5-chloro-2-(2'-pyridyl)indole | 475993-68-1

• 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: 5-chloro-2-(2'-pyridyl)indole
• 英文别名: 5-chloro-2-(pyridin-2-yl)-indole；5-chloro-2-pyridin-2-yl-1H-indole
• CAS: 475993-68-1
• 化学式: C₁₃H₉ClN₂
• 分子量: 228.681
• InChiKey: RRIKQUALGYFGPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 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：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(2'-pyridyl)indole 、 三苯基硼烷 以 甲苯 为溶剂， 以50%的产率得到5-Chloro-16,16-diphenyl-1-aza-15-azonia-16-boranuidatetracyclo[7.7.0.02,7.010,15]hexadeca-2(7),3,5,8,10,12,14-heptaene
  参考文献：
  名称：

  Tuning the Luminescence and Electroluminescence of Diphenylboron Complexes of 5-Substituted 2-(2‘-Pyridyl)indoles

  摘要：

  To examine the effect of substituent groups on the luminescence of BPh2(X-2-PI) complexes, three new air-stable boron complexes BPh2(F-2-PI) (5a), BPh2(Cl-2-PI) (5b), and BPh2(CH3O2-PI) (5c) were synthesized and characterized, where F-2-PI = 5-fluoro-2-(2'-pyridyl)indole, Cl-2-PI = 5-chloro-2-(2'-pyridyl)indole, and CH3O-2-PI = 5-methoxyl-2-(2'-pyridyl)indole. In these complexes, the 5-substituted 2-PI ligand chelates in a tretrahedral fashion to the boron center. Compounds 5a-c are luminescent, with 5a having the highest emission efficiency. Compared with the emission maximum of BPh2(2-PI) (516 nm), the emission maximum of 5a and 5b is blue-shifted to 490 and 487 nm, respectively, while the emission of 5c is red-shifted to 532 nm, indicating the possibility of tuning the luminescence of these complexes by varying the substituent groups on the 2-PI ligand. An electroluminescent device using compound 5a as the emitter and the electron transport material has been fabricated.

  DOI：

  10.1021/om020446j
• 作为产物：
  描述：

  2-acetylpyridine-para-chlorophenylhydrazone 在 PPA 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.67h， 以57%的产率得到5-chloro-2-(2'-pyridyl)indole
  参考文献：
  名称：

  3-乙烯基吲哚对吡啶并[2,3- a ]-，吡啶并[4,3- a ]-和噻吩并[2,3- a ]-咔唑的光化学电环化：设计，合成，DNA结合和抗肿瘤细胞毒性

  摘要：

  在DNA配体的设计和合成过程中，合成了一些新的戊烯退火的咔唑。作为铅结构，考虑了插入的四环体系吡啶并[2,3- a ]-和吡啶并[4,3- a ]-咔唑，在一种情况下考虑了噻吩并[2,3- a ]-咔唑。将二烷基氨基酰胺链引入平面发色体系，目的是产生较小的凹槽结合性能。通过NCI抗肿瘤筛选检查了某些化合物的细胞毒性。此外，进行了生物物理和生化研究，以便获得有关此新系列分子的DNA结合特性和对DNA相关功能酶的抑制作用的一些信息。

  DOI：

  10.1016/j.ejmech.2009.03.026

文献信息

• Photochemical electrocyclisation of 3-vinylindoles to pyrido[2,3-a]-, pyrido[4,3-a]- and thieno[2,3-a]-carbazoles: Design, synthesis, DNA binding and antitumor cell cytotoxicity
  作者：Thomas Lemster、Ulf Pindur、Gaelle Lenglet、Sabine Depauw、Christelle Dassi、Marie-Hélène David-Cordonnier

  DOI：10.1016/j.ejmech.2009.03.026

  日期：2009.8

  In the context of the design and synthesis of DNA ligands, some new hetarene annelated carbazoles were synthesized. As lead structure the intercalating tetracyclic systems pyrido[2,3-a]- and pyrido[4,3-a]-carbazoles and in one case a thieno[2,3-a]-carbazole were taken into account. A dialkyl amino amidic chain was introduced to the planar chromophoric system with the intent to generate minor groove

  在DNA配体的设计和合成过程中，合成了一些新的戊烯退火的咔唑。作为铅结构，考虑了插入的四环体系吡啶并[2,3- a ]-和吡啶并[4,3- a ]-咔唑，在一种情况下考虑了噻吩并[2,3- a ]-咔唑。将二烷基氨基酰胺链引入平面发色体系，目的是产生较小的凹槽结合性能。通过NCI抗肿瘤筛选检查了某些化合物的细胞毒性。此外，进行了生物物理和生化研究，以便获得有关此新系列分子的DNA结合特性和对DNA相关功能酶的抑制作用的一些信息。
• Synthesis, characterization and photophysical study of a series of neutral isocyano rhodium(I) complexes with pyridylindolide ligands
  作者：Wing-Kin Chu、Larry Tso-Lun Lo、Shek-Man Yiu、Chi-Chiu Ko

