(2S,12S,22S)-2,6-cyclo-12,16-cyclo-22,26-cyclo-29-(benzyloxycarbonylamino)-6,10,16,20,26-pentaaza-11,21-dioxononanoic acid methyl ester | 350028-11-4

• 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: (2S,12S,22S)-2,6-cyclo-12,16-cyclo-22,26-cyclo-29-(benzyloxycarbonylamino)-6,10,16,20,26-pentaaza-11,21-dioxononanoic acid methyl ester
• CAS: 350028-11-4
• 化学式: C₃₃H₅₂N₆O₆
• 分子量: 628.812
• InChiKey: IZJWJWJWGPCOES-AWCRTANDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  45.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  132.55
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,12S,22S)-2,6-cyclo-12,16-cyclo-22,26-cyclo-29-(benzyloxycarbonylamino)-6,10,16,20,26-pentaaza-11,21-dioxononanoic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  The synthesis of l-proline derived hexaazamacrocyclic ligands of C3 symmetry via intramolecular methyl ester aminolysis

  摘要：

  A convenient synthesis of enantiomerically pure 18-, 21-. and 24-membered hexaaza-crown ligands is presented. Linear alpha,omega -aminoesters, prepared from L-proline, undergo intramolecular aminolysis to afford the corresponding 18-, 21-, and 24-membered macrocyclic amides in satisfactory yields (42, 65. and 22%, respectively). These were subsequently transformed into the title macrocyclic hexamines via exhaustive reduction with a borane-dimethylsulfide complex. X-Ray structures of two larger macrocyclic amides are also presented. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00068-4
• 作为产物：
  描述：

  (2S)-N-(N'-(benzyloxycarbonyl)-3'-aminopropyl)-proline 、 methyl (2S)-1-[3-[[(2S)-1-(3-aminopropyl)pyrrolidine-2-carbonyl]amino]propyl]pyrrolidine-2-carboxylate 在 三乙胺 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(2S,12S,22S)-2,6-cyclo-12,16-cyclo-22,26-cyclo-29-(benzyloxycarbonylamino)-6,10,16,20,26-pentaaza-11,21-dioxononanoic acid methyl ester
  参考文献：
  名称：

  The synthesis of l-proline derived hexaazamacrocyclic ligands of C3 symmetry via intramolecular methyl ester aminolysis

  摘要：

  A convenient synthesis of enantiomerically pure 18-, 21-. and 24-membered hexaaza-crown ligands is presented. Linear alpha,omega -aminoesters, prepared from L-proline, undergo intramolecular aminolysis to afford the corresponding 18-, 21-, and 24-membered macrocyclic amides in satisfactory yields (42, 65. and 22%, respectively). These were subsequently transformed into the title macrocyclic hexamines via exhaustive reduction with a borane-dimethylsulfide complex. X-Ray structures of two larger macrocyclic amides are also presented. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00068-4