(2S,3R)-2,3-(cyclohexylidenedioxy)-hex-4-yne | 1356477-74-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-2,3-(cyclohexylidenedioxy)-hex-4-yne
• CAS: 1356477-74-1
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: SMVUNMGTQLCBBO-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2,3-(cyclohexylidenedioxy)-hex-4-yne 在 sodium periodate 、 ruthenium(IV) oxide hydrate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 0.08h， 生成 (4S,5S)-4,5-(cyclohexylidenedioxy)-hexane-2,3-dione
  参考文献：
  名称：

  Stereochemical diversity of AI-2 analogs modulates quorum sensing in Vibrio harveyi and Escherichia coli

  摘要：

  Bacteria coordinate population-dependent behaviors such as virulence by intra-and inter-species communication (quorum sensing). Autoinducer-2 (AI-2) regulates inter-species quorum sensing. AI-2 derives from the spontaneous cyclisation of linear (S)-4,5-dihydroxypentanedione (DPD) into two isomeric forms in dynamic equilibrium. Different species of bacteria have different classes of AI-2 receptors (LsrB and LuxP) which bind to different cyclic forms. In the present work, DPD analogs with a new stereocenter at C-5 (4,5-dihydroxyhexanediones (DHDs)) have been synthesized and their biological activity tested in two bacteria. (4S, 5R)-DHD is a synergistic agonist in Escherichia coli (which contains the LsrB receptor), while it is an agonist in Vibrio harveyi (LuxP), displaying the strongest agonistic activity reported so far (EC50 = 0.65 mu M) in this organism. Thus, modification at C-5 opens the way to novel methods to manipulate quorum sensing as a method for controlling bacteria. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.007
• 作为产物：
  描述：

  (2S)-2-t-butyldiphenylsilyloxyhex-4-yn-3-one 在 (-)-(S)-alpine-borane 、 硫酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 (2S,3R)-2,3-(cyclohexylidenedioxy)-hex-4-yne
  参考文献：
  名称：

  Stereochemical diversity of AI-2 analogs modulates quorum sensing in Vibrio harveyi and Escherichia coli

  摘要：

  Bacteria coordinate population-dependent behaviors such as virulence by intra-and inter-species communication (quorum sensing). Autoinducer-2 (AI-2) regulates inter-species quorum sensing. AI-2 derives from the spontaneous cyclisation of linear (S)-4,5-dihydroxypentanedione (DPD) into two isomeric forms in dynamic equilibrium. Different species of bacteria have different classes of AI-2 receptors (LsrB and LuxP) which bind to different cyclic forms. In the present work, DPD analogs with a new stereocenter at C-5 (4,5-dihydroxyhexanediones (DHDs)) have been synthesized and their biological activity tested in two bacteria. (4S, 5R)-DHD is a synergistic agonist in Escherichia coli (which contains the LsrB receptor), while it is an agonist in Vibrio harveyi (LuxP), displaying the strongest agonistic activity reported so far (EC50 = 0.65 mu M) in this organism. Thus, modification at C-5 opens the way to novel methods to manipulate quorum sensing as a method for controlling bacteria. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.007