4-methyl-2,3-dihydrofuro[2,3-b]quinoline | 49664-53-1

• 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: 4-methyl-2,3-dihydrofuro[2,3-b]quinoline
• 英文别名: 4-methyl-2,3-dihydro[2,3-b]quinoline；furoquinoline；4-methyl-2,3-dihydro-furo[2,3-b]quinoline；4-Methyl-2,3-dihydro-furo[2,3-b]chinolin；4-Methyl-2,3-dihydro-furo<2.3-b>chinolin；4-Methyl-2,3:2',3'-dihydro-furano-chinolin
• CAS: 49664-53-1
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: BGVLSDUMLSASEB-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C
• 沸点：
  347.7±21.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 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：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-acetyl-N-phenylcyclopropanecarboxamide 在 tin (IV) chloride pentahydrate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 4-methyl-2,3-dihydrofuro[2,3-b]quinoline
  参考文献：
  名称：

  Facile synthesis of furoquinoline and effects on radical-induced oxidation of DNA

  摘要：

  The aim of this work was to clarify the influences of the position of hydroxyl group and furo[2,3-b] moiety on the antioxidant effectiveness of quinoline. Thus, 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-6-ol (PFQ), 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-8-ol (OFQ), and 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-7-ol (MFQ) were synthesized by a recyclization reaction of 1-acetyl-N-phenylcyclopropanecarboxamide in the presence of SnCl4 as the catalyst. The antioxidant capacities of PFQ, OFQ, and MFQ were evaluated in the experimental system of the oxidation of DNA caused by Cu2+/glutathione (GSH), (OH)-O-aEuro cent, and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH). OFQ and PFQ were able to protect DNA against Cu2+/GSH- and (OH)-O-aEuro cent-induced oxidation because the furo[2,3-b] moiety was beneficial for stabilizing the produced furoquinoline radical. Moreover, MFQ can decrease the oxidation rate of AAPH-induced oxidation of DNA, while PFQ and OFQ can inhibit AAPH-induced oxidation of DNA for a period. The data obtained from AAPH-induced oxidation of DNA were treated by chemical kinetic method; it was found that PFQ and OFQ can trap 1.3 and 1.5 radicals, respectively. Therefore, the hydroxyl group at different positions changed the mechanism of furoquinoline in protecting DNA against radical-induced oxidation.Effects on Cu2+/glutathione-, (OH)-O-aEuro cent-, and peroxyl radical-induced oxidation of DNA.

  DOI：

  10.1007/s00044-012-0157-0

文献信息

• Thermally induced formal [3+2] cyclization of ortho-aminoaryl-tethered alkylidenecyclopropanes: facile synthesis of furoquinoline and thienoquinoline derivatives
  作者：Liu-Zhu Yu、Xu-Bo Hu、Qin Xu、Min Shi

  DOI：10.1039/c5cc09218c

  日期：——

  A facile synthetic method to access furoquinoline and thienoquinoline derivatives has been disclosed via a thermal induced ring-opening and cyclization reaction from aniline-tethered alkylidenecyclopropanes with in situ generated isocyanates or...

  通过热诱导的开环和环化反应，由苯胺系链的亚烷基亚环丙烷与原位生成的异氰酸酯或环戊二烯反应，公开了一种简便的合成方法来获取呋喃喹啉和噻吩并喹啉衍生物。
• Copper-catalyzed C(sp)–H aryl amination enables modular synthesis of quinolines and 2-quinolinones
  作者：Yang Gao、Haixia Li、Simin Yang、Yanping Huo、Qian Chen、Xianwei Li、Zhe Wang、Xiao-Qiang Hu

  DOI：10.1007/s11426-023-1739-y

  日期：2024.2

  Herein, we disclose a novel copper-catalyzed C(sp)–H aryl amination of terminal alkynes with anthranils, enabling the rapid generation of highly reactive secondary N-aryl ynamines for the modular synthesis of structurally diverse C2-substituted quinolines and 2-quinolinones. The in-situ formed carbonyl-ynamines are prone to tautomerize to carbonyl-ketenimines, which can efficiently react with a series

  在此，我们公开了一种新型的铜催化末端炔烃与邻氨基苯酚的C(sp)-H芳基胺化反应，能够快速生成高反应性仲N-芳基炔胺，用于结构多样的C2取代喹啉和2-喹啉酮的模块化合成。原位形成的羰基烯胺易于互变异构为羰基烯酮亚胺，可与一系列亲核试剂，包括胺、醇、酚、硫醇、苯硫酚、活性亚甲基化合物，甚至水有效反应，生成各种喹啉衍生物，产生 H 2 O 作为唯一的绿色副产品。该方法还开辟了创建各种喹啉稠合杂环的实用途径，并可成功应用于复杂分子的后期修饰和生物活性靶标的简洁合成。机理研究揭示了使用邻氨基苯甲醚作为新型芳基氮烯前体的铜催化内球氮烯转移过程。
• 一种喹啉稠环衍生物的制备方法
  申请人：广东工业大学

  公开号：CN117003760A

  公开（公告）日：2023-11-07

  本专利申请提供了一种喹啉稠环衍生物的制备方法：在反应瓶中，加入含铜催化剂，配体以及碱作为促进剂，通入惰性气体，加入溶剂，依次加入氨茴内酐(式III)、末端炔醇或末端炔胺(式II)，在低于100℃的条件下，搅拌反应8‑18小时，反应结束后冷却至室温，反应液经过水洗，再通过乙酸乙酯萃取除去溶剂，无水硫酸镁干燥，纯化得到系列所述的喹啉稠环衍生物(式I)。本专利申请喹啉稠环衍生物的合成方法原料廉价、易得，操作安全、简单，对官能团适应性好，对底物适应性广，且环境友好有利于工业生产，在农药、医药及天然产物合成中应用潜力较大。
• Synthesis of Carbocyclic and Heterocyclic Fused Quinolines by Cascade Radical Annulations of Unsaturated <i>N</i>-Aryl Thiocarbamates, Thioamides, and Thioureas
  作者：Wu Du、Dennis P. Curran

  DOI：10.1021/ol0344319

  日期：2003.5.1

  [GRAPHICS]Tandem radical cyclizations of suitably substituted N-aryl thiocarbamates, thioamides, and thioureas are induced by exposure to tris(trimethylsilyl)silane (TTMSH) and UV light and provide furoquinolines, isofuroquinolines, cyclopentaquinolines, indoloquinollnes, and related ring systems. The intermediacy of an alpha-thioalkylamino radical, which is the synthetic equivalent of an imidoyl radical, is invoked.
• Domino Ring-Opening/Recyclization Reactions of Doubly Activated Cyclopropanes as a Strategy for the Synthesis of Furoquinoline Derivatives
  作者：Zhiguo Zhang、Qian Zhang、Shaoguang Sun、Tao Xiong、Qun Liu

  DOI：10.1002/anie.200604276

  日期：2007.2.26