2,6-bis(decyloxy)naphthalene | 1257135-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-bis(decyloxy)naphthalene
• 英文别名: 2,6-(1,5-Didecyloxy)naphthalene；2,6-didecoxynaphthalene
• CAS: 1257135-20-8
• 化学式: C₃₀H₄₈O₂
• 分子量: 440.71
• InChiKey: YKQQBARJPMYPBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  32
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,6-萘二酚 、 癸基溴 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以33.9%的产率得到2,6-bis(decyloxy)naphthalene
  参考文献：
  名称：

  Behavior of 2,6-Bis(decyloxy)naphthalene Inside Lipid Bilayer

  摘要：

  Interactions between small organic molecules and lipid or cell membranes are important because of their role in the distribution of biologically active substances inside the membrane and their permeation through the cell membranes. In the current paper, we have explored the effect of the attachment of long hydrocarbon tails on the behavior of small organic molecule inside the lipid membrane. Naphthalene with two decyloxy groups attached at the opposite sites of the ring (2,6-bis(decyloxy)naphthalene, 3) was synthesized and incorporated into phosphatidylcholine (PC) vesicles. Fluorescence methods as well as molecular dynamic (MD) simulations were used to estimate the position, orientation, and migration of compound 3 in PC bilayer. It was found that the naphthalene ring of compound 3 resides in the upper acyl chain region of the bilayer and the hydrocarbon tails are directed to the center of the bilayer. As was shown with cryotransmission electron microscopy (cryo-TEM), such lipidlike conformation enables compound 3 to be incorporated into liposomes at a very high content without their disintegration. Moreover, compound 3 can migrate from one leaflet to other. The mechanism of this process is, however, different from that characteristic of the flip-flop event of lipid molecules in the membrane. Finally, the possible application of compound 3 as a rotational molecular probe for monitoring fluidity of liposornal membrane in the acyl side chain region was checked by studies of the effect of cholesterol on the fluoresce ice anisotropy of 3.

  DOI：

  10.1021/jp103753f

文献信息

• Behavior of 2,6-Bis(decyloxy)naphthalene Inside Lipid Bilayer
  作者：Mariusz Kepczynski、Marta Kumorek、Michał Stepniewski、Tomasz Róg、Bartłomiej Kozik、Dorota Jamróz、Jan Bednar、Maria Nowakowska

  DOI：10.1021/jp103753f

  日期：2010.12.2

  Interactions between small organic molecules and lipid or cell membranes are important because of their role in the distribution of biologically active substances inside the membrane and their permeation through the cell membranes. In the current paper, we have explored the effect of the attachment of long hydrocarbon tails on the behavior of small organic molecule inside the lipid membrane. Naphthalene with two decyloxy groups attached at the opposite sites of the ring (2,6-bis(decyloxy)naphthalene, 3) was synthesized and incorporated into phosphatidylcholine (PC) vesicles. Fluorescence methods as well as molecular dynamic (MD) simulations were used to estimate the position, orientation, and migration of compound 3 in PC bilayer. It was found that the naphthalene ring of compound 3 resides in the upper acyl chain region of the bilayer and the hydrocarbon tails are directed to the center of the bilayer. As was shown with cryotransmission electron microscopy (cryo-TEM), such lipidlike conformation enables compound 3 to be incorporated into liposomes at a very high content without their disintegration. Moreover, compound 3 can migrate from one leaflet to other. The mechanism of this process is, however, different from that characteristic of the flip-flop event of lipid molecules in the membrane. Finally, the possible application of compound 3 as a rotational molecular probe for monitoring fluidity of liposornal membrane in the acyl side chain region was checked by studies of the effect of cholesterol on the fluoresce ice anisotropy of 3.