11,11,12,12,13,13,14,14,15,15,16,16,16-Tridecafluoro-hexadecanoic acid | 187867-08-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 11,11,12,12,13,13,14,14,15,15,16,16,16-Tridecafluoro-hexadecanoic acid
• 英文别名: 11,11,12,12,13,13,14,14,15,15,16,16,16-Tridecafluorohexadecanoic acid
• CAS: 187867-08-9
• 化学式: C₁₆H₁₉F₁₃O₂
• 分子量: 490.305
• InChiKey: AQWWREXKYXXCKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  11,11,12,12,13,13,14,14,15,15,16,16,16-Tridecafluoro-hexadecanoic acid 在 aluminum oxide 、 草酰氯 作用下， 以 正己烷 为溶剂， 生成 2,3-Bis(11,11,12,12,13,13,14,14,15,15,16,16,16-tridecafluorohexadecanoyloxy)propyl 11,11,12,12,13,13,14,14,15,15,16,16,16-tridecafluorohexadecanoate
  参考文献：
  名称：

  甘油的高度氟化脂肪酸酯的合成：甘油三棕榈酸酯-F 39

  摘要：

  由甘油和R F-棕榈酸-F 13的酰氯经固相氧化铝催化反应制备甘油三棕榈酸酯-F 39。该产物已通过电喷雾质谱和1 H，19 F和13 C NMR方法进行了表征。

  DOI：

  10.1016/j.jfluchem.2006.04.016
• 作为产物：
  描述：

  9-癸烯酸 、 全氟己基碘烷 在 偶氮二异丁腈 、 溶剂黄146 、 锌 作用下， 以52%的产率得到11,11,12,12,13,13,14,14,15,15,16,16,16-Tridecafluoro-hexadecanoic acid
  参考文献：
  名称：

  Nanoscale Patterning in Mixed Fluorocarbon−Hydrocarbon Phospholipid Bilayers

  摘要：

  A growing body of literature suggests that fluorocarbons can direct self-assembly within hydrocarbon environments. We report here the fabrication and characterization of supported lipid bilayers (SLBs) composed of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and a synthetic, fluorocarbon-functionalized analogue, 1. AFM investigation of these model membranes reveals an intricate, composition-dependent domain structure consisting of similar to 50 nm stripes interspersed between similar to 1 mu m sized domains. Although DSC of 1 showed a phase transition near room temperature, DSC of DPPC:1 mixtures exhibited complex phase behavior suggesting domain segregation. Finally, temperature-dependent AFM of DPPC:1 bilayers shows that, while the stripe structures can be melted above the T-m of 1, the stripes and domains result from immiscibility of the hydrocarbon and fluorocarbon lipid gel phases. Fluorination appears to be a promising strategy for chemical self-assembly in two dimensions. In particular, because no modification is made to the lipid headgroups, it may be useful for nanopatterning biologically relevant ligands on bilayers in vitro or in living cells.

  DOI：

  10.1021/ja070950l

文献信息

• Fluorinated Lipid Constructs Permit Facile Passage of Molecular Cargo into Living Cells
  作者：Laila Dafik、Venkateshwarlu Kalsani、Anthony Kar Lun Leung、Krishna Kumar

  DOI：10.1021/ja902777d

  日期：2009.9.2

  Fluorinated lipids get rapidly internalized into living cells and are also displayed on the cell surface. The uptake of lipids is energy dependent and is likely via the clathrin-mediated endocytic pathway. Fluorinated lipids are 3-5-fold more efficient in acting as molecular transporters of noncovalently bound proteins than their hydrocarbon counterparts. These materials could serve as efficient molecular transporters for molecules that function in the cytoplasm such as short interfering RNAs (siRNAs)
• Reaction of RF-palmitic acid-F13 with dicyclohexylcarbodiimide
  作者：Gerald W. Buchanan、Majid F. Rastegar、Gary Enright

  DOI：10.1016/j.jfluchem.2007.05.005

  日期：2007.9

  The 1,3-dicyclohexylcarbodiimide (DCC) adduct of R-F-palmitic acid-F-13 I has been synthesized and characterized. The X-ray crystal structure shows that the product arises from an O- to N-acyl migration of an initially formed N,N' -dicyclohexyl-O-R-F-palmitoyl-F-13-isourea 2 to give 1-R-F-palmitoyl-F-13-1,3-dicyclohexylurea 3. X-ray data for an R-F-palmitic acid-F-13 unit are reported for the first time. The product of the reaction of DCC with palmitic acid is also the urea derivative which has been characterized by IR and NMR methods. (c) 2007 Elsevier B.V. All rights reserved.