  DOI：10.1016/j.jorganchem.2011.06.032

  日期：2011.10

  Pyridylindole ligand and its chloro substituted derivatives have been synthesized and incorporated into the square planar bis(phenylisocyano) rhodium(I) complexes to give a series of neutral rhodium(I) complexes with general formula of [Rh(X-pyind)(CNR)2] (R = 2,6-(CH3)2-4-BrC6H2, 2,4-Cl2-6-(CH3O)C6H2, 2,4,6-Br3C6H2, 2,4,6-Cl3C6H2; L = 2-(2′-pyridyl)indole, 5-chloro-2-(2′-pyridyl)indole, 4,6-dichl

  合成了吡啶基吲哚配体及其氯取代的衍生物，并将其掺入方形平面双（苯基异氰基）铑（I）配合物中，得到一系列通式为[Rh（X-pyind）（CNR）的中性铑（I）配合物2〕（R = 2,6-（CH 3）2 -4-BRC 6 ħ 2，2,4-CL 2 -6（CH 3 ℃）6 ħ 2，2,4,6-溴3 ç 6 ħ 2，2,4,6-氯3 c ^ 6 ħ 2; L ＝ 2-（2′-吡啶基）吲哚，5-氯-2-（2′-吡啶基）吲哚，4，6-二氯-2-（2′-吡啶基）吲哚）。两种络合物前体[Rh（cod）（Cl-pyind）]和[Rh（cod）（Cl 2 pyind）]和目标络合物[Rh（pyind）（CNC 6 H 2 -2,4-Cl）的结构通过X射线晶体学测定2 -6-（OCH 3））2 ]。还研究了这些配合物的紫外可见吸收特性及其对温度变化的响应。
• Cerium(III)-catalyzed C3-acylation of indoles with nitroolefins
  作者：Cheng-Tao Feng、Hui-Zhi Zhu、Zhong Li、Zaigang Luo、Song-Song Wu、Shi-Tang Ma

  DOI：10.1016/j.tetlet.2016.01.029

  日期：2016.2

  A novel and efficient cerium(III)-catalyzed C3-selective acylation of N–H indoles using nitroolefins as acylating reagents was first developed. It was found that the use of CeCl3 as a catalyst achieves an unexpected and highly efficient C–C bond cleavage.

  首次开发了一种新型高效的铈（III）催化的硝基苯吲哚的C3选择性C3选择性酰化反应，该反应使用硝基烯烃作为酰化试剂。发现使用CeCl 3作为催化剂可实现意想不到且高效的C–C键裂解。
• Olefin Hydroarylation Catalyzed by (pyridyl-indolate)Pt(II) Complexes: Catalytic Efficiencies and Mechanistic Aspects
  作者：Benjamin A. Suslick、Allegra L. Liberman-Martin、Truman C. Wambach、T. Don Tilley

  DOI：10.1021/acscatal.7b01560

  日期：2017.7.7

  A series of Pt(II) complexes of the type (N–N)PtPh(SR2) (N–N = 2,2′-pyridyl-indolate) were prepared, and their performance as catalysts for the hydroarylation of olefins was assessed. Evidence that the catalysis is homogeneous and is Pt-mediated is provided by control experiments with added hindered base (2,6-di-tert-butyl-4-methylpyridine) and Hg(0). Two potential catalytic intermediates, (tBuPyInd)PtPh(C2H4)

  制备了一系列（N–N）PtPh（SR 2）（N–N = 2,2'-吡啶基-吲哚酸酯）类型的Pt（II）配合物，并评估了它们作为烯烃加氢芳基化反应的催化剂的性能。 。对照实验提供了添加受阻碱（2,6-二叔丁基-4-甲基吡啶）和Hg（0）的证据，证明了催化是均相的并且是Pt介导的。两种潜在的催化中间体（t BuPyInd）PtPh（C 2 H 4）和（t BuPyInd）Pt（CH 2 CH 2 Ph）（C 2 H 4），合成，并探索其催化功效。此外，还确定了分解和失活途径，包括通过β-氢化物消除和配体还原性脱金属形成苯乙烯。
• Tuning the Luminescence and Electroluminescence of Diphenylboron Complexes of 5-Substituted 2-(2‘-Pyridyl)indoles
  作者：Qinde Liu、Maria S. Mudadu、Hartmut Schmider、Randolph Thummel、Ye Tao、Suning Wang

  DOI：10.1021/om020446j

  日期：2002.10.1

  To examine the effect of substituent groups on the luminescence of BPh2(X-2-PI) complexes, three new air-stable boron complexes BPh2(F-2-PI) (5a), BPh2(Cl-2-PI) (5b), and BPh2(CH3O2-PI) (5c) were synthesized and characterized, where F-2-PI = 5-fluoro-2-(2'-pyridyl)indole, Cl-2-PI = 5-chloro-2-(2'-pyridyl)indole, and CH3O-2-PI = 5-methoxyl-2-(2'-pyridyl)indole. In these complexes, the 5-substituted 2-PI ligand chelates in a tretrahedral fashion to the boron center. Compounds 5a-c are luminescent, with 5a having the highest emission efficiency. Compared with the emission maximum of BPh2(2-PI) (516 nm), the emission maximum of 5a and 5b is blue-shifted to 490 and 487 nm, respectively, while the emission of 5c is red-shifted to 532 nm, indicating the possibility of tuning the luminescence of these complexes by varying the substituent groups on the 2-PI ligand. An electroluminescent device using compound 5a as the emitter and the electron transport material has been fabricated.