N,N',N''-Tritosyl-2,6,10-triaza<11>(1,4)naphthalenecyclophane

• 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',N''-Tritosyl-2,6,10-triaza<11>(1,4)naphthalenecyclophane
• 英文别名: 3,7,11-Tris-(4-methylphenyl)sulfonyl-3,7,11-triazatricyclo[11.6.2.014,19]henicosa-1(20),13(21),14,16,18-pentaene
• 化学式: C₃₉H₄₃N₃O₆S₃
• 分子量: 745.985
• InChiKey: BLNWHTJPCAOVIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  51
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,5,9-Tritosyl-1,5,9-triazanonane 、 1,4-双(溴甲基)萘 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 30.0h， 以82%的产率得到N,N',N''-Tritosyl-2,6,10-triaza<11>(1,4)naphthalenecyclophane
  参考文献：
  名称：

  N-Tosylated Polyaza[n](1,4)naphthalenophanes. Synthesis and Conformational Studies

  摘要：

  N-Tosylated polyaza[n](1,4)naphthalenophanes containing from 3 to 6 nitrogen atoms and from 9 to 18 atoms in the saturated bridge can be prepared in high yields from 1,4-bis(bromomethyl)naphthalene and the appropriate N-tosylated polyamine chains. NMR data and molecular mechanics calculations suggest the prevalence of conformations in which the polyamine bridge is located above the aromatic ring. Variable-temperature NMR experiments show that internal rotation of the aromatic ring is not allowed, on the NMR time scale, even at 180 degrees C for naphthalenophanes having chain lengths of 12 or less. For naphthalenophanes with chain lengths of 14 or 15 atoms, the rotational barrier is on the order of 12 kcal mol(-1) as calculated from VT-NMR data.

  DOI：

  10.1021/jo00084a024

文献信息

• N-Tosylated Polyaza[n](1,4)naphthalenophanes. Synthesis and Conformational Studies
  作者：M. Isabel Burguete、Beatriz Escuder、Enrique Garcia-Espana、Santiago V. Luis、Juan F. Miravet

  DOI：10.1021/jo00084a024

  日期：1994.3

  N-Tosylated polyaza[n](1,4)naphthalenophanes containing from 3 to 6 nitrogen atoms and from 9 to 18 atoms in the saturated bridge can be prepared in high yields from 1,4-bis(bromomethyl)naphthalene and the appropriate N-tosylated polyamine chains. NMR data and molecular mechanics calculations suggest the prevalence of conformations in which the polyamine bridge is located above the aromatic ring. Variable-temperature NMR experiments show that internal rotation of the aromatic ring is not allowed, on the NMR time scale, even at 180 degrees C for naphthalenophanes having chain lengths of 12 or less. For naphthalenophanes with chain lengths of 14 or 15 atoms, the rotational barrier is on the order of 12 kcal mol(-1) as calculated from VT-NMR data.