3,6,13,17-tetramethyl-3,6,14,17,23,24-hexaazatricyclo[17.3.1.1^8,12]tetracosa-1(23),8,10,12(24),19,21-hexaene-2,7,13,18-tetraone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 3,6,13,17-tetramethyl-3,6,14,17,23,24-hexaazatricyclo[17.3.1.1^8,12]tetracosa-1(23),8,10,12(24),19,21-hexaene-2,7,13,18-tetraone
• 英文别名: 3,6,14,17-Tetramethyl-3,6,14,17,23,24-hexazatricyclo[17.3.1.18,12]tetracosa-1(23),8(24),9,11,19,21-hexaene-2,7,13,18-tetrone
• 化学式: C₂₂H₂₆N₆O₄
• 分子量: 438.486
• InChiKey: MHTGDGWVKFTALK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  pyridine-2,6-dicarbonyl chloride hydrochloride 、 N,N'-二甲基乙二胺 在 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以26%的产率得到3,6,13,17-tetramethyl-3,6,14,17,23,24-hexaazatricyclo[17.3.1.1^8,12]tetracosa-1(23),8,10,12(24),19,21-hexaene-2,7,13,18-tetraone
  参考文献：
  名称：

  Bis-pyridine-tetramide 18-membered macrocycles. Role of increased preorganisation on selectivity

  摘要：

  Enhanced preorganisation induced by four substituted amide groups in macrocycles 4a and 4b increases the Ag+ extraction efficiency by >30% to 74 - 81% and Ag+/Pb2+ selectivity by >300% to 245 - 283 times than in 1. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02234-4

文献信息

• Factors Influencing the Course of the Macrocyclization ofα,ω-Diamines with Esters ofα,ω-Dicarboxylic Acids
  作者：Dorota Gryko、Daniel T. Gryko、Hanna Sierzputowska-Gracz、Piotr Pi??tek、Janusz Jurczak

  DOI：10.1002/hlca.200490004

  日期：2004.1

  The efficient synthesis of eight new macrocyclic amides (lactams) via reaction of diesters with diamines under normal dilution conditions is described. The role of intermolecular H-bond formation and steric hindrance is discussed based on 1H- and 15N-NMR studies of appropriate model compounds. Principles for the optimal choice of esters that can be efficiently transformed into diamides have been developed

  描述了通过二酯与二胺在正常稀释条件下的反应有效合成八种新的大环酰胺（内酰胺）。基于适当模型化合物的1 H-和15 N-NMR研究，讨论了分子间H键形成和位阻的作用。已经开发出可以有效转化为二酰胺的最佳选择酯的原理。
• Synthetic ionophores 16. Synthesis and association behaviour of bis-pyridine tetramide macrocycles: Role of increased preorganisation on Ag+ selectivity
  作者：Subodh Kumar、Maninder Singh Hundal、Geeta Hundal、Navneet Kaur、Harjit Singh

  DOI：10.1016/s0040-4020(97)00691-1

  日期：1997.8

  Pyridine based tetramide macrocycles (6-9) have been synthesized by nucleophilic displacement in pyridine-2,6-dicarbonyl dichloride with appropriate diamines. The 18-membered macrocycles 6 and 7 have well organized structures and 20-membered macrocycles 8 and 9 exist as mixtures of configurational isomers. The comparison of X-ray single crystal and energy minimized structures of previously reported diamide diester macrocycle(1) with those of macrocycles 6, 7 and 1.AgNO3 show that the macrocyles 6 and 7 possess type of preorganised structure attained by macrocycle 1 on complexation. This enhanced preorganisation in macrocycles 6 and 7 increases the Ag+ extraction efficiency by >30% to 74 - 81% and Ag+ / Pb2+ selectivity by >300% to 245 - 283 times than in 1. (C) 1997 Elsevier Science Ltd.
• Bis-pyridine-tetramide 18-membered macrocycles. Role of increased preorganisation on selectivity
  作者：Subodh Kumar、Geeta Hundal、Navneet Kaur、Maninder Singh Hundal、Harjit Singh

  DOI：10.1016/s0040-4039(96)02234-4

  日期：1997.1

  Enhanced preorganisation induced by four substituted amide groups in macrocycles 4a and 4b increases the Ag+ extraction efficiency by >30% to 74 - 81% and Ag+/Pb2+ selectivity by >300% to 245 - 283 times than in 1. Copyright (C) 1996 Published by Elsevier Science Ltd