(3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene | 951172-79-5

• 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: (3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene
• 英文别名: (3R,8R)-3,8-dimethyl-8-(phenylmethoxycarbonylamino)-2,4,6,7-tetrahydropyrrolo[1,2-a]pyrimidine-3-carboxylic acid
• CAS: 951172-79-5
• 化学式: C₁₈H₂₃N₃O₄
• 分子量: 345.398
• InChiKey: CSYIFMOWUZQKOW-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene 、 叠氮磷酸二苯酯 、 叔丁醇 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 36.0h， 以45%的产率得到(3S,7S)-7-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene diphenylphosphate
  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 劳森试剂 、 lithium hydroxide 、 sodium cyanoborohydride 、 臭氧 、 溶剂黄146 、 mercury dichloride 、 lithium hexamethyldisilazane 、 肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 164.0h， 生成 (3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene
  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.