ethyl 5-(4-methoxyphenyl)-2-methylfuran-3-carboxylate | 62596-45-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 5-(4-methoxyphenyl)-2-methylfuran-3-carboxylate
• 英文别名: Ethyl 5-(4-methoxyphenyl)-2-methyl-3-furoate
• CAS: 62596-45-6
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: RMSHLICXMPLWJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-methoxyphenyl)-2-methylfuran-3-carboxylate 在 喹啉 、 copper oxide-chromium oxide 作用下， 生成 2-(4-甲氧基苯基)-5-甲基呋喃
  参考文献：
  名称：

  The Synthesis of 3-(p-Hydroxyphenyl)-cyclopentanone-1 and Related Compounds

  摘要：

  DOI：

  10.1021/ja01218a042
• 作为产物：
  描述：

  ethyl 1-(3-methoxyphenyl)-1,4-pentandione-3-carboxylate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以52%的产率得到ethyl 5-(4-methoxyphenyl)-2-methylfuran-3-carboxylate
  参考文献：
  名称：

  Porretta; Scalzo; Chimenti, Farmaco, Edizione Scientifica, 1987, vol. 42, # 5, p. 629 - 639

  摘要：

  DOI：

文献信息

• Cu(I)-catalyzed reaction of diazo compounds with terminal alkynes: a direct synthesis of trisubstituted furans
  作者：Mohammad Lokman Hossain、Fei Ye、Yan Zhang、Jianbo Wang

  DOI：10.1016/j.tet.2014.07.086

  日期：2014.9

  method for the synthesis of tri-substituted furans has been developed based on Cu(I)-catalyzed reaction of terminal alkynes with β-keto α-diazoesters. This method for the synthesis of 2,3,5-trisubstituted furans is operationally simple and applicable to wide substrate scope. Moreover, this synthesis employs cheap Cu(MeCN)4PF6 as the catalyst and no additional ligand is needed. Similar reaction has also been

  基于Cu（I）催化的末端炔烃与β-酮α-重氮酸酯的反应，已经开发了一种三取代呋喃的合成方法。该合成2,3,5-三取代呋喃的方法操作简单，适用于广泛的底物范围。此外，该合成采用廉价的Cu（MeCN）4 PF 6作为催化剂，不需要其他配体。类似的反应也已用于（E）-2-重氮-3-（甲氧基亚氨基）丁酸乙酯，用于合成2,3,5-三取代的N-甲氧基吡咯，但效果有限。
• One-Pot Synthesis of Furans Using Base- and Acid-Supported Reagents ‘Na2CO3/Al2O3-PPA/SiO2'
  作者：Tadashi Aoyama、Takashi Nagaoka、Toshio Takido、Mitsuo Kodomari

  DOI：10.1055/s-0030-1258402

  日期：2011.2

  convenient method for the one-pot synthesis of furans from β-keto esters and α-halo ketones was developed using an acid- and base-supported reagent system ‘Na2CO3/Al2O3-PPA/SiO2’. The condensation reaction of triketones, which are formed from the reaction of β-keto esters with α-halo ketones in the presence of Na2CO3/Al2O3, was promoted by PPA/SiO2 to give the corresponding furans in good yields. This method

  开发了一种方便的方法，可使用酸和碱支持的试剂系统'Na 2 CO 3 / Al 2 O 3 -PPA / SiO 2 '从β-酮酯和α-卤代酮一锅合成呋喃。PPA / SiO 2促进了β-酮酸酯与α-卤代酮在Na 2 CO 3 / Al 2 O 3存在下的反应而形成的三酮缩合反应，得到了相应的呋喃。产量。与分步法相比，该方法简单易行，收率好。 呋喃-一锅合成-支持的试剂
• Copper-Mediated [3 + 2] Oxidative Cyclization Reaction of <i>N</i>-Tosylhydrazones and β-Ketoesters: Synthesis of 2,3,5-Trisubstituted Furans
  作者：Yubing Huang、Xianwei Li、Yue Yu、Chuanle Zhu、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.6b00568

  日期：2016.6.17

  The first attempt utilizing N-tosylhydrazones as two-carbon synthons has been successfully achieved, which underwent a copper-mediated [3 + 2] oxidative cyclization reaction to afford 2,3,5-trisubstituted furans in moderate to good yields. The features of this method include inexpensive metal catalyst, readily available substrates, high regioselectivity and convenient operation. The studies provide

  已成功实现了使用N-甲苯磺酰hydr作为二碳合成子的首次尝试，该尝试进行了铜介导的[3 + 2]氧化环化反应，以中等至良好的收率提供了2,3,5-三取代的呋喃。该方法的特征包括廉价的金属催化剂，易于获得的底物，高区域选择性和方便的操作。这些研究为进一步探索N-甲苯磺酰hydr的强大而多样的反应能力提供了重要的途径。
• Copper-Catalyzed Coupling Cyclization of <i>gem</i>-Difluoroalkenes with Activated Methylene Carbonyl Compounds: Facile Domino Access to Polysubstituted Furans
  作者：Xuxue Zhang、Wenpeng Dai、Wei Wu、Song Cao

  DOI：10.1021/acs.orglett.5b01123

  日期：2015.6.5

  A novel and efficient CuI-catalyzed synthesis of 2,3,5-trisubstituted furans was developed via coupling cyclization of gem-difluoroalkenes with active methylene carbonyl compounds such as 1,3-dicarbonyl compounds, acetoacetonitrile, and phenylsulfonylacetone with the assistance of a base. Commercial availability of substrates or reagents, good to high isolated yields, and excellent functional group

  通过宝石-二氟烯烃与活性亚甲基羰基化合物（例如1,3-二羰基化合物，乙酰乙腈和苯磺酰丙酮）的偶联环化，开发了新颖，高效的CuI催化的2,3,5-三取代呋喃合成方法。底物或试剂的商业可得性，良好或较高的分离产率以及出色的官能团相容性，使这种转化成为合成各种呋喃的有力工具。提出了一种可能的机制，涉及到烯丙基酮。
• Copper-Catalyzed Coupling of 2-Siloxy-1-alkenes and Diazocarbonyl Compounds: Approach to Multisubstituted Furans, Pyrroles, and Thiophenes
  作者：Wei Wen Tan、Naohiko Yoshikai

  DOI：10.1021/acs.joc.6b00904

  日期：2016.7.1

  We report herein copper(II)-catalyzed cyclization reactions of silyl enol ethers derived from methyl ketones with α-diazo-β-ketoesters or α-diazoketones to afford 2-siloxy-2,3-dihydrofuran derivatives or 2,3,5-trisubstituted furans, respectively, under mild conditions. The former cyclization products serve as versatile 1,4-diketone surrogates, allowing facile preparation of 2,3,5-trisubstituted furans

  我们在本文中报道了铜（II）催化的甲基酮衍生的甲硅烷基烯醇醚与α-重氮-β-酮酸酯或α-二氮酮的环化反应，从而提供2-siloxy-2,3-dihydrofuran衍生物或2,3,5-三取代的呋喃，分别在温和的条件下。以前的环化产品可以用作通用的1,4-二酮替代物，从而可以轻松制备2,3,5-三取代的呋喃，吡咯和噻吩。