N-(3-phenpropyl)maleimide | 1184631-54-6

• 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: N-(3-phenpropyl)maleimide
• 英文别名: N-phenylpropyl-3-methylmaleimide；2-methyl-N-(phenylpropyl)maleimide；3-Methyl-1-(3-phenylpropyl)pyrrole-2,5-dione
• CAS: 1184631-54-6
• 化学式: C₁₄H₁₅NO₂
• mdl: MFCD13233947
• 分子量: 229.279
• InChiKey: HWEUBSDLGVNYJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 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：

  N-(3-phenpropyl)maleimide 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-methyl-N-(phenylpropyl)succinimide
  参考文献：
  名称：

  Efficient asymmetric hydrogenation of the C–C double bond of 2-methyl- and 2,3-dimethyl-N-phenylalkylmaleimides by Aspergillus fumigatus

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2010.02.017
• 作为产物：
  描述：

  柠康酸酐 、 3-苯基-1-丙胺 在 sodium acetate 、 乙酸酐 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以65%的产率得到N-(3-phenpropyl)maleimide
  参考文献：
  名称：

  Efficient asymmetric hydrogenation of the C–C double bond of 2-methyl- and 2,3-dimethyl-N-phenylalkylmaleimides by Aspergillus fumigatus

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2010.02.017

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
• 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.