4-(1H,1H,2H,2H,3H,3H-全氟庚氧基)苄醇 | 892154-51-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-(1H,1H,2H,2H,3H,3H-全氟庚氧基)苄醇
• 中文别名: 4-[3-(全氟丁基)-1-丙氧基]苄醇；4-(4,4,5,5,6,6,7,7,7-九氟庚氧基)苄醇
• 英文名称: p-(perfluorobutylpropyloxy)benzyl alcohol
• 英文别名: 4-(4,4,5,5,6,6,7,7,7-Nonafluoroheptyloxy)benzyl alcohol；[4-(4,4,5,5,6,6,7,7,7-nonafluoroheptoxy)phenyl]methanol
• CAS: 892154-51-7
• 化学式: C₁₄H₁₃F₉O₂
• 分子量: 384.242
• InChiKey: FVFREHJGVAWXEQ-UHFFFAOYSA-N

物化性质

• 熔点：
  58-62 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  11

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36
• 安全说明：
  S26

反应信息

• 作为反应物：
  描述：

  4-(1H,1H,2H,2H,3H,3H-全氟庚氧基)苄醇 在 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 、 mineral oil 为溶剂， 反应 26.08h， 生成 (S)-methyl 3-(4-(4,4,5,5,6,6,7,7,7-nonafluoroheptyloxy)benzyloxy)-2-methylpropanoate
  参考文献：
  名称：

  Synthesis and Spectroscopic Analysis of a Stereoisomer Library of the Phytophthora Mating Hormone α1 and Derived Bis-Mosher Esters

  摘要：

  Fluorous mixture synthesis provided all eight diastereomers of the phytophthora hormone alpha 1 with the R configuration at C11 as individual samples after demixing and detagging. The library of all possible bis-Mosher esters (16) was then made by esterification. Complete sets of H-1, C-13, and (for the Mosher esters) F-19 NMR spectra were recorded, assigned, and compared with each other and with published spectra. Not all of the spectra are unique, and the H-1 NMR spectra of the Mosher esters provided the most information. The previous assignment of the natural sample as an "all-R" stereoisomer mixed with its 3S-epimer was confirmed.

  DOI：

  10.1021/ja2082679

文献信息

• Synthesis of a Resorcylic Acid Lactone (RAL) Library Using Fluorous-Mixture Synthesis and Profile of its Selectivity Against a Panel of Kinases
  作者：Rajamalleswaramma Jogireddy、Pierre-Yves Dakas、Gaëlle Valot、Sofia Barluenga、Nicolas Winssinger

  DOI：10.1002/chem.200901375

  日期：2009.11.2

  A library of resorcylic acid lactones (RAL) containing a cis‐enone moiety targeting kinases bearing a cysteine residue within the ATP‐binding pocket was prepared using a fluorous‐mixture synthesis and evaluated against a panel of 19 kinases thus providing important structure–activity trends. Two new analogues were then profiled for their selectivity against a panel of 402 kinases providing the broadest

  使用氟混合物合成方法制备了含有顺式-烯酮部分靶向激酶的顺式-烯酮部分文库的间苯二酸内酯（RAL），该激酶在ATP结合袋中带有半胱氨酸残基，并针对一组19种激酶进行了评估，从而提供了重要的结构-活性趋势。然后，针对两个新的类似物针对一组402种激酶的选择性进行了分析，从而对该药效基团的选择性进行了最广泛的评估。
• Total Synthesis of a 28-Member Stereoisomer Library of Murisolins
  作者：Dennis P. Curran、Qisheng Zhang、Cyrille Richard、Hejun Lu、Venugopal Gudipati、Craig S. Wilcox

  DOI：10.1021/ja061801q

  日期：2006.7.1

  library, fluorous PMB (p-methoxybenzyl) groups encode configurations, and four mixtures of four dihydroxy-tetrahydrofurans are prepared by Shi epoxidation followed (optionally) by Mitsunobu reaction. The mixtures are coupled by Kocienski-Julia reaction with a single hydroxybutenolide followed by hydrogenation. Demixing and detagging provide the 16 pure stereoisomers. In the second synthesis, a single

  报道了两个 16 人库的 murisolin 异构体的总合成。在第一个库中，含氟 PMB（对甲氧基苄基）基团编码构型，通过 Shi 环氧化和（可选）Mitsunobu 反应制备四种二羟基四氢呋喃的四种混合物。混合物通过 Kocienski-Julia 反应与单一羟基丁烯内酯偶联，然后氢化。分层和去标签提供 16 种纯立体异构体。在第二个合成中，四种含氟标记的二羟基四氢呋喃的单一混合物与带有 DMB（二甲氧基苄基）基团衍生物的羟基丁烯内酯的四化合物混合物偶联，其中低聚乙二醇 (OEG) 单元编码 C4 和 C34 的构型. 16-化合物混合物进行氢化、双重分层、并去标签以提供 16 种异构纯的 murisolins。这些异构体中有 12 个是新的，而第一个库中的四个匹配样品。
• Synthesis and Spectroscopic Analysis of a Stereoisomer Library of the Phytophthora Mating Hormone α1 and Derived Bis-Mosher Esters
  作者：Reena Bajpai、Dennis P. Curran

  DOI：10.1021/ja2082679

  日期：2011.12.21

  Fluorous mixture synthesis provided all eight diastereomers of the phytophthora hormone alpha 1 with the R configuration at C11 as individual samples after demixing and detagging. The library of all possible bis-Mosher esters (16) was then made by esterification. Complete sets of H-1, C-13, and (for the Mosher esters) F-19 NMR spectra were recorded, assigned, and compared with each other and with published spectra. Not all of the spectra are unique, and the H-1 NMR spectra of the Mosher esters provided the most information. The previous assignment of the natural sample as an "all-R" stereoisomer mixed with its 3S-epimer was confirmed.