2,2-difluoro-3-hydroxy-N-[(3S)-2-oxooxolan-3-yl]dodecanamide | 260807-02-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2-difluoro-3-hydroxy-N-[(3S)-2-oxooxolan-3-yl]dodecanamide
• CAS: 260807-02-1
• 化学式: C₁₆H₂₇F₂NO₄
• 分子量: 335.391
• InChiKey: HVSIMNGQZWOFJD-UEWDXFNNSA-N

物化性质

• 沸点：
  531.8±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-3-hydroxy-N-[(3S)-2-oxooxolan-3-yl]dodecanamide 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(S)-2,2-difluoro-3-oxododecanyl homoserine lactone
  参考文献：
  名称：

  Novel synthetic analogs of the Pseudomonas autoinducer

  摘要：

  Release of virulence factors in Pseudomonas aeruginosa is regulated by two N-acylhomoserine lactones, PAI-I and PAI-2, that activate the respective transcription factors LasR and RhlR. With the goal of developing novel therapeutic agents, we synthesized constrained analogs of PAI-I and evaluated them in P. aeruginosa, Two of the novel analogs bound to LasR and showed agonist activity in LasR stimulation of a lasI-lacZ reporter construct. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00626-5
• 作为产物：
  描述：

  2,2-difluoro-3-hydroxydodecanoic acid ethyl ester 在 氢氧化钾 、 N-羟基-7-氮杂苯并三氮唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,2-difluoro-3-hydroxy-N-[(3S)-2-oxooxolan-3-yl]dodecanamide
  参考文献：
  名称：

  Novel synthetic analogs of the Pseudomonas autoinducer

  摘要：

  Release of virulence factors in Pseudomonas aeruginosa is regulated by two N-acylhomoserine lactones, PAI-I and PAI-2, that activate the respective transcription factors LasR and RhlR. With the goal of developing novel therapeutic agents, we synthesized constrained analogs of PAI-I and evaluated them in P. aeruginosa, Two of the novel analogs bound to LasR and showed agonist activity in LasR stimulation of a lasI-lacZ reporter construct. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00626-5

文献信息

• Novel synthetic analogs of the Pseudomonas autoinducer
  作者：T. Kline、J. Bowman、B.H. Iglewski、T. de Kievit、Y. Kakai、L. Passador

  DOI：10.1016/s0960-894x(99)00626-5

  日期：1999.12

  Release of virulence factors in Pseudomonas aeruginosa is regulated by two N-acylhomoserine lactones, PAI-I and PAI-2, that activate the respective transcription factors LasR and RhlR. With the goal of developing novel therapeutic agents, we synthesized constrained analogs of PAI-I and evaluated them in P. aeruginosa, Two of the novel analogs bound to LasR and showed agonist activity in LasR stimulation of a lasI-lacZ reporter construct. (C) 1999 Elsevier Science Ltd. All rights reserved.