2,3-dihydro-1H-cyclopenta[c]quinoline | 65733-51-9

• 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: 2,3-dihydro-1H-cyclopenta[c]quinoline
• 英文别名: 2,3-dihydro-1H-cyclopenta[c]quinoline；2,3-Dihydro-1H-cyclopenta[c]chinolin；2,3-Dihydro-1H-cyclopentachinolin
• CAS: 65733-51-9
• 化学式: C₁₂H₁₁N
• mdl: MFCD18803392
• 分子量: 169.226
• InChiKey: MEYVKMHZYZXWHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2,3-dihydro-1H-cyclopenta[c]quinoline 、 碘甲烷 生成 5-methyl-2,3-dihydro-1H-cyclopenta[c]quinolin-5-ium;iodide
  参考文献：
  名称：

  EISCH J. J.; GOPAL H.; KUO C. T., J. ORG. CHEM., 1978, 43, NO 11, 2190-2196

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴环戊烯-1-甲醛 在 palladium on activated charcoal 、 tris(dibenzylideneacetone)dipalladium (0) 氢气 、 铜 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 18.0~80.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 2,3-dihydro-1H-cyclopenta[c]quinoline
  参考文献：
  名称：

  Synthesis of Quinolines, 2-Quinolones, Phenanthridines, and 6(5H)-Phenanthridinones via Palladium[0]-Mediated Ullmann Cross-Coupling of 1-Bromo-2-nitroarenes with β-Halo-enals, -enones, or -esters

  摘要：

  Palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitrobenzene (1 R = H) and its derivatives with a range of beta-halo-enals, -enones, or -esters readily affords the corresponding beta-aryl derivatives, which are converted into the corresponding quinolines, 2-quinolones, phenanthridines, or 6(5H)-phenanthridinones on reaction with dihydrogen in the presence of Pd on C or with TiCl3 in aqueous acetone.

  DOI：

  10.1021/ol0490375

文献信息

• Aerobic oxidative dehydrogenation of N-heterocycles over OMS-2-based nanocomposite catalysts: preparation, characterization and kinetic study
  作者：Xiuru Bi、Tao Tang、Xu Meng、Mingxia Gou、Xiang Liu、Peiqing Zhao

  DOI：10.1039/c9cy01968e

  日期：——

  aerobic oxidative dehydrogenation of N-heterocycles were examined in detail. Many tetrahydroquinoline derivatives and a broad range of other N-heterocycles could be tolerated by the catalytic system using a biomass-derived solvent as a reaction medium. Newly generated mixed crystal phases, noticeably enhanced surface areas and labile lattice oxygen of the OMS-2-based nanocomposite catalysts might contribute

  首次制备了掺有钨的基于OMS-2的纳米复合材料，并详细研究了它们在N杂环的好氧氧化脱氢中的显着增强的催化活性和可回收性。使用生物质衍生的溶剂作为反应介质的催化体系可以耐受许多四氢喹啉衍生物和各种其他N-杂环。OMS-2基纳米复合催化剂的新生成的混合晶体相，显着增加的表面积和不稳定的晶格氧可能有助于其出色的催化性能。此外，进行了广泛的动力学研究，得出的结论是1,2,3,4-四氢喹啉的脱氢是一级反应，表观活化能为29.66 kJ mol -1。
• MnOx/catechol/H2O: A cooperative catalytic system for aerobic oxidative dehydrogenation of N-heterocycles at room temperature
  作者：Tao Tang、Xiuru Bi、Xu Meng、Gexin Chen、Mingxia Gou、Xiang Liu、Peiqing Zhao

  DOI：10.1016/j.tetlet.2019.151425

  日期：2020.1

  Amorphous manganese oxide doped by Na+ ion (Na-AMO) was successfully prepared and found to be an efficient heterogeneous catalyst in aerobic oxidative dehydrogenation of N-heterocycles, cooperate with catachol. Na-AMO was fully characterized by XRD, XPS BET H2-TPR, CO2-TPD FT-IR, TEM, SEM and had rich amounts of surface absorbed active oxygen species which are responsible for superior catalytic performance

  成功制备了Na +离子掺杂的无定形锰氧化物（Na-AMO），发现它是N-杂环好氧氧化脱氢的有效多相催化剂，与催化裂化反应配合使用。Na-AMO通过XRD，XPS BET H 2 -TPR，CO 2 -TPD FT-IR，TEM，SEM进行了全面表征，并具有大量的表面吸收活性氧，这些都具有优异的催化性能。Na-AMO和邻苯二酚之间的协同相互作用使催化系统高效且具有耐受性，在温和条件下，该系统可提供各种N-杂环化合物，收率好至极佳。
• Substituted 1,10-Phenanthrolines. IX. Cycloalkeno Derivatives¹
  作者：FRANCIS H. CASE

  DOI：10.1021/jo01116a005

  日期：1956.10
• New protocols for the synthesis of 3,4-annulated and 4-substituted quinolines from β-bromo-α,β-unsaturated aldehydes and 1-bromo-2-nitrobenzene or 2-bromoacetanilide
  作者：Surajit Some、Jayanta K. Ray、Martin G. Banwell、Matthew T. Jones

  DOI：10.1016/j.tetlet.2007.03.078

  日期：2007.5

  The palladium[0]-mediated Ullmann cross-coupling of readily available beta-bromo-alpha,beta-unsaturated aldehydes of the general form 2 with 1-bromo-2-nitrobenzene (3, X = Br) delivers products, 4, that undergo reductive cyclization to novel quinolines (5) upon exposure to indium in aqueous ammonium chloride or to Raney-nickel in the presence of dihydrogen. Analogous cross-coupling of 2-bromoacetanilide (6) with 2 affords products of type 7 that undergo in situ and K2CO3-mediated cyclization to give the same types of quinolines (5). (C) 2007 Elsevier Ltd. All rights reserved.