2,2',2''-tris<(pentafluorophenyl)amino>triethylamine | 155019-77-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,2',2''-tris<(pentafluorophenyl)amino>triethylamine
• 英文别名: 2,2',2''-tris((pentafluorophenyl)amino)triethylamine；N',N'-bis[2-(2,3,4,5,6-pentafluoroanilino)ethyl]-N-(2,3,4,5,6-pentafluorophenyl)ethane-1,2-diamine
• CAS: 155019-77-5
• 化学式: C₂₄H₁₅F₁₅N₄
• 分子量: 644.386
• InChiKey: HUCGVJDWKLWITQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.3
• 氢给体数：
  3
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2,2',2''-tris<(pentafluorophenyl)amino>triethylamine 在 Et₃N 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 生成
  参考文献：
  名称：

  含三酰胺氨基配体的钛配合物的合成

  摘要：

  我们报告了各种钛配合物的合成，这些配合物包含（Et 3 SiNCH 2 CH 2）3 N，（C 6 F 5 NCH 2 CH 2）3 N或（Me 3 SiNCH 2 CH 2 CH 2）3 N配体。第一类络合物包括[（Et 3 SiNCH 2 CH 2）3 N] TiCl，[（Et 3 SiNCH 2 CH 2）3 N] Ti（OTf）和[（Et 3 SiNCH2 CH 2）3 N] Ti（t -Bu）。第二类络合物包括[（C 6 F 5 NCH 2 CH 2）3 N] TiX（X = Cl，Br，I，OTf）和[（C 6 F 5 NCH 2 CH 2）3 N] TiR（R =我，等等）。第三类络合物包括[（Me 3 SiNCH 2 CH 2 CH 2）3 N] TiCl和[（Me 3 SiNCH 2 CH 2 CH 2）3 N] TiCH3。在X射线研究中，[（Me 3 SiNCH 2 CH

  DOI：

  10.1021/om9508389
• 作为产物：
  描述：

  六氟苯 、 三(2-氨基乙基)胺 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以73%的产率得到2,2',2''-tris<(pentafluorophenyl)amino>triethylamine
  参考文献：
  名称：

  Synthesis of Molybdenum and Tungsten Complexes That Contain Triamidoamine Ligands of the Type (C6F5NCH2CH2)3N and Activation of Dinitrogen by Molybdenum

  摘要：

  Three new ligands of the type (ArNHCH2CH2)(3)N (Ar = 3,5-bis(trifluoromethyl)phenyl, 2-(trifluoromethyl)phenyl, and pentafluorophenyl) have been prepared. Only Mo and W complexes containing the [(C6F5NCH2CH2)(3)N](3-) ([N3N](3-)) ligand were found to be stable. Stable complexes that have been prepared include Mo[N3N](NMe(2)), M[N3N]Cl(M = Mo or W), Mo[N3N](OTf) (M = Mo or W), [N3N]M=N (M = Mo or W), and {[N3N]Mo=NMe}(OTf). An X-ray study of Mo[N3N]Cl showed it to be a monomeric distorted trigonal bipyramidal species having a pseudo-C-3 symmetry (space group P (1) over bar, a = 11.265(2) Angstrom, b = 11.371(2) Angstrom, c = 21.805(4) Angstrom, alpha = 82.40(1)degrees, beta = 79.07(1)degrees, gamma = 74.89(1)degrees, V = 2637.4 Angstrom(3), Z = 4, fw = 772.75, rho(calcd) = 1.946 g/cm(3), R = 0.032, R(W) = 0.034). Reduction of Mo[N3N](OTf) with 1 equiv of sodium amalgam yields a dinuclear bridging dinitrogen species, [N3N]Mo(mu N-2)Mo[N3N]. In the presence of 2 equiv of sodium amalgam in ether Mo[N3N](OTf) is reduced to [N3N]Mo(N-2)[Na(ether)(x)] (1 < x < 2). A more stable 15-crown-5 derivative can be prepared and more fully characterized. [N3N]Mo(mu-N-2)Mo[N3N] can be reduced to [N3N]Mo(N-2)[NaL(x)] by sodium amalgam under dinitrogen and the latter can be oxidized to the former by ferrocenium triflate or air. [N3N]Mo(N-2)[NaL(x)] reacts with Mo[N3N](OTf) to give [N3N]Mo(mu-N-2)Mo[N3N], with triisopropylsilyl chloride to give [N3N]MoN=NSi(i-Pr)(3), and with tributyltin chloride to give [N3N]MoN=NSn(Bu)(3). An X-ray study of [N3N]MoN=NSi(i-Pr)(3) (space group P2(1)/n, a 13.524(3) Angstrom, b = 18.016(4) Angstrom, c = 16.248(3) Angstrom, beta = 98.74(2)degrees, V = 3913(1) Angstrom(3), Z = 4, fw = 922.67, rho(calcd) = 1.566 g/cm(3), R = 0.069, R(W) = 0.072) showed it to be a trigonal bipyramidal complex containing a slightly bent diazenido ligand (Mo-N-alpha = 1.788(9) Angstrom, Mo-N-alpha-N-beta = 171.1(8)degrees, N-alpha-N-beta-Si = 154(1)degrees).

