(R)-(+)-2-methyl-N-phenethylsuccinimide | 1233225-39-2

• 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: (R)-(+)-2-methyl-N-phenethylsuccinimide
• 英文别名: (3R)-3-methyl-1-phenethyl-pyrrolidine-2,5-dione；(3R)-3-methyl-1-(2-phenylethyl)pyrrolidine-2,5-dione
• CAS: 1233225-39-2
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: UBZXKPRYHFHJRA-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-methyl-1-phenethyl-1H-pyrrole-2,5-dione 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-phenethylsuccinimide
  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

• 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.