1-(6-deoxy-β-L-mannopyranosyl)-2-(2,4-dinitrophenyl)hydrazine | 918800-47-2

• 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: 1-(6-deoxy-β-L-mannopyranosyl)-2-(2,4-dinitrophenyl)hydrazine
• 英文别名: (2S,3R,4R,5R,6S)-2-[2-(2,4-dinitrophenyl)hydrazinyl]-6-methyloxane-3,4,5-triol
• CAS: 918800-47-2
• 化学式: C₁₂H₁₆N₄O₈
• 分子量: 344.281
• InChiKey: MFFNUFUBLGCPNW-RYIKZVKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  24
• 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：
  186
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(6-deoxy-β-L-mannopyranosyl)-2-(2,4-dinitrophenyl)hydrazine 、 乙酰氯 反应 2.0h， 以49%的产率得到2,3,4,5-tetra-O-acetyl-6-deoxy-L-mannose 2,4-dinitrophenylhydrazone
  参考文献：
  名称：

  Density functional theory calculations and experimental parameters for mutarotation of 6-deoxy-l-mannopyranosyl hydrazine

  摘要：

  The geometry and energy profiles of the mutarotation pathway present in the equilibrium of 6-deoxy-beta-L-mannopyranosyl 2,4-dinitropheny1hydrazine (1a), 6-deoxy-L-mannose 2,4-dinitrophenylhydrazone (1b), and 6-deoxy-alpha-L-mannopyranosyl 2,4-dinitrophenylhydrazine (1c) were modeled by DFT calculations at B3LYP/6-31G(d) level affording Delta G(DFT)=0.000 kcal/mol, Delta G(DFT)=0.174 kcal/mol, and Delta G(DFT)=3.411 kcal/mol, respectively. Experimentally, the beta-L-pyranose 1a occurs in 50% followed by the acyclic structure 1b in 44% as well as by the alpha-L-anomer 1c in 6%. The conformations of 1a-c and their corresponding 2,3,4-triacetyl derivatives 2a-c were studied by molecular modeling and NMR spectroscopy. IR frequencies, NMR chemical shifts, and X-ray diffraction analysis were employed to compare theoretical with experimental structural parameters. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.090
• 作为产物：
  描述：

  L-rhamnopyranose 、 2,4-二硝基苯肼 在 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 19.0h， 以33%的产率得到1-(6-deoxy-β-L-mannopyranosyl)-2-(2,4-dinitrophenyl)hydrazine
  参考文献：
  名称：

  Density functional theory calculations and experimental parameters for mutarotation of 6-deoxy-l-mannopyranosyl hydrazine

  摘要：

  The geometry and energy profiles of the mutarotation pathway present in the equilibrium of 6-deoxy-beta-L-mannopyranosyl 2,4-dinitropheny1hydrazine (1a), 6-deoxy-L-mannose 2,4-dinitrophenylhydrazone (1b), and 6-deoxy-alpha-L-mannopyranosyl 2,4-dinitrophenylhydrazine (1c) were modeled by DFT calculations at B3LYP/6-31G(d) level affording Delta G(DFT)=0.000 kcal/mol, Delta G(DFT)=0.174 kcal/mol, and Delta G(DFT)=3.411 kcal/mol, respectively. Experimentally, the beta-L-pyranose 1a occurs in 50% followed by the acyclic structure 1b in 44% as well as by the alpha-L-anomer 1c in 6%. The conformations of 1a-c and their corresponding 2,3,4-triacetyl derivatives 2a-c were studied by molecular modeling and NMR spectroscopy. IR frequencies, NMR chemical shifts, and X-ray diffraction analysis were employed to compare theoretical with experimental structural parameters. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.090