{2-(CH₂NMe₂)C₆H₄-κC,N}(n-Bu)₂SnF | 712351-39-8

• 英文名称: {2-(CH₂NMe₂)C₆H₄-κC,N}(n-Bu)₂SnF
• 英文别名: (2-(N,N-dimethylaminomethyl)phenyl)(n-Bu)2SnF；[2-[(CH3)2NCH2]C6H4]2(Bu)4SnF；{2-(CH2NMe2)C6H4-κC,N}(n-Bu)2SnF；2-[(N,N-dimethylaminomethyl)phenyl]di-n-butylstannylfluoride
• CAS: 712351-39-8
• 化学式: C₁₇H₃₀FNSn
• 分子量: 386.14
• InChiKey: HDOXGBFCSBFNOF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  {2-(CH₂NMe₂)C₆H₄-κC,N}(n-Bu)₂SnF 、 (η⁵-C₅H₄(Xylf))₂TiCl₂ 以 二氯甲烷 为溶剂， 反应 14.0h， 以88%的产率得到(η⁵-C₅H₄₍Xylf₎)(η⁵-C₅H₄(Xylf))TiF₂
  参考文献：
  名称：

  Titanocene Dihalides and Ferrocenes Bearing a Pendant α-d-Xylofuranos-5-yl or α-d-Ribofuranos-5-yl Moiety. Synthesis, Characterization, and Cytotoxic Activity

  摘要：

  Titanocene dichlorides of general formula [(eta(5)-C5H5)(eta(5)-C5H4R)TiCl2] (where R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-alpha-D-xylofuranos-5-yl (Xylf) (8a); R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-alpha-D-ribofuranos-5-yl (Ribf) (8b)) and [(eta(5)-C5H4R)(2)TiCl2] (R = Xylf (9a); R = Ribf (9b)) were prepared by reaction of the corresponding lithium cyclopentadienides 7a,b with an equimolar amount of [(eta(5)-C5H5)TiCl3] or a 0.5 mol amount of [TiCl4(THF)(2)]. Titanocene difluorides of the general formula [(eta(5)-C5H4R1)(eta(5)-C5H4R2)TiF2] (R-1 = H and R-2 = Ribf (10); R-1 = R-2 = Xylf (11a); R-1 = R-2 = Ribf (11b)) were obtained by fluorination of the corresponding titanocene dichlorides 8b and 9 with the fluorinating agent {2-(CH2NMe2)C6H4-kappa C,N}(n-Bu)(2)SnF in high yields. Alternatively, complexes 11 were prepared in a straightforward way by direct reaction of [TiF4(THF)(2)] with 2 equiv of the corresponding lithium cyclopentadienide 7a,b. Ferrocene complexes [(eta(5)-C5H4R)(2)Fe] (R = Xylf (12a); R = Ribf (12b)) were synthesized by metathesis of 2 equiv of lithium cyclopentadienide 7a,b and 1 equiv of anhydrous FeCl2. Deprotection of the benzyl group in ferrocenes 12 proceeded cleanly by a catalytic hydrogenation on Pd/C and afforded the ferrocene diols [(eta(5)-C3H4R)(2)Fe] (R = 5-deoxy-1,2-di-O-isopropylidene-alpha-D-xylofuranos-5-yl (Xylf-OH) (14a); R = 5-deoxy-1,2-di-O-isopropylidene-alpha-D-ribofuranos-5-yl (Ribf-OH) (14b)). A scaled up benzyl deprotection with Et3SiH as a hydrogen source led to the replacement of only one benzyl group, which gave the ferrocene alcohol [(eta(5)-C5H4R1)(eta(5)-C5H4R2)Fe] (R-1 = Xylf and R-2 = Xylf-OH (13)). The prepared complexes were characterized by elemental analysis, melting point determination, NMR, IR, and ESI-MS, and the molecular structure of 9b was determined by X-ray diffraction analysis. The cytotoxic activity of complexes 8-14 against A2780 and A2780cis cancer cells was evaluated by MTT tests. Titanocene difluorides 10 and 11 and ferrocene diol 14a showed cytotoxicity against A2780 cells in the medium to low micromolar range, while the most active species, 11b, displayed about 40% higher cytotoxicity against A2780cis in comparison to a cisplatin standard.

  DOI：

  10.1021/om500200r
• 作为产物：
  描述：

  potassium fluoride 、 [2-(N,N-二甲基氨基甲基)苯基]二正丁基锡(IV)氯化物 以 乙醚 、 水 为溶剂， 以73%的产率得到{2-(CH₂NMe₂)C₆H₄-κC,N}(n-Bu)₂SnF
  参考文献：
  名称：

  Monomeric Triorganotin(IV) Fluorides Containing a C,N-Chelating Ligand

  摘要：

  The set of four triorganotin(IV) fluorides of general formula {2-[(CH3)(2)NCH2]C6H4}R2SnF, where R is Me (5), n-Bu (6), t-Bu (7), and Ph (8), respectively, has been prepared and characterized using NMR and ESI-MS techniques. The structures of crystalline compounds 5 and 8 were determined using X-ray methods. All compounds are monomeric both in solution using different solvents and in the solid state. The tin central atom is five-coordinated with all carbon atoms in equatorial positions and fluorine and nitrogen, from the intramolecularly coordinated dimethylamino group, in the axial positions of the distorted trigonal bipyramid. The ability of compounds 6 and 8 to perform fluorination of organometallic chlorides was tested on titanocene dichloride. A quantitative yield Of CP2TiF2 was obtained.

