methyl 4-(1H,1H,2H,2H-perfluorodecyl)benzoate | 495388-45-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-(1H,1H,2H,2H-perfluorodecyl)benzoate
• 英文别名: methyl 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)benzoate；Methyl 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)benzoate
• CAS: 495388-45-9
• 化学式: C₁₈H₁₁F₁₇O₂
• 分子量: 582.257
• InChiKey: BGKDUXCRTBCCNE-UHFFFAOYSA-N

物化性质

• 沸点：
  333.9±42.0 °C(Predicted)
• 密度：
  1.511±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  methyl 4-(1H,1H,2H,2H-perfluorodecyl)benzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以93%的产率得到4-十七氟癸基苄醇
  参考文献：
  名称：

  Fluorous synthesis of mono-dispersed poly(ethylene glycols)

  摘要：

  Mono-dispersed poly(ethylene glycols) (PEGs) are of great value in the development of biopharmaceuticals. However, tedious synthesis limits the availability of mono-dispersed PEGs. To address this issue, a fluorous synthesis of mono-dispersed PEGs, discretely PEGylated surfactants and F-19 magnetic resonance imaging (MRI) agents has been developed. During the synthesis, both fluorous and normal phase silica gel-based solid-phase extractions were successfully employed to simplify the purifications. This synthesis provided an easy access to valuable mono-dispersed PEGs and related molecules for biomedical application on multi-gram scales. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.047
• 作为产物：
  描述：

  1H,1H,2H-全氟-1-癸烯 在 palladium on activated charcoal 、 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) 氢气 、 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 125.0 ℃ 、300.0 kPa 条件下， 反应 17.0h， 生成 methyl 4-(1H,1H,2H,2H-perfluorodecyl)benzoate
  参考文献：
  名称：

  Use of benzyloxycarbonyl (Z)-based fluorophilic tagging reagents in the purification of synthetic peptides

  摘要：

  Three novel fluorous reagents (i.e. 1-3), derived from benzyl chloroformate (Z-Cl), have been synthesized and used for the tagging of peptides prepared following a Fmoc-based solid-phase approach. It is shown that the implementation of a benzyloxycarbonyl (Z)-based fluorophilic tag facilitates purification of peptides using fluorous reverse phase chromatography. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01723-9

文献信息

• Fluorous oligonucleotide reagents and affinity purification of oligonucleotides
  申请人：Berry A. David

  公开号：US20060178507A1

  公开（公告）日：2006-08-10

  Fluorous-tagged oligonucleotide reagents and an oligonucleotide purification methodology making use thereof, the method comprising: Synthesizing oligonucleotides using oligonucleotide reagents each bearing at least one fluorous group to yield a mixture of synthesis products and reagents, the mixture including at least one target synthesized oligonucleotide bearing at least one fluorous group; passing the mixture through a separation medium having an affinity for the at least one fluorous group so that the target synthesized oligonucleotide bearing at least one fluorous group is adsorbed by the separation medium; washing the separation medium with at least a first solvent to selectively dissociate therefrom substantially all synthesis products and reagents of the heterogenous mixture other than the at least one target synthesized oligonucleotide bearing at least one fluorous group; and subsequently dissociating the at least one synthesized oligonucleotide from the separation medium, with or without the fluorous group.

  使用含有至少一个氟亲和基团的寡核苷酸试剂和一种利用该方法的寡核苷酸纯化方法，该方法包括：使用每个带有至少一个氟亲和基团的寡核苷酸试剂合成寡核苷酸，以产生合成产物和试剂的混合物，混合物包括至少一个带有至少一个氟亲和基团的目标合成寡核苷酸；将混合物通过具有亲和性的分离介质，使带有至少一个氟亲和基团的目标合成寡核苷酸被分离介质吸附；用至少一种溶剂洗涤分离介质，以选择性地从异质混合物中溶解除了至少一个带有至少一个氟亲和基团的目标合成寡核苷酸之外的几乎所有合成产物和试剂；随后从分离介质中解离至少一个合成寡核苷酸，带有或不带有氟亲和基团。
• Fluorous Oligonucleotide Reagents and Affinity Purification of Oligonucleotides
  申请人：Berry David A.

  公开号：US20100087634A1

  公开（公告）日：2010-04-08

  Fluorous-tagged oligonucleotide reagents and an oligonucleotide purification methodology making use thereof, the method comprising: Synthesizing oligonucleotides using oligonucleotide reagents each bearing at least one fluorous group to yield a mixture of synthesis products and reagents, the mixture including at least one target synthesized oligonucleotide bearing at least one fluorous group; passing the mixture through a separation medium having an affinity for the at least one fluorous group so that the target synthesized oligonucleotide bearing at least one fluorous group is adsorbed by the separation medium; washing the separation medium with at least a first solvent to selectively dissociate therefrom substantially all synthesis products and reagents of the heterogenous mixture other than the at least one target synthesized oligonucleotide bearing at least one fluorous group; and subsequently dissociating the at least one synthesized oligonucleotide from the separation medium, with or without the fluorous group.

  含氟标记的寡核苷酸试剂及其利用的寡核苷酸纯化方法，该方法包括：使用每个带有至少一个氟基团的寡核苷酸试剂合成寡核苷酸，以产生一种合成产物和试剂的混合物，其中包括至少一种带有至少一个氟基团的目标合成寡核苷酸；将混合物通过具有亲和力的分离介质，使带有至少一个氟基团的目标合成寡核苷酸被分离介质吸附；使用至少一种第一溶剂清洗分离介质，以选择性地分离除带有至少一个氟基团的目标合成寡核苷酸之外的异质混合物中的所有合成产物和试剂；随后将至少一个合成寡核苷酸与或不与氟基团从分离介质中解离。
• Synthesis and Reactions of Fluorous Carbobenzyloxy (^FCbz) Derivatives of α-Amino Acids
  作者：Dennis P. Curran、Muriel Amatore、David Guthrie、Matthew Campbell、Eisan Go、Zhiyong Luo

  DOI：10.1021/jo0344283

  日期：2003.6.1

  Fluorous carbobenzyloxy ((F)Cbz) reagents RfCH(2)CH(2)C(6)H(4)CH(2)OC(O)OSU (where Su is succinimidoyl and Rf is C6F13 and C8F17) have been used to make FCbz derivatives of 18 of the 20 natural amino acids. The potential utility of this new family of reagents in both standard fluorous synthesis with spe separation and fluorous quasiracemic synthesis is illustrated with representative reactions of the (F)Cbz-Phe derivatives.
• Fluorous Affinity Purification of Oligonucleotides
  作者：William H. Pearson、David A. Berry、Patrick Stoy、Kee-Yong Jung、Anthony D. Sercel

  DOI：10.1021/jo050795y

  日期：2005.9.1

  Nucleoside phosphoramidites bearing a fluorous dimethoxytrityl (FDMT) group were used to synthesize fluorous-tagged oligonucleotides, which were subjected to solid-phase extraction using a pH-stable fluorinated adsorbent. On-column detritylation afforded the purified oligonucleotides. The fluorous affinity purification method offers one-pass loading without ammonia removal, high selectivity for the removal of failure sequences, high recoveries (typically 70-100%), and the ability to purify long oligonucleotides (e.g., 50-100-mers).
• FLUOROUS OLIGONUCLEOTIDE REAGENTS AND AFFINITY PURIFICATION OF OLIGONUCLEOTIDES
  申请人：Berry & Associates , Inc.

  公开号：EP1831238A2

  公开（公告）日：2007-09-12