tris-(2-perfluorohexylethyl)stannane | 175354-32-2

• 物质功能分类: 有机原料 - 有机金属类化合物 - 有机锡
• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: tris-(2-perfluorohexylethyl)stannane
• 英文别名: tris(1H,1H,2H,2H-perfluorooctyl)tinhydride；tris[(2-perfluorohexyl)ethyl]tin hydride；tris(3,3,4,4,5,5,6,6,7,7,8,8,8,-tridecafluorooctyl)stannane；F-Oct3SnH；Tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)tin hydride；tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)stannane
• CAS: 175354-32-2
• 化学式: C₂₄H₁₃F₃₉Sn
• 分子量: 1161.01
• InChiKey: XDEOXVCAUPQFMU-UHFFFAOYSA-N

物化性质

• 沸点：
  133-40°C/0.02mmHg
• 稳定性/保质期：

  在常温常压下保持稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  64
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  39

安全信息

• TSCA：
  No
• 危险品标志：
  Xi
• 安全说明：
  S61
• 危险类别码：
  R36/37/38
• WGK Germany：
  1
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中。

反应信息

• 作为反应物：
  描述：

  tris-(2-perfluorohexylethyl)stannane 、 亚乙基丙二酸二乙酯 在 2,2'-azobisisobutyronitrile 作用下， 以 further solvent(s) 为溶剂， 以86%的产率得到
  参考文献：
  名称：

  氟化锡氢化物：在自由基反应中使用和重复使用的一系列新试剂

  摘要：

  已经合成并研究了一个新的高度氟化（氟）锡氢化物家族的八个成员作为自由基反应的试剂。已制备通式为 [Rf(CH2)n]3SnH 和 [Rf(CH2)n]Me2SnH 的锡氢化物，其中 Rf 为 C4F9、C6F13、C8F17 或 C10F21，n 为 2 或 3。这些试剂在氟化溶剂，以及全氟己烷和几种有机溶剂之间的分配系数已被测量。这些试剂通常可用于通常用氢化三丁基锡进行的还原自由基反应和氢化锡化反应。化学计量和催化程序已经开发出来，两者的特点是通过方便的液-液或固-液萃取，可以非常容易地将锡产品与有机产品分离。锡试剂以高产率从反应中回收并经常重复使用。速率常数测量表明，氟化锡氢化物的反应性与（或在某些情况下，略有……

  DOI：

  10.1021/ja990069a
• 作为产物：
  描述：

  1-碘-1H,1H,2H,2H-全氟辛烷 在 lithium aluminium tetrahydride 、 溴 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 18.25h， 生成 tris-(2-perfluorohexylethyl)stannane
  参考文献：
  名称：

  SYNTHESIS OF TRIS(2-PERFLUOROHEXYLETHYL)TIN HYDRIDE: A HIGHLY FLUORINATED TIN HYDRIDE WITH ADVANTAGEOUS FEATURES OF EASY PURIFICATION

  摘要：

  DOI：

  10.15227/orgsyn.079.0001
• 作为试剂：
  描述：

  碘环己烷 、 丙烯腈 在 tris-(2-perfluorohexylethyl)stannane 、 sodium cyanoborohydride 作用下， 以 叔丁醇 为溶剂， 以75%的产率得到3-环己基丙腈
  参考文献：
  名称：

  Tris(2-(perfluorohexyl)ethyl)tin Hydride:  A New Fluorous Reagent for Use in Traditional Organic Synthesis and Liquid Phase Combinatorial Synthesis

  摘要：

  DOI：

  10.1021/ja953287m

文献信息

• A hybrid solid-fluorous phase radioiodination and purification platform
  作者：James P. K. Dzandzi、Denis R. Beckford Vera、John F. Valliant

  DOI：10.1002/jlcr.3214

  日期：2014.7

  A new class of fluorous materials was developed to create a hybrid solid-solution phase strategy for the expedient preparation and HPLC-free purification of 125I-labeled compounds. The system is referred to as a hybrid platform in that it combines solution phase labeling and fluorous solid-phase purification in one step as opposed to two separate individual processes. Treatment of fluorous arylstannanes coated on fluorous silica with [125I]NaI and the appropriate oxidant made it possible to produce and selectively isolate the nonfluorous radiolabeled products in high purity (>98%) free from excess starting material and unreacted radioiodine. Examples included simple aryl and heterocyclic (click) derivatives, known radiopharmaceuticals including meta-iodobenzylguanidine (MIBG) and iododeoxyuridine (IUdR), and a new agent with high affinity for prostate-specific membrane antigen. The coated fluorous silica kits are simple to prepare, and reactions can be performed at room temperature using different oxidants generating products in minutes in biocompatible solutions.

