1,8-二氮杂双环[6.3.1]十二烷 | 100098-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1,8-二氮杂双环[6.3.1]十二烷
• 英文名称: 1,8-diazabicyclo<6.3.1>dodecane
• 英文别名: 1,8-Diazabicyclo[6.3.1]dodecane
• CAS: 100098-22-4
• 化学式: C₁₀H₂₀N₂
• 分子量: 168.282
• InChiKey: INBYVNOVCKAAGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 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：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,8-二氮杂双环[5.4.0]十一碳-7-烯 在 二异丁基氢化铝 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 56.0h， 生成 1,8-二氮杂双环[6.3.1]十二烷
  参考文献：
  名称：

  The out,out to out,in transition for 1,(n+2)-diazabicyclo[n.3.1]alkanes

  摘要：

  Hexahydropyrimidines N,N-bridged by a chain of n methylene groups (1,(n + 2)-diazabicyclo[n.3.1]alkanes) adopt out,out (axial,axial) structures for n = 2, 3, and 4. When n = 5, the photoelectron spectrum shows evidence of the presence of some of the out,in (axial,equatorial) isomer in the gas phase, although none can be found in solution. When n = 6, the compound is apparently entirely out,in in the gas phase but exists as a mixture of out,out and out,in conformers in solution. For n = 7, only the diamond lattice out,in isomer can be detected in solution. These experimental data are correlated with,force field (MM2) calculations; multiple minimum search methods have been used to locate all low-energy conformations. Semiempirical calculations (MNDO, AMI, and PM3) have been carried out on model systems. Related tricyclic bis-aminals having 10- and 12-membered rings have also been studied. They adopt [2323] and [3333] conformations, respectively, each having out,in (equatorial,axial) bridged hexahydropyrimidine rings. For several of the compounds, dynamic NMR processes are observed, and possible mechanisms for these are discussed.

  DOI：

  10.1021/ja00068a015

文献信息

• The out,out to out,in transition for 1,(n+2)-diazabicyclo[n.3.1]alkanes
  作者：Roger W. Alder、Edgar Heilbronner、Evi Honegger、Alan B. McEwen、Richard E. Moss、Edward Olefirowicz、Peter A. Petillo、Richard B. Sessions、Gary R. Weisman

  DOI：10.1021/ja00068a015

  日期：1993.7

  Hexahydropyrimidines N,N-bridged by a chain of n methylene groups (1,(n + 2)-diazabicyclo[n.3.1]alkanes) adopt out,out (axial,axial) structures for n = 2, 3, and 4. When n = 5, the photoelectron spectrum shows evidence of the presence of some of the out,in (axial,equatorial) isomer in the gas phase, although none can be found in solution. When n = 6, the compound is apparently entirely out,in in the gas phase but exists as a mixture of out,out and out,in conformers in solution. For n = 7, only the diamond lattice out,in isomer can be detected in solution. These experimental data are correlated with,force field (MM2) calculations; multiple minimum search methods have been used to locate all low-energy conformations. Semiempirical calculations (MNDO, AMI, and PM3) have been carried out on model systems. Related tricyclic bis-aminals having 10- and 12-membered rings have also been studied. They adopt [2323] and [3333] conformations, respectively, each having out,in (equatorial,axial) bridged hexahydropyrimidine rings. For several of the compounds, dynamic NMR processes are observed, and possible mechanisms for these are discussed.