D-glucose hydrazon | 190259-02-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-glucose hydrazon
• 英文别名: glucose hydrazone；(2R,3R,4R,5S,6E)-6-hydrazinylidenehexane-1,2,3,4,5-pentol
• CAS: 190259-02-0
• 化学式: C₆H₁₄N₂O₅
• 分子量: 194.188
• InChiKey: GBNXMEVVZBZIAC-ZXENJKTBSA-N

物化性质

• 沸点：
  614.0±65.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  D-glucose hydrazon 在 一水合肼 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 β-D-glucopyranosyl hydrazine
  参考文献：
  名称：

  NMR Studies of Saccharide Hydrazones, Thiosemicarbazones and Azines: Model Compounds for Immobilisation Studies

  摘要：

  To evaluate possible chemical strategies for the solid-phase immobilization of sugars, studies on the formation and stability of hydrazones, thiosemicarbazones and azines of D-glucose and 2-acetamido-2-deoxy-D-glucose, and the subsequent release of sugars, were carried out. Hydrazone formation was observed to occur under milder conditions than previously reported, thereby minimising the accompanying N-deacetylation which occurs with N-acetamido sugars. The cyclic beta-pyranosyl structures of the saccharide hydrazones, thiosemicarbazones and azines were the preferred isomers in aqueous solution.

  DOI：

  10.1080/07328309808005766
• 作为产物：
  描述：

  D-葡萄糖 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以97%的产率得到D-glucose hydrazon
  参考文献：
  名称：

  合成取代的4-咪唑啉酮类化合物作为潜在抗病毒和抗肿瘤药物的新方法

  摘要：

  5-（（Z）-亚芳基）-2-（（2-（E）-亚苄基）hydr）-4-咪唑啉酮7a-d和5-（（Z）-亚芳基）-2-（（2-（E由5-（（Z）-亚芳基）-2-甲基巯基乙内酰脲3a-d与2-（E）-亚苄基6或5-（（Z）-亚芳基）-2-甲基巯基乙内酰脲3a-d的反应制备）-聚羟基亚烷基））基）-4-咪唑啉酮11a-d至15a-d。 2-（E）-单糖9a-e，其依次通过缩合苯甲醛或适当的单糖8a-e制备与水合肼。AM1的半经验计算表明，对于CNNC ，嗪体系具有反式几何构型和平面构象。测试了所有新化合物的潜在抗病毒和抗肿瘤活性。

  DOI：

  10.1016/s0040-4020(98)00170-7

文献信息

• Synthesis of some novel 2-thioxoimidazolidin-4-one substituted glycosyl hydrazone derivatives
  作者：N. M. Khalifa、M. A. Al-Omar、A. A. Sediek、A. E. Amr

  DOI：10.1134/s1070363217039239

  日期：2017.3

  A series of novel 2-thioxoimidazolidine glycosides were prepared via reaction of the key intermediate 2-(benzylsulfanyl)-5-[4-(3-hydroxypropoxy)-3-(methoxybenzylidene)]-3-phenyl-1H-imidazol-4-one with different sugar aldose or sugar hydrazones to give the corresponding glycosides. The newly synthesized compounds were confirmed by physical and spectral data.

  通过关键中间体2-（苄基硫烷基）-5- [4-（3-羟基丙氧基）-3-（甲氧基苄叉）]-3-苯基-1H-咪唑-4的反应制备了一系列新颖的2-硫代氧杂咪唑烷糖苷。-与不同的糖醛糖或糖一起得到相应的糖苷。通过物理和光谱数据证实了新合成的化合物。
• Tautomerism of saccharide hydrazones in solution and their reaction with nitrous acid
  作者：J.Michael Williams

  DOI：10.1016/0008-6215(83)88077-x

  日期：1983.6

  rapid and the latter preponderate; exceptions are the hydrazones of d -ribose and l -arabinose which give almost equal proportions of acyclic and cyclic tautomers at pH 6. Reaction of representative saccharide hydrazones with nitrous acid gives a mixture of the corresponding saccharide and the β-glycosyl azide, the latter being formed from the glycosylhydrazine tautomer.

  摘要Nmr光谱（13 C和1 H）已显示出肼溶液中的糖主要以顺式无环互变异构体的形式存在。在氧化氘溶液中，发生缓慢的互变异构，生成糖基肼。在pH 6时，互变异构作用迅速，后者互为优势。d-核糖和l-阿拉伯糖的在pH 6时具有几乎相等比例的无环和环状互变异构体。只有代表性的糖与亚硝酸反应生成相应的糖和β-糖基叠氮化物的混合物，后者由糖基肼互变异构体形成。
• Auge, Jacques; Lubin-Germain, Nadege, Journal of Carbohydrate Chemistry, 2000, vol. 19, # 3, p. 378 - 392
  作者：Auge, Jacques、Lubin-Germain, Nadege

  DOI：——

  日期：——
• Heterocyclic derivatives of sugars: an NMR study of the formation of 1-glycosyl-3,5-dimethyl-1 H-pyrazoles from hydrazones
  作者：Warren C Kett、Michael Batley、John W Redmond

  DOI：10.1016/s0008-6215(97)00007-4

  日期：1997.4

  Hydrazones were prepared by treatment of monosaccharides and disaccharides with hydrazine hydrate and converted in high yield to mixtures of 1-glycosyl-3,5-dimethyl-1 H-pyrazoles by reaction with pentan-2,4-dione (acetylacetone). The isomeric products were separated by HPLC and characterized by NMR spectroscopy. This represents a new approach to the introduction of a heteroaromatic label into sugars under nonacidic and nonreducing conditions, and it is a process likely to be especially useful for glycan hydrazones obtained from glycoproteins by hydrazinolysis or beta elimination in the presence of hydrazine. (C) 1997 Elsevier Science Ltd.
• Discussion
  作者：Khodair, Ahmed I.

  DOI：10.1016/s0008-6215(98)00024-x

  日期：1998.1

  A series of 5-[(Z)-(4-(2-(E)-arylidene)hydrazonosulfonylbenzylidene)]-2, 4-imidazolidinediones 6a-h and 5-[(Z)-(4-(2-beta-D-glycopyranosyl) hydrazinosulfonylbenzylidene)]-2,4-imidazolidinediones 10a-j were synthesized via two different routes. The compounds did not display any antiviral and antitumoral activity.