methyl 4-(4-bromophenyl)-3-methoxycarbonyl-4-oxo-2-butenoate

• 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: methyl 4-(4-bromophenyl)-3-methoxycarbonyl-4-oxo-2-butenoate
• 英文别名: (E)-2-(4-bromobenzoyl)but-2-enedioic acid dimethyl ester；dimethyl (2E)-2-(4-bromobenzoyl)but-2-enedioate；dimethyl (E)-2-(4-bromobenzoyl)but-2-enedioate
• 化学式: C₁₃H₁₁BrO₅
• 分子量: 327.131
• InChiKey: LEOAOUJRFOFKKK-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-(4-bromophenyl)-3-methoxycarbonyl-4-oxo-2-butenoate 、 三氟乙酸酐 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到dimethyl 2-(4-bromophenyl)-5-(trifluoromethyl)furan-3,4-dicarboxylate
  参考文献：
  名称：

  A Powerful Cascade Approach for Expeditious Synthesis of Trifluoromethylated Furans

  摘要：

  A powerful approach to synthesize trifluoromethylated furans has been developed. The method is operationally simple, broad in substrate scope, and amenable to scale-up using trifluoroacetic anhydride. Meanwhile, the strategy not only provided a versatile approach to synthesize trifluoromethylated furans but also provides a new method for exploring the new reactivity of trifluoroacetic anhydride.

  DOI：

  10.1021/ol2022092
• 作为产物：
  描述：

  methyl 5-(4-bromophenyl)-2-methoxy-4-methylfuran-3-carboxylate 在 盐酸 、 氧气 、 亚甲兰 作用下， 以 丙酮 为溶剂， 反应 3.5h， 生成 methyl 4-(4-bromophenyl)-3-methoxycarbonyl-4-oxo-2-butenoate
  参考文献：
  名称：

  Photosensitized Oxidation of Furans; Part 17:¹A Simple Method for the Synthesis of 5-Hydroperoxyfuran-2(5H)-ones

  摘要：

  5-氢过氧呋喃-2(5H)-酮3是通过对二氢呋喃1进行酸水解合成的。这些二氢呋喃1是在一次性反应过程中，通过相应的呋喃4与单线态氧和甲醇反应制备的。该合成方法具有广泛的应用范围；然而，无法制备在C-4位上未经取代的化合物3，因为相应的二氢呋喃1不会形成。

  DOI：

  10.1055/s-1994-25610

文献信息

• A new ferrocene-based bulky pyridine as an efficient reusable homogeneous catalyst
  作者：Bishwapran Kashyap、Prodeep Phukan

  DOI：10.1039/c3ra41674g

  日期：——

  An effective approach to reusing a homogeneous catalyst has been demonstrated. A ferrocene-based bulky pyridine has been synthesized and utilized as a homogeneous catalyst for the synthesis of benzoylfumarates as well as for acetylation. After the reaction, the catalyst was separated by simple precipitation and reused without appreciable loss of activity.

  已经证明了一种有效的方法来重复使用均相催化剂。合成了基于二茂铁的大体积吡啶，并将其用作均相催化剂，用于合成苯甲酰富马酸酯以及乙酰化反应。反应后，催化剂通过简单的沉淀分离出来，并且可以重复使用而不会显著损失活性。
• Photosensitized Oxidation of Furans; Part 18: A Simple Method for a One-Pot Synthesis of Functionalized Methyl cis-4-Oxoalk-2-enoates
  作者：M. Rosaria Iesce、Flavio Cermola、Alfonso Piazza、Rachele Scarpati、M. Liliana Graziano

  DOI：10.1055/s-1995-3922

  日期：1995.4

  Functionalized methyl cis-4-oxoalk-2-enoates 2 are synthesized in a one-pot procedure by singlet oxygen oxygenation of the corresponding 2-methoxyfurans 1 in methanol and reduction of the resulting hydroperoxides 4 and 5 by the sulfides 6 which are selectively oxidized into the sulfoxides 7. The synthetic method has a wide range of applicability and affords compounds 2 stereoselectively and in good yields; concomitantly the sulfoxides 7 are obtained in excellent yields.

  功能化的甲基顺-4-氧烯-2-酸酯2通过单氧对相应的2-甲氧基呋喃1在甲醇中的氧化，随后用硫化物6选择性还原生成的过氧化物4和5，采用一锅法合成。该合成方法具有广泛的适用性，能够立体选择性地高产量地获得化合物2；同时，亚砜7也以优异的产率获得。
• Reactions of Arylaldehydes and N-Sulfonated Imines with Dimethyl Acetylenedicarboxylate Catalyzed by Nitrogen and Phosphine Lewis Bases
  作者：Chao-Qun Li、Min Shi

  DOI：10.1021/ol0354324

  日期：2003.11.1

  [reaction: see text] In the reaction of arylaldehydes or N-sulfonated imines (0.5 mmol) with dimethyl acetylenedicarboxylate (DMAD) (0.6 mmol) catalyzed by pyridine or DMAP (20 mol %), we found that (E)-2-aryl-but-2-enedioic acid dimethyl ester 1 or (E)-2-[aryl-(toluene-4-sulfonylimino)methyl]-but-2-enedioic acid dimethyl ester 2 was formed in good yields at 60 degrees C in THF. A plausible mechanism

  [反应：参见正文]在吡啶或DMAP（20 mol％）催化下，芳醛或N-磺化亚胺（0.5 mmol）与乙酰二羧酸二甲酯（DMAD）（0.6 mmol）的反应中，我们发现（E）-2-在60℃下，以良好的收率形成了芳基-丁-2-烯二酸二甲酯1或（E）-2- [芳基-（甲苯-4-磺酰亚胺基）甲基]-丁-2-烯二酸二甲酯2。四氢呋喃。已经提出了一种合理的机制。
• Nicotinic acid functionalized organomodified silica as an efficient heterogeneous catalyst for the synthesis of benzoyl fumarate
  作者：Rana Sanjay Kumar Singh、Bishwapran Kashyap、Prodeep Phukan

  DOI：10.1016/j.tetlet.2013.09.057

  日期：2013.12

  A new hybrid catalyst has been developed by incorporating nicotinic acid onto an organomodified silica. The catalyst was applied as a heterogeneous catalyst for the synthesis of benzoyl fumarate. The reactions work well in the presence of 20 wt % of the catalyst at room temperature to produce the desired products in high yield. The catalyst could be recovered and reused without appreciable change in activity. (C) 2013 Elsevier Ltd. All rights reserved.
• Poly(4-vinylpyridine-co-ethylvinylbenzene) as heterogeneous reusable catalyst for the synthesis of benzoyl fumarate
  作者：Bishwapran Kashyap、Prodeep Phukan

  DOI：10.1007/s00706-015-1531-7

  日期：2016.4

  Poly(4-vinylpyridine-co-ethylvinylbenzene) 25 % cross-linked (with divinylbenzene) has been found to be an effective heterogeneous catalyst for the synthesis of benzoyl fumarate from aldehyde and dimethyl acetylenedicarboxylate. Various aromatic aldehydes undergo this reaction with good yield in presence of 15 wt% of the catalyst. The catalyst was recovered and reused six times without appreciable alteration in activity.