5-Fluoro-2-(2-pyridyl)-indole | 80030-94-0

• 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-Fluoro-2-(2-pyridyl)-indole
• 英文别名: 5-fluoro-2-(2'-pyridyl)indole；5-Fluor-2-(2'-pyridyl)indol (Germ.)；5-Fluoro-2-(pyridin-2-yl)-1H-indole；5-fluoro-2-pyridin-2-yl-1H-indole
• CAS: 80030-94-0
• 化学式: C₁₃H₉FN₂
• mdl: MFCD05224234
• 分子量: 212.226
• InChiKey: CAFROQGRGCAGJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  2

反应信息

• 作为反应物：
  描述：

  5-Fluoro-2-(2-pyridyl)-indole 在 苄基三乙基氯化铵 sodium hydroxide 、 对甲苯磺酰叠氮 作用下， 以 苯 为溶剂， 反应 18.0h， 以80%的产率得到3-Diazo-5-fluoro-2-pyridin-2-yl-3H-indole
  参考文献：
  名称：

  Application of Phase-Transfer Catalysis to the Synthesis of 3-Diazo-3H-indoles

  摘要：

  DOI：

  10.1055/s-1981-29585
• 作为产物：
  描述：

  2-acetylpyridine 4-fluorophenylhydrazone 在 PPA 作用下， 反应 0.25h， 以68%的产率得到5-Fluoro-2-(2-pyridyl)-indole
  参考文献：
  名称：

  Application of Phase-Transfer Catalysis to the Synthesis of 3-Diazo-3H-indoles

  摘要：

  DOI：

  10.1055/s-1981-29585

文献信息

• 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。
• Formic Acid as Carbon Monoxide Source in the Palladium-Catalyzed N-Heterocyclization of <i>o</i>-Nitrostyrenes to Indoles
  作者：Manar Ahmed Fouad、Francesco Ferretti、Fabio Ragaini

  DOI：10.1021/acs.joc.2c02613

  日期：——

  generation of CO from nontoxic and affordable sources. Among several CO sources that have been previously explored for the generation of gaseous CO, here we report the use of cheap and readily available formic acid as an effective reductant for the reductive cyclization of o-nitrostyrenes. The reaction is air and water tolerant and provides the desired indoles in yields up to 99%, at a low catalyst loading

  使用 CO 作为廉价还原剂，研究了邻硝基苯乙烯生成吲哚的还原环化反应已有 30 年，但它仍然是一个有趣的研究和改进领域。然而，使用有毒的 CO 气体有几个缺点。因此，非常优选使用安全有效的替代品从无毒且负担得起的来源原位生成 CO。在先前探索用于产生气态 CO 的几种 CO 来源中，我们在此报告使用廉价且容易获得的甲酸作为有效还原剂，用于还原环化o-硝基苯乙烯。该反应具有空气和水耐受性，并以高达 99% 的收率提供所需的吲哚，催化剂负载量较低 (0.5 mol%)，并且不会产生有毒或难以分离的副产物。可以使用便宜的玻璃厚壁“压力管”代替较少可用的高压灭菌器，即使在 2 g 的规模上，从而扩大了我们协议的适用性。
• 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.
• Heilmann-Brohl, Julia; Schoedel, Frauke; Bolte, Michael, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2011, vol. 66, # 11, p. 1151 - 1160
  作者：Heilmann-Brohl, Julia、Schoedel, Frauke、Bolte, Michael、Wagner, Matthias、Lerner, Hans-Wolfram

  DOI：——

  日期：——