3-methyl-1-phenethyl-1H-pyrrole-2,5-dione | 140369-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-methyl-1-phenethyl-1H-pyrrole-2,5-dione
• 英文别名: N-(β-phenylethyl)-3-methylmaleimide；N-phenethyl-3-methylmaleimide；2-methyl-N-phenethylmaleimide；3-Methyl-1-(2-phenylethyl)pyrrole-2,5-dione
• CAS: 140369-62-6
• 化学式: C₁₃H₁₃NO₂
• mdl: MFCD11642982
• 分子量: 215.252
• InChiKey: RCHHHICSPDBKAN-UHFFFAOYSA-N

物化性质

• 熔点：
  54-56 °C
• 沸点：
  362.0±21.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-1-phenethyl-1H-pyrrole-2,5-dione 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 5-acetoxy-2,5-dihydro-3-methyl-1-phenethyl-1H-pyrrol-2-one
  参考文献：
  名称：

  Intermolecular and Intramolecular α-Amidoalkylation Reactions Using Bismuth Triflate as the Catalyst

  摘要：

  Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).

  DOI：

  10.1021/jo062077x
• 作为产物：
  描述：

  柠康酸酐 、 2-苯乙胺 在 溶剂黄146 作用下， 以76.4%的产率得到3-methyl-1-phenethyl-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  一系列马来酰亚胺的抗Leishmanial和细胞毒活性：合成，生物学评估和结构活性关系。

  摘要：

  在本研究中，已经合成了45种马来酰亚胺，并评估了其对体外杜氏乳酸杆菌的抗利什曼活性和对THP1细胞的细胞毒性。所有化合物均表现出明显的抗利什曼活性。在所测试的化合物中，有10种具有比标准药物两性霉素B更高的抗利什曼活性的马来酰亚胺，和32种具有比标准药物戊tam具有更好的抗利什曼活性的马来酰亚胺，尤其是化合物16（IC50 <0.0128μg/ mL）和42（IC50 <0.0128μg/ mL），在体外测试中显示出非凡的功效，并且细胞毒性低（CC50> 10μg/ mL）。16和42的抗Leishmanial活性比两性霉素B强10倍。结构和活性关系（SAR）研究表明，3，与3-甲基-马来酰亚胺和3,4-二氯-马来酰亚胺相比，4-未取代的马来酰亚胺显示出最强的抗利什曼活性。与3-甲基-马来酰亚胺和3,4-非取代的马来酰亚胺相比，3,4-二氯-马来酰亚胺的细胞毒性最小。结果表明，一些已报道的

  DOI：

  10.3390/molecules23112878

文献信息

• Antifungal, cytotoxic and SAR studies of a series of N-alkyl, N-aryl and N-alkylphenyl-1,4-pyrrolediones and related compounds
  作者：M. Sortino、F. Garibotto、V. Cechinel Filho、M. Gupta、R. Enriz、S. Zacchino

  DOI：10.1016/j.bmc.2011.03.038

  日期：2011.5

  The synthesis, in vitro evaluation and SAR studies of 67 maleimides and derivatives acting as antifungal agents are reported. A detailed SAR study supported by theoretical calculations led us to determine that: an intact maleimido ring appears to be necessary for a strong antifungal activity, dissimilarly affected by the substituents in positions 2 and 3. The best activities were shown by 2,3-nonsubstituted

