(3,5-dibromo-2-(methoxymethoxy)phenyl)methanamine | 1276560-33-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3,5-dibromo-2-(methoxymethoxy)phenyl)methanamine
• CAS: 1276560-33-8
• 化学式: C₉H₁₁Br₂NO₂
• 分子量: 325.0
• InChiKey: XAPBYXHGJYGDOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  371.0±42.0 °C(predicted)
• 密度：
  1.722±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3,5-dibromo-2-(methoxymethoxy)phenyl)methanamine 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.5h， 生成 2,4-dibromo-6-((2-nitrobenzamido)methyl)phenyl 2-chlorobenzoate
  参考文献：
  名称：

  Synthesis and Molecular Modeling Provide Insight into a Pseudomonas aeruginosa Quorum Sensing Conundrum

  摘要：

  The triphenyl amide/ester 12 was originally reported to be a potent mimic of the natural 3-oxo-dodecanoyl homoserine lactone quorum sensing molecule in Pseudomonas aeruginosa. However, explicit synthesis/chemical characterization was lacking, and a later report providing protein crystallographic data inferred 12 to be incorrect, with 9 now being the surmised structure. Because of these inconsistencies and our interest in quorum sensing molecules utilized by Gram-negative bacteria, we found it necessary to synthesize 9 and 12 to test for agonistic activity in a P. aeruginosa reporter assay. Despite distinct regiochemical differences, both 9 and 12 were found to have comparable EC(50) values. To reconcile these unanticipated findings, modeling studies were conducted, and both compounds were revealed to have comparable properties for binding to the LasR receptor.

  DOI：

  10.1021/ja111138y
• 作为产物：
  描述：

  2-(3,5-dibromo-2-(methoxymethoxy)benzyl)isoindoline-1.3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 17.0h， 以85%的产率得到(3,5-dibromo-2-(methoxymethoxy)phenyl)methanamine
  参考文献：
  名称：

  Synthesis and Molecular Modeling Provide Insight into a Pseudomonas aeruginosa Quorum Sensing Conundrum

  摘要：

  The triphenyl amide/ester 12 was originally reported to be a potent mimic of the natural 3-oxo-dodecanoyl homoserine lactone quorum sensing molecule in Pseudomonas aeruginosa. However, explicit synthesis/chemical characterization was lacking, and a later report providing protein crystallographic data inferred 12 to be incorrect, with 9 now being the surmised structure. Because of these inconsistencies and our interest in quorum sensing molecules utilized by Gram-negative bacteria, we found it necessary to synthesize 9 and 12 to test for agonistic activity in a P. aeruginosa reporter assay. Despite distinct regiochemical differences, both 9 and 12 were found to have comparable EC(50) values. To reconcile these unanticipated findings, modeling studies were conducted, and both compounds were revealed to have comparable properties for binding to the LasR receptor.

  DOI：

  10.1021/ja111138y