rac-5-((tert-butyldimethylsilyl)oxy)-4-hexyloxypentane-2,3-dione | 1392009-73-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-5-((tert-butyldimethylsilyl)oxy)-4-hexyloxypentane-2,3-dione
• CAS: 1392009-73-2
• 化学式: C₁₇H₃₄O₄Si
• 分子量: 330.54
• InChiKey: ZFFPDUQMGMVBAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  22.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  rac-5-((tert-butyldimethylsilyl)oxy)-4-hexyloxypentane-2,3-dione 在 水 、 氘代硫酸 作用下， 以 氘代二甲亚砜 、 water-d2 为溶剂， 以100%的产率得到4-hexyloxy-3,3,5-trihydroxypentan-2-one
  参考文献：
  名称：

  C4-Alkoxy-HPD: A Potent Class of Synthetic Modulators Surpassing Nature in AI-2 Quorum Sensing

  摘要：

  Bacteria have developed cell-to-cell communication mechanisms, termed quorum sensing (QS), that regulate bacterial gene expression in a cell population dependent manner. Autoinducer-2 (AI-2), a class of QS signaling molecules derived from (4S)-4,5-dihydroxy-2,3-pentanedione (DPD), has been identified in both Gramnegative and Gram-positive bacteria. Despite considerable interest in the AI-2 QS system, the biomolecular communication used by distinct bacterial species still remains shrouded. Herein, we report the synthesis and evaluation of a new class of DPD analogues, C4-alkoxy-5-hydroxy-2,3-pentanediones, termed C4-alkoxy-HPDs. Remarkably, two of the analogues were more potent QS agonists than the natural ligand, DPD, in Vibrio harveyi. The findings presented extend insights into ligand - receptor recognition/signaling in the AI-2 mediated QS system.

  DOI：

  10.1021/ja305532y
• 作为产物：
  描述：

  rac-1-[(tert-butyldimethylsilyl)oxy]pent-3-yn-2-ol 在 sodium periodate 、 ruthenium(IV) oxide hydrate 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 四氯化碳 、 乙腈 、 mineral oil 为溶剂， 反应 4.58h， 生成 rac-5-((tert-butyldimethylsilyl)oxy)-4-hexyloxypentane-2,3-dione
  参考文献：
  名称：

  C4-Alkoxy-HPD: A Potent Class of Synthetic Modulators Surpassing Nature in AI-2 Quorum Sensing

  摘要：

  Bacteria have developed cell-to-cell communication mechanisms, termed quorum sensing (QS), that regulate bacterial gene expression in a cell population dependent manner. Autoinducer-2 (AI-2), a class of QS signaling molecules derived from (4S)-4,5-dihydroxy-2,3-pentanedione (DPD), has been identified in both Gramnegative and Gram-positive bacteria. Despite considerable interest in the AI-2 QS system, the biomolecular communication used by distinct bacterial species still remains shrouded. Herein, we report the synthesis and evaluation of a new class of DPD analogues, C4-alkoxy-5-hydroxy-2,3-pentanediones, termed C4-alkoxy-HPDs. Remarkably, two of the analogues were more potent QS agonists than the natural ligand, DPD, in Vibrio harveyi. The findings presented extend insights into ligand - receptor recognition/signaling in the AI-2 mediated QS system.

  DOI：

  10.1021/ja305532y