ethyl 2-(4-nitrophenyl)furan-3-carboxylate

• 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: ethyl 2-(4-nitrophenyl)furan-3-carboxylate
• 英文别名: Ethyl 2-(4-nitrophenyl)furan-3-carboxylate
• 化学式: C₁₃H₁₁NO₅
• 分子量: 261.234
• InChiKey: YCUAOSMKBTYKAL-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：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对硝基苯甲酰醋酸乙酯 在 三氟甲磺酸 、 cobalt(II) chloride 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 ethyl 2-(4-nitrophenyl)furan-3-carboxylate
  参考文献：
  名称：

  叔丁基过氧化物的重排用于建设多取代呋喃

  摘要：

  布朗斯台德酸催化的叔丁基过氧化物的重排提供了一种新的策略，可通过1,2-芳基迁移来构建2,3-二取代的呋喃。此外，叔丁基过氧化物也可以通过一系列碱催化的Kornblum-DelaMare重排和酸促进的Paal-Knorr反应转化为2,3,5-三取代或2,5-二取代的呋喃。

  DOI：

  10.1021/ol402509u

文献信息

• Rhodium-catalyzed synthesis of 2,3 – Disubstituted N -methoxy pyrroles and furans via [3+2] cycloaddition between metal carbenoids and activated olefins
  作者：Bharath Kumar Kuruba、Samuel Vasanthkumar、Lourdusamy Emmanuvel

  DOI：10.1016/j.tet.2017.04.007

  日期：2017.6

  the synthesis of 2-substituted N-alkoxy pyrrole 3-carboxylate and furan 3-carboxylate via Rh-catalyzed [3+2] cycloaddition between α-diazo oxime ether or α-diazo carbonyl compounds with vinyl equivalents in a one-pot process. We have demonstrated ethyl vinyl ether as well as vinyl acetate as vinyl equivalents and both were found to give excellent yields. We have also demonstrated the synthesis of N-alkoxy

  我们首次报道了通过α-重氮肟醚或具有乙烯基当量的α-重氮羰基化合物之间的Rh催化的[3 + 2]环加成反应合成2-取代的N-烷氧基吡咯3-羧酸盐和呋喃3-羧酸盐在一锅法过程中。我们已经证明乙基乙烯基醚以及乙酸乙烯酯作为乙烯基当量，并且发现两者均具有优异的产率。我们还证明了通过在低温下进行反应可以合成N-烷氧基二氢吡咯衍生物。
• Transition-Metal-Free Approach to Polysubstituted Furans
  作者：Changming You、Zhenming Zhang、Yongliang Tu、Hong Tang、Yuanfeng Wang、Da Long、Junfeng Zhao

  DOI：10.1021/acs.joc.9b03006

  日期：2020.3.6

  A convenient and straightforward strategy for the synthesis of 2,3-disubstituted and 2,3,5-trisubstituted furans via a base-promoted domino reaction of β-keto compounds with vinyl dichlorides is described. This transition-metal-free approach proceeds under operationally simple reaction conditions featuring easily available starting materials, a broad substrate scope, and good functional group tolerance

  描述了一种通过β-酮化合物与二氯乙烯的碱促进的多米诺反应合成2,3-二取代和2,3,5-三取代的呋喃的便捷方法。这种无过渡金属的方法在操作简单的反应条件下进行，该条件具有容易获得的起始原料，广泛的底物范围和良好的官能团耐受性。
• Phosphine-Mediated Reductive Condensation of γ-Acyloxy Butynoates:  A Diversity Oriented Strategy for the Construction of Substituted Furans
  作者：Cheol-Kyu Jung、Jian-Cheng Wang、Michael J. Krische

  DOI：10.1021/ja049377l

  日期：2004.4.1

  gamma-acyloxy butynoates to stoichiometric quantities of triphenylphosphine results in reductive condensation to afford substituted furans, by way of allenic ester intermediates. As gamma-acyloxy butynoates are readily obtained through condensation of ethyl propiolate with aldehydes followed by acylation, this method represents a powerful and mechanistically novel protocol for the convergent three-component

  γ-酰氧基丁酸酯暴露于化学计量量的三苯基膦导致还原缩合，通过丙二烯酯中间体提供取代的呋喃。由于丙炔酸乙酯与醛缩合然后酰化很容易获得 γ-酰氧基丁酸酯，因此该方法代表了一种强大且机械新颖的协议，用于取代呋喃的收敛三组分构建。
• Regioselective Palladium-Catalyzed Arylation of 3-Carboalkoxy Furan and Thiophene
  作者：Bobby Glover、Kimberly A. Harvey、Bing Liu、Matthew J. Sharp、Maria F. Tymoschenko

  DOI：10.1021/ol027266q

  日期：2003.2.1

  [GRAPHICS]The regioselective palladium(0)-catalyzed arylation of 3-furoate and 3-thiophenecarboxylate esters with aryl bromides is described. Conditions were developed that allow for the selective synthesis of either 2-aryl or 5-aryl products.
• The Rearrangement of <i>tert</i>-Butylperoxides for the Construction of Polysubstituted Furans
  作者：Xiaojian Zheng、Shenglin Lu、Zhiping Li

  DOI：10.1021/ol402509u

  日期：2013.11

  The Brønsted acid catalyzed rearrangement of tert-butyl peroxides provides a new strategy to construct 2,3-disubstituted furans via 1,2-aryl migration. In addition, tert-butyl peroxides could also be transformed into 2,3,5-trisubstituted or 2,5-disubstituted furans through a sequence of base-catalyzed Kornblum–DelaMare rearrangements and acid-promoted Paal–Knorr reactions.

  布朗斯台德酸催化的叔丁基过氧化物的重排提供了一种新的策略，可通过1,2-芳基迁移来构建2,3-二取代的呋喃。此外，叔丁基过氧化物也可以通过一系列碱催化的Kornblum-DelaMare重排和酸促进的Paal-Knorr反应转化为2,3,5-三取代或2,5-二取代的呋喃。