Ethyl 3-F-pentyl propynoate | 117643-84-2

• 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: Ethyl 3-F-pentyl propynoate
• 英文别名: Ethyl 4,4,5,5,6,6,7,7,8,8,8-undecafluorooct-2-ynoate
• CAS: 117643-84-2
• 化学式: C₁₀H₅F₁₁O₂
• 分子量: 366.131
• InChiKey: ZPRBMVHPGMIWLY-UHFFFAOYSA-N

物化性质

• 沸点：
  190.2±40.0 °C(Predicted)
• 密度：
  1.522±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Ethyl 3-F-pentyl propynoate 在 palladium on activated charcoal 氢气 作用下， 以92%的产率得到Ethyl 4,4,5,5,6,6,7,7,8,8,8-undecafluorooctanoate
  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：

  (F-hexanoylcarbethoxymethylene)triphenylphosphorane 150.0~220.0 ℃ 、2.67 kPa 条件下， 以90%的产率得到Ethyl 3-F-pentyl propynoate
  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

• Synthèse de perfluoroalkyl indoles via la cycloaddition dipolaire-1,3
  作者：Joel Fayn、Antoine Nezis、Aime Cambon

  DOI：10.1016/s0022-1139(00)81989-2

  日期：1987.9

  An unusual synthesis of functionalized F-alkyl indoles using ethyl perfluoroalkynoates and C,N diphenyl nitrone is described. Two isomers, 2- F-alkyl (90%) and 3- F-alkyl (10%) are obtained with short perfluoro alkyl chains (CF3, nC3F7). Regiospecifity is obtained with longer chains (C5F11, C6F13, C7F15).

  描述了使用全氟链烷酸乙酯和C，N二苯基硝酮不寻常地合成官能化的F-烷基吲哚的方法。获得具有短的全氟烷基链（CF 3，nC 3 F 7）的两种异构体，2-F-烷基（90％）和3-F-烷基（10％）。区域特异性是通过更长的链（C 5 F 11，C 6 F 13，C 7 F 15）获得的。
• Reactivite des f-alkyl-3 propynoates d'ethyle: addition d'esters α et β amines. synthese de f-heptyl pyrrolidone
  作者：Alain Chauvin、Joelle Fabron、M.O. Ait Yahia、Raphaël Pastor、Aimé Cambon

  DOI：10.1016/s0040-4020(01)87860-1

  日期：1990.1

  N-ethylaminopropanoate (secondary amine) to ethyl 3-F-alkylpropynoate leads in excellent yields to enaminoesters of Z and E configuration respectively. Heterocyclic compounds (pyrrolidone) are obtained from Z enaminoesters in three steps: hydrogenation followed by methylation and cyclisation in alkaline medium.

  将甘氨酸乙酯（伯胺）和N-乙基氨基丙酸乙酯（仲胺）加到3-F-烷基丙酸乙酯中可分别得到Z和E构型的烯胺酯。杂环化合物（吡咯烷酮）可通过三个步骤从Z烯脂酸酯中获得：氢化，然后甲基化，并在碱性介质中环化。
• Stereoselective synthesis of F-alkyl α,β-unsaturated esters and their epoxidation
  作者：Marion Lanier、Mustapha Haddach、Raphael Pastor、Jean G. Riess

  DOI：10.1016/s0040-4039(00)60443-4

  日期：1993.4

  Strong electrophilic Z and E 3-F-alkyl 2-propenoates have been prepared stereoselectively. Their extremely difficult epoxidation has been achieved with retention of stereohemistry using t-BuO2Li, leading to F-alkyl glycidic esters, which are useful building blocks for the synthesis of new amphiphiles.

  已经立体选择性地制备了强亲电的Z和E 3- F-烷基2-丙酸酯。通过使用t-BuO 2 Li保留立体异构，已经实现了其极其困难的环氧化作用，从而导致F-烷基缩水甘油酯，这是合成新两亲物的有用组成部分。
• Stabilite et reactivite anormales des perfluoroalkyl azirines et aziridines
  作者：Mustapha Haddach、Raphaël Pastor、Jean G Riess

  DOI：10.1016/s0040-4039(00)88896-6

  日期：1990.1

  The presence of an F-alkyl chain induces particular reactivity and stability in azirinic and aziridinic rings. The newly synthesized F-alkyl azirine carboxylates undergo addition reactions. The F-alkyl aziridine carboxylates are extremely stable towards both nucleophilic and electrophilic reactants, whether the medium be neutral, acidic or basic.

  F-烷基链的存在在叠氮和叠氮环中引起特别的反应性和稳定性。新合成的F-烷基叠氮基羧酸盐发生加成反应。无论介质是中性，酸性还是碱性，F-烷基氮丙啶羧酸盐对亲核和亲电反应物都极为稳定。
• Synthese de nouveaux acides amines F-alkyles derives de la lysine. L'arginine et la cysteine
  作者：M. Haddach、R. Pastor、J.G. Riess

  DOI：10.1016/s0022-1139(00)80290-0

  日期：1991.2

  Ethyl-2-F-alcynoates are good substrates for Michael additions. Such additions allowed the preparation of three new families of F-alkylated aminoacids derived from lysine, arginine and cysteine. However, their transformation into betaines has proved more difficult than in the hydrocarbon series.