  开发了一种新的氟聚合物材料，以创建一种混合固态-溶液相策略，使125I标记化合物的快速制备和无HPLC纯化成为可能。该系统被称为混合平台，因为它将溶液相标记和氟固相纯化结合在一步中，而不是两个单独的过程。用[125I]NaI和适当的氧化剂处理涂覆在氟硅氧烷上的氟芳基锡化合物，使得能够高纯度（>98%）地生产并选择性分离出无氟的放射性标记产物，且不含多余的起始材料和未反应的放射性碘。例子包括简单的芳香族和杂环（点击）衍生物，已知的放射药物包括美托碘苯基胍（MIBG）和碘脱氧尿苷（IUdR），以及一种对前列腺特异性膜抗原具有高亲和力的新试剂。涂覆的氟硅氧烷试剂盒易于制备，可以在室温下使用不同的氧化剂进行反应，在生物相容溶液中几分钟内生成产物。
• Fluorous reaction systems
  申请人：University of Pittsburgh

  公开号：US05777121A1

  公开（公告）日：1998-07-07

  The present invention provides a method for carrying out a chemical reaction comprising the steps of forming an organic/fluorous solubilizing liquid phase comprising a solvent system. The solvent system is selected or adapted to substantially solubilize a fluorous reaction component or components (that is, a fluorous reagent, a fluorous catalyst and/or a fluorous reactant). The "fluorous reaction component" is functionalized to comprise at least one fluorous moiety having the formula -(R).sub.d (Rf).sub.e. (Rf).sub.e is at least one fluorous group and e is a whole number. (R).sub.d is an organic (for example, hydrocarbon) spacer group, which may be present or absent, and d is an integer equal to at least zero. The solvent system is also adapted to substantially solubilize an organic reaction component or components. After the reaction occurs in the organic/fluorous solubilizing liquid phase, a phase separation into at least a fluorous phase and an organic phase is effected. The present invention also provides a chemical compound of the formula XM\x9b(R) (Rf)!.sub.3, wherein M is Ge or Sn and X is an atom or group selected to react with an organic reaction component or components.

  本发明提供了一种进行化学反应的方法，包括形成包含溶剂系统的有机/氟溶解液相的步骤。所选或适应的溶剂系统被选择为或被适应为基本上溶解氟反应组分或组分（即，氟试剂，氟催化剂和/或氟反应物）。“氟反应组分”被官能化为至少包含一个具有式-(R).sub.d(Rf).sub.e的氟基团。 (Rf).sub.e至少是一个氟基团，e是一个整数。 (R).sub.d是一个有机（例如，烃）空间基团，可能存在或不存在，d是至少为零的整数。溶剂系统还被适应为基本上溶解有机反应组分。在有机/氟溶解液相中发生反应后，进行至少氟相和有机相的相分离。本发明还提供了一个化学化合物的公式XM\x9b(R)(Rf)!_3，其中M为Ge或Sn，X是选定用于与有机反应组分反应的原子或基团。
• Fluorous reaction and separation systems
  申请人：University of Pittsburgh

  公开号：US05859247A1

  公开（公告）日：1999-01-12

  The present invention provides several methods of synthesis and separation in which organic/fluorous phase separation techniques are used to effect separations. The present invention also provides novel compositions of matter comprising fluorous Si, Sn and Ge compounds.

  本发明提供了几种合成和分离方法，其中利用有机/氟相分离技术来实现分离。本发明还提供了包括氟硅、锡和锗化合物的新颖物质组合。
• Fluorous tin compounds an methods of using fluorous tin compounds
  申请人：Curran Dennis P.

