methyl 4-(4-ethylphenylamino)-1-(4-ethylphenyl)-2,5-dihydro-5-oxo-1H-pyrrole-3-carboxylate | 1374118-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: methyl 4-(4-ethylphenylamino)-1-(4-ethylphenyl)-2,5-dihydro-5-oxo-1H-pyrrole-3-carboxylate
• 英文别名: methyl 4-(4-ethylanilino)-1-(4-ethylphenyl)-5-oxo-2H-pyrrole-3-carboxylate
• CAS: 1374118-81-6
• 化学式: C₂₂H₂₄N₂O₃
• 分子量: 364.444
• InChiKey: WHIDYTJFEOKCNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 丁炔二酸二甲酯 、 4-乙基苯胺 在 咖啡因 作用下， 以 甲醇 为溶剂， 反应 3.75h， 以82%的产率得到methyl 4-(4-ethylphenylamino)-1-(4-ethylphenyl)-2,5-dihydro-5-oxo-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Caffeine as a naturally green and biodegradable catalyst promoted convenient and expedient synthetic route for the synthesis of polysubstituted dihydro-2-oxypyrroles

  摘要：

  研究人员研究了一种绿色、便捷、高产和一锅法合成高取代度二氢-2-氧吡咯的方法，该方法是在环境温度下，在催化量咖啡因作为绿色、天然、便捷和可生物降解催化剂的存在下，通过芳香族/脂肪族胺、乙炔二甲酸二烷基酯和甲醛之间的多米诺四组份缩合反应合成高取代度二氢-2-氧吡咯。这种绿色方法的突出特点是操作和工作程序简单，无需色谱纯化步骤；使用安全、不挥发、无腐蚀性的绿色催化剂；这种固体催化剂易于获得和处理；单锅反应；经济和清洁合成。

  DOI：

  10.4314/bcse.v33i1.15

文献信息

• Glutamic acid as green and bio-based α-amino acid catalyst promoted one-pot access to polyfunctionalized dihydro-2-oxypyrroles
  作者：Farzaneh Mohamadpour

  DOI：10.2298/jsc180720006m

  日期：——

  route for biologically act­ive α -amino acid, glutamic acid catalyzed facile and mild preparation of poly­functionalized dihydro-2-oxypyrroles via one-pot, four condensation dom­ino reaction between aromatic/aliphatic amines, dialkyl acetylenedicar­boxyl­ates and formaldehyde have been studied. The route includes green, biodegradable and inexp­ensive α -amino acid catalyst, high atom-economy, simplicity

  通过一锅，芳香族/脂肪族胺，二烷基乙酰二羧酸二烷基酯和甲醛之间的一锅，四次缩合多米诺反应，已获得了高度通用和便捷的合成途径，用于生物活性的α-氨基酸，谷氨酸催化的轻度制备多官能化的二氢-2-氧基吡咯。研究过。该路线包括绿色，可生物降解且廉价的α-氨基酸催化剂，高原子经济性，操作简便和后处理程序，无需色谱纯化步骤。固体催化剂无毒或有害，在温和的反应条件下易于处理，并具有优异的收率，是高效高效合成这些产品的显着优势。
• BF₃/nano-sawdust as a green, biodegradable and inexpensive catalyst for the synthesis of highly substituted dihydro-2-oxopyrroles
  作者：Bi Bi Fatemeh Mirjalili、Reza Zare Reshquiyea

  DOI：10.1039/c4ra16625f

  日期：——

  BF₃/nano-sawdust was used as a readily available, inexpensive, biodegradable and environmentally benign heterogeneous solid acid catalyst for the one-pot cascade synthesis of highly functionalized dihydro-2-oxypyrroles.

  使用BF₃/纳米锯末作为一种易得、廉价、可生物降解和环境友好的异相固体酸催化剂，进行一锅法级联合成高度官能化的二氢-2-氧吡咯。
• Imin-based synthesis of polyfunctionalized dihydro-2-oxypyrroles catalyzed by glycine amino acid via tandem Michael–Mannich cyclocondensation reaction under ambient temperature
  作者：Farzaneh Mohamadpour

  DOI：10.1007/s11164-019-04072-z

  日期：2020.3

  and mild synthetic route to the convenient one-pot preparation of polyfunctionalized dihydro-2-oxypyrroles has been developed and catalyzed via glycine amino acid as a natural bio-based and biodegradable catalyst using imin-based four condensation domino reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde via tandem Michael–Mannich cyclocondensation reaction under ambient temperature

  已经开发了一种高效，温和的合成途径，以方便的一锅制备多官能化二氢-2-氧基吡咯，并通过甘氨酸氨基酸作为天然生物基和可生物降解的催化剂，使用基于亚胺的胺，二烷基四胺基缩合多米诺反应进行催化。在环境温度下，通过迈克尔-曼尼希串联缩合反应生成乙炔二羧酸盐和甲醛。反应在较短的时间内完成，但是以优异的产率获得了产物。这种对环境友好的方法包括引人注目的特性，例如生物基和绿色催化剂，无需柱色谱分离即可直接进行后处理，具有成本效益，温和简单的合成，一锅法和高原子经济性。
• One-pot four-component domino reaction for the synthesis of substituted dihydro-2-oxypyrrole catalyzed by molecular iodine
  作者：Abu T. Khan、Arindam Ghosh、Md. Musawwer Khan

  DOI：10.1016/j.tetlet.2012.03.046

  日期：2012.5

  The synthesis of multi-functionalized dihydro-2-oxypyrrole can be achieved using one-pot four-component domino reaction from dialkylacetylene dicarboxylate, amines, and formaldehyde by employing molecular iodine as catalyst at room temperature. The salient features of the present method are: simple, straightforward, cost-effective, environmentally benign, and no column chromatographic separation is applicable on a broad range of substrates. (C) 2012 Elsevier Ltd. All rights reserved.
• Nano-TiCl4/SiO2: an efficient catalyst for the one-pot synthesis of highly substituted dihydro-2-oxopyrroles
  作者：Abdolhamid Bamoniri、Bi Bi Fatemeh Mirjlili、Reza Tarazian

  DOI：10.1007/s00706-015-1481-0

  日期：2015.12

  Nano-TiCl4/SiO2 was used as a readily available, inexpensive, efficient, and environmentally benign heterogeneous solid acid catalyst for the one-pot cascade synthesis of highly functionalized dihydro-2-oxopyrroles. Four-component reaction (4CR) of dialkyl acetylenedicarboxylates, aniline derivatives, and formaldehyde was employed for the synthesis of these compounds under thermal conditions.