  DOI：

  10.1021/ja00089a028

文献信息

• Synthesis of Rhenium Complexes That Contain the [(C₆F₅NCH₂CH₂)₃N]³^- Ligand
  作者：Steven M. Reid、Brigitte Neuner、Richard R. Schrock、William M. Davis

  DOI：10.1021/om980220+

  日期：1998.8.1

  The reaction between [Et4N]2[ReOCl5] and (C6F5NHCH2CH2)3N (H3[N3NF]) in CH3CN at room temperature in the presence of NEt3 yielded air stable, emerald green, diamagnetic [(C6F5NCH2CH2)2NCH2CH2NHC6F5]Re(O)Cl (1). The reaction between 1 and Ta(CH-t-Bu)(THF)2Br3 gave paramagnetic [N3NF]ReBr (2). An X-ray structure of a sample of 2 showed it to be analogous to that of [N3NF]MoCl. Reduction of 2 by methyllithium

  在室温下在NEt 3存在下，[Et 4 N] 2 [ReOCl 5 ]与（C 6 F 5 NHCH 2 CH 2）3 N（H 3 [N 3 N F ]）在CH 3 CN中的反应产生空气稳定，翠绿色，抗磁性[（C 6 F 5 NCH 2 CH 2）2 NCH 2 CH 2 NHC 6 F 5 ] Re（O）Cl（1）。1之间的反应和Ta（CH-t-Bu）（THF）2 Br 3给出顺磁性的[N 3 N F ] ReBr（2）。2样品的X射线结构表明它与[N 3 N F ] MoCl相似。在各种双电子配体的存在下，通过甲基锂（或更方便地通过Mg）还原2得到[N 3 N F ] Re（L）类型的配合物（L = H 2，乙烯，丙烯，CO， N 2，膦，吡啶，四氢噻吩，乙腈或硅烷）。[N 3 N F ] Re（乙烯）的X射线结构显示为η2-乙烯以其C-C轴位于N ax -Re-N eq平面之一中的方式结合在顶端的“口袋”中。PMe
• Redox-Controlled Reactivity at Boron: Parallels to Frustrated Lewis/Radical Pair Chemistry
  作者：Anthony Wong、Jiaxiang Chu、Guang Wu、Joshua Telser、Roman Dobrovetsky、Gabriel Ménard

  DOI：10.1021/acs.inorgchem.0c01464

  日期：2020.7.20

  -N)B(C6F5)2 (1b). Redox control of the VIV/V couple resulted in switchable borane versus “hidden” boron radical reactivity, mimicking frustrated Lewis versus frustrated radical pair (FLP/FRP) chemistry, respectively. Whereas heterolytic FLP-type addition reactions were observed with the VV complex (1b) in the presence of a bulky phosphine, homolytic peroxide, or Sn–hydride bond cleavage reactions were

  我们报告了拴在氧化还原活性钒中心，（Ph 2 N）3 V（μ-N）B（C 6 F 5）2（1a）和（N（CH 2 CH 2 N （C 6 F 5））3）V（μ-N）B（C 6 F 5）2（1b）。V IV / V的氧化还原控制偶合导致硼烷与“隐藏”硼自由基反应性可切换，分别模拟沮丧的Lewis和沮丧的自由基对（FLP / FRP）化学。在大型膦存在下，V V络合物（1b）发生了杂合FLP型加成反应，而V IV络合物[CoCp 2 * ] [（ N（CH 2 CH 2 N（C 6 F 5））3）V（μ-N）B（C 6 F 5）2 ]（3b），表示硼自由基阴离子的性质。自由基特征的程度通过光谱和计算手段探究。总之，这些结果表明，通过控制V IV / V氧化态，可以使这些化合物获得在FLP和FRP化学中均观察到的反应性。
• Rhenium(III) and Rhenium(V) Complexes That Contain the (C₆F₅NCH₂CH₂)₃N Ligand
  作者：Brigitte Neuner、Richard R. Schrock

  DOI：10.1021/om950581e

  日期：1996.1.9

  The reaction between [Et4N]2[ReOCl5] and (C6F5NHCH2CH2)3N in THF at room temperature in the presence of NEt3 yielded air-stable emerald green diamagnetic [(C6F5NCH2CH2)2NCH2CH2NHC6F5]Re(O)Cl (1). The reaction between 1 and Ta(CH-t-Bu)(THF)2Br3 gave paramagnetic [(C6F5NCH2CH2)3N]ReBr}Br (2). Reduction of 2 by methyllithium under dinitrogen gave diamagnetic [(C6F5NCH2CH2)3N]Re(N2), under carbon monoxide

