2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)quinoline | 917471-42-2

• 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-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)quinoline
• 英文别名: 2-(2,3-Dihydro-1,4-benzodioxin-6-yl)quinoline
• CAS: 917471-42-2
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: LNGSANHXKPZUQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-nitroquinoline 在 盐酸 、 tin 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以76%的产率得到2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)quinoline
  参考文献：
  名称：

  An unusual de-nitro reduction of 2-substituted-4-nitroquinolines

  摘要：

  The treatment of a variety of 2-substituted-4-nitroquinolines with Sn in the presence of concentrated hydrochloric acid in ethanol at 70 degrees C for 2-4 h afforded unusual de-nitro products 2-substituted-quinolines in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.140

文献信息

• Catalytic Arylation of a CH Bond in Pyridine and Related Six-Membered N-Heteroarenes Using Organozinc Reagents
  作者：Isao Hyodo、Mamoru Tobisu、Naoto Chatani

  DOI：10.1002/asia.201100971

  日期：2012.6

  Despite significant advances in the catalytic direct arylation of heteroarenes, the application of this reaction to pyridines has been met with limited success. An oxidative nucleophilic arylation strategy has been developed to overcome this problem. Pyridine, pyrazine, quinolone, and related electron‐deficient N‐heteroarenes can be arylated at the most electrophilic site using the developed nickel‐catalyzed

  尽管在杂芳烃的催化直接芳基化方面取得了重大进展，但该反应在吡啶上的应用却取得了有限的成功。为了克服该问题，已经开发了一种氧化亲核芳基化策略。吡啶，吡嗪，喹诺酮和相关的电子不足的N-杂芳烃可以通过发达的镍催化反应在最亲电的位置被芳基化。该协议可作为催化直接芳基化反应的补充方法。
• π‐Allylpalladium Species in Micelles of FI‐750‐M for Sustainable and General Suzuki‐Miyaura Couplings of Unactivated Quinoline Systems in Water
  作者：Sachin Handa、Faisal Ibrahim、Tharique N. Ansari、Fabrice Gallou

  DOI：10.1002/cctc.201800958

  日期：2018.10.9

  General, clean, and sustainable Suzuki‐Miyaura cross‐couplings of 2‐and 4‐quinoline and isoquinoline systems have been demonstrated with use of π‐allyl Pd catalyst in the nanomicelles of environmentally benign, proline‐derived surfactant FI‐750‐M. Optimized reaction conditions mostly provided good‐to‐excellent yields up to gram‐scale with high selectivity and functional group tolerance. Control studies

  在环境友好的脯氨酸衍生表面活性剂FI-750-M的纳米胶束中使用π-烯丙基Pd催化剂已证明，2-，4-喹啉和异喹啉体系具有常规，清洁和可持续的Suzuki-Miyaura交叉偶联。优化的反应条件主要提供了高达克级的良好至优异的收率，高选择性和官能团耐受性。对照研究表明，该催化剂在FI‐750‐M中具有长期稳定性。催化剂和胶束反应介质均已再循环。纳米胶束的行为已通过DLS和冷冻TEM测量得以阐明，并且机理研究表明，喹啉氮与钯的可逆结合竞争性地抑制了反应速率。
• Organometal-Free Arylation and Arylation/Trifluoroacetylation of Quinolines by Their Reaction with CF₃-ynones and Base-Induced Rearrangement
  作者：Vasiliy M. Muzalevskiy、Kseniya V. Belyaeva、Boris A. Trofimov、Valentine G. Nenajdenko

  DOI：10.1021/acs.joc.0c01277

  日期：2020.8.7

  The reaction of quinolines with CF3-ynones resulted in the formation of 1,3-oxazinoquinolines. Subsequent treatment of the reaction mixture with a base initiated deep structural transformation of primary products. Both steps proceed in very high yield. As a result, unusual rearrangement of 1,3-oxazinoquinolines to form either 2-arylquinolines or 2-aryl-3-trifluoroacetylquinolines was discovered. The

  喹啉与CF 3-炔酮的反应导致形成1，3-恶嗪基喹啉。用碱对反应混合物的后续处理引发了初级产物的深度结构转化。这两个步骤都以很高的产率进行。结果，发现了1，3-恶嗪基喹啉的异常重排以形成2-芳基喹啉或2-芳基-3-三氟乙酰基喹啉。显示了碱在反应方向上的决定性作用。使用这些反应，通过简单的一锅法，精心设计了通往2-芳基喹啉和2-芳基-3-三氟乙酰基喹啉的高效途径，以高收率提供了相应的化合物。讨论了可能的重排机制。
• [EN] PHOSPHORESCENT MATERIALS<br/>[FR] MATÉRIAUX PHOSPHORESCENTS
  申请人：UNIVERSAL DISPLAY CORP

  公开号：WO2012064499A1

  公开（公告）日：2012-05-18

  Compounds comprising a ligand having a quinoline or isoquinoline moiety and a phenyl moiety, e.g., (iso)pq ligands. In particular, the ligand is further substituted with electron donating groups. The compounds may be used in organic light emitting devices, particularly devices with emission in the deep red part of the visible spectrum, to provide devices having improved properties.
• An unusual de-nitro reduction of 2-substituted-4-nitroquinolines
  作者：Yu Zhou、Jian Li、Hong Liu、Linxiang Zhao、Hualiang Jiang

  DOI：10.1016/j.tetlet.2006.09.140

  日期：2006.11

  The treatment of a variety of 2-substituted-4-nitroquinolines with Sn in the presence of concentrated hydrochloric acid in ethanol at 70 degrees C for 2-4 h afforded unusual de-nitro products 2-substituted-quinolines in good yields. (c) 2006 Elsevier Ltd. All rights reserved.