  报道了67种马来酰亚胺及其衍生物作为抗真菌剂的合成，体外评估和SAR研究。由理论计算支持的详细SAR研究使我们确定：完整的马来酰亚胺环似乎对于强的抗真菌活性是必需的，与位置2和3上的取代基不同。然后是2,3二氯和2-甲基取代的马来酰亚胺。它们都是杀真菌剂，而不是抑真菌剂，增强了其抗真菌活性的重要性。2,3-二甲基和2,3-二苯基-马来酰亚胺具有边际活性或无效活性。N中存在灵活的连接链-苯基烷基马来酰亚胺似乎不是抗真菌活性所必需的，尽管其长度显示出与抗真菌行为的相关性，显示出烷基链为n  = 3和n  = 4的马来酰亚胺是大多数真菌中最佳的抗真菌活性。苯环上的不同取代基对活性没有明显的影响。化学势性质以及能量的值不能充分区分活性化合物和非活性化合物。尽管如此，发现尽管log  P单凭其强度不足以正确预测其抗真菌活性，对同一亚型化合物的抗真菌活性值的比较表明，抗真菌活性随亲脂性的增加而增强。另
• An efficient synthesis of substituted spiro[isoxazolopyrroloisoquinolines] via diastereoselective N-acyliminium ion cyclization
  作者：Maria S. Ledovskaya、Alexander V. Stepakov、Alexander P. Molchanov、Rafael R. Kostikov

  DOI：10.1016/j.tet.2015.08.007

  日期：2015.10

  A simple and efficient strategy is reported for the synthesis of spiro-fused pyrrolo[2,1-a]isoquinoline ring systems. The spiro[isoxazolopyrroloisoquinolines] are readily prepared via diastereoselective N-acyliminium ion cyclization of 6-hydroxy-7-(2-arylethyl)-1-oxa-2,7-diazaspiro[4.4]non-2-en-8-ones derived from the corresponding spirocyclic dihydroisoxazoles.

  一个简单的，高效的策略被报告螺稠合的吡咯并[2,1-的合成一个]异喹啉环系统。的螺[isoxazolopyrroloisoquinolines]经由非对映选择性容易地制备Ñ -acyliminium离子环化的6-羟基-7-（2-芳基乙基）-1-氧杂-2,7-二氮杂螺[4.4]壬-2-烯-8-酮衍生从相应的螺环dihydroisoxazoles。
• Chemo‐ and Diastereoselective Synthesis of Polyheterocycles by Rhodium(III)‐Catalyzed <i>sp</i>^<i>2</i>/<i>sp</i>^<i>3</i> C−H Activation of 2‐Arylquinazolin‐4(3<i>H</i>)‐ones with 3‐Methylmaleimides
  作者：Shreedhar Devkota、Muhammad Saeed Akhtar、Yong Rok Lee

  DOI：10.1002/adsc.202300147

  日期：2023.5.12

  Rhodium(III)-catalyzed sp2/sp3 C−H activation/annulation of 2-arylquinazolin-4(3H)-ones with 3-methylmaleimides is explored. This protocol provides diversely functionalized isoindoloquinazolinones in good yields upon reaction with various maleimides. This Rh(III)-catalyzed protocol can be applied for the chemo- and diastereoselective synthesis of various polyheterocycles.

  探索了铑 (III) 催化的sp 2 / sp 3 C−H 活化/环化 2-arylquinazolin-4(3 H )-ones 与 3-methylmaleimides。该协议在与各种马来酰亚胺反应后，提供了多种功能化的 isoindoloquinazolinones，产量很高。这种 Rh(III) 催化的方案可用于各种多杂环化合物的化学和非对映选择性合成。
• Correa; Rosa; Bella Cruz, Pharmaceutical Sciences, 1996, vol. 2, # 8, p. 353 - 355
  作者：Correa、Rosa、Bella Cruz、Savi、Cechinel Filho、Nunes

  DOI：——

  日期：——
• Efficient asymmetric hydrogenation of the C–C double bond of 2-methyl- and 2,3-dimethyl-N-phenylalkylmaleimides by Aspergillus fumigatus
  作者：Maximiliano Sortino、Susana Alicia Zacchino

  DOI：10.1016/j.tetasy.2010.02.017

  日期：2010.3

  Eight N-phenylalkylmaleimides (four 2-methyl-N-phenylalkylmaleimides and four 2,3-dimethyl-N-phenylalkylmaleimides with an alkyl chain (CH(2))(n) (n = 1-4) between the imide N and the benzene ring) were subjected to biotransformation using the fungal strain Aspergillus fumigatus ATCC 26934. All compounds were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)(3) showed that enantiomeric excesses were >99%. (C) 2010 Elsevier Ltd. All rights reserved.