dimethyl (2E)-2-(4-methoxybenzoyl)but-2-enedioate | 1224593-08-1

• 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: dimethyl (2E)-2-(4-methoxybenzoyl)but-2-enedioate
• 英文别名: dimethyl 2-(4-methoxybenzoyl)fumarate；dimethyl (E)-2-(4-methoxybenzoyl)but-2-enedioate
• CAS: 1224593-08-1
• 化学式: C₁₄H₁₄O₆
• 分子量: 278.262
• InChiKey: BRGXUZSIPWWZAD-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl (2E)-2-(4-methoxybenzoyl)but-2-enedioate 、 三氟乙酸酐 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到dimethyl 2-(4-methoxyphenyl)-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：

  4-甲氧基苯甲醛 、 丁炔二酸二甲酯 在 N,N'-dimethyl-N,N'-di(pyridin-4-yl)ferrocene-1,1'-dicarboxamide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 7.0h， 以66%的产率得到dimethyl (2E)-2-(4-methoxybenzoyl)but-2-enedioate
  参考文献：
  名称：

  A new ferrocene-based bulky pyridine as an efficient reusable homogeneous catalyst

  摘要：

  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。

  DOI：

  10.1039/c3ra41674g

文献信息

• 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.
• 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。
• A Powerful Cascade Approach for Expeditious Synthesis of Trifluoromethylated Furans
  作者：Yao Wang、Yong-Chun Luo、Xiu-Qin Hu、Peng-Fei Xu

  DOI：10.1021/ol2022092

  日期：2011.10.7

  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.