  DOI：

  10.1021/om049912q

文献信息

• C,N-chelated dicyclopentadienylzirconium complexes and their possible use as hydrogenation catalysts
  作者：Josef Bareš、Zdeňka Padělková、Philippe Meunier、Nadine Pirio、Didier Poinsot、Aleš Růžička

  DOI：10.1016/j.inoche.2010.08.030

  日期：2010.12

  Abstract In situ generated Cp2Zr(n-Bu)Cl (6) reacts with 2-[(CH3)2NCH2]C6H4}2Pb to form exclusively 2-[(CH3)2NCH2]C6H4}Cp2ZrCl (7), [(CH3)2NCH2]C6H5, butene and elemental lead. The further derivatization of chloride (7) to fluoride (8), hydride (9), methyl derivative (10), and a reduction of 7 are also described. The crystal structures of 7–10 were determined. The catalytic activity of 9 and 10 in

  摘要 原位生成的 Cp2Zr(n-Bu)Cl (6) 与 2-[(CH3)2NCH2]C6H4}2Pb 反应，仅形成 2-[( )2NCH2]C6H4}Cp2ZrCl (7), [( )2NCH2]C6H5、丁烯和元素铅。还描述了氯化物 (7) 进一步衍生为氟化物 (8)、氢化物 (9)、甲基衍生物 (10) 和 7 的还原。确定了 7-10 的晶体结构。还初步测试了9和10在苯乙烯加氢中的催化活性。
• C, N-chelated antimony and bismuth complexes; oxidation and fluorination
  作者：Petr Švec、Iva Vránová、Zdeňka Růžičková、Maksim A. Samsonov、Libor Dostál、Aleš Růžička

  DOI：10.1016/j.jorganchem.2023.122644

  日期：2023.5

  R = n-Bu or Ph) and/or XeF2 as fluorinating agents. All species were characterised by the combination of elemental analysis and multinuclear solution NMR spectroscopy. Solid-state structures of all complexes were established by the sc-XRD analysis. In addition, theoretical calculations were carried out to corroborate the experimental results. Preparation and structural characterisation of LSbI2 is also

  一组带有 2-[(2,6-二异丙基苯基)亚氨基] 的有机锑 (III/V) 和有机铋 (V) 氟化物（即LSbF 2、LSbClF、LPh 2 SbF 2、LSbF 4和 LPh 2 BiF 2 ）甲基}苯基-作为C，N-螯合配体(L)已经使用L CN R 2 SnF制备(其中L CN  = 2-( N,N-二甲基氨基甲基)苯基)；R =  n -Bu 或 Ph) 和/或 XeF 2作为氟化剂。所有物种均通过元素分析和多核溶液 NMR 光谱学的组合进行表征。通过 sc-XRD 分析建立了所有复合物的固态结构。此外，还进行了理论计算以证实实验结果。还报道了LSbI 2的制备和结构表征。
• Tri- and diorganostannates containing 2-(N,N-dimethylaminomethyl)phenyl ligand
  作者：Petr Švec、Eva Černošková、Zdeňka Padělková、Aleš Růžička、Jaroslav Holeček

  DOI：10.1016/j.jorganchem.2010.08.006

  日期：2010.11

  The C,N-chelated tri and diorganotin(IV) chlorides react with both protic mineral acids and carboxylic acids. The nitrogen atom of the L-CN ligand (where L-CN is 2-(dimethylaminomethyl)phenyl) is thus quarternized e protonated and new Sn-X bond (X = Cl, Br, I or the remainder of the starting acid used) is simultaneously formed. The set of zwitterionic tri and diorganostannates containing protonated 2-(dimethylaminomethyl) phenyl-moiety was prepared and structurally characterized by multinuclear NMR spectroscopy and XRD techniques. In all these cases, the intramolecular N-H center dot center dot center dot X bond is present in the molecule. Despite the central tin atom remains five-coordinated (except for the [(HLH)-H-CN](+)[(n-Bu)(2)SnCl(NO3)(2)](-)) and reveals a distorted trigonal bipyramidal geometry, the Sn-119 NMR chemical shift values of these zwitterionic stannates are somewhat shifted to the higher field than corresponding starting C, N-chelated tri and diorganotin(IV) halides. Reactions of C,N-chelated organotin(IV) halides with various Lewis acids are also discussed. (C) 2010 Elsevier B.V. All rights reserved.