  [Et 4 N] 2 [ReOCl 5 ]和（C 6 F 5 NHCH 2 CH 2）3 N在THF中，在室温下，在NEt 3存在下的反应产生了空气稳定的翡翠绿抗磁性[[C 6 F 5 NCH 2 CH 2）2 NCH 2 CH 2 NHC 6 F 5 ] Re（O）Cl（1）。1与Ta（CH- t- Bu）（THF）2 Br 3之间的反应得到顺磁性的[（（C 6 F 5 NCH 2 CH 2）3 N] ReBr} Br（2）。在氮气下用甲基锂还原2，得到抗磁性的[（C 6 F 5 NCH 2 CH 2）3 N] Re（N 2），在一氧化碳下得到[（C 6 F 5 NCH 2 CH 2）3 N] Re（CO ），在二氢下产生[（C 6 F 5 NCH 2 CH 2）3 N] ReH 2并在乙烯下得到[（C 6 F 5 NCH 2 CH 2）3 N] Re（C 2 H 4）。
• Syntheses of monomeric iron and manganese complexes using bulky tripodal ligands: catalytic alkene epoxidations
  作者：Jinyuan Chen、L.Keith Woo

  DOI：10.1016/s0022-328x(00)00022-x

  日期：2000.4

  showed efficient catalytic activity with high selectivity and reaction rate for epoxidation, in comparison to control experiments without a catalyst. Complex 4 with O2 and isobutyraldehyde also catalyzed the epoxidation of stilbenes to epoxides. Both cis- and trans-stilbenes are converted mainly to the trans-stilbene oxide. The possible role of the metal complexes as the active epoxidation catalysts is

  检查了立体阻碍的单体过渡金属络合物作为环氧化催化剂。使用大体积的配体，例如[（RNCH 2 CH 2）3 N] 3-型四齿三酰胺胺和三齿三（3-叔丁基吡唑基）硼酸酯，可通过μ-氧代二聚作用减少催化剂的失活。几种单体锰和铁配合物，包括M [（RNCH 2 CH 2）3 N] [R =三甲基甲硅烷基：M = Mn 3+（1）；R = C 6 F 5：M = Fe 3+（2），Mn 3+（3）]，η 3 -HB（3-吨BuPz）3 }的MC1 [M =的Fe 2+（4），锰2+（6）]和η 3 -HB（3-吨BuPz）3 } FeOTf（合成并检查了5）作为降冰片烯和苯乙烯的选择性环氧化的可能催化剂。氧原子来源是PhIO或分子O 2-异丁醛。与PhIO作为氧化剂时，复合物1，3，和6氧化降冰片烯和苯乙烯催化在高选择性的相应的环氧化物，而复合物2和4表现出低的环氧化活性。采用使用了O 2与异丁
• Synthesis of Vanadium(III), -(IV), and -(V) Complexes That Contain the Pentafluorophenyl-Substituted Triamidoamine Ligand [(C₆F₅NCH₂CH₂)₃N]³^-
  作者：Kotohiro Nomura、Richard R. Schrock、W. M. Davis

  DOI：10.1021/ic951433j

  日期：1996.1.1

  [N3N]V=O ([N3N](3-) = [(C6F5NCH2CH2)(3)N](3-)) was prepared from VOCl3 and H-3[N3N] in the presence of Et(3)N. Related arylimido complexes, [N3N]V=NAr (Ar = p-MeC(6)H(4), p-CF3C6H4, or p-FC6H4), were prepared in high yields from the known V(NAr)Cl-3(THF) complexes in a similar manner or by treating [N3N]V=O with an aryl isocyanate in refluxing m-xylene. New imido complexes also were prepared by reacting an imido complex with an aryl isocyanate over a period of 2 days in refluxing mesitylene. The reaction between VCl3(THF)(3) and H-3[N3N] in the presence of triethylamine gave [HNEt(3)][N3N]VCl} (3) when the reaction was carried out in ether and [N3N]V(CH3CN) (4a) when carried out in acetonitrile, while the reaction between VCl3(THF)(3) and H-3[N3N] in the presence of triethylamine and tert-butyl isocyanide gave green [N3N]V(t-BuNC). [N3N]V(CH3CN) reacts with propylene oxide to give [N3N]V=O and with diazoalkanes to give [N3N]V=NN=CHR (R = SiMe(3), CO2C2H5). An X-ray structure determination of 4a (C26H15N5F15V, a = 13.021(1) Angstrom, b = 13.021(1) Angstrom, c = 14.221(1) Angstrom, gamma = 120 degrees, rhombohedral, R3 (h), Z = 3) shows it to be a pseudo-trigonal-bipyramidal species with acetonitrile coordinated in the apical position. An attempt to prepare the iodo analog of 3 by adding Me(3)SiI in THF to it yielded green crystalline [N3N]V(THF) (5). An X-ray structure determination of 5 (C28H20N4F15OV, a = 15.390(7) Angstrom, b = 12.189(6) Angstrom, c = 16.368(7) Angstrom, beta = 109.96 (3)degrees, monoclinic, P2(1)/n, Z = 4) shows it to be a pseudo trigonal bipyramid containing 1 equiv of THF in the axial position in a structure that otherwise is similar to that of 4a. [HNEt(3)][N3N]VCl} reacts with ferrocenium triflate to yield [N3N]VCl, a species that can be reduced to 5 in THF by sodium amalgam.