2,7-di(p-toluenesulfonamido)naphthalene | 118477-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,7-di(p-toluenesulfonamido)naphthalene
• 英文别名: 2.7-Bis--naphthalin；N,N'-naphthalene-2,7-diyl-bis-toluene-4-sulfonamide；N,N'-Naphthalin-2,7-diyl-bis-toluol-4-sulfonamid；2,7-Bis-toluol-4-sulfonylamino-naphthalin
• CAS: 118477-42-2
• 化学式: C₂₄H₂₂N₂O₄S₂
• 分子量: 466.582
• InChiKey: KMBHSTAFFBVJKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  92.34
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,7-di(p-toluenesulfonamido)naphthalene 在 palladium on activated charcoal 硫酸 、 氢气 、 硝酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 28.0h， 生成 1,2,7,8-tetraaminonaphthalene
  参考文献：
  名称：

  peri-Naphthylenediamines. 38. Naphthalene and acenaphthene “proton sponges” with +M substituents in ortho positions with respect to peri-dimethylamino groups

  摘要：

  Previously unknown 4,5,6,7-tetrakis(dimethylamino)acenaphthene, which is the first acenaphthene derivative containing four vicinal dialkylamino groups, was synthesized based on 5,6-bis(dimethylamino)-4,7-dinitroacenaphthene. The total synthesis of 1,2,7,8-tetrakis(dimethylamino) naphthalene was carried out starting from 3,6-dinitronaphthalic anhydride. Other "proton sponges" of this type, viz., 1,7,8-tris((dimethylamino)-2-methoxy- and 1, 8 -bis(dimethylamino)-2,7-dipiperidinonaphthalenes, were prepared by the nucleophilic substitution in 2,7-dimethoxy-1,8-dinitronaphthalene. In solutions, 1,2,7,8-tetrakis(dimethylamino)naphthalene and its analogs can form di- and trications in the presence of acids. The basicity constants pK(a)(1) of the compounds measured in DMSO depend in a complex way on their structures but correlate with the basicity index B, which is determined by changes in the Chemical Shifts 811 after the addition of the first proton. Due to low C-nucleophilicity of ortho-disubstituted "proton sponges" in combination with high basicity, these compounds hold considerable promise as reagents in organic synthesis.

  DOI：

  10.1023/b:rucb.0000030818.70534.6b
• 作为产物：
  描述：

  2,7-二氨基萘 、 对甲苯磺酰氯 在 吡啶 作用下， 生成 2,7-di(p-toluenesulfonamido)naphthalene
  参考文献：
  名称：

  Bell et al., Journal of the Chemical Society, 1956, p. 2335,2339

  摘要：

  DOI：