6-bromo-2,6-dideoxy-D-lyxo-hexono-1,4-lactone | 109986-36-9

• 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-2,6-dideoxy-D-lyxo-hexono-1,4-lactone
• 英文别名: 6-bromo-2,6-dideoxy-D-xylo-hexono-1,4-lactone；(4S,5R)-5-[(1S)-2-bromo-1-hydroxyethyl]-4-hydroxyoxolan-2-one
• CAS: 109986-36-9
• 化学式: C₆H₉BrO₄
• 分子量: 225.039
• InChiKey: BCAGVZZOCCCQBE-MRKVFDINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-bromo-2,6-dideoxy-D-lyxo-hexono-1,4-lactone 以 水 为溶剂， 反应 2.0h， 以94%的产率得到3,6-anhydro-2-deoxy-D-lyxo-hexono-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
• 作为产物：
  描述：

  D-(-)-古洛糖酸-gamma-内酯 在 甲醇 、 氢溴酸 、 一水合肼 、 溶剂黄146 作用下， 反应 2.0h， 生成 6-bromo-2,6-dideoxy-D-lyxo-hexono-1,4-lactone
  参考文献：
  名称：

  Bock, Klaus; Lundt, Inge; Pedersen, Christian, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 9, p. 740 - 744

  摘要：

  DOI：