1-(2-bromophenyl)-(1,2-dideoxy-α-D-glucofurano)<2,1-d>imidazolidine-2-thione | 223396-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(2-bromophenyl)-(1,2-dideoxy-α-D-glucofurano)<2,1-d>imidazolidine-2-thione
• 英文别名: (3aS,5S,6R,6aR)-3-(2-bromophenyl)-5-[(1R)-1,2-dihydroxyethyl]-6-hydroxy-3a,5,6,6a-tetrahydro-1H-furo[2,3-d]imidazole-2-thione
• CAS: 223396-45-0
• 化学式: C₁₃H₁₅BrN₂O₄S
• 分子量: 375.243
• InChiKey: OHMLYFCFPNDSCB-OOCWMUITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-(2-bromophenyl)-(1,2-dideoxy-α-D-glucofurano)<2,1-d>imidazolidine-2-thione 在 吡啶 作用下， 反应 24.0h， 以69%的产率得到3,5,6-tri-O-acetyl-1-(2-bromophenyl)-(1,2-dideoxy-α-D-glucofurano)<2,1-d>imidazolidine-2-thione
  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：

  Acetic acid (2R,3S,4R)-4-[(4R,5R)-1-(2-bromo-phenyl)-5-hydroxy-2-thioxo-imidazolidin-4-yl]-2,3,4-trihydroxy-butyl ester 在 溶剂黄146 作用下， 反应 0.5h， 以74%的产率得到1-(2-bromophenyl)-(1,2-dideoxy-α-D-glucofurano)<2,1-d>imidazolidine-2-thione
  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