  公开号：US06861544B1

  公开（公告）日：2005-03-01

  A method of carrying out a reaction comprising the steps of: mixing at least one organic reaction component with at least one fluorous reaction component having the formula: X 1 Sn(R) n [Rs(Rf)] 3-n , X 1 X 2 Sn[Rs(Rf)] 2 or O═Sn[Rs(Rf)] 2 wherein n is 1 or 2, R is a C 1 -C 6 alkyl group, X 1 and X 2 are independently, the same or different, H, F, Cl, Br, I, N 3 , OR 1 , OOR 1 SR 1 , SeR 1 , CN, NC, NR 1 R 2 , an aryl group, a heteroaryl group, an alkyl group of 1 to 20 carbons, an alkenyl group, an alkynyl group, —C(O)R 3 , M((Rs′)(Rf′)) 3 , OM((Rs′)(Rf′)) 3 or OOM((Rs′)Rf′)) 3 , wherein M is Si, Ge, or Sn, and wherein R 1 and R 2 are each independently the same or different H, an alkyl group, —SO 2 R 3 or —C(O)R 3 , wherein R 3 is an alkyl group or an aryl group, and wherein Rs and Rs′ are each independently the same or different a spacer group, and wherein Rf and Rf′ are each independently the same or different a fluorous group; carrying out a reaction to produce an organic product; and after producing the organic product, separating any excess of the fluorous reaction component and any fluorous byproduct of the fluorous reaction component using a fluorous separation technique. Several compounds have the formula: X 1 Sn(R) n [Rs(Rf) 3-n , X 1 X 2 Sn[Rs(Rf)] 2 or O═Sn[Rs(Rf)] 2 .

  一种进行反应的方法，包括以下步骤：将至少一个有机反应组分与至少一个具有以下式子的氟烷反应组分混合：X1Sn（R）n [Rs（Rf）] 3-n，X1X2Sn [Rs（Rf）] 2或O═Sn [Rs（Rf）] 2，其中n为1或2，R为C1-C6烷基，X1和X2分别是相同或不同的H、F、Cl、Br、I、N3、OR1、OOR1SR1、SeR1、CN、NC、NR1R2、芳基、杂环芳基、1至20碳的烷基、烯丙基、炔基、—C（O）R3、M（（Rs'）（Rf'））3、OM（（Rs'）（Rf'））3或OOM（（Rs'）Rf'）3，其中M为Si、Ge或Sn，R1和R2分别是相同或不同的H、烷基、—SO2R3或—C（O）R3，其中R3是烷基或芳基，而Rs和Rs'分别是相同或不同的间隔基，而Rf和Rf'分别是相同或不同的氟烷基；进行反应以产生有机产物；在产生有机产物之后，使用氟烷分离技术分离任何剩余的氟烷反应组分和任何氟烷反应组分的氟烷副产物。多种化合物具有以下式子：X1Sn（R）n [Rs（Rf）] 3-n，X1X2Sn [Rs（Rf）] 2或O═Sn [Rs（Rf）] 2。
• Synthesis and Evaluation of Radioiodinated Acyloxymethyl Ketones as Activity-Based Probes for Cathepsin B
  作者：Patricia E. Edem、Shannon Czorny、John F. Valliant

  DOI：10.1021/jm501357r

  日期：2014.11.26

  Dipeptidyl (acyloxy)methyl ketones (AOMKs) were functionalized with different iodine-containing prosthetic groups to generate a library of candidate cathepsin B probes. Compound 23a, (S)-20-[(S)-2-[(benzyloxy)carbonyl]amino}-3-phenylpropanamido]-1-(4-iodophenyl)-1,14,21-trioxo-5,8,11-trioxa-2,15-diazadocosan-22-yl 2,4,6-trimethylbenzoate, was identified as a potential lead through in vitro screening, having a K-i = 181 +/- 9 nM and demonstrating the ability to effectively label active cathepsin B in vitro. Its less potent analogue 11a, (S)-3-[(S)-2-[(benzyloxy)carbonyl]amino}-3-phenylpropanamido]-7-[6-(4-iodobenzamido)hexanamido]-2-oxoheptyl 2,4,6-trimethylbenzoate, was also tested as a comparison. Biodistribution studies of the iodine-125-labeled compounds in MDA-MB-231 mouse xenografts exhibited tumor uptake of 0.58% +/- 0.06% injected dose per gram (ID/g) for [I-125]11a and 1.12% +/- 0.08% ID/g for [I-125]23a at 30 min. The tumor-to-blood ratios reached 1.2 for [I-125]23a and 1.6 for [I-125]11a after 23 h. The more hydrophilic [I-125]23a showed an improved clearance profile with a superior tumor-to-muscle ratio of 7.0 compared to 3.4 for [I-125]11a at 23 h. Iodinated AOMK ligands are suitable in vitro probes for cathepsin B and hold promise as a platform to develop molecular imaging probes.