(3R)-3-benzyloxycarbonylamino-3-methyl-1-(p-methoxyphenyl)pyrrolidin-2-one | 951172-62-6

• 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: (3R)-3-benzyloxycarbonylamino-3-methyl-1-(p-methoxyphenyl)pyrrolidin-2-one
• 英文别名: benzyl N-[(3R)-1-(4-methoxyphenyl)-3-methyl-2-oxopyrrolidin-3-yl]carbamate
• CAS: 951172-62-6
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: HWSMWKQMUQLRLR-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R)-3-benzyloxycarbonylamino-3-methyl-1-(p-methoxyphenyl)pyrrolidin-2-one 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以69%的产率得到(3R)-3-benzyloxycarbonylamino-3-methylpyrrolidin-2-one
  参考文献：
  名称：

  Preparation of Diazabicyclo[4.3.0]nonene-Based Peptidomimetics

  摘要：

  Several functionalized diazabicyclo[4.3.0]nonenes and other heterocycles have been prepared as potential peptidomimetic scaffolds. A novel and efficient method has been developed for the preparation of N-substituted gamma-lactams 13. Preparation of amidine-containing 1,5-diazabicyclo[4.3.0]nonenes 43 and 44 has been achieved through Hg-mediated cyclization of the precursor N-aminopropyl-gamma-thiolactams and subsequent functional group manipulation. Bicycle 43 represents a novel scaffold for potential peptide turn mimetics, whereas 44 could potentially be employed as an alpha-helix template attached to the C-terminus of peptides. These compounds are novel additions to the current range of small-molecule constrained peptidomimetics.

  DOI：

  10.1021/jo071074x
• 作为产物：
  描述：

  (2S,4S)-3-苄氧羰基-4-甲基-2-苯基-1,3-恶唑啉-5-酮 在 sodium cyanoborohydride 、 臭氧 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 94.5h， 生成 (3R)-3-benzyloxycarbonylamino-3-methyl-1-(p-methoxyphenyl)pyrrolidin-2-one
  参考文献：
  名称：

  Preparation of Diazabicyclo[4.3.0]nonene-Based Peptidomimetics

  摘要：

  Several functionalized diazabicyclo[4.3.0]nonenes and other heterocycles have been prepared as potential peptidomimetic scaffolds. A novel and efficient method has been developed for the preparation of N-substituted gamma-lactams 13. Preparation of amidine-containing 1,5-diazabicyclo[4.3.0]nonenes 43 and 44 has been achieved through Hg-mediated cyclization of the precursor N-aminopropyl-gamma-thiolactams and subsequent functional group manipulation. Bicycle 43 represents a novel scaffold for potential peptide turn mimetics, whereas 44 could potentially be employed as an alpha-helix template attached to the C-terminus of peptides. These compounds are novel additions to the current range of small-molecule constrained peptidomimetics.

  DOI：

  10.1021/jo071074x

文献信息

• Preparation of Diazabicyclo[4.3.0]nonene-Based Peptidomimetics
  作者：Craig A. Hutton、Paul A. Bartlett

  DOI：10.1021/jo071074x

  日期：2007.8.31

  Several functionalized diazabicyclo[4.3.0]nonenes and other heterocycles have been prepared as potential peptidomimetic scaffolds. A novel and efficient method has been developed for the preparation of N-substituted gamma-lactams 13. Preparation of amidine-containing 1,5-diazabicyclo[4.3.0]nonenes 43 and 44 has been achieved through Hg-mediated cyclization of the precursor N-aminopropyl-gamma-thiolactams and subsequent functional group manipulation. Bicycle 43 represents a novel scaffold for potential peptide turn mimetics, whereas 44 could potentially be employed as an alpha-helix template attached to the C-terminus of peptides. These compounds are novel additions to the current range of small-molecule constrained peptidomimetics.