11-(全氟己基)十一烷酰氯 | 118624-66-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 中文名称: 11-(全氟己基)十一烷酰氯
• 英文名称: 11-(perfluorohexyl)undecanoyl chloride
• 英文别名: 11-(F-hexyl)-undecanoyl chloride；11-(F-hexyl)undecanoyl chloride；12,12,13,13,14,14,15,15,16,16,17,17,17-Tridecafluoroheptadecanoyl chloride
• CAS: 118624-66-1
• 化学式: C₁₇H₂₀ClF₁₃O
• 分子量: 522.777
• InChiKey: CLTPPAJDTWVGMU-UHFFFAOYSA-N

物化性质

• 沸点：
  118-119 °C(Press: 0.01 Torr)
• 密度：
  1.344±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  11-(全氟己基)十一烷酰氯 在 吡啶 、 三氟乙酸 作用下， 以 氯仿 、 水 为溶剂， 生成 5-O-<11'-(F-hexyl)undecanoyl>xylitol
  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：

  11-(F-hexyl)-undecanoic acid 在 氯化亚砜 作用下， 以91%的产率得到11-(全氟己基)十一烷酰氯
  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

• Synthesis and evaluation of the in vivo tolerance of amido fiuorocarbon/fluorocarbon and fluorocarbon/hydrocarbon double-chain phosphocholines deriving from diaminopropanols and serine
  作者：Laurence Clary、Catherine Santaella、Pierre Vierling

  DOI：10.1016/0040-4020(95)00837-x

  日期：1995.11

  The syntheses of various fluorocarbon/fluorocarbon and fluorocarbon/hydrocarbon amido-connected phosphocholines derived from diaminopropanols and serine are described. They were best obtained by phosphorylation of suitable alcohol precursors using 2-chloro-2-oxo-1,3,2-dioxaphospholane and subsequent ring opening with trimethylamine. The di-alkylamidopropanols were prepared by acylation, using perfluoroalkylated

  描述了衍生自二氨基丙醇和丝氨酸的各种碳氟化合物/碳氟化合物和碳氟化合物/烃基酰胺连接的磷胆碱的合成。它们最好通过使用2-氯-2-氧代-1,3,2-二氧戊环烷对合适的醇前体进行磷酸化并随后用三甲胺进行开环来获得。通过使用全氟烷基化的酰氯酰化1，3-二氨基-2-丙醇或2，3-二氨基-1-丙酸甲基酯，然后还原酯键，来制备二烷基酰胺基丙醇。通过Boc- O的缩合制备全氟烷基化的N-烷酰基-丝氨酸烷基酰胺-Bn-L-丝氨酸与脂族或全氟烷基化的胺，Boc脱保护，酰化，然后氢解苄基脱保护。急性毒性评估表明，这些系列的酰胺基连接的化合物在体内的耐受性非常好。
• Synthesis and characterization of new perfluoroalkylated side-chain ferrocenes and ferricinium salts
  作者：Christophe Guillon、Pierre Vierling

  DOI：10.1016/0022-328x(95)05723-3

  日期：1996.1

  The synthesis and characterization of various mono- and 1,1′-bis-[ω-(F-alkyl)acyl]ferrocenes, 1,1′-bis-[ω-(F-alkyl)alkyl]ferrocenes and 1,1′-bis-[ω-(F-alkyl)-α-(hydroxy)-alkyl]ferrocenes are described (where F-alkyl denotes perfluoroalkylation). The [(F-alkyl)acyl]ferrocenes were obtained by Friedel-Crafts acylation of ferrocene with (F-alkyl)acyl chlorides. The (F-alkyl)alkyl and (F-alsyl)-α-(hydroxyl)alkyl

  各种单和1,1'-双-[ ω-（F-烷基）酰基]二茂铁，1,1'-双-[ ω-（F-烷基）烷基]二茂铁和1,1的合成与表征描述了′-双-[ ω-（F-烷基）-α-（羟基）-烷基]二茂铁（其中F-烷基表示全氟烷基化）。[（F-烷基）酰基]二茂铁是通过二茂铁与（F-烷基）酰氯的弗瑞德-克来福特（Friedel-Crafts）酰化获得的。通过用LiAlH 4还原酰基衍生物，选择性地制备了（F-烷基）烷基和（F-烷基）-α-（羟基）烷基类似物。AlCl 3和的LiAlH 4分别。这些反应说明了（F-烷基）酰基和（F-烷基）烷基链在强烈还原条件下的化学惰性。当用ω- [2-（F-烷基）乙烯基]酰氯对二茂铁进行酰化时，得到了二茂铁，但它们的侧链含有（Z）CFCHCH（CL）-序列。这些链的形成是由于高度立体有择（E）CF 2 CHCH-至（Z）CFCHCH（Cl）的转化，其涉及在
• synthesis of single- and double-chain fluorocarbon and hydrocarbon β-linked galactose amphiphiles derived from serine
  作者：Laurence Clary、Jacques Greiner、Catherine Santaella、Pierre Vierling

  DOI：10.1016/0040-4039(94)02335-9

  日期：1995.1

  Single- and double-chain β-linked galactose amphiphiles derived from serine were synthesized. Both types of compounds have potential as material for the formulation of liposomal drug carrier and targeting systems and as HIV inhibitors.

  合成了衍生自丝氨酸的单链和双链β-连接的半乳​​糖两亲物。两种类型的化合物均具有作为脂质体药物载体和靶向系统的配制材料以及作为HIV抑制剂的潜力。
• Synthèse d’acides α-aminés racémiques à chaı̂ne perfluoroalkylée
  作者：D TraAnh、H Blancou、A Commeyras

  DOI：10.1016/s0022-1139(98)00340-6

  日期：1999.2

  The simple and effective syntheses of racemic alpha-amino-acids of general formula R-F(CH2)(n-1)Y (Y=CH(NH2)CO2H) (R-F=C6F13, C8F17; n=3,10) have been described, (C) 1999 Elsevier Science S.A. All rights reserved.
• Manfredi, Alexandre; Abouhilale, Samir; Greiner, Jacques, Bulletin de la Societe Chimique de France, 1989, # 6, p. 872 - 878
  作者：Manfredi, Alexandre、Abouhilale, Samir、Greiner, Jacques、Riess, Jean

  DOI：——

  日期：——