1-(perfluorooctyl)-3-dodecanol | 147694-91-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(perfluorooctyl)-3-dodecanol
• CAS: 147694-91-5
• 化学式: C₂₀H₂₅F₁₇O
• 分子量: 604.391
• InChiKey: XGKAIVIYXXFSSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.28
• 重原子数：
  38.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(perfluorooctyl)-3-dodecanol 在 lithium aluminium tetrahydride 、 叠氮磷酸二苯酯 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  Vesicles and other supramolecular systems from biocompatible synthetic glycolipids with hydrocarbon and/or fluorocarbon chains

  摘要：

  A series of double-tailed hydrocarbon and/or fluorocarbon glycolipids derived from galactose and glucose have been prepared. These compounds were obtained upon opening a lactono- and maltonolactone moiety by the amino group of either a glycine, glycylglycine or lysine residue. The carboxyl terminus of the glycyl and glycylglycine conjugates was further reacted with the appropriate double-tailed amine. In the case of lysine, the lactonamide conjugate was functionalized with a hydrocarbon and/or fluorocarbon fatty amine and acid, respectively. The ability of such glycolipids to disperse in water, the morphology of self-assemblies formed and the stability of the supramolecular structure obtained were shown to depend on the presence or absence and on the nature of the aminoacid spacer. Most of the compounds described were shown by conventional techniques (TEM, Cryo-TEM, LLS, etc.) to produce stable vesicular systems.

  DOI：

  10.1016/0009-3084(94)90099-x
• 作为产物：
  描述：

  癸醛 、 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-十七氟-10-碘庚烷 在 magnesium 作用下， 生成 1-(perfluorooctyl)-3-dodecanol
  参考文献：
  名称：

  Vesicles and other supramolecular systems from biocompatible synthetic glycolipids with hydrocarbon and/or fluorocarbon chains

  摘要：

  A series of double-tailed hydrocarbon and/or fluorocarbon glycolipids derived from galactose and glucose have been prepared. These compounds were obtained upon opening a lactono- and maltonolactone moiety by the amino group of either a glycine, glycylglycine or lysine residue. The carboxyl terminus of the glycyl and glycylglycine conjugates was further reacted with the appropriate double-tailed amine. In the case of lysine, the lactonamide conjugate was functionalized with a hydrocarbon and/or fluorocarbon fatty amine and acid, respectively. The ability of such glycolipids to disperse in water, the morphology of self-assemblies formed and the stability of the supramolecular structure obtained were shown to depend on the presence or absence and on the nature of the aminoacid spacer. Most of the compounds described were shown by conventional techniques (TEM, Cryo-TEM, LLS, etc.) to produce stable vesicular systems.

  DOI：

  10.1016/0009-3084(94)90099-x

文献信息

• Synthesis of double-tailed (perfluoroalkyl)alkyl phosphosugars: new components for drug-carrying and -targeting systems
  作者：Frédéric Guillod、Jacques Greiner、Jean G. Riess

  DOI：10.1016/0008-6215(94)80004-9

  日期：1994.8

  corresponding O -protected glycose phosphate diesters. O -Deisopropylidenation of the latter by aqueous trifluoroacetic acid afforded the target compound in 70% yield, based on the protected glycosides. Condensation of 1,2,3,4-tetra- O -acetyl-β- d -glucopyranose or -mannopyranose with double-tailed (perfluoroalkyl)alkyl hydrogenphosphonates or 10-eicosyl hydrogenphosphonate, via the coupling and oxidation

  摘要：通过氢膦酸法合成了双尾d-葡萄糖3-和6-[[全氟烷基]烷基磷酸钠]。由双尾（全氟烷基）链烷醇和PCl 3-咪唑制得的稳定的双尾（全氟烷基）烷基氢膦酸酯，与1,2：3,4-二-O-异亚丙基-α-d-吡喃半乳糖反应，或与1，在Me 3 CCOCl作为缩合剂存在下的2：5,6-二-O-异亚丙基-α-d-葡萄糖基呋喃糖，在用碘水溶液氧化后，得到相应的O-保护的糖基磷酸二酯。基于被保护的糖苷，后者通过三氟乙酸水溶液的O-异异丙基亚胺化以70％的收率得到目标化合物。1,2,3的凝结 经由上述偶联和氧化步骤，具有双尾（全氟烷基）烷基氢膦酸酯或10-二十烷基氢膦酸酯的4-四-O-乙酰基-β-d-吡喃葡萄糖或-甘露吡喃糖提供了全-O-乙酰基葡萄糖磷酸二酯。基于保护的糖，用MeONa-MeOH的O-脱乙酰基以65％的收率实现。所有化合物均通过19 F，1 H，13 C和31 P NMR数据表征。初步的
• New anionic glycophospholipids with two perfluorocarbon or two hydrocarbon or mixed hydrophobic chains
  作者：Frédéric Guillod、Jacques Greiner、Jean G. Riess

  DOI：10.1016/0009-3084(95)02492-2

  日期：1995.11

  Novel amphiphilic anionic sugar phosphates esterified by various hydrophobic double-chain tails were synthesized. They differ primarily by the design of their hydrophobic tail. Amphiphile 12a derives from phosphogalactose and has two perfluoroalkylated hydrophobic chains; 12b has a pentenyloxy spacer between the mixed hydrocarbon/fludrocarbon double-chain and the same head group; 12c and 14c are galactose and glucose derivatives with two hydrocarbon tail chains. All were prepared through a three-step H-phosphonate route: reaction of the hydrophobic double-chain alcohol on phosphorus trichloride (27-60%), followed by the addition of the appropriately protected sugar, by oxidation (50-81%), and finally by deprotection of the sugar (58-95%). The starting alcohols were prepared through conventional reactions. Their synthesis was however, difficult, essentially as a result of lesser reactivity, and of low solubility of some of the intermediates related to the presence of the bulky, strongly hydrophobic chains. Preliminary biocompatibility assays indicate a reduction in hemolytic activity by increasing the number of fluorinated chains or by increasing the total length, hence the hydrophobicity of the amphiphile. Acute toxicity tests indicate maximum intravenously tolerated doses in mice of ca. 500 mg/kg body weight for 12a and 12b.