N,N'-ditosyl-1,6-diaza-3,4-dehydro<6>metacyclophane | 145285-52-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-ditosyl-1,6-diaza-3,4-dehydro<6>metacyclophane
• 英文别名: N,N'-ditosyl-1,6-diaza-3,4-dehydro[6]metacyclophane；(4Z)-2,7-bis[(4-methylphenyl)sulfonyl]-2,7-diazabicyclo[6.3.1]dodeca-1(12),4,8,10-tetraene；(4Z)-2,7-bis-(4-methylphenyl)sulfonyl-2,7-diazabicyclo[6.3.1]dodeca-1(12),4,8,10-tetraene
• CAS: 145285-52-5
• 化学式: C₂₄H₂₄N₂O₄S₂
• 分子量: 468.598
• InChiKey: YIHXZPHZUXDFFW-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  91.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  顺式-1,4-二氯-2-丁烯 、 N,N'-ditosyl-metaphenylenediamine 在 caesium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以46%的产率得到N,N'-ditosyl-1,6-diaza-3,4-dehydro<6>metacyclophane
  参考文献：
  名称：

  Synthesis and conformational behaviour of ditosyldiaza[2.2]orthometacyclophanes

  摘要：

  The N,N'-ditosyl-diaza[2.2]orthometacyclophanes 5 a, b were synthesized from N,N-ditosyl-metaphenylenediamine by reaction with (Z)-1,4-dichlorobutene and 1,2-bis-bromomethylbenzene, respectively. Low temperature NMR studies showed that the compound 5 b exists as a 1:1 mixture of chair and boat form of the strained (EZ)-diazanonadiene ring. At room temperature all corresponding resonances are averaged on the NMR time scale (including all four ethylene bridge protons). Going to lower temperatures, in a first step the methylene bridge inversion is frozen (giving two exo H and two endo H, DELTA-G(not-equal) ca. 52 kJ mol-1). In a second step the chair and boat form can be observed separately (DELTA-G(not-equal) ca. 43.5 kJ mol-1 for the chair/boat flip). The assignments were confirmed by 2D NMR experiments.

  DOI：

  10.1007/bf00812332

文献信息

• Synthesis and conformational behaviour of ditosyldiaza[2.2]orthometacyclophanes
  作者：E. Kleinpeter、J. Hartmann、W. Schroth、O. Hofer、H. Kalchhauser、G. Wurz

  DOI：10.1007/bf00812332

  日期：——

  The N,N'-ditosyl-diaza[2.2]orthometacyclophanes 5 a, b were synthesized from N,N-ditosyl-metaphenylenediamine by reaction with (Z)-1,4-dichlorobutene and 1,2-bis-bromomethylbenzene, respectively. Low temperature NMR studies showed that the compound 5 b exists as a 1:1 mixture of chair and boat form of the strained (EZ)-diazanonadiene ring. At room temperature all corresponding resonances are averaged on the NMR time scale (including all four ethylene bridge protons). Going to lower temperatures, in a first step the methylene bridge inversion is frozen (giving two exo H and two endo H, DELTA-G(not-equal) ca. 52 kJ mol-1). In a second step the chair and boat form can be observed separately (DELTA-G(not-equal) ca. 43.5 kJ mol-1 for the chair/boat flip). The assignments were confirmed by 2D NMR experiments.

表征谱图