3-methylene-8,11-bis(2-hydroxyethyl)-1,5-dioxa-8,11-diazacyclotridecane | 143065-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 3-methylene-8,11-bis(2-hydroxyethyl)-1,5-dioxa-8,11-diazacyclotridecane
• 英文别名: 2-[7-(2-hydroxyethyl)-12-methylidene-1,10-dioxa-4,7-diazacyclotridec-4-yl]ethanol
• CAS: 143065-56-9
• 化学式: C₁₄H₂₈N₂O₄
• 分子量: 288.387
• InChiKey: ZRCBXOUTCLTSKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  460.4±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  65.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-methylene-8,11-bis(2-hydroxyethyl)-1,5-dioxa-8,11-diazacyclotridecane 在 lithium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 6,16-bis(hydroxymethyl)-4,8,14,18-tetraoxa-1,11-diazabicyclo<9.9.2>docosane
  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：

  2,2'-(2-methylenepropane-1,3-diyldioxy)bisethanol 在 sodium hydroxide 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 74.0h， 生成 3-methylene-8,11-bis(2-hydroxyethyl)-1,5-dioxa-8,11-diazacyclotridecane
  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