1-(2-methoxyphenyl)-(1,2-dideoxy-α-D-glucofurano)<2,1-d>imidazolidine-2-one | 223396-33-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-methoxyphenyl)-(1,2-dideoxy-α-D-glucofurano)<2,1-d>imidazolidine-2-one
• 英文别名: (3aS,5S,6R,6aR)-5-[(1R)-1,2-dihydroxyethyl]-6-hydroxy-3-(2-methoxyphenyl)-3a,5,6,6a-tetrahydro-1H-furo[2,3-d]imidazol-2-one
• CAS: 223396-33-6
• 化学式: C₁₄H₁₈N₂O₆
• 分子量: 310.307
• InChiKey: LYTVPQKBBQMQSD-WECGXBHGSA-N

物化性质

• 熔点：
  226-229 °C
• 密度：
  1.454±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-(2-methoxyphenyl)-(1,2-dideoxy-α-D-glucofurano)<2,1-d>imidazolidine-2-one 在 吡啶 作用下， 反应 24.0h， 以60%的产率得到1-(2-methoxyphenyl)-(3,5,6-tri-O-acetyl-1,2-dideoxy-α-D-glucofurano)<2,1-d>imidazolidine-2-one
  参考文献：
  名称：

  Non-biaryl atropisomers derived from carbohydrates. Part 2. Atropisomeric behavior of monocyclic and bicyclic imidazolidine-2-ones and 2-thiones

  摘要：

  High-yielding syntheses of bicyclic imidazolidine-2-ones and 2-thiones bearing an ortho-substituted aromatic ring have been described. Their atropisomeric behavior has been studied in depth taking into account the effects of substituents in the ortho position, the length of the exocyclic C=X bond, and the presence of substituents at C-5 in the heterocyclic ring. The barriers to rotation were independently estimated by dynamic NMR spectroscopy and molecular mechanics. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00110-6
• 作为产物：
  描述：

  2-deoxy-2-<3-(2-methoxyphenylureido)>-α-D-glucopyranose 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.0h， 以60%的产率得到1-(2-methoxyphenyl)-(1,2-dideoxy-α-D-glucofurano)<2,1-d>imidazolidine-2-one
  参考文献：
  名称：

  Non-biaryl atropisomers derived from carbohydrates. Part 2. Atropisomeric behavior of monocyclic and bicyclic imidazolidine-2-ones and 2-thiones

  摘要：

  High-yielding syntheses of bicyclic imidazolidine-2-ones and 2-thiones bearing an ortho-substituted aromatic ring have been described. Their atropisomeric behavior has been studied in depth taking into account the effects of substituents in the ortho position, the length of the exocyclic C=X bond, and the presence of substituents at C-5 in the heterocyclic ring. The barriers to rotation were independently estimated by dynamic NMR spectroscopy and molecular mechanics. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00110-6