9,13-dioxo-4,11,17,25,31-pentaoxa-1,8,14,20-tetraazatricyclo<18.5^1,14.6^8,20.2>tritriacontane | 143065-53-6

• 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: 9,13-dioxo-4,11,17,25,31-pentaoxa-1,8,14,20-tetraazatricyclo<18.5^1,14.6^8,20.2>tritriacontane
• 英文别名: 4,10,18,24,29-Pentaoxa-1,7,14,21-tetrazatricyclo[12.12.5.27,21]tritriacontane-27,31-dione
• CAS: 143065-53-6
• 化学式: C₂₄H₄₄N₄O₇
• 分子量: 500.636
• InChiKey: NSRURKDYEQRBAC-UHFFFAOYSA-N

物化性质

• 沸点：
  706.2±60.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  35
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9,13-dioxo-4,11,17,25,31-pentaoxa-1,8,14,20-tetraazatricyclo<18.5^1,14.6^8,20.2>tritriacontane 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到4,11,17,25,31-pentaoxa-1,8,14,20-tetraazatricyclo<18.5^1,14.6^8,20.2>tritriacontane
  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 、 1,8-双二甲氨基萘 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 乙腈 、 苯 为溶剂， 反应 52.0h， 生成 9,13-dioxo-4,11,17,25,31-pentaoxa-1,8,14,20-tetraazatricyclo<18.5^1,14.6^8,20.2>tritriacontane
  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.