N-benzyl-1-(2,3,4-trifluorophenyl)methanimine | 159627-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-1-(2,3,4-trifluorophenyl)methanimine
• CAS: 159627-03-9
• 化学式: C₁₄H₁₀F₃N
• 分子量: 249.235
• InChiKey: SNNVYQAMLBBSNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-1-(2,3,4-trifluorophenyl)methanimine 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Cyclometalated Platinum(II) Compounds with Fluorinated Iminic Ligands: Synthesis and Reactivity Tuning. Crystal Structures of the Compounds [PtMe(RCH:NCH2C6H5)(PPh3)] (R = 2,3,4-C6HF3 and 2,3-C6H2F2)

  摘要：

  [Pt(2)Me(4)(mu-SMe(2))(2)] (1) reacts with fluorinated imines ArCH=NCH2C6H5 (2; Ar = 2,3,4-C6H2F3, 2,4,5-C6H2F3, 2,3-C6H3F2) to yield the C,N-cyclometalated platinum(II) compounds [PtMe(RCH=NCH2C6H5)(SMe(2))] (3) by ortho metalation with loss of methane. Complexes 3 react with triphenylphosphine to give cyclometalated compounds [PtMe(RCH=N-CH2C6H5)(PPh(3))] (4). For R = 2,4,5-C6HF3, an excess of PPh(3) produces metallacycle cleavage, and [PtMe(RCH=NCH2C6H5)(PPh(3))(2)] (5) is formed with the imine acting as a [C-] unidentate ligand. Similarly, reactions of the previously reported compounds [PtMe{RCH=NCH2(2-C6H4Cl)}(SMe(2))] (R = 3,5-C6H2F2, 2-C6H3F, 5-C6H3F) with PPh(3) produce the cyclometalated compounds 4. When an excess of PPh(3) is used, compounds 5 are obtained only if there is a fluorine atom adjacent to platinum (F-5). 3-5 were characterized by elemental analyses and NMR spectroscopy, and [PtMe(2,3,4-C6HF3CH=NCH2C6H5)(PPh(3))] (4a) and [PtMe(2,3-C6H2F2CH=NCH2C6H5)(PPh(3))] (4c) were characterized crystallographically. 4a crystallizes in the monoclinic space group P2(1)/c, with a = 12.475(3) Angstrom, b = 21.642(5) Angstrom, c = 10.497(2) Angstrom, 12.031(2) Angstrom, beta = 96.92(2)degrees, and Z = 4. 4c crystallizes in the triclinic space group P ($) over bar 1, with a = 13.757(2) Angstrom, c = 9.768(2) Angstrom, alpha = 72.91(2)degrees, beta = 114.91(1)degrees, gamma = 104.20(2)degrees, and Z = 2. Structural and NMR parameters for compounds 4 are discussed in relation to the observed reactivity of these compounds.

  DOI：

  10.1021/om00001a051

文献信息

• Nickel-Catalyzed Csp²Csp³Bond Formation by CarbonFluorine Activation
  作者：Alex D. Sun、Kaylyn Leung、Anita D. Restivo、Nicole A. LaBerge、Harumi Takasaki、Jennifer A. Love

  DOI：10.1002/chem.201303809

  日期：2014.3.10

  method for Csp2Csp3 bond formation through CF activation. The process uses an inexpensive nickel complex with either diorganozinc or alkylzinc halide reagents, including those with β‐hydrogen atoms. A variety of fluorine substitution patterns and functional groups can be readily incorporated. Sequential reactions involving different precatalysts and coupling partners permit the synthesis of densely

  我们在此报告为CSP的一般催化方法2  CSP 3至C键形成 ˚F活化。该方法使用廉价的镍配合物与任一或diorganozinc烷基锌卤化物试剂，包括那些具有β氢原子。多种氟取代模式和官能团可以容易地并入。涉及不同预催化剂和偶合剂的