(R)-1,2-cyclohexylidenedioxypent-3-yne | 848035-00-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1,2-cyclohexylidenedioxypent-3-yne
• 英文别名: (3R)-3-prop-1-ynyl-1,4-dioxaspiro[4.5]decane
• CAS: 848035-00-7
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: OZJBPNLAYPOFGI-SNVBAGLBSA-N

物化性质

• 沸点：
  271.6±35.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (R)-1,2-cyclohexylidenedioxypent-3-yne 在 sodium periodate 、 ruthenium(IV) oxide hydrate 、 水 作用下， 以 四氯化碳 、 乙腈 为溶剂， 生成 6-甲基-2-硫代-2,3-二氢-4H-1,3-苯并噁嗪-4-酮
  参考文献：
  名称：

  An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing

  摘要：

  Autoinducer-2 (AI-2) is a signalling molecule for bacterial inter-species communication. A synthesis of (S)-4,5-dihydroxypentane-2,3-dione (DPD), the precursor of AI-2, is described starting from methyl glycolate. The key step was an asymmetric reduction of a ketone with (S)-Alpine borane. This new method was highly reproducible affording DPD for biological tests without contaminants. The biological activity was tested with the previously available assays and compared with a new method using an Escherichia coli reporter strain thus avoiding the use of the pathogenic Salmonella reporter. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.036
• 作为产物：
  描述：

  5-((2S)-1,4-dioxaspiro[4.5]dec-2-yl)(3S,4R,5S)-3,4-dihydroxy-3,4,5-trihydrofuran-2-one 在 正丁基锂 、 potassium metaperiodate 、 potassium hydrogencarbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 21.5h， 生成 (R)-1,2-cyclohexylidenedioxypent-3-yne
  参考文献：
  名称：

  An Expeditious Synthesis of DPD and Boron Binding Studies

  摘要：

  A practical synthesis has been developed for DPD (4,5-dihydroxypentane-2,3-dione), an unstable small molecule that is proposed to be the source of universal signaling agents for quorum sensing in bacteria. The synthesis allows preparation of isotopically labeled DPD and entDPD as well as detailed studies of spontaneous binding to borate to give the unusual borate complex 6, the signal for marine bacteria such as Vibrio harveyi.

  DOI：

  10.1021/ol047695j

文献信息

• [EN] EXPEDITIOUS SYNTHESIS OF DPD<br/>[FR] SYNTHESE RAPIDE DE DPD
  申请人：UNIV PRINCETON

  公开号：WO2006034269A1

  公开（公告）日：2006-03-30

  This invention provides a practical synthesis route for 4,5-dihydroxypentane-2,3-dione (DPD), an unstable small molecule which is proposed to be the source of universal signaling agents for quorum sensing in bacteria. The synthesis route includes new intermediates and allows preparation of isotopically-labeled DPD and ent-DPD. The method provides sufficient quantities of DPD for study of spontaneous binding of borate to DPD, the signal for the marine bacteria V. harveyi

  这项发明提供了一种实用的合成途径，用于合成4,5-二羟基戊烷-2,3-二酮（DPD），这是一种不稳定的小分子，被认为是细菌群体感应通用信号物质的来源。该合成途径包括新的中间体，并允许制备同位素标记的DPD和ent-DPD。该方法提供了足够数量的DPD，以研究硼酸与DPD的自发结合，这是海洋细菌V. harveyi的信号。
• An Unexpected Switch in the Modulation of AI-2-Based Quorum Sensing Discovered through Synthetic 4,5-Dihydroxy-2,3-pentanedione Analogues
  作者：Colin A. Lowery、Junguk Park、Gunnar F. Kaufmann、Kim D. Janda

  DOI：10.1021/ja802353j

  日期：2008.7.1

  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.
• Inhibition of Pseudomonas aeruginosa quorum sensing by AI-2 analogs
  作者：Hadas Ganin、Xu Tang、Michael M. Meijler

  DOI：10.1016/j.bmcl.2009.03.163

  日期：2009.7

  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.
• Pyrogallol and its analogs can antagonize bacterial quorum sensing in Vibrio harveyi
  作者：Nanting Ni、Gaurav Choudhary、Minyong Li、Binghe Wang

  DOI：10.1016/j.bmcl.2008.01.081

  日期：2008.3

  Bacteria can coordinate community-wide behaviors through quorum sensing, that is, the secretion and sensing of autoinducer (AI) molecules. Bacterial quorum sensing is implicated in the regulation of pathologically relevant events such as biofilm formation, bacterial virulence, and drug resistance. Inhibitors of bacterial quorum sensing could therefore be useful therapeutics. Herein we report for the first time the discovery of several pyrogallol compounds as single digit micromolar inhibitors of bacterial quorum sensing in Vibrio harveyi. (c) 2008 Elsevier Ltd. All rights reserved.
• An Expeditious Synthesis of DPD and Boron Binding Studies
  作者：Martin F. Semmelhack、Shawn R. Campagna、Michael J. Federle、Bonnie L. Bassler

  DOI：10.1021/ol047695j

  日期：2005.2.1

  A practical synthesis has been developed for DPD (4,5-dihydroxypentane-2,3-dione), an unstable small molecule that is proposed to be the source of universal signaling agents for quorum sensing in bacteria. The synthesis allows preparation of isotopically labeled DPD and entDPD as well as detailed studies of spontaneous binding to borate to give the unusual borate complex 6, the signal for marine bacteria such as Vibrio harveyi.