(S)-1,2-cyclohexylidenedioxypent-3-yne | 848035-10-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1,2-cyclohexylidenedioxypent-3-yne
• 英文别名: (3S)-3-prop-1-ynyl-1,4-dioxaspiro[4.5]decane
• CAS: 848035-10-9
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: OZJBPNLAYPOFGI-JTQLQIEISA-N

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：

  (S)-1,2-cyclohexylidenedioxypent-3-yne 在 ruthenium(IV) oxide sodium periodate 、 水 作用下， 以 四氯化碳 、 氯仿 、 乙腈 为溶剂， 生成 (R)-4,5-cyclohexylidenedioxy-2,3-pentanedione
  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
• 作为产物：
  描述：

  1-(tert-butyldiphenylsilyloxy)pent-3-yne-2-one 在 (-)-(S)-alpine-borane 、 硫酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 (S)-1,2-cyclohexylidenedioxypent-3-yne
  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

文献信息

• 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.
• <i>O</i>-Directed Free-Radical Hydrostannations of Propargyl Ethers, Acetals, and Alcohols with Ph₃SnH and Et₃B
  作者：Paschalis Dimopoulos、Audrey Athlan、Soraya Manaviazar、Jonathan George、Marcus Walters、Linos Lazarides、Abil E. Aliev、Karl J. Hale

  DOI：10.1021/ol051936l

  日期：2005.11.1

  The O-directed hydrostannation of various propargyloxy substrates is reported with Ph(3)SnH/Et(3)B.
• An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing
  作者：Osvaldo S. Ascenso、João C. Marques、Ana Rita Santos、Karina B. Xavier、M. Rita Ventura、Christopher D. Maycock

  DOI：10.1016/j.bmc.2010.12.036

  日期：2011.2

  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.