5-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoro-1-nonyl-undecyloxy)-pentan-1-ol | 172916-15-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoro-1-nonyl-undecyloxy)-pentan-1-ol
• CAS: 172916-15-3
• 化学式: C₂₅H₃₅F₁₇O₂
• 分子量: 690.525
• InChiKey: SLJUFPCRSOYMSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.46
• 重原子数：
  44.0
• 可旋转键数：
  23.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoro-1-nonyl-undecyloxy)-pentan-1-ol 在 吡啶 、 咪唑 、 sodium hydroxide 、 Amberlite IR-120 (H⁺ form) 、 水 、 碘 、 三甲基乙酰氯 、 三乙胺 、 三氟乙酸 、 三氯化磷 作用下， 反应 5.75h， 生成 D-galactose 6-{sodium 6-oxa-7-[2-(perfluorooctyl)ethyl]hexadecyl phosphate}
  参考文献：
  名称：

  New anionic glycophospholipids with two perfluorocarbon or two hydrocarbon or mixed hydrophobic chains

  摘要：

  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.

  DOI：

  10.1016/0009-3084(95)02492-2
• 作为产物：
  描述：

  1-mesyloxy-5-tetrahydropyranyloxy-pentane 在 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 5-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoro-1-nonyl-undecyloxy)-pentan-1-ol
  参考文献：
  名称：

  New anionic glycophospholipids with two perfluorocarbon or two hydrocarbon or mixed hydrophobic chains

  摘要：

  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.

  DOI：

  10.1016/0009-3084(95)02492-2

文献信息

• 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.