2-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine | 265647-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 2-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine
• 英文别名: 2-(2-pyridyl)-7-azaindole；2-pyridin-2-yl-1H-pyrrolo[2,3-b]pyridine
• CAS: 265647-77-6
• 化学式: C₁₂H₉N₃
• 分子量: 195.224
• InChiKey: HBNIHJMRARVJNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 palladium on activated charcoal 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 58.0h， 以29%的产率得到2-(哌啶-2-基)-1H-吡咯并[2,3-b]吡啶
  参考文献：
  名称：

  Benzyl Piperidine Compounds as Lysophosphatidic Acid (LPA) Receptor Antagonist

  摘要：

  该发明提供了根据式（I）提供的新型取代苄基哌啶化合物，作为赖氨酸磷脂酸（LPA）受体拮抗剂，其制造和用于治疗增生性或炎症性疾病，如癌症、纤维化或关节炎。

  公开号：

  US20150011557A1
• 作为产物：
  描述：

  7-氮杂吲哚 在 sodium hydroxide 、 四丁基溴化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 环己烷 、 苯 为溶剂， 反应 9.0h， 生成 2-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  Syntheses, Structures, and Electroluminescence of New Blue/Green Luminescent Chelate Compounds:  Zn(2-py-in)₂(THF), BPh₂(2-py-in), Be(2-py-in)₂, and BPh₂(2-py-aza) [2-py-in = 2-(2-pyridyl)indole; 2-py-aza = 2-(2-pyridyl)-7-azaindole]

  摘要：

  Four novel blue/green luminescent compounds, Zn(2-py-in)(2)(THF) (1), BPh2(2-py-in) (2), Be(2-py-in)(2) (3), and BPh2(2-py-aza) (4), where 2-py-in = 2-(2-pyridyl)indole and 2-py-aza = 2-(2-pyridyl)-7-azaindole, have been synthesized and fully characterized. The 2-py-in ligand and 2-py-aza ligand in the new compounds are chelated to the central atom; Compounds 2-4 are air stable and readily sublimable, with a melting point above 250 degrees C. In the solid state, compounds 1-4 have an emission maximum at lambda 488, 516, 490, and 476 nm, respectively. The structures of compounds 2 and 4 are similar. The blue shift of emission energy displayed by compound 4, in comparison to that of 2, is attributed to the presence of an extra nitrogen atom in the 2-py-aza ligand as confirmed by ab initio calculations on compounds 2 and 4. Electroluminescent devices of compounds 3 and 4 were fabricated by using N,N'-di-1-naphthyl-N,N'-diphenylbenzidine (NPB) as the hole transporting layer, Alq(3) (q = 8-hydroxyquinolato) as the electron transporting layer, and compound 3 or 4 as the light emitting layer. At 20 mA/cm(2) the EL device of 3 has an external efficiency of 1.06 cd/A while the EL device of 4 has an external efficiency of 2.34 cd/A, demonstrating that compounds 3 and 4 are efficient and promising emitters in electroluminescent devices.

  DOI：

  10.1021/ja9944249

文献信息

• Expedient Copper-Free One-Pot Alkynylation–Cyclization Sequence for the Preparation of 2-Substituted 7-Azaindoles
  作者：Thomas Müller、Timo Lessing、Fabian Sterzenbach

  DOI：10.1055/s-0034-1379907

  日期：——

  2-Substituted 7-azaindoles are rapidly and efficiently prepared in a one-pot copper-free alkynylation-cyclization sequence starting from 2-aminopyridyl halides and terminal alkynes. Most importantly the amino nitrogen atom neither requires activation nor protection throughout the sequence.
• [EN] BENZYL PIPERIDINE COMPOUNDS AS LYSOPHOSPHATIDIC ACID (LPA) RECEPTOR ANTAGONIST<br/>[FR] COMPOSÉS DE BENZYLPIPÉRIDINE UTILISÉS COMME ANTAGONISTES DES RÉCEPTEURS À L'ACIDE LYSOPHOSPHATIDIQUE (LPA)
  申请人：MERCK PATENT GMBH

  公开号：WO2013045028A9

  公开（公告）日：2014-12-24
• Lui, Shi-Feng; Wu, Qingguo; Schmider, Hartmut L., Journal of the American Chemical Society, 2000, vol. 122, p. 3671 - 3678
  作者：Lui, Shi-Feng、Wu, Qingguo、Schmider, Hartmut L.、Aziz, Hany、Hu, Nan-Xing、et al.

  DOI：——

  日期：——
• BENZYL PIPERIDINE COMPOUNDS AS LYSOPHOSPHATIDIC ACID (LPA) RECEPTOR ANTAGONIST
  申请人：Merck Patent GmbH

  公开号：EP2844648B1

  公开（公告）日：2016-11-09
• US9527850B2
  申请人：——

  公开号：US9527850B2

  公开（公告）日：2016-12-27