5-(4-(methoxycarbonyl)phenyl)furan-2-carboxylic acid methyl ester | 53355-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-(methoxycarbonyl)phenyl)furan-2-carboxylic acid methyl ester
• 英文别名: methyl 5-(4-methoxycarbonylphenyl)furan-2-carboxylate；Methyl 5-(4-(methoxycarbonyl)phenyl)furan-2-carboxylate
• CAS: 53355-35-4
• 化学式: C₁₄H₁₂O₅
• 分子量: 260.246
• InChiKey: WPDICMVQAFHQQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-溴-2-糠酸甲酯 、 4-碘苯甲酸甲酯 在 potassium phosphate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以82%的产率得到5-(4-(methoxycarbonyl)phenyl)furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Visible light induced cross-coupling synthesis of asymmetrical heterobiaryls using Pd/CeO2 nanocomposite photocatalyst

  摘要：

  A simple, mild and green approach has been developed for the synthesis of asymmetrical heterobiaryls under the irradiation of visible light without any oxidants and promoting reagents through using Pd/CeO2 nanocomposite photocatalyst. This method can tolerate considerable functional groups such as electron donating groups and electron-withdrawing groups through C-C cross-coupling. Moreover, we obtain the products with moderate yields in an efficient way. Finally, a plausible mechanism is proposed. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2018.01.002

文献信息

• Methyl 2-Furoate: An Alternative Reagent to Furan for Palladium-Catalysed Direct Arylation
  作者：Hai Yan Fu、Henri Doucet

  DOI：10.1002/ejoc.201101102

  日期：2011.12

  The palladium-catalysed direct arylation of methyl 2-furoate with aryl bromides was studied. The use of KOAc as the base, dimethylacetamide (DMAc) as the solvent and Pd(OAc)2 as the catalyst was found to give 5-arylfurans regioselectively and without decarboxylation. These methyl 5-aryl-2-furoates gave 2,5-diarylfurans by decarboxylative coupling by using Pd(OAc)2 as the catalyst. Methyl 2-furoate

  研究了钯催化的 2-糠酸甲酯与芳基溴化物的直接芳基化反应。发现使用 KOAc 作为碱、二甲基乙酰胺 (DMAc) 作为溶剂和 Pd(OAc) 2 作为催化剂可以区域选择性地得到 5-芳基呋喃并且没有脱羧。这些5-芳基-2-糠酸甲酯通过使用Pd(OAc) 2 作为催化剂的脱羧偶联得到2,5-二芳基呋喃。因此，2-糠酸甲酯代表了一种方便的替代呋喃的底物，用于合成单或多芳基化呋喃。
• Biphenyl dicarboxylates from ethene and bifuran dimethyl esters
  作者：Mingchun Ye、Mi Jen Kuo、Raul F. Lobo

  DOI：10.1016/j.mcat.2023.112949

  日期：2023.2

  The substrate scope of the Diels-Alder-Dehydration reaction was expanded to the deactivated bifuran structure. Dimethyl biphenyl-4,4′-dicarboxylate (1) and methyl 5- [4-(methoxycarbonyl)phenyl]-2-furoate (2) were synthesized from dimethyl 2,2′-bifuran-5,5′-dicarboxylate (3) via metal-triflate-catalyzed Diels-Alder-Dehydration reaction with ethene. A 31% yield of (1) was obtained using Sc(OTf)3 catalyst

  Diels-Alder-Dehydration 反应的底物范围扩展到失活的双呋喃结构。4,4'-二羧酸联苯二甲酯 ( 1 ) 和 5-[4-(甲氧基羰基)苯基]-2-糠酸甲酯 ( 2 ) 由 2,2'-联呋喃-5,5'-二羧酸二甲酯 ( 3 ) 合成) 通过金属-三氟甲磺酸盐催化的 Diels-Alder-Dehydration 反应与乙烯。使用Sc (OTf) 3催化剂获得( 1 )的产率为31%，使用La(OTf) 3获得( 2 )的产率为76.6%温和反应条件下的催化剂。这种方法对 4,4'-二羧酸盐具有固有的选择性，并绕过了二甲基-联苯路线的甲基氧化步骤。
• Visible light induced cross-coupling synthesis of asymmetrical heterobiaryls using Pd/CeO2 nanocomposite photocatalyst
  作者：Yanqin Ge、Pinhui Diao、Chen Xu、Nannan Zhang、Cheng Guo

  DOI：10.1016/j.cclet.2018.01.002

  日期：2018.6

  A simple, mild and green approach has been developed for the synthesis of asymmetrical heterobiaryls under the irradiation of visible light without any oxidants and promoting reagents through using Pd/CeO2 nanocomposite photocatalyst. This method can tolerate considerable functional groups such as electron donating groups and electron-withdrawing groups through C-C cross-coupling. Moreover, we obtain the products with moderate yields in an efficient way. Finally, a plausible mechanism is proposed. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.