methyl 2-(4-methoxy)phenylquinoline-3-carboxylate | 115307-42-1

• 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: methyl 2-(4-methoxy)phenylquinoline-3-carboxylate
• 英文别名: methyl 2-(4-methoxyphenyl)-3-quinolinecarboxylate；methyl 2-(4-methoxyphenyl)quinoline-3-carboxylate
• CAS: 115307-42-1
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: ATTDYIBPCIYRLU-UHFFFAOYSA-N

物化性质

• 熔点：
  98-98.5 °C
• 沸点：
  454.3±45.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-nitrocinnamic acid 在 boron trifluoride methanol complex 、 magnesium sulfate 、 氯化铵 、 sodium sulfate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 112.0h， 生成 methyl 2-(4-methoxy)phenylquinoline-3-carboxylate
  参考文献：
  名称：

  A convenient synthesis of substituted quinolines by thermal electrocyclic rearrangement of o-vinyl anils under nonacidic conditions

  摘要：

  DOI：

  10.1021/jo00253a011

文献信息

• FeCl3-promoted formation of C–C bonds: synthesis of substituted quinolines from imines and electron-deficient alkynes
  作者：Yu-feng Li、Zheng-guang Wu、Jie Shi、Yi Pan、Hong-zhong Bu、Hong-fei Ma、Jia-chao Gu、Hao Huang、Yao-zhu Wang、Lin Wu

  DOI：10.1016/j.tet.2014.05.051

  日期：2014.11

  An efficient method for the synthesis of substituted quinolines is described. By FeCl3-promoted C–C bond formation, 2,3-disubstituted and 2,3,4-trisubstituted quinolines were successfully synthesized from the reaction between imines and electron-deficient alkynes in good yields. The reaction can also be performed in a sequential three-component manner by using aromatic amines and aromatic aldehydes

  描述了一种合成取代喹啉的有效方法。通过FeCl 3促进的CC键形成，成功地从亚胺和电子不足的炔烃之间的反应中成功合成了2,3-二取代和2,3,4-三取代的喹啉。该反应还可以通过使用芳族胺和芳族醛代替相应的亚胺以连续的三组分方式进行。
• Controlled and Efficient Synthesis of Quinoline Derivatives from Morita–Baylis–Hillman Adducts by Palladium-Catalyzed Heck Reaction and Cyclization
  作者：Kodirajan Selvakumar、Kandapalam Lingam、Rama Varma、Veerappan Vijayabaskar

  DOI：10.1055/s-0034-1379938

  日期：——

  An efficient synthesis of 2,3-disubstituted quinoline derivatives from easily accessible (het)aryl-substituted Morita–Baylis–Hillman (MBH) adducts was achieved by an approach involving a palladium-catalyzed Heck reaction and cyclization. This strategy converts the MBH adducts into α-benzyl β-keto ester derivatives that can cyclize into the corresponding quinolines in good yields.

  通过涉及钯催化的 Heck 反应和环化的方法，实现了从易于获得的（杂）芳基取代的 Morita-Baylis-Hillman (MBH) 加合物有效合成 2,3-二取代喹啉衍生物。该策略将 MBH 加合物转化为 α-苄基 β-酮酯衍生物，该衍生物可以高产率环化成相应的喹啉。
• Zircon PrVO4: An Efficient Heterogeneous Catalyst for Tandem Oxidative Synthesis of 2,3-Disubstituted Quinoline Derivatives
  作者：Neetu Yadav、Gopalaiah Kovuru、Jyoti Pandey、Rajamani Nagarajan

  DOI：10.1039/d3dt00435j

  日期：——

  PrVO4 was also confirmed from electron microscopic and vibrational spectroscopic measurements. From XPS analysis, the existence of redox couplets Pr3+/Pr4+ and V4+/V5+ in PrVO4 was established. The catalytic utility of zircon PrVO4 for one-pot synthesis of 2,3-disubstituted quinolines through the oxidative tandem reaction of 2-aminobenzylalcohols with 1,3-dicarbonyl compounds has been demonstrated. This

  当前的研究解决了 PrVO 4中固有氧化还原对的使用，该 PrVO 4在锆石型结构中结晶以进行串联氧化转化。使用溶液燃烧合成法合成的单相PrVO 4在其PXRD图(SG I 4 1 / amd )中显示出四方锆石型结构。电子显微镜和振动光谱测量也证实了锆石 PrVO 4的四方对称性。XPS分析表明PrVO 4中存在氧化还原对Pr 3+ /Pr 4+和V 4+ /V 5+建立了。锆石 PrVO 4通过 2-氨基苄醇与 1,3-二羰基化合物的氧化串联反应一锅法合成 2,3-二取代喹啉的催化效用已得到证实。这种高效的方法在分子氧下进行，容忍不同的官能团，并以良好到极好的收率生产各种取代的喹啉衍生物。该工艺的重要特点是易于后处理、催化剂回收简单和可重复使用。
• Selective Co/Ti Cooperatively Catalyzed Biaryl Couplings of Aryl Halides with Aryl Metal Reagents
  作者：Jing Zeng、Kun Ming Liu、Xin Fang Duan

  DOI：10.1021/ol402599f

  日期：2013.10.18

  Various aryl bromides or chlorides, including those bearing a free COOH, OH, CONHR, and SO2NHR group, coupled with aryl magnesium or lithium reagents in the presence of 7.5 mol % CoCl2/15 mol % PBu3 and substoichiometric Ti(OEt)(4) (40 mol % to ArM) at room temperature in high yields with high chemo- and regioslectivity. This simple reaction represents the first example of Co/Ti cooperative catalysis which plays a key role in suppressing undesired homocouplings.
• Polythiophene-Encapsulated Bimetallic Au-Fe₃O₄ Nano-Hybrid Materials: A Potential Tandem Photocatalytic System for Nondirected C(sp²)–H Activation for the Synthesis of Quinoline Carboxylates
  作者：Mandeep Kaur、Subhamay Pramanik、Manoj Kumar、Vandana Bhalla

  DOI：10.1021/acscatal.6b02681

  日期：2017.3.3

  Hetero-oligophenylene derivative 3 appended with thiophene moieties has been designed and synthesized which undergoes aggregation to form J-typefluorescent aggregates in in H2O/THF (7/3) media. These aggregates served as reactors for the preparation of bimetallic Au-Fe3O4 NPs. During the reduction process, aggregates of derivative 3 were oxidized to the polythiophene species 4. Interestingly, the polythiophene species 4, having a fibrous morphology, served as a shape-and morphology-directed template for assembly of bimetallic Au-Fe3O4 NPs in a flower-like arrangement. Furthermore, polythiophene-encapsulated bimetallic 4:AuFe3O4 nanohybrid materials served as an efficient and recyclable catalytic system for C(sp(2)) H bond activation of unprotected electron-rich anilines for the construction of synthetically versatile quinoline carboxylates via C H activation, carbonylation, and subsequent annulation under mild and eco-friendly conditions (aqueous media, room temperature, visible-light irradiation, and aerial conditions).