5-O-<3'-(F-hexyl)-2'-iodopropyl>-1,2:3,4-di-O-isopropylidenexylitol | 125024-81-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-<3'-(F-hexyl)-2'-iodopropyl>-1,2:3,4-di-O-isopropylidenexylitol
• 英文别名: 5-O-[3'-(F-hexyl)-2'-iodopropyl]-1,2:3,4-di-O-isopropylidenexylitol；(4S,5R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-5-[(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodononoxy)methyl]-1,3-dioxolane
• CAS: 125024-81-9
• 化学式: C₂₀H₂₄F₁₃IO₅
• 分子量: 718.291
• InChiKey: GSZFYMFSEVMDHZ-WSWARRKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-O-<3'-(F-hexyl)-2'-iodopropyl>-1,2:3,4-di-O-isopropylidenexylitol 在 C.I.酸性橙108 作用下， 以 乙醇 为溶剂， 反应 1.33h， 以95%的产率得到(Z)-5-O-<3'-(F-hexyl)-2'-propenyl>-1,2:3,4-di-O-isopropylidenexylitol
  参考文献：
  名称：

  Synthesis of perfluoroalkylated xylitol ethers and esters: new surfactants for biomedical uses

  摘要：

  New, well-defined surfactants and cosurfactants were synthesized with the objective of enhancing the stability of fluorocarbon emulsions destined to serve as oxygen carriers for biomedical applications. Monoperfluoroalkylated ethers of xylitol were achieved by addition of perfluoroalkyl iodide on the double bond of a protected xylitol allyl ether in a one-step addition-elimination reaction. Monoesters were obtained specifically on position 5 by treating 1,2:3,4-di-O-isopropylidenexylitol with perfluoroalkylated acid chlorides of various chain lengths in pyridine at room temperature. The products display strong surface activity and produce a remarkable synergistic stabilization of a fluorocarbon/Pluronic F-68 type emulsion. Biocompatibility data are reported, which include in vitro toxicity tests on Namalva cell cultures and hemolysis tests on human blood cells; the latter was found to decrease as the length of the F-alkyl chain increased. IV injection in mice (n = 10) showed that these products were innocuous at 400-1000 mg/kg of body weight. Preliminary exchange-perfusion experiments on rats with an emulsion containing the F-octyl xylitol ether were encouraging.

  DOI：

  10.1021/jm00166a028
• 作为产物：
  描述：

  Xylitol 在 硫酸 、 sodium hydride 、 copper(II) sulfate 、 过氧化苯甲酰 作用下， 反应 65.0h， 生成 5-O-<3'-(F-hexyl)-2'-iodopropyl>-1,2:3,4-di-O-isopropylidenexylitol
  参考文献：
  名称：

  Synthesis of perfluoroalkylated xylitol ethers and esters: new surfactants for biomedical uses

  摘要：

  New, well-defined surfactants and cosurfactants were synthesized with the objective of enhancing the stability of fluorocarbon emulsions destined to serve as oxygen carriers for biomedical applications. Monoperfluoroalkylated ethers of xylitol were achieved by addition of perfluoroalkyl iodide on the double bond of a protected xylitol allyl ether in a one-step addition-elimination reaction. Monoesters were obtained specifically on position 5 by treating 1,2:3,4-di-O-isopropylidenexylitol with perfluoroalkylated acid chlorides of various chain lengths in pyridine at room temperature. The products display strong surface activity and produce a remarkable synergistic stabilization of a fluorocarbon/Pluronic F-68 type emulsion. Biocompatibility data are reported, which include in vitro toxicity tests on Namalva cell cultures and hemolysis tests on human blood cells; the latter was found to decrease as the length of the F-alkyl chain increased. IV injection in mice (n = 10) showed that these products were innocuous at 400-1000 mg/kg of body weight. Preliminary exchange-perfusion experiments on rats with an emulsion containing the F-octyl xylitol ether were encouraging.

  DOI：

  10.1021/jm00166a028

文献信息

• ZARIF, LEILA;GREINER, JACQUES;PACE, SIMONNE;RIESS, JEAN G., J. MED. CHEM., 33,(1990) N, C. 1262-1269
  作者：ZARIF, LEILA、GREINER, JACQUES、PACE, SIMONNE、RIESS, JEAN G.

  DOI：——

  日期：——