4,5,9,10-tetraazatetracyclo[6.2.2.2^3,6.0^2,7]tetradecan-4,9-diene | 136276-57-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,5,9,10-tetraazatetracyclo[6.2.2.2^3,6.0^2,7]tetradecan-4,9-diene
• CAS: 136276-57-8
• 化学式: C₁₀H₁₄N₄
• 分子量: 190.248
• InChiKey: VGLBUSTXTPYBIG-UXAOAXNSSA-N

反应信息

• 作为反应物：
  描述：

  甲基锂 、 4,5,9,10-tetraazatetracyclo[6.2.2.2^3,6.0^2,7]tetradecan-4,9-diene 、 叔丁醇 在 四氟硼酸-二乙醚络合物 作用下， 生成 4,10-bis(dimethylethyl)-5,9-dimethyl-4,5,9,10-tetraazatetracyclo<6.2.2.2^3,6.0^2,7>tetradecane 、 4,9-bis(dimethylethyl)-5,10-dimethyl-4,5,9,10-tetraazatetracyclo<6.2.2.2^3,6.0^2,7>tetradecane
  参考文献：
  名称：

  Torsional effects on the conformations of two diastereomeric tetracyclic bis(hydrazines)

  摘要：

  The symmetrical tetraazatetracyclotetradecadiene (1) is bis(tert-butylated) (tert-butyl alcohol/H+) and bis(methylated) (methyllithium) to a 1:1 mixture of diastereomeric bis(tert-butylmethylhydrazines) with like alkyl groups anti (9a) and syn (9s). 9a has the expected C2 symmetry on the NMR time scale (both tert-butyl groups are directed away from the central CC bond, conformation Oi,Oi in Scheme II). 9s does not have the expected C(s) symmetry, but has one tert-butyl group directed away from the central CC bond and one directed toward it (conformations Oi,oI and Io,iO in Scheme II). Both diastereomers also crystallize in these conformations. AM1 calculations carried out using VAMP both predict this result and show it to be caused by tetracyclic ring torsion (experimentally approximately 12.7-degrees about the central CC bond for crystalline 9a, approximately 13.2-degrees for 9s).

  DOI：

  10.1021/ja00021a009
• 作为产物：
  描述：

  4,5,9,10-tetrakis(ethoxycarbonyl)-4,5,9,10-tetraazatetracyclo<6.2.2.2^3,6.0^2,7>tetradeca-11,13-diene 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 24.33h， 生成 4,5,9,10-tetraazatetracyclo[6.2.2.2^3,6.0^2,7]tetradecan-4,9-diene
  参考文献：
  名称：

  Torsional effects on the conformations of two diastereomeric tetracyclic bis(hydrazines)

  摘要：

  The symmetrical tetraazatetracyclotetradecadiene (1) is bis(tert-butylated) (tert-butyl alcohol/H+) and bis(methylated) (methyllithium) to a 1:1 mixture of diastereomeric bis(tert-butylmethylhydrazines) with like alkyl groups anti (9a) and syn (9s). 9a has the expected C2 symmetry on the NMR time scale (both tert-butyl groups are directed away from the central CC bond, conformation Oi,Oi in Scheme II). 9s does not have the expected C(s) symmetry, but has one tert-butyl group directed away from the central CC bond and one directed toward it (conformations Oi,oI and Io,iO in Scheme II). Both diastereomers also crystallize in these conformations. AM1 calculations carried out using VAMP both predict this result and show it to be caused by tetracyclic ring torsion (experimentally approximately 12.7-degrees about the central CC bond for crystalline 9a, approximately 13.2-degrees for 9s).

  DOI：

  10.1021/ja00021a009