4-(2-carboxy-2-methylpropyl)pyridine-1-oxide | 1374840-04-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 4-(2-carboxy-2-methylpropyl)pyridine-1-oxide
• 英文别名: 2,2-dimethyl-3-(1-oxidopyridin-1-ium-4-yl)propanoic acid
• CAS: 1374840-04-6
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: BEARVEGUPIRXCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-carboxy-2-methylpropyl)pyridine-1-oxide 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  A New and Useful Method for the Macrocyclization of Linear Peptides

  摘要：

  A new and useful procedure for the macrocyclization of linear peptides is described. The natural amino acid side chains of tyrosine (phenol), lysine (alkylamine), and histidine (imidazole) react in an Intramolecular fashion with a pendent pyridine-N-oxide-carboxamide, which is selectively activated by the phosphonium salt, PyBroP. The reaction is mild, rapid, and efficient with a potentially large substrate scope. Multiple examples are provided with full characterization and analyses, including a novel aza-variant of the C-O-D ring system of vancomycin.

  DOI：

  10.1021/ol301173m
• 作为产物：
  描述：

  2,2-dimethyl-3-(pyridin-4-yl)propanoic acid 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到4-(2-carboxy-2-methylpropyl)pyridine-1-oxide
  参考文献：
  名称：

  A New and Useful Method for the Macrocyclization of Linear Peptides

  摘要：

  A new and useful procedure for the macrocyclization of linear peptides is described. The natural amino acid side chains of tyrosine (phenol), lysine (alkylamine), and histidine (imidazole) react in an Intramolecular fashion with a pendent pyridine-N-oxide-carboxamide, which is selectively activated by the phosphonium salt, PyBroP. The reaction is mild, rapid, and efficient with a potentially large substrate scope. Multiple examples are provided with full characterization and analyses, including a novel aza-variant of the C-O-D ring system of vancomycin.

  DOI：

  10.1021/ol301173m