺 ( 3 ) 的双 N-芳基化反应中表现出优异的催化性能，以良好的产率提供官能化咔唑。该Pd 2 (dba) 3 / L-Sb催化的双N-芳基化反应是三价有机锑化合物作为配体应用于N-芳基化反应的首例，具有催化剂负载量小、官能团耐受性广、化学稳定性好等优点。产率以及克级合成的简易性。
• CuCl-Catalyzed Ullmann-Type C–N Cross-Coupling Reaction of Carbazoles and 2-Bromopyridine Derivatives
  作者：Xiangdong Zhao、Yuanbin She、Kun Fang、Guijie Li

  DOI：10.1021/acs.joc.6b02595

  日期：2017.1.20

  A CuCl-catalyzed Ullmann-type C-N cross coupling reaction of carbazoles and 2-bromopyridine deriva tives has been developed for the synthesis of N-heteroarylcarbazole derivatives employing 1-methyl-imidazole and t-BuOLi as ligand and base, respectively, both of which are found to significantly promote the reaction. Low cost and low loading of both catalyst and ligand, together with high reaction yields, render this practical reaction to be suitable for large-scale preparations and could be useful in material science.
• Palladium(II)-Catalyzed Direct Ortho Arylation of 4-Methyl-<i>N</i>-phenylpyridin-2-amines via C–H Activation/C–C Coupling and Synthetic Applications
  作者：Jean-Ho Chu、Hao-Ping Huang、Wen-Ting Hsu、Shih-Tien Chen、Ming-Jung Wu

  DOI：10.1021/om401195w

  日期：2014.3.10

  The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C-H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of H-1 NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications.
• Pd(II) catalyzed regioselective ortho arylation of 2-arylpyridines, 1-phenyl-1H-pyrazoles, and N-pyridinylcarbazoles with diaryliodonium salts
  作者：M. V. Niladri Raju、G. Manohar Reddy、B. Jaganmohan Reddy、V. Jayathirtha Rao、Sai Prathima Parvathaneni

  DOI：10.1007/s00706-022-02990-0

  日期：2022.12