2-methyl-N-(phenylbutyl)maleimide | 1233225-36-9

• 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: 2-methyl-N-(phenylbutyl)maleimide
• 英文别名: 3-Methyl-1-(4-phenylbutyl)pyrrole-2,5-dione
• CAS: 1233225-36-9
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: IJIWCSDLVXSVSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-methyl-N-(phenylbutyl)maleimide 在 Aspergillus fumigatus ATCC 26934, fungi 、 Czapek broth medium 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 生成 (R)-(+)-2-methyl-N-(phenylbutyl)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 、 苯基-4-丁胺 在 sodium acetate 、 乙酸酐 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以71%的产率得到2-methyl-N-(phenylbutyl)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
• Maleimide‐Controlled Formation of Indanonylpyrrolinediones and Spiroindanonylpyrrolinediones <i>via</i> Rh(III)‐Catalyzed C−H Activation of Sulfoxonium Ylides
  作者：Perumal Muthuraja、Muhammad Saeed Akhtar、Purushothaman Gopinath、Yong Rok Lee

  DOI：10.1002/adsc.202301010

  日期：2023.12.19

  A substrate‐controlled [4+1] annulation of sulfoxonium ylides with maleimides via Rh(III)‐catalyzed C−H bond activation is developed. The reaction of sulfoxonium ylides with 2‐methyl‐N‐arylmaleimides in the presence of AgNTf₂ diastereoselectively provides diversely functionalized indanonylpyrroline‐2,5‐dione derivatives. Furthermore, in the presence of AgBF₄, the subsequent reaction with maleimides leads to biologically intriguing various spiroindanonylpyrroline‐2,5‐diones. This methodology offers a broad substrate scope, good functional group tolerance, and diastereoselectivity.

  摘要 通过Rh(III)催化的C-H键活化，开发了一种底物可控的[4+1]环化磺酰亚胺马来酰亚胺反应。在 AgNTf2 非对映选择性存在下，砜酰化物与 2-甲基-N-芳基马来酰亚胺的反应可提供多种官能化的茚并吡咯啉-2,5-二酮衍生物。此外，在 AgBF4 的存在下，与马来酰亚胺的后续反应还能产生各种具有生物意义的螺茚基吡咯啉-2,5-二酮。这种方法具有广泛的底物范围、良好的官能团耐受性和非对映选择性。
• 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.