tert-butyl Nα-Boc-Nδ-(5-amino-2H-1,2,4-triazol-3-yl)-L-ornithinate | 149971-01-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl Nα-Boc-Nδ-(5-amino-2H-1,2,4-triazol-3-yl)-L-ornithinate
• 英文别名: tert-butyl N^α-Boc-N^δ-(5-amino-2H-1,2,4-triazol-3-yl)-L-ornithinate
• CAS: 149971-01-7
• 化学式: C₁₆H₃₀N₆O₄
• 分子量: 370.452
• InChiKey: LJZCOHXAJKZZGE-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  144.25
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl Nα-Boc-Nδ-(5-amino-2H-1,2,4-triazol-3-yl)-L-ornithinate 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以30 mg的产率得到N^δ-(5-amino-2H-1,2,4-triazol-3-yl)-L-ornithine
  参考文献：
  名称：

  Methodology for the preparation of N-guanidino-modified arginines and related derivatives

  摘要：

  Methods for the preparation of N(G)-modified arginines and N(delta)-heterocyclic ornithines are described. The reactive cyanamide intermediate tert-butyl N(alpha)-Boc-N(delta)-cyano-L-ornithinate (2). prepared either by treatment of tert-butyl N(alpha)-BOC-L-ornithinate (5) with cyanogen bromide or by dehydration of tert-butyl N(alpha)-Boc-L-citrullinate (6), was utilized to prepare N(G)-hydroxy-L-arginine, N(G)-amino-L-arginine, and N(G)-methoxy-L-arginine. Intermediates 3a and 3b, derived from treatment of 5 with diphenyl cyanocarbonimidate (19), reacted with nitrogen nucleophiles to produce novel N(G)-cyano-L-arginine and N(delta)-heterocyclic L-ornithine analogs.

  DOI：

  10.1021/jo00068a031
• 作为产物：
  描述：

  tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate 在 一水合肼 、 三乙胺 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 3.0h， 生成 tert-butyl Nα-Boc-Nδ-(5-amino-2H-1,2,4-triazol-3-yl)-L-ornithinate
  参考文献：
  名称：

  Methodology for the preparation of N-guanidino-modified arginines and related derivatives

  摘要：

  Methods for the preparation of N(G)-modified arginines and N(delta)-heterocyclic ornithines are described. The reactive cyanamide intermediate tert-butyl N(alpha)-Boc-N(delta)-cyano-L-ornithinate (2). prepared either by treatment of tert-butyl N(alpha)-BOC-L-ornithinate (5) with cyanogen bromide or by dehydration of tert-butyl N(alpha)-Boc-L-citrullinate (6), was utilized to prepare N(G)-hydroxy-L-arginine, N(G)-amino-L-arginine, and N(G)-methoxy-L-arginine. Intermediates 3a and 3b, derived from treatment of 5 with diphenyl cyanocarbonimidate (19), reacted with nitrogen nucleophiles to produce novel N(G)-cyano-L-arginine and N(delta)-heterocyclic L-ornithine analogs.

  DOI：

  10.1021/jo00068a031