1-chloropent-3-yn-2-one | 89283-52-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-chloropent-3-yn-2-one
• 英文别名: 1-Chlor-pentin-(3)-on-(2)
• CAS: 89283-52-3
• 化学式: C₅H₅ClO
• mdl: MFCD19233420
• 分子量: 116.547
• InChiKey: CIBRBASEOITFKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-chloropent-3-yn-2-one 在 咪唑 、 甲醇 、 sodium tetrahydroborate 、 sodium periodate 、 cerium(III) chloride heptahydrate 、 (x)H₂O*O₂Ru 、 重水 、 氘代硫酸 作用下， 以 四氯化碳 、 氘代二甲亚砜 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 42.47h， 生成 5-chloro-4-hydroxypentane-2,3-dione
  参考文献：
  名称：

  Dissecting AI-2-mediated quorum sensing through C5-analogue synthesis and biochemical analysis

  摘要：

  Autoinducer-2 (AI-2)-mediated quorum sensing (QS) is utilised for both intra- and inter-species communication by a wide variety of bacteria. An understanding of the mechanism of this communication has the potential to elucidate new targets for antibacterial therapeutics. Herein, we report the synthesis of DPD analogues with modified dynamic equilibria and the evaluation of their behaviour in Gram-negative bacteria. None of the compounds showed modulation of QS in Salmonella Typhimurium, and although no antagonism of Vibrio harveyi was observed, chloro-analogue C5-Cl-DPD showed modest agonism in this marine bacterium. This raises the possibility that access to a cyclic form of DPD may not be required for AI-2-mediated QS in V. harveyi. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.063
• 作为产物：
  描述：

  1-(三甲基硅基)丙炔 、 氯乙酰氯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 1-chloropent-3-yn-2-one
  参考文献：
  名称：

  Dissecting AI-2-mediated quorum sensing through C5-analogue synthesis and biochemical analysis

  摘要：

  Autoinducer-2 (AI-2)-mediated quorum sensing (QS) is utilised for both intra- and inter-species communication by a wide variety of bacteria. An understanding of the mechanism of this communication has the potential to elucidate new targets for antibacterial therapeutics. Herein, we report the synthesis of DPD analogues with modified dynamic equilibria and the evaluation of their behaviour in Gram-negative bacteria. None of the compounds showed modulation of QS in Salmonella Typhimurium, and although no antagonism of Vibrio harveyi was observed, chloro-analogue C5-Cl-DPD showed modest agonism in this marine bacterium. This raises the possibility that access to a cyclic form of DPD may not be required for AI-2-mediated QS in V. harveyi. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.063

文献信息

• 693. The synthesis of acetylenes and allenes from enol phosphates
  作者：J. Cymerman Craig、M. Moyle

  DOI：10.1039/jr9630003712

  日期：——
• Dissecting AI-2-mediated quorum sensing through C5-analogue synthesis and biochemical analysis
  作者：Karen C. Collins、Kyoji Tsuchikama、Colin A. Lowery、Jie Zhu、Kim D. Janda

  DOI：10.1016/j.tet.2015.08.063

  日期：2016.6

  Autoinducer-2 (AI-2)-mediated quorum sensing (QS) is utilised for both intra- and inter-species communication by a wide variety of bacteria. An understanding of the mechanism of this communication has the potential to elucidate new targets for antibacterial therapeutics. Herein, we report the synthesis of DPD analogues with modified dynamic equilibria and the evaluation of their behaviour in Gram-negative bacteria. None of the compounds showed modulation of QS in Salmonella Typhimurium, and although no antagonism of Vibrio harveyi was observed, chloro-analogue C5-Cl-DPD showed modest agonism in this marine bacterium. This raises the possibility that access to a cyclic form of DPD may not be required for AI-2-mediated QS in V. harveyi. (C) 2015 Elsevier Ltd. All rights reserved.