1-(4-bromo-phenyl)-4-hydroxy-5-oxo-2-p-tolyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester | 1443221-99-5

• 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: 1-(4-bromo-phenyl)-4-hydroxy-5-oxo-2-p-tolyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester
• 英文别名: methyl 1-(4-bromophenyl)-4-hydroxy-5-oxo-2-p-tolyl-2,5-dihydro-1H-pyrrole-3-carboxylate；1-(4-bromophenyl)-5-(4-methylphenyl)-3-hydroxy-4-methoxycarbonyl-3-pyrrolin-2-one；methyl 1-(4-bromophenyl)-4-hydroxy-2-(4-methylphenyl)-5-oxo-2H-pyrrole-3-carboxylate
• CAS: 1443221-99-5
• 化学式: C₁₉H₁₆BrNO₄
• 分子量: 402.244
• InChiKey: GHVSMXXWMORTQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 、 对溴苯甲醛 、 丁炔二酸二甲酯 在 titanium(IV) oxide 、 十六烷基三甲基溴化铵 作用下， 以 水 为溶剂， 反应 18.0h， 以85%的产率得到1-(4-bromo-phenyl)-4-hydroxy-5-oxo-2-p-tolyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Admicellar catalysis in multicomponent synthesis of polysubstituted pyrrolidinones

  摘要：

  A multicomponent green methodology was developed to synthesize 3-hydroxy-2-pyrrolidinones under admicellar catalysis by TiO2 nano-particles at room temperature (30 degrees C). TiO2 nano-particles in aqueous CTAB solution promote the formation of admicelles and the reaction occurs in admicellar environment. The methodology was successfully applied to synthesize a variety of 3-hydroxy-2-pyrrolidinones and 3'-hydroxyspiro-2'-pyrrolidinone derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.017

文献信息

• Chromatography free expeditious green synthesis of 3-hydroxy-2-pyrrolidone derivatives under eco-friendly conditions via the oxidation of benzyl amines without catalyst
  作者：Kajal Mal、Chhanda Mukhopadhyay

  DOI：10.1016/j.molstruc.2022.133377

  日期：2022.10

  sustainable and atom economic one-pot synthesis of biologically significant 3-hydroxy-2-pyrrolidone moieties via the reaction of benzyl amine, aniline (or another benzyl amine) and dialkylacetylenedicarboxylate without catalyst in green solvent has been developed. Some remarkable features of our green procedure are aqueous ethanol solvent, reaction without catalyst, no column chromatography for isolation

  通过苄胺、苯胺（或另一种苄胺）和二烷基乙炔二羧酸盐在绿色溶剂中的反应，开发了一种可持续且原子经济的一锅法合成具有生物学意义的 3-羟基-2-吡咯烷酮部分。我们绿色工艺的一些显着特点是水性乙醇溶剂、无催化剂反应、无需柱色谱分离产物、较高的原子经济性 (AE) 值（高达 94.30 %）和较低的 E 因子值（高达0.23 克/克）。该反应主要展示了苄胺氧化和环化的范围。该合成路线也适​​用于克级合成。
• AmberChrom/brine as a Green Catalytic System for Synthesis of Pyrrolin-2-ones
  作者：Parya Hamdi Mohamadabad、Davood Setamdideh

  DOI：10.1080/00304948.2022.2141044

  日期：——

  Published in Organic Preparations and Procedures International: The New Journal for Organic Synthesis (Vol. 55, No. 3, 2023)
• Admicellar catalysis in multicomponent synthesis of polysubstituted pyrrolidinones
  作者：Rajib Sarkar、Chhanda Mukhopadhyay

  DOI：10.1016/j.tetlet.2013.05.017

  日期：2013.7

  A multicomponent green methodology was developed to synthesize 3-hydroxy-2-pyrrolidinones under admicellar catalysis by TiO2 nano-particles at room temperature (30 degrees C). TiO2 nano-particles in aqueous CTAB solution promote the formation of admicelles and the reaction occurs in admicellar environment. The methodology was successfully applied to synthesize a variety of 3-hydroxy-2-pyrrolidinones and 3'-hydroxyspiro-2'-pyrrolidinone derivatives. (C) 2013 Elsevier Ltd. All rights reserved.