2-Hexadecyloxy-1,4-dimethylbenzene | 1118246-26-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Hexadecyloxy-1,4-dimethylbenzene
• 英文别名: 2-Hexadecoxy-1,4-dimethylbenzene；2-hexadecoxy-1,4-dimethylbenzene
• CAS: 1118246-26-6
• 化学式: C₂₄H₄₂O
• 分子量: 346.597
• InChiKey: YNPYCHSGTQZERP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Hexadecyloxy-1,4-dimethylbenzene 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 以28%的产率得到1-tetradecyloxy-2,5-bis(bromomethyl)benzene
  参考文献：
  名称：

  Bicephalic amphiphile architecture affects antibacterial activity

  摘要：

  A series of cationic amphiphiles, each with an aromatic core, was prepared and investigated for antimicrobial properties. The synthesized amphiphiles in this study are bicephalic (double-headed) in that they each possess two trimethylammonium head groups and a single linear alkoxy tail. Minimum inhibitory and minimum bactericidal concentrations of these amphiphiles were in the low micromolar range. Antimicrobial activities are highly sensitive to the chain length of the hydrophobic region, and modestly reliant on the relative positioning of the head groups on the aromatic core. These trends were more pronounced in time kill assays, wherein longer chain compounds required significantly shorter times to completely kill bacteria. Microscopy suggested that the mode of cell death was lysis. Strong inhibition was observed with both biscationic compounds and monocationic comparisons against Gram-positive bacteria: only biscationic amphiphiles maintained good activity versus the Gram-negative bacteria tested. These observations provide direction for future antimicrobial structural investigations. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.026
• 作为产物：
  描述：

  2,5-二甲基苯酚 、 溴代十六烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以72%的产率得到2-Hexadecyloxy-1,4-dimethylbenzene
  参考文献：
  名称：

  Bicephalic amphiphile architecture affects antibacterial activity

  摘要：

  A series of cationic amphiphiles, each with an aromatic core, was prepared and investigated for antimicrobial properties. The synthesized amphiphiles in this study are bicephalic (double-headed) in that they each possess two trimethylammonium head groups and a single linear alkoxy tail. Minimum inhibitory and minimum bactericidal concentrations of these amphiphiles were in the low micromolar range. Antimicrobial activities are highly sensitive to the chain length of the hydrophobic region, and modestly reliant on the relative positioning of the head groups on the aromatic core. These trends were more pronounced in time kill assays, wherein longer chain compounds required significantly shorter times to completely kill bacteria. Microscopy suggested that the mode of cell death was lysis. Strong inhibition was observed with both biscationic compounds and monocationic comparisons against Gram-positive bacteria: only biscationic amphiphiles maintained good activity versus the Gram-negative bacteria tested. These observations provide direction for future antimicrobial structural investigations. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.026

文献信息

• Bicephalic amphiphile architecture affects antibacterial activity
  作者：Jade E. LaDow、David C. Warnock、Kristina M. Hamill、Kaitlin L. Simmons、Robert W. Davis、Christian R. Schwantes、Devon C. Flaherty、Jon A.L. Willcox、Kelsey Wilson-Henjum、Kevin L. Caran、Kevin P.C. Minbiole、Kyle Seifert

  DOI：10.1016/j.ejmech.2011.06.026

  日期：2011.9

  A series of cationic amphiphiles, each with an aromatic core, was prepared and investigated for antimicrobial properties. The synthesized amphiphiles in this study are bicephalic (double-headed) in that they each possess two trimethylammonium head groups and a single linear alkoxy tail. Minimum inhibitory and minimum bactericidal concentrations of these amphiphiles were in the low micromolar range. Antimicrobial activities are highly sensitive to the chain length of the hydrophobic region, and modestly reliant on the relative positioning of the head groups on the aromatic core. These trends were more pronounced in time kill assays, wherein longer chain compounds required significantly shorter times to completely kill bacteria. Microscopy suggested that the mode of cell death was lysis. Strong inhibition was observed with both biscationic compounds and monocationic comparisons against Gram-positive bacteria: only biscationic amphiphiles maintained good activity versus the Gram-negative bacteria tested. These observations provide direction for future antimicrobial structural investigations. (C) 2011 Elsevier Masson SAS. All rights reserved.