N-(p-bromophenyl)-β-D-galactopyranosylamine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(p-bromophenyl)-β-D-galactopyranosylamine
• 英文别名: galactosyl-p-bromoaniline；(2R,3R,4S,5R,6R)-2-(4-bromoanilino)-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₂H₁₆BrNO₅
• 分子量: 334.167
• InChiKey: MVAHLHJIWOAWSB-YBXAARCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-吡喃葡萄糖 、 4-溴苯胺 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 N-(p-bromophenyl)-β-D-galactopyranosylamine
  参考文献：
  名称：

  Molecular and crystal structures of N-aryl-β-d-glycopyranosylamines from mannose and galactose

  摘要：

  The molecular and crystal structures of 12 N-aryl-beta -D-glycopyranosylamines have been determined by X-ray crystallography. Six of these are mannose derivatives, the N-p-bromophenyl (1), N-p-tolyl (2), N-m-chlorophenyl (3), N-p-methoxyphenyl (4), N-o-chloroyhenyl (5), and N-o-tolyl (6) derivatives that are formed by reaction with the corresponding substituted anilines. The remaining six are galactose derivatives, the N-phenyl (7), N-p-chlorophenyl (8), N-p-bromophenyl (9), N-p-iodophenyl (10), N-p-nitrophenyl (11) and N-p-tolyl (12), derivatives prepared similarly. Compounds 1 3 assume the same packing arrangement. Compounds 4, 5, and 6 assume unique packing an arrangements, although that assumed by 4 is closely related to that assumed by 1-3. Compounds 7-11 assume the same packing arrangement; that assumed by 12 is closely related to that assumed by 7-11. That the same packing arrangements can be maintained in spite of substantial changes in the electronic and steric nature of the substituent on the aryl ring reflects the strength of the hydrogen bond network connecting the monosaccharide portions of the molecules in the solid state. A hydrogen bonding motif found in all six mannose structures is a mutual interaction between translationally related molecules involving 0-3-(HO)-O-...-5 and O-6-(HO)-O-...-4 hydrogen bonds. The recurrence of this motif throughout this group of mannosylamines suggests that it is an especially favorable interaction that might be expected to occur also in related macromolecular systems. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00117-3

文献信息

• Molecular and crystal structures of N-aryl-β-d-glycopyranosylamines from mannose and galactose
  作者：Charles R Ojala、Joanne M Ostman、Summer E Hanson、William H Ojala

  DOI：10.1016/s0008-6215(01)00117-3

  日期：2001.6

  The molecular and crystal structures of 12 N-aryl-beta -D-glycopyranosylamines have been determined by X-ray crystallography. Six of these are mannose derivatives, the N-p-bromophenyl (1), N-p-tolyl (2), N-m-chlorophenyl (3), N-p-methoxyphenyl (4), N-o-chloroyhenyl (5), and N-o-tolyl (6) derivatives that are formed by reaction with the corresponding substituted anilines. The remaining six are galactose derivatives, the N-phenyl (7), N-p-chlorophenyl (8), N-p-bromophenyl (9), N-p-iodophenyl (10), N-p-nitrophenyl (11) and N-p-tolyl (12), derivatives prepared similarly. Compounds 1 3 assume the same packing arrangement. Compounds 4, 5, and 6 assume unique packing an arrangements, although that assumed by 4 is closely related to that assumed by 1-3. Compounds 7-11 assume the same packing arrangement; that assumed by 12 is closely related to that assumed by 7-11. That the same packing arrangements can be maintained in spite of substantial changes in the electronic and steric nature of the substituent on the aryl ring reflects the strength of the hydrogen bond network connecting the monosaccharide portions of the molecules in the solid state. A hydrogen bonding motif found in all six mannose structures is a mutual interaction between translationally related molecules involving 0-3-(HO)-O-...-5 and O-6-(HO)-O-...-4 hydrogen bonds. The recurrence of this motif throughout this group of mannosylamines suggests that it is an especially favorable interaction that might be expected to occur also in related macromolecular systems. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of glycoconjugates of physiologically active compounds
  作者：D. V. Bessonov、I. V. Kulakov、A. M. Gazaliev、O. A. Nurkenov

  DOI：10.1134/s1070427207030329

  日期：2007.3

  Synthesis of N-glycosylamines derived from D-glucose and D-galactose (glycoconjugates of aniline derivatives and of d-pseudoephedrine and cytisine alkaloids) was studied with the aim to develop new pharmaceuticals.