tert-butyl 3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-propanoate | 353246-10-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: tert-butyl 3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-propanoate
• 英文别名: Tert-butyl 3-(3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-yl)propanoate
• CAS: 353246-10-3
• 化学式: C₁₈H₃₀N₄O₂
• 分子量: 334.462
• InChiKey: OEMWWLLFYRVVHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-propanoate 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 3,96-bis(carboxymethyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-propanoic acid
  参考文献：
  名称：

  Regioselective synthesis of N-functionalized 12-membered azapyridinomacrocycles bearing trialkylcarboxylic acid side chains

  摘要：

  Selective protection of primary amine moieties of diethylenetriamine by 2-nitrophenylsulfonyl chloride followed by alkylation of the central N atom generates functionalized disulfonamide building blocks. When reacted with 2,6-bis(bromomethyl)pyridine following the Richman-Atkins methodology, such compounds yield the corresponding pyridine-containing azamacrocycles. Smooth removal of the N-sulfonyl groups provides versatile azamacrocyclic intermediates with transannular secondary amine functions. Subsequent N-alkylation regioselectively leads to tri N-functionalized 12-membered azapyridinomacrocycles bearing a sequence of N-acetate and N-propionate side chains. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00328-3
• 作为产物：
  描述：

  tert-butyl 3,9-bis(2-nitrophenylsulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-propanoate 在 sodium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到tert-butyl 3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-propanoate
  参考文献：
  名称：

  Regioselective synthesis of N-functionalized 12-membered azapyridinomacrocycles bearing trialkylcarboxylic acid side chains

  摘要：

  Selective protection of primary amine moieties of diethylenetriamine by 2-nitrophenylsulfonyl chloride followed by alkylation of the central N atom generates functionalized disulfonamide building blocks. When reacted with 2,6-bis(bromomethyl)pyridine following the Richman-Atkins methodology, such compounds yield the corresponding pyridine-containing azamacrocycles. Smooth removal of the N-sulfonyl groups provides versatile azamacrocyclic intermediates with transannular secondary amine functions. Subsequent N-alkylation regioselectively leads to tri N-functionalized 12-membered azapyridinomacrocycles bearing a sequence of N-acetate and N-propionate side chains. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00328-3