(1E,4S)-2,2-dimethyl-4-(prop-1-enyl)-1,3-dioxalane | 1228078-23-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1E,4S)-2,2-dimethyl-4-(prop-1-enyl)-1,3-dioxalane
• 英文别名: (4S)-2,2-dimethyl-4-[(E)-prop-1-enyl]-1,3-dioxolane
• CAS: 1228078-23-6
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: SZQALDVLJRMTFN-KPJROHGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1E,4S)-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,4R)-1-(2,2-dimethyl-1,3-dioxalane-4-yl)-propane-1,2-diol 、 (1S,2R,4R)-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
• 作为产物：
  描述：

  乙基三苯基溴化膦 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以70%的产率得到(1E,4S)-2,2-dimethyl-4-(prop-1-enyl)-1,3-dioxalane
  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

文献信息

• Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer
  作者：Manikandan Kadirvel、William T. Stimpson、Souad Moumene-Afifi、Biljana Arsic、Nicola Glynn、Nigel Halliday、Paul Williams、Peter Gilbert、Andrew J. McBain、Sally Freeman、John M. Gardiner

  DOI：10.1016/j.bmcl.2010.02.064

  日期：2010.4

  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.