(R)-1,2-cyclohexylidenedioxyoct-3-yne | 1042719-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1,2-cyclohexylidenedioxyoct-3-yne
• CAS: 1042719-11-8
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: XIPIQGGPCLKPSL-CYBMUJFWSA-N

物化性质

• 沸点：
  321.0±37.0 °C(predicted)
• 密度：
  1.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (R)-1,2-cyclohexylidenedioxyoct-3-yne 在 sodium periodate 、 ruthenium(IV) oxide hydrate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 0.5h， 以62%的产率得到(S)-1,2-cyclohexylidenedioxy-3,4-octadione
  参考文献：
  名称：

  Inhibition of Pseudomonas aeruginosa quorum sensing by AI-2 analogs

  摘要：

  Autoinducer-2 (AI-2) has been suggested to serve as a universal interspecies quorum sensing signaling molecule. We have synthesized a set of AI-2 analogs with small incremental changes in alkyl substitution on C-2 and evaluated them for their agonistic and antagonistic potential as quorum sensing (QS) attenuators in two different bacterial species: Pseudomonas aeruginosa and Vibrio harveyi. Unexpectedly, several of the analogs were found to function as synergistic QS agonists in V. harveyi, while two of these analogs inhibit QS in P. aeruginosa. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.163
• 作为产物：
  描述：

  1-碘丁烷 、 1,2-cyclohexylidenedioxybut-3-yne 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.5h， 以69%的产率得到(R)-1,2-cyclohexylidenedioxyoct-3-yne
  参考文献：
  名称：

  An Unexpected Switch in the Modulation of AI-2-Based Quorum Sensing Discovered through Synthetic 4,5-Dihydroxy-2,3-pentanedione Analogues

  摘要：

  Quorum sensing (QS) has traditionally referred to a mechanism of communication within a species of bacteria. However, emerging research implicates QS in interspecies communication and competition, and such systems have been proposed in a wide variety of bacteria, The AI-2-based QS system represents the most studied of these proposed interspecies systems, and has been proposed to regulate diverse functions such as bioluminescence, expression of virulence factors, and biofilm formation. As such, the development of modulatory compounds, both agonists and antagonists, is of great interest for the treatment of bacterial infections and the study of unknown AI-2-based QS systems. Toward this end, we have designed and synthesized a panel of 4,5-dihydroxy-2,3-pentanedione/AI-2 analogues and evaluated their effects on the AI-2 QS of various bacteria. The panel of compounds exhibited differential effects in the bacterial cell lines examined, providing a platform for the development of broad-spectrum modulators of AI-2-based QS.

  DOI：

  10.1021/ja802353j