10-vinylbenzo[h]-quinoline | 1203589-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 10-vinylbenzo[h]-quinoline
• 英文别名: 10-Ethenylbenzo[h]quinoline
• CAS: 1203589-74-5
• 化学式: C₁₅H₁₁N
• 分子量: 205.259
• InChiKey: QARIJRQQBMOWQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Umicore M31 、 10-vinylbenzo[h]-quinoline 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 dichloro-((κ²(C,N)-(2-(benzo[h]quinolin-10-yl)methylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene))Ru
  参考文献：
  名称：

  Variation of the Sterical Properties of the N-Heterocyclic Carbene Coligand in Thermally Triggerable Ruthenium-Based Olefin Metathesis Precatalysts/Initiators

  摘要：

  A series of ruthenium complexes based on the kappa(2)( C,N) - (2- (benzo [h] quinolin-10-yl)methylidene ruthenium dichloride fragment featuring different neutral coligands L (L = 1,3-bis (2,6-diis opropylp henyl) -4, S- dihydroimidazol-2-ylidene (SIPr), 1,3-bis(2,4,6-trimethylpheny1)-4,5-dihydroimidazol-2-ylidene (SIMcs), 1,3-bis(2,4-dimethylpheny1)-4,5-dihydroimidazol-2-ylidene (81Xyl), and 1,3-bis(2-methylpheny1)4,5-dihydroimidazol-2-ylidene (SITO1)) was prepared, characterized, and tested in the thermally induced ring-opening metathesis polymerization of dicydopentadiene. In addition, the corresponding tricydohe#1phosphine derivative was investigated for comparison. All compounds were isolated as their trans-clichloro isomers. NMR spectroscopic features as well as structural features are, particularly within the NHC-bearing complexes, very similar, but their polymerization activity at elevated temperatures is distinctly different. While the SIMes derivatiie shows the desired properties, i.e., latency at room temperature and pronouneed polymerization activity at elevated temperature, 'all other preinitiators do not. The preinitiator featuring the SIPr coligarid is the most latent one, needing temperatures > 140 degrees C to show moderate: activity in the polymerization of dicydopentadiene. Compounds bearing the smaller N-heterocyclic carbene congeners are stable and latent at room temperature, but decompose upon heating, diminishing the polymerization activity at elevated temperatures. Density functional calculations show that the SIMes -derivative is the easiest to activate and yields the most stable 14-electron intermediate. Finally calculations reveal a distinct influence of the nature Of the N-heterocyclic carbene ligand on the position of the equilibrium of cis- and trans-dichloro isbrhers of the Complexes. -While the SLPr and the SIMes derivatives prefer the cisconfiguration, all other derivatives favor, at least in solvents with low dielectric constants, the trans-configuration. These computational findings were supported by the isolation and full characterization of the cis-dichloro isomer of the SIMes-bearing preinitiator obtained upon heating of its trans-isomer at 140 degrees C.

  DOI：

  10.1021/acs.organomet.5b00715
• 作为产物：
  描述：

  7,8-苯并喹啉 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 palladium diacetate 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 58.0h， 生成 10-vinylbenzo[h]-quinoline
  参考文献：
  名称：

  钯催化的羰基化环化反应，可通过将芳族C═N键正式插入Pd-酰基键实现。

  摘要：

  通过还原消除和氧化加成序列的组合，一种有效的新形式插入策略被报道，其中通过烃基化形成的瞬态N-酰基亚胺离子起关键中间体的作用。该策略通过将C═C键，CO和C bondN键顺序插入氢化钯键中，使新颖的钯催化的氮杂芳烃系链烯烃或二烯的烃基化环化反应成为可能。该方法为具有扩展的π-共轭体系，具有可调的发射波长和良好的光致发光能力的喹喔啉酮及其衍生物提供了一种新的高效合成方法。

  DOI：

  10.1021/acs.orglett.9b03503

文献信息

• Triorganoindium Reagents in Rh-Catalyzed C–H Activation/C–C Cross-Coupling Reactions of 2-Arylpyridines
  作者：Ricardo Riveiros、Rubén Tato、José Pérez Sestelo、Luis Sarandeses

  DOI：10.3390/molecules23071582

  日期：——

  catalytic reactions using transition metals is an important challenge in organic chemistry in which the intermediates are related to those produced in the classical cross-coupling reactions. As part of our research program devoted to the development of metal-catalyzed reactions using indium organometallics, a protocol for the C⁻H activation and C⁻C coupling of 2-arylpyridines with triorganoindium reagents

