3-(perfluorodecyl)prop-1-ene | 40798-36-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 3-(perfluorodecyl)prop-1-ene
• 英文别名: 3-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-henicosafluorodecyl)-propene；4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-heneicosafluorotridec-1-ene；4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-eicosafluoro-1-tridecene；4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-henicosafluoro-tridec-1-ene；4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-henicosafluorotridec-1-ene
• CAS: 40798-36-5
• 化学式: C₁₃H₅F₂₁
• 分子量: 560.149
• InChiKey: JTKRDKDKUCALFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  3-(perfluorodecyl)prop-1-ene 在 吡啶 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 丙酮 为溶剂， 反应 21.0h， 以87%的产率得到3-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-henicosafluorodecyl)-propane 1,2-diol
  参考文献：
  名称：

  The synthesis and application of fluorous boronates without perfluorinated solvents

  摘要：

  The synthesis of a fluorous diol 4 bearing a perfluorodecyl chain was described. A series of boronic acid were attached to 4 by esterification. The purification of the products was fulfilled by facile filtration instead of expensive and environmental troublesome fluorous liquid-liquid extraction. The Suzuki cross-coupling reactions of the formed fluorous boronates 5 underwent smoothly and the fluorous diol 4 was recycled in good yields. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2004.12.014
• 作为产物：
  描述：

  1-碘全氟癸烷 在 溶剂黄146 、 锌 、 过氧化苯甲酰 作用下， 以 异丙醇 为溶剂， 反应 15.0h， 生成 3-(perfluorodecyl)prop-1-ene
  参考文献：
  名称：

  The synthesis and application of fluorous boronates without perfluorinated solvents

  摘要：

  The synthesis of a fluorous diol 4 bearing a perfluorodecyl chain was described. A series of boronic acid were attached to 4 by esterification. The purification of the products was fulfilled by facile filtration instead of expensive and environmental troublesome fluorous liquid-liquid extraction. The Suzuki cross-coupling reactions of the formed fluorous boronates 5 underwent smoothly and the fluorous diol 4 was recycled in good yields. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2004.12.014

文献信息

• “Propylene spaced” allyl tin reagents: A new class of fluorous tin reagents for allylations under radical and metal-catalyzed conditions
  作者：Dennis P. Curran、Zhiyong Luo、Peter Degenkolb

  DOI：10.1016/s0960-894x(98)00435-1

  日期：1998.9

  A new generation of propylene-spaced fluorous allyltin reagents [(Rf(CH2)3)3SnCH2CH = CH2] is described. These succeed in radical allylations where their lower homologs (ethylene-spaced) fail, and they provide improved performance in transition metal catalyzed allylations. The reagents and byproducts are readily separated by simple fluorous-organic liquid-liquid or solid-liquid extractions.

  描述了新一代的丙烯间隔氟烯丙基锡试剂[（Rf（CH2）3）3SnCH2CH = CH2]。这些在低级同系物（乙烯间隔的）失效的自由基烯丙基化中成功，并且在过渡金属催化的烯丙基化中提供了改进的性能。试剂和副产物可通过简单的氟有机液-液或固-液萃取轻松分离。
• Thermomorphic fluorous phosphines as organocatalysts for Michael addition reactions
  作者：Carolina Gimbert、Adelina Vallribera、John A. Gladysz、Markus Jurisch

  DOI：10.1016/j.tetlet.2010.06.136

  日期：2010.9

  fluorous phosphines P[(CH2)mRfn]3 (Rfn = (CF2)n−1CF3; m/n = 2/8, 3/8, 3/10) are efficient nucleophilic catalysts of Michael addition reactions. They can be easily recycled based upon their highly temperature-dependent solubilities (thermomorphism), with recovery by simple liquid/solid phase separation. The phosphonium salt formed by reaction of the nucleophilic phosphine with the α,β-unsaturated system

