1-nitro-11-bromo-3,6,9-trioxaundecane | 203740-61-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-nitro-11-bromo-3,6,9-trioxaundecane
• 英文别名: 1-[2-[2-(2-Bromoethoxy)ethoxy]ethoxy]-2-nitroethane
• CAS: 203740-61-8
• 化学式: C₈H₁₆BrNO₅
• 分子量: 286.123
• InChiKey: MCGHDBHYKZCTHO-UHFFFAOYSA-N

物化性质

• 沸点：
  364.7±32.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-nitro-11-bromo-3,6,9-trioxaundecane 在 异氰酸苯酯 、 三乙胺 、 四丁基亚硝酸铵 作用下， 以 硝基甲烷 、 甲苯 为溶剂， 反应 25.5h， 生成 3,6,9,12,16,19,22,26-Octaoxa-13,25-diazatricyclo[22.2.1.111,14]octacosa-1(27),11(28),13,24-tetraene
  参考文献：
  名称：

  Organic metal-complexes. XXI. Synthesis and structure of 3,5,15,17-tetraoxo-1,7,10,13,19,22-hexaoxa-cyclotetracosane and 2,12,14,24-tetraoxo-4,7,10,16,19,22-hexaoxa-25-mercurato-bicyclo[11.11.1]pentacosane

  摘要：

  A new synthesis of the title crown via isoxazolo crown ether 7 and macrocyclic bis-peneaminoketone 10 is described. 7 can be synthesized in 14% yield by a non-template double-[3+2] cycloaddition of dinitrileoxide 5 prepared in situ from dinitropolyether 19 by dehydration with Ph-NCO and alkyne 6. The compounds 16, 17 and 18 are synthesized by the same synthetic strategy. Comparable IR and H-1 NMR spectroscopic data of macrocyclic and non-cyclic compounds show, that macrocyclic conformation stabilizing effects can be ruled out. The structures of the macrocycles 1, 7, 10 and that of the Hg(II)-complex 25, synthesized by reaction of 1 with Hg(OAc)(2) were established by single-crystal X-ray structure analyses. Both inter-and intramolecular hydrogen bonds are observed for the macrocyclic bis-beta-eneaminoketone 10, whereas only intramolecular hydrogen bonds are formed by 1. In the Hg(II)-complex of 1 the mercury is bonded to two methylene groups. C-Hg-C is almost linear [177(1)degrees], the mean Hg-C distance amounts to 215(1) pm. In addition to the Hg-C bonds, each Hg makes a short contact to a carbonyl oxygen in a neighbouring molecule in the plane perpendicular to the C-Hg-C axis [Hg(1)-O(1) = 279(1) pm, Hg(2)-O(5)= 284(1) pm].

  DOI：

  10.1002/prac.19983400207
• 作为产物：
  描述：

  1-溴-2-(2-(2-(2-溴乙氧基)乙氧基)乙氧基)乙烷 在 四丁基亚硝酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 以45%的产率得到1-nitro-11-bromo-3,6,9-trioxaundecane
  参考文献：
  名称：

  Organic metal-complexes. XXI. Synthesis and structure of 3,5,15,17-tetraoxo-1,7,10,13,19,22-hexaoxa-cyclotetracosane and 2,12,14,24-tetraoxo-4,7,10,16,19,22-hexaoxa-25-mercurato-bicyclo[11.11.1]pentacosane

  摘要：

  A new synthesis of the title crown via isoxazolo crown ether 7 and macrocyclic bis-peneaminoketone 10 is described. 7 can be synthesized in 14% yield by a non-template double-[3+2] cycloaddition of dinitrileoxide 5 prepared in situ from dinitropolyether 19 by dehydration with Ph-NCO and alkyne 6. The compounds 16, 17 and 18 are synthesized by the same synthetic strategy. Comparable IR and H-1 NMR spectroscopic data of macrocyclic and non-cyclic compounds show, that macrocyclic conformation stabilizing effects can be ruled out. The structures of the macrocycles 1, 7, 10 and that of the Hg(II)-complex 25, synthesized by reaction of 1 with Hg(OAc)(2) were established by single-crystal X-ray structure analyses. Both inter-and intramolecular hydrogen bonds are observed for the macrocyclic bis-beta-eneaminoketone 10, whereas only intramolecular hydrogen bonds are formed by 1. In the Hg(II)-complex of 1 the mercury is bonded to two methylene groups. C-Hg-C is almost linear [177(1)degrees], the mean Hg-C distance amounts to 215(1) pm. In addition to the Hg-C bonds, each Hg makes a short contact to a carbonyl oxygen in a neighbouring molecule in the plane perpendicular to the C-Hg-C axis [Hg(1)-O(1) = 279(1) pm, Hg(2)-O(5)= 284(1) pm].

  DOI：

  10.1002/prac.19983400207