  通过使用过渡金属的催化反应来活化C⁻H键是有机化学中的重要挑战，在有机化学中，中间体与经典交叉偶联反应中产生的中间体有关。作为我们致力于开发使用铟有机金属的金属催化反应的研究计划的一部分，据报道，在Rh（I）催化下，2-芳基吡啶与三有机铟试剂进行C⁻H活化和C⁻C偶联的方案。在优化的条件下，我们发现Me₃In和Ar₃In试剂在Rh（PPh₃）：Cl的存在下于PhCl / THF（9：1）中与2-芳基吡啶和相关化合物在120°C下反应48小时，得到中等产量的邻偶合产物。
• Rhodium-Catalyzed Direct C-H Vinylation of Arenes To Access Styrenes with Vinyl Acetate as a Vinyl Source
  作者：Shu-Tao Mei、Kun Jiang、Nan-Jin Wang、Li Shuai、Yi Yuan、Ye Wei

  DOI：10.1002/ejoc.201500945

  日期：2015.10

  RhIII-catalyzed aryl C–H vinylation for the preparation of styrenes by using vinyl acetate, a commercially available and inexpensive compound, as the vinyl source was successfully realized. This method enables various aromatics including N-sulfonyl ketimines, pyridines, azoles, and amides to be vinylated in moderate to good yields.

  RhIII 催化芳基 C-H 乙烯基化，以醋酸乙烯酯（一种市售且廉价的化合物）作为乙烯基源制备苯乙烯。该方法能够以中等至良好的收率对包括 N-磺酰基酮亚胺、吡啶、唑类和酰胺在内的各种芳烃进行乙烯基化。
• Latent Thermo-Switchable Olefin Metathesis Initiators Bearing a Pyridyl-Functionalized Chelating Carbene: Influence of the Leaving Group’s Rigidity on the Catalyst’s Performance
  作者：Anna Szadkowska、Xaver Gstrein、Daniel Burtscher、Katarzyna Jarzembska、Krzysztof Woźniak、Christian Slugovc、Karol Grela

  DOI：10.1021/om900857w

  日期：2010.1.11

  The synthesis and characterization of two ruthenium complexes bearing chelating carbene ligands is described. Carbene precursors, 2-(2-vinylphenyl)pyridine and 10-vinylbenzo[h]quinoline, are applied to prepare (SPY-5-31)-dichloro-(κ2(C,N)-N-2-(2-vinylbenzylidene)pyridine(1,3-bis(2,4,6-trimethylphenyl)4,5-dihydroimidazol-2-ylidene)ruthenium (VIII) and (SPY-5-31)-dichloro-(κ2(C,N)-2-(benzo[h]quinoli

  描述了带有螯合卡宾配体的两种钌配合物的合成和表征。卡宾前体，2-（2-乙烯基苯基）吡啶和10乙烯基苯并[ ħ ]喹啉，被施加到制备（SPY-5-31） -二氯- （κ 2（C，N）-N-2-（2- vinylbenzylidene）吡啶（1,3-双（2,4,6-三甲基苯基）-4,5-二氢咪唑-2-亚基）钌（VIII）和（SPY-5-31） -二氯- （κ 2（C，N ）-2-（苯并[ h ]喹啉-10-基）亚甲基）（1,3-双（2,4,6-三甲基苯基）4,5-二氢咪唑-2-亚烷基）钌（IX）。两种催化剂/引发剂均用于进行开环复分解（RCM）和开环复分解聚合（ROMP）。RCM实验表明，在强迫反应条件下（如甲苯沸腾48小时），催化剂具有显着的热稳定性。甚至具有挑战性的底物，例如二乙基烯丙基（2-甲基烯丙基）丙二酸酯也可以在低催化剂负载下（在110°C时为0.1 mol％）完全转化。高的热稳定
• Directed C−H Activation and Tandem Cross-Coupling Reactions Using Palladium Nanocatalysts with Controlled Oxidation
  作者：Kiseong Kim、Younjae Jung、Suyeon Lee、Mijong Kim、Dongwoo Shin、Hyeeun Byun、Sung June Cho、Hyunjoon Song、Hyunwoo Kim

  DOI：10.1002/anie.201700301

  日期：2017.6.6

  palladium nanoparticles provided high‐valent PdIV oxo‐clusters which efficiently promote directed C−H halogenation reactions. In addition, palladium nanoparticles can undergo changes in oxidation states to provide both high‐valent PdIV and low‐valent Pd0 species within one system, and thus a tandem reaction of C−H halogenation and cross‐coupling (C−N, C−C, and C−S bond formation) was successfully established

  钯纳米颗粒的可控氧化提供了高价的Pd IV氧簇，可有效促进定向的CH卤化反应。此外，钯纳米粒子可能会经历氧化态的变化，从而在一个系统中同时提供高价Pd IV和低价Pd 0物种，因此发生了CH卤化和交叉偶联（C，N，C -C和C-S键的形成已成功建立。