  氟膦化合物P [（CH 2）m R f n ] 3（R f n  =（CF 2）n -1 CF 3；m / n  = 2 / 8，3 / 8，3/10）是有效的亲核催化剂迈克尔加成反应。基于它们高度依赖温度的溶解度（热同质性），可以轻松地对其进行回收，并通过简单的液相/固相分离进行回收。由亲核膦与α，β-不饱和体系反应形成的phospho盐似乎是催化剂静止状态的重要组成部分。
• Separation of fluorous compounds
  申请人：Curran P. Dennis

  公开号：US20050283032A1

  公开（公告）日：2005-12-22

  A method of separating at least a first non-fluorous compound from a mixture of compounds including at least the first non-fluorous compound and a second fluorous compound includes: charging the of compounds to a non-fluorous solid (stationary) phase and eluting with a fluorous eluting fluid (mobile phase). In one embodiment, the non-fluorous solid phase is polar in nature. The method can further include a second phase elution with a suitable organic solvent. A method conducting a chemical reaction, includes: mixing at least a first fluorous compound and a second compound, the first fluorous compound differing in fluorous nature from the second compound; exposing the first mixture to conditions to convert at least one of the first fluorous compound and the second compound to give a second mixture containing at least a third compound, charging the second mixture to a non-fluorous solid phase; and eluting with a fluorous fluid

  将至少一个非氟化合物从包括至少第一个非氟化合物和第二个氟化合物的混合物中分离出来的方法包括：将化合物充电到非氟固体（静态）相，并用氟溶剂流体（移动相）洗脱。在一个实施例中，非氟固相具有极性特性。该方法还可以包括使用适当的有机溶剂进行第二相洗脱。一种进行化学反应的方法包括：混合至少一个第一氟化合物和第二化合物，第一个氟化合物在氟性质上与第二化合物不同；将第一混合物暴露在条件下，将至少一个第一个氟化合物和第二化合物转化为至少包含第三化合物的第二混合物，将第二混合物充电到非氟固相；并用氟溶剂洗脱。
• Base-Promoted C–C Bond Activation Enables Radical Allylation with Homoallylic Alcohols
  作者：Maximilian Lübbesmeyer、Emily G. Mackay、Mark A. R. Raycroft、Jonas Elfert、Derek A. Pratt、Armido Studer

  DOI：10.1021/jacs.9b12343

  日期：2020.2.5

  C-radical addition to the double bond of the title reagents and subsequent base-promoted homolytic Cα–Cβ cleavage leads to the formation of the corresponding allylated products along with ketyl radicals that act as single electron reductants to sustain the chain reactions. Substrate scope is documented and the role of base in the C–C bond activation is studied by computation.

  高烯丙醇中的 Cα-Cβ 键可以在碱性条件下被激活，使这些非应变无环系统成为自由基烯丙基化试剂。这种反应性通过光引发（用可见光和/或蓝色 LED）使全氟烷基和分别从全氟烷基碘化物和烷基吡啶鎓盐产生的烷基与高烯丙醇进行烯丙基化反应来举例说明。C-自由基加成到标题试剂的双键和随后的碱促进均裂 Cα-Cβ 裂解导致形成相应的烯丙基化产物以及作为单电子还原剂维持链反应的羰基自由基。记录了底物范围，并通过计算研究了碱在 C-C 键活化中的作用。
• Darstellung von polyfluororganotrichlorsilanen
  作者：Alois Haas、Juergen Koehler

  DOI：10.1016/s0022-1139(00)82259-9

  日期：1981.6

  The following substances could be prepared by Grignard reactions or by conversions with trichlorosilane: C6F5CH2CHCH2, C6F5(CH2)3SiCl3, CF3(CF2)9CH2CHCH2, CF3(CF2)7(CH2)2SiCl3, CF3(CF2)11(CH2)3CHCH2 und CF3(CF2)11(CH2)5SiCl3.

  C：下列物质可以通过格氏试剂或通过用三氯硅烷的转化来制备6 ˚F 5 CH 2 CHCH 2，C 6 ˚F 5（CH 2）3的SiCl 3，CF 3（CF 2）9 CH 2 CHCH 2，CF 3（CF 2）7（CH 2）2 SiCl 3，CF 3（CF 2）11（CH 2）3CHCH 2和CF 3（CF 2）11（CH 2）5的SiCl 3。