4,7,13,16,22,28-hexaoxa-1,10,19,25-tetraazabicyclo<17.11.2>dotriacontane | 143065-63-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,7,13,16,22,28-hexaoxa-1,10,19,25-tetraazabicyclo<17.11.2>dotriacontane
• 英文别名: 4,7,13,16,22,28-Hexaoxa-1,10,19,25-tetrazabicyclo[17.11.2]dotriacontane
• CAS: 143065-63-8
• 化学式: C₂₂H₄₆N₄O₆
• 分子量: 462.63
• InChiKey: ICYBIEBJKWIXKU-UHFFFAOYSA-N

物化性质

• 沸点：
  616.7±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  85.9
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,7,13,16,22,28-hexaoxa-1,10,19,25-tetraazabicyclo<17.11.2>dotriacontane 在 硼烷 、 1,8-双二甲氨基萘 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 34.0h， 生成 4,7,13,19,27,32,35-heptaoxa-1,10,16,22-tetraazatricyclo<20.5^1,16.8^10,22.2>heptatriacontane
  参考文献：
  名称：

  Synthesis and complexation properties of suitcase-shaped macrotricyclic and butterfly-shaped macrobicyclic polyether ligands

  摘要：

  Ten suitcase-shaped macrotricyclic polyethers (1-10) containing nitrogen and carbon bridgehead atoms have been synthesized. These new cage compounds were prepared by connecting together two hydroxymethyl-substituted or two secondary amine-containing butterfly-shaped macrobicyclic polyethers by means of linear bifunctional connecting groups. Intermediate bis(hydroxymethyl)-substituted butterfly-shaped macrobicyclic polyether 14 was prepared by treating N,N'-bis(2-hydroxyethyl)ethylenediamine with 5-methylene-3,7-dioxanonane-1,9-diyl ditosylate to give bislariat 1,4-diaza-13-crown-4 (11) which was cyclized with 3-chloro-2-(chloromethyl)-l-propene followed by hydroboration. Intermediate bissecondary amine-contaminating butterfly shaped macrobicyclic polyethers 18 and 19 were prepared by treating N,N'-bis(2-hydroxyethyl)ethylenediamine with 6-tosyl-3,9-dioxa-6-aza-1,11-undecanediyl ditosylate (33) to give N-tosyl-N,N"-bis(2-hydroxyethyl)triaza-15-crown-5 (12). Lariat crown ether 12 was cyclized with 33 followed by reduction with LiAlH4 to give 18, or with 4-tosyl-4-aza-1,7-heptanediyl ditosylate (36) to give 19. Some of the suitcase-shaped macrotricycles interacted with various cations. One was selective for Pb2+ ions and another interacted strongly with Hg2+. A crystal structure for the 13-NaClO4 complex also is reported.

  DOI：

  10.1021/jo00044a040
• 作为产物：
  描述：

  N,N-bis<2-(2-hydroxyethoxy)ethyl>-p-toluenesulfonamide 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 11.0h， 生成 4,7,13,16,22,28-hexaoxa-1,10,19,25-tetraazabicyclo<17.11.2>dotriacontane
  参考文献：
  名称：

  Synthesis and complexation properties of suitcase-shaped macrotricyclic and butterfly-shaped macrobicyclic polyether ligands

  摘要：

  Ten suitcase-shaped macrotricyclic polyethers (1-10) containing nitrogen and carbon bridgehead atoms have been synthesized. These new cage compounds were prepared by connecting together two hydroxymethyl-substituted or two secondary amine-containing butterfly-shaped macrobicyclic polyethers by means of linear bifunctional connecting groups. Intermediate bis(hydroxymethyl)-substituted butterfly-shaped macrobicyclic polyether 14 was prepared by treating N,N'-bis(2-hydroxyethyl)ethylenediamine with 5-methylene-3,7-dioxanonane-1,9-diyl ditosylate to give bislariat 1,4-diaza-13-crown-4 (11) which was cyclized with 3-chloro-2-(chloromethyl)-l-propene followed by hydroboration. Intermediate bissecondary amine-contaminating butterfly shaped macrobicyclic polyethers 18 and 19 were prepared by treating N,N'-bis(2-hydroxyethyl)ethylenediamine with 6-tosyl-3,9-dioxa-6-aza-1,11-undecanediyl ditosylate (33) to give N-tosyl-N,N"-bis(2-hydroxyethyl)triaza-15-crown-5 (12). Lariat crown ether 12 was cyclized with 33 followed by reduction with LiAlH4 to give 18, or with 4-tosyl-4-aza-1,7-heptanediyl ditosylate (36) to give 19. Some of the suitcase-shaped macrotricycles interacted with various cations. One was selective for Pb2+ ions and another interacted strongly with Hg2+. A crystal structure for the 13-NaClO4 complex also is reported.

  DOI：

  10.1021/jo00044a040

文献信息

• Synthesis and complexation properties of suitcase-shaped macrotricyclic and butterfly-shaped macrobicyclic polyether ligands
  作者：Haoyun An、Jerald S. Bradshaw、Krzysztof E. Krakowiak、Chengyue Zhu、N. Kent Dalley、Reed M. Izatt

  DOI：10.1021/jo00044a040

  日期：1992.8

  Ten suitcase-shaped macrotricyclic polyethers (1-10) containing nitrogen and carbon bridgehead atoms have been synthesized. These new cage compounds were prepared by connecting together two hydroxymethyl-substituted or two secondary amine-containing butterfly-shaped macrobicyclic polyethers by means of linear bifunctional connecting groups. Intermediate bis(hydroxymethyl)-substituted butterfly-shaped macrobicyclic polyether 14 was prepared by treating N,N'-bis(2-hydroxyethyl)ethylenediamine with 5-methylene-3,7-dioxanonane-1,9-diyl ditosylate to give bislariat 1,4-diaza-13-crown-4 (11) which was cyclized with 3-chloro-2-(chloromethyl)-l-propene followed by hydroboration. Intermediate bissecondary amine-contaminating butterfly shaped macrobicyclic polyethers 18 and 19 were prepared by treating N,N'-bis(2-hydroxyethyl)ethylenediamine with 6-tosyl-3,9-dioxa-6-aza-1,11-undecanediyl ditosylate (33) to give N-tosyl-N,N"-bis(2-hydroxyethyl)triaza-15-crown-5 (12). Lariat crown ether 12 was cyclized with 33 followed by reduction with LiAlH4 to give 18, or with 4-tosyl-4-aza-1,7-heptanediyl ditosylate (36) to give 19. Some of the suitcase-shaped macrotricycles interacted with various cations. One was selective for Pb2+ ions and another interacted strongly with Hg2+. A crystal structure for the 13-NaClO4 complex also is reported.