ethyl 5-(4-methoxyphenyl)-2-furoate | 60336-07-4

• 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-furoate
• 英文别名: ethyl 5-(4-methoxyphenyl)furan-2-carboxylate；4-(4-methoxyphenyl)-1-furoic acid ethyl ester；5-(4-methoxy-phenyl)-furan-2-carboxylic acid ethyl ester；2-Furancarboxylic acid, 5-(4-methoxyphenyl)-, ethyl ester
• CAS: 60336-07-4
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: WXKTYPNLQJFAFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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-furoate 以51%的产率得到
  参考文献：
  名称：

  OLEJNIK A. F.; VOZYAKOVA T. I.; NOVITSKIJ K. YU.; ZYKOVA T. N.; GUSKOVA T+, XIM.-FARMATSEVT. ZH. , 1976, 10, HO 4, 46-49

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(4-甲氧苯基)-2-糠酸 以24%的产率得到
  参考文献：
  名称：

  OLEJNIK A. F.; VOZYAKOVA T. I.; NOVITSKIJ K. YU.; ZYKOVA T. N.; GUSKOVA T+, XIM.-FARMATSEVT. ZH. , 1976, 10, HO 4, 46-49

  摘要：

  DOI：

文献信息

• Cobalt-Catalyzed Cross-Coupling Reactions of Heterocyclic Chlorides with Arylmagnesium Halides and of Polyfunctionalized Arylcopper Reagents with Aryl Bromides, Chlorides, Fluorides and Tosylates
  作者：Paul Knochel、Tobias Korn、Matthias Schade、Murthy Cheemala、Stefan Wirth、Simon Guevara、Gérard Cahiez

  DOI：10.1055/s-2006-950290

  日期：2006.11

  A range of aromatic organocopper or organomagnesium compounds undergo smooth cross-coupling reactions with aryl bromides, chlorides, fluorides and tosylates, leading to polyfunctionalized aromatics or heterocycles in the presence of cobalt salts (5-7.5 mol%) as catalysts. Very mild reaction conditions are needed and, in the case of cross-coupling with organocopper compounds, Bu4NI (1 equiv) and 4-fluorostyrene (20 mol%) are essential as promoters for successful couplings.

  一系列芳香族有机铜或有机镁化合物与芳基溴、氯、氟及托烯磺酸酯进行平滑的交叉偶联反应，在钴盐（5-7.5 mol%）作为催化剂的情况下，产生多功能化的芳香族化合物或杂环化合物。反应条件非常温和，且在与有机铜化合物交叉偶联的情况下，四丁基氮化铵（1当量）和4-氟苯乙烯（20 mol%）是成功偶联所必需的促进剂。
• Manganese-Catalyzed Oxidative Cross-Coupling of Grignard Reagents with Oxygen as an Oxidant
  作者：Gérard Cahiez、Christophe Duplais、Julien Buendia

  DOI：10.1002/anie.200902188

  日期：2009.8.24

  Oxidative heterocoupling between two Grignard reagents RMgX and R′MgX is made possible by manganese catalysis with O2 as an oxidant. This procedure, development of which was based on mechanistic analysis of the corresponding homocoupling reaction, can be steered towards the heterocoupling product at the expense of the homocoupling products by judicious choice of the R and R′ groups (see examples).

  通过以O 2为氧化剂的锰催化，可以实现两种格氏试剂RMgX和R'MgX之间的氧化杂化。该方法的开发是基于对相应的均偶联反应的机理分析，可以通过明智地选择R和R'基团，以牺牲均偶联产物为导向，转向异偶联产物（参见示例）。
• Mono- and Biscouplings Using Triarylbismuths for the Atom-Efficient Arylations of Functionalized Furans under Palladium Catalysis
  作者：Maddali Rao、Dheeraj Awasthi、Jalindar Talode

  DOI：10.1055/s-0032-1316567

  日期：2012.8

  Palladium-catalyzed cross-coupling reactions of functionalized bromofurans with triarylbismuths have been described for the atom-economic synthesis of functionalized arylfuran systems. The coupling reactions using triarylbismuths with various 2-bromofurans and 2,5-dibromofuran underwent smoothly to afford the corresponding 2-arylfurans and 2,5-diarylfurans in high yields in a short reaction time (one

  钯催化的功能化溴呋喃与三芳基铋的交叉偶联反应已被描述用于功能化芳基呋喃系统的原子经济合成。使用三芳基铋与各种 2-溴呋喃和 2,5-二溴呋喃的偶联反应顺利进行，在短反应时间（1 小时）内以高产率得到相应的 2-芳基呋喃和 2,5-二芳基呋喃。
• Palladium-Catalyzed Denitrative α-Arylation of Heteroarenes with Nitroarenes via C–H and C–NO2 Bond Activations
  作者：Jiaxin Yao、Yuxuan Xiao、Haiyan Li、Xun Yang、Jiahui Du、Ying Yin、Lin Feng、Wengui Duan、Lin Yu

  DOI：10.1021/acs.orglett.4c02340

  日期：2024.9.6

  can be arylated at the α-position in moderate to good yields. Mechanistic studies demonstrate that the reaction proceeds via a CMD pathway, with C–H bond activation as the rate-determining step. Furthermore, the scalability and applicability in the synthesis of a drug molecule exemplify the utility of this protocol.

  首次报道了通过脱硝偶联将杂芳烃与硝基芳烃进行 α-芳基化的通用方法。各种杂芳烃，包括呋喃、苯并呋喃、吡咯、吲哚、噻吩和苯并噻吩的衍生物，可以在α位以中等至良好的产率芳基化。机理研究表明，该反应通过 CMD 途径进行，其中 C-H 键激活作为速率决定步骤。此外，药物分子合成的可扩展性和适用性例证了该协议的实用性。
• Triflic Acid-Catalyzed Cycloisomerization Reactions of Donor–Acceptor Cyclopropanes: Access to Alkyl 5-Arylfuran-2-carboxylates
  作者：Yuequan Zhu、Panpan Xu、Yuefa Gong

  DOI：10.1021/acs.joc.6b00161

  日期：2016.6.3

  A direct synthetic strategy starting from alkyl 1-alkoxy-2-aroylcyclopropanecarboxylates was developed for the construction of alkyl 5-arylfuran-2-carboxylates. These donor acceptor cyclopropanes smoothly undergo a simple ring opening reaction or/and cycloisomerization reaction in the presence of acid at room temperature;, which greatly depends on the properties of the acid used in the experiment, Alkyl 5-arylfuran-2-carboxylates were afforded in high yields in triflic acid, whereas alkyl 2,5-dioxo-5-phenylpentanoate became the major product in other protic acids and Lewis acids.