(2S)-2-t-butyldiphenylsilyloxyhex-4-yn-3-one | 1356477-62-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S)-2-t-butyldiphenylsilyloxyhex-4-yn-3-one
• CAS: 1356477-62-7
• 化学式: C₂₂H₂₆O₂Si
• 分子量: 350.533
• InChiKey: MBCIXWWELORXHY-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-t-butyldiphenylsilyloxyhex-4-yn-3-one 在 (-)-(S)-alpine-borane 、 水 、 氯化铵 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以36%的产率得到(2S,3R)-hex-4-yne-2,3-diol
  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：

  (S)-2-[(1,1-dimethylethyl)diphenylsilyl]oxypropanoic acid 在 N-甲基吗啉 、 正丁基锂 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 7.75h， 生成 (2S)-2-t-butyldiphenylsilyloxyhex-4-yn-3-one
  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