10-<(N,N-Diethylcarbamoyl)methyl>-1,4,7-trioxa-10-azacyclododecane | 166886-05-1

• 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: 10-<(N,N-Diethylcarbamoyl)methyl>-1,4,7-trioxa-10-azacyclododecane
• 英文别名: N,N-diethyl-2-(1,4,7-trioxa-10-azacyclododec-10-yl)acetamide
• CAS: 166886-05-1
• 化学式: C₁₄H₂₈N₂O₄
• 分子量: 288.387
• InChiKey: SXEMWGUJRSRRLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  10-<(N,N-Diethylcarbamoyl)methyl>-1,4,7-trioxa-10-azacyclododecane 在 硼烷 作用下， 以70%的产率得到10-<(N,N-Diethylamino)ethyl>-1,4,7-trioxa-10-azacyclododecane
  参考文献：
  名称：

  Li+ Ion-Selective Binding and Transport Properties of 12-Membered Ring Lariat Ethers: Experimental and Computational Studies on Crown Ring-Sidearm Cooperativity

  摘要：

  A variety of lariat ethers were prepared in which amine, ether, ester, amide, nitrile, and pyridine moieties were attached as cation-ligating sidearms to azacrown rings. Among them, amine-armed aza-12-crown-4 compounds specifically accommodated a Li+ cation in a three dimensional fashion and clearly distinguished it from other metal cations. FAB-MS and Li-7/C-13 NMR binding and liquid membrane transport studies confirmed that amine-armed aza-12-crown-4s formed stable and encapsulated Li+ complexes suitable for specific recognition and transport, while other aza-12-crown-4 derivatives exhibited Naf ion selectivity. Using the density functional method, stabilization energies were estimated for some lariat ether-metal complexes. Since this nonempirical calculation offered results consistent with several experimental observations, combined studies of lariat ether chemistry and computer calculation may provide a new and interesting approach to the design of a specific cation receptor.

  DOI：

  10.1021/jo00105a021
• 作为产物：
  描述：

  氮杂-12-冠醚-4 、 N,N-二乙基-2-氯乙酰胺 以70%的产率得到10-<(N,N-Diethylcarbamoyl)methyl>-1,4,7-trioxa-10-azacyclododecane
  参考文献：
  名称：

  Li+ Ion-Selective Binding and Transport Properties of 12-Membered Ring Lariat Ethers: Experimental and Computational Studies on Crown Ring-Sidearm Cooperativity

  摘要：

  A variety of lariat ethers were prepared in which amine, ether, ester, amide, nitrile, and pyridine moieties were attached as cation-ligating sidearms to azacrown rings. Among them, amine-armed aza-12-crown-4 compounds specifically accommodated a Li+ cation in a three dimensional fashion and clearly distinguished it from other metal cations. FAB-MS and Li-7/C-13 NMR binding and liquid membrane transport studies confirmed that amine-armed aza-12-crown-4s formed stable and encapsulated Li+ complexes suitable for specific recognition and transport, while other aza-12-crown-4 derivatives exhibited Naf ion selectivity. Using the density functional method, stabilization energies were estimated for some lariat ether-metal complexes. Since this nonempirical calculation offered results consistent with several experimental observations, combined studies of lariat ether chemistry and computer calculation may provide a new and interesting approach to the design of a specific cation receptor.

  DOI：

  10.1021/jo00105a021

文献信息

• Li+ Ion-Selective Binding and Transport Properties of 12-Membered Ring Lariat Ethers: Experimental and Computational Studies on Crown Ring-Sidearm Cooperativity
  作者：Hiroshi Tsukube、Takayuki Inoue、Kenzi Hori

  DOI：10.1021/jo00105a021

  日期：1994.12

  A variety of lariat ethers were prepared in which amine, ether, ester, amide, nitrile, and pyridine moieties were attached as cation-ligating sidearms to azacrown rings. Among them, amine-armed aza-12-crown-4 compounds specifically accommodated a Li+ cation in a three dimensional fashion and clearly distinguished it from other metal cations. FAB-MS and Li-7/C-13 NMR binding and liquid membrane transport studies confirmed that amine-armed aza-12-crown-4s formed stable and encapsulated Li+ complexes suitable for specific recognition and transport, while other aza-12-crown-4 derivatives exhibited Naf ion selectivity. Using the density functional method, stabilization energies were estimated for some lariat ether-metal complexes. Since this nonempirical calculation offered results consistent with several experimental observations, combined studies of lariat ether chemistry and computer calculation may provide a new and interesting approach to the design of a specific cation receptor.