(1S,4S)-5-(3-aminopropyl)-2-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane | 191280-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (1S,4S)-5-(3-aminopropyl)-2-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane
• 英文别名: tert-butyl (1S,4S)-5-(3-aminopropyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
• CAS: 191280-84-9
• 化学式: C₁₃H₂₅N₃O₂
• 分子量: 255.36
• InChiKey: GUJYEETYNFSPNT-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  58.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三氟乙酸乙酯 、 (1S,4S)-5-(3-aminopropyl)-2-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane 以 乙醇 为溶剂， 以67.6%的产率得到
  参考文献：
  名称：

  Conformationally Restrained Chiral Analogues of Spermine:  Chemical Synthesis and Improvements in DNA Triplex Stability

  摘要：

  The synthesis of novel chiral analogues of spermine, 11 (2R,4S) and 14 (2S,4R), is reported starting from trans-4-hydroxy-L-proline 3. These cyclic analogues are generated from linear, achiral spermine by incorporating a pyrrolidine ring on the backbone to effect conformational rigidity, with simultaneous creation of two asymmetric centers. The chiral analogues bind both AT and CG rich DNA duplexes as effectively as spermine and exhibit even better association with DNA tripler than spermine. The newer analogues have features for structural elaboration to novel molecular entities of potential importance in therapeutics and material design.

  DOI：

  10.1021/jo970414j
• 作为产物：
  描述：

  N-Boc-反式-4-羟基-L-脯氨酸甲酯 在 锂硼氢 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 56.0h， 生成 (1S,4S)-5-(3-aminopropyl)-2-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Conformationally Restrained Chiral Analogues of Spermine:  Chemical Synthesis and Improvements in DNA Triplex Stability

  摘要：

  The synthesis of novel chiral analogues of spermine, 11 (2R,4S) and 14 (2S,4R), is reported starting from trans-4-hydroxy-L-proline 3. These cyclic analogues are generated from linear, achiral spermine by incorporating a pyrrolidine ring on the backbone to effect conformational rigidity, with simultaneous creation of two asymmetric centers. The chiral analogues bind both AT and CG rich DNA duplexes as effectively as spermine and exhibit even better association with DNA tripler than spermine. The newer analogues have features for structural elaboration to novel molecular entities of potential importance in therapeutics and material design.

  DOI：

  10.1021/jo970414j

文献信息

• Conformationally Restrained Chiral Analogues of Spermine:  Chemical Synthesis and Improvements in DNA Triplex Stability
  作者：Kallanthottathil G. Rajeev、Gangadhar J. Sanjayan、Krishna N. Ganesh

  DOI：10.1021/jo970414j

  日期：1997.7.1

  The synthesis of novel chiral analogues of spermine, 11 (2R,4S) and 14 (2S,4R), is reported starting from trans-4-hydroxy-L-proline 3. These cyclic analogues are generated from linear, achiral spermine by incorporating a pyrrolidine ring on the backbone to effect conformational rigidity, with simultaneous creation of two asymmetric centers. The chiral analogues bind both AT and CG rich DNA duplexes as effectively as spermine and exhibit even better association with DNA tripler than spermine. The newer analogues have features for structural elaboration to novel molecular entities of potential importance in therapeutics and material design.