(1S,2R,4S)-1-(2,2-dimethyl-1,3-dioxalane-4-yl)-propane-1,2-diol | 443642-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,4S)-1-(2,2-dimethyl-1,3-dioxalane-4-yl)-propane-1,2-diol
• 英文别名: (1S,2R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propane-1,2-diol
• CAS: 443642-75-9
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: BPVVSRACGYQKRD-VQVTYTSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4R)-2,2-dimethyl-4-(prop-1-enyl)-1,3-dioxalane 在 N-甲基吗啉氧化物 、 四氧化锇 作用下， 以 水 、 丙酮 为溶剂， 生成 (1R,2S,4S)-1-(2,2-dimethyl-1,3-dioxalane-4-yl)-propane-1,2-diol 、 (1S,2R,4S)-1-(2,2-dimethyl-1,3-dioxalane-4-yl)-propane-1,2-diol
  参考文献：
  名称：

  Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer

  摘要：

  The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from D-mannitol via (2R)2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescenceinducing properties in the Vibrio harveyi BB170 strain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.064