1,3-bis(3-chloro-6-oxopyridazin-1-yl)propane | 674309-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,3-bis(3-chloro-6-oxopyridazin-1-yl)propane
• 英文别名: 2,2'-(Propane-1,3-diyl)bis(6-chloropyridazin-3(2H)-one)；6-chloro-2-[3-(3-chloro-6-oxopyridazin-1-yl)propyl]pyridazin-3-one
• CAS: 674309-08-1
• 化学式: C₁₁H₁₀Cl₂N₄O₂
• 分子量: 301.132
• InChiKey: OEQYXLCXPPWBSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-bis(3-chloro-6-oxopyridazin-1-yl)propane 在 potassium tert-butylate 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 10,14,22,26-tetraoxa-1,5,31,32,33-pentaazatetracyclo[25.3.1.1^5,9.1^16,20]tritriaconta-7,9(32),16,18,20(33),27(31),28-heptaen-6,30-dione
  参考文献：
  名称：

  A new series of heteroaromatic receptors containing the 1,3-bis(6-oxopyridazin-1-yl)propane unit: their selective transport ability towards NH4+ in relation to Na+, K+ and Ca2+

  摘要：

  The synthesis of a new series of heteroaromatic macrocycles 6-9 containing the 1,3-bis(6-oxopyridazin-1-yl)propane and pyridine units is reported. The acyclic compounds 11-15 had to be prepared as the intermediates in the synthetic sequence. Evaluation of the ionophoric properties of 6-9 and 11-15 shows that 8 and 13 behave as good ammonium ion carriers and exhibit a high selectivity for ammonium with respect to spherically symmetric metallic ions like Na+, K+, and Ca2+. Molecular modelling of the ammonium complexes suggests that the host's oxyimino groups play a more relevant part in effective complexation than the pyridine unit, and that the high complexating efficiency of 13 might be related to the formation of a pseudocavity by intramolecular hydrogen bonding. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.040
• 作为产物：
  描述：

  3-羟基-6-氯哒嗪 、 1,3-二溴丙烷 在 氢氧化钾 、 四丁基氯化铵 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 100.0h， 以67%的产率得到1,3-bis(3-chloro-6-oxopyridazin-1-yl)propane
  参考文献：
  名称：

  A new series of heteroaromatic receptors containing the 1,3-bis(6-oxopyridazin-1-yl)propane unit: their selective transport ability towards NH4+ in relation to Na+, K+ and Ca2+

  摘要：

  The synthesis of a new series of heteroaromatic macrocycles 6-9 containing the 1,3-bis(6-oxopyridazin-1-yl)propane and pyridine units is reported. The acyclic compounds 11-15 had to be prepared as the intermediates in the synthetic sequence. Evaluation of the ionophoric properties of 6-9 and 11-15 shows that 8 and 13 behave as good ammonium ion carriers and exhibit a high selectivity for ammonium with respect to spherically symmetric metallic ions like Na+, K+, and Ca2+. Molecular modelling of the ammonium complexes suggests that the host's oxyimino groups play a more relevant part in effective complexation than the pyridine unit, and that the high complexating efficiency of 13 might be related to the formation of a pseudocavity by intramolecular hydrogen bonding. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.040

文献信息

• A new series of heteroaromatic receptors containing the 1,3-bis(6-oxopyridazin-1-yl)propane unit: their selective transport ability towards NH4+ in relation to Na+, K+ and Ca2+
  作者：Lucrecia Campayo、Mercedes Pardo、Ana Cotillas、Oscar Jaúregui、Maria J.R Yunta、Carmen Cano、Fernando Gomez-Contreras、Pilar Navarro、Ana M Sanz

  DOI：10.1016/j.tet.2003.11.040

  日期：2004.1

  The synthesis of a new series of heteroaromatic macrocycles 6-9 containing the 1,3-bis(6-oxopyridazin-1-yl)propane and pyridine units is reported. The acyclic compounds 11-15 had to be prepared as the intermediates in the synthetic sequence. Evaluation of the ionophoric properties of 6-9 and 11-15 shows that 8 and 13 behave as good ammonium ion carriers and exhibit a high selectivity for ammonium with respect to spherically symmetric metallic ions like Na+, K+, and Ca2+. Molecular modelling of the ammonium complexes suggests that the host's oxyimino groups play a more relevant part in effective complexation than the pyridine unit, and that the high complexating efficiency of 13 might be related to the formation of a pseudocavity by intramolecular hydrogen bonding. (C) 2003 Elsevier Ltd. All rights reserved.