6-bromo-6-deoxy-D-idono-1,4-lactone | 161085-46-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 6-bromo-6-deoxy-D-idono-1,4-lactone
• CAS: 161085-46-7
• 化学式: C₆H₉BrO₅
• 分子量: 241.038
• InChiKey: DIFBGJIRMFVVKL-STGXQOJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.61
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  86.99
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-bromo-6-deoxy-D-idono-1,4-lactone 在 sodium tetrahydroborate 、 ion exchange resin (IR-120, H+) 作用下， 生成 1,4-anhydro-D-iditol
  参考文献：
  名称：

  Enantiomerically pure, highly functionalized tetrahydrofurans from simple carbohydrate precursors

  摘要：

  6-Bromo-6-deoxy-1,4-aldonolactones and 6-bromo-6-deoxy-alditols with D-galacto-, D-altro-, D-manno- and D-ido-configuration were selectively converted into hydroxylated tetrahydrofuran derivatives by simple heating in water. The 6-bromo-6-deoxy-D-altritol (10) and 6-bromo-6-deoxy-D-iditol (25) reacted even at room temperature. Likewise, the 6-bromo-2,6-dideoxy-aldonolactones with D-arabino- (29) and D-lyxo-configuration (31) gave the corresponding 2-deoxy-3,6-anhydrides, when heated in water. The rate of formation of the furan ring by intramolecular nucleophilic substitution was determined by the conformation of the bromopolyols in water.

  DOI：

  10.1016/s0040-4020(01)89337-6
• 作为产物：
  描述：

  D-idono-1,4-lactone 在 氢溴酸 作用下， 以56%的产率得到6-bromo-6-deoxy-D-idono-1,4-lactone
  参考文献：
  名称：

  Enantiomerically pure, highly functionalized tetrahydrofurans from simple carbohydrate precursors

  摘要：

  6-Bromo-6-deoxy-1,4-aldonolactones and 6-bromo-6-deoxy-alditols with D-galacto-, D-altro-, D-manno- and D-ido-configuration were selectively converted into hydroxylated tetrahydrofuran derivatives by simple heating in water. The 6-bromo-6-deoxy-D-altritol (10) and 6-bromo-6-deoxy-D-iditol (25) reacted even at room temperature. Likewise, the 6-bromo-2,6-dideoxy-aldonolactones with D-arabino- (29) and D-lyxo-configuration (31) gave the corresponding 2-deoxy-3,6-anhydrides, when heated in water. The rate of formation of the furan ring by intramolecular nucleophilic substitution was determined by the conformation of the bromopolyols in water.

  DOI：

  10.1016/s0040-4020(01)89337-6