N-(p-nitrophenyl)-β-D-galactopyranosylamine | 25876-26-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(p-nitrophenyl)-β-D-galactopyranosylamine
• 英文别名: β-D-p-nitrophenylgalactosylamine；N-(4-nitro-phenyl)-β-D-galactopyranosylamine；N-(4-Nitro-phenyl)-β-D-galactopyranosylamin；D-Galactose-(4-nitro-phenylimin)；N-(p-Nitrophenyl)-D-galactosylamin；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(4-nitroanilino)oxane-3,4,5-triol
• CAS: 25876-26-0
• 化学式: C₁₂H₁₆N₂O₇
• 分子量: 300.268
• InChiKey: ONVNCZJMOXIVHT-YBXAARCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 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：
  148
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(p-nitrophenyl)-β-D-galactopyranosylamine 、 乙酸酐 在 zinc(II) chloride 作用下， 生成 N,O2,O3,O4,O6-pentaacetyl-N-(4-nitro-phenyl)-ξ-D-glucopyranosylamine
  参考文献：
  名称：

  Frerejacque, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1938, vol. 207, p. 638

  摘要：

  DOI：
• 作为产物：
  描述：

  mixture of anomers of D-p-nitrophenylgalactosylamine tetraacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以20%的产率得到α-D-p-nitrophenylgalactosylamine
  参考文献：
  名称：

  Kaletina, N. I.; Bezzubov, A. A.; Stepanenko, B. N., Journal of general chemistry of the USSR, 1981, vol. 51, p. 2408 - 2411

  摘要：

  DOI：

文献信息

• Oral hygiene compositions containing amino sugars as antiplaque agents
  申请人：UNILEVER N.V.

  公开号：EP0550099A1

  公开（公告）日：1993-07-07

  Oral hygiene antiplaque compositions which include as an active ingredient an amino sugar containing a sugar moiety recognized by lectins on oral bacteria (e.g., β-D-galactose, β-D-N-acetyl galactosamine, L-rhamnose and β-D-fucose) and in which nitrogen is linked to carbon number 1. The amino sugars singly or in combination with each other provide enhanced inhibition of bacterial aggregation, surfactancy, and antimicrobial activity.

  口腔卫生抗结膜组合物，其活性成分包括含有口腔细菌凝集素识别的糖分子的氨基糖（如β-D-半乳糖、β-D-N-乙酰半乳糖胺、L-鼠李糖和β-D-岩藻糖），其中氮与碳原子数 1 相连。这些氨基糖单独使用或相互组合使用，可增强对细菌聚集的抑制、表面活性和抗菌活性。
• Weygand et al., Chemische Berichte, 1951, vol. 84, p. 594,596,599
  作者：Weygand et al.

  DOI：——

  日期：——
• 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.
• Barclay et al., Journal of the Chemical Society, 1955, p. 1541,1545
  作者：Barclay et al.

  DOI：——

  日期：——
• US5362480A
  申请人：——

  公开号：US5362480A

  公开（公告）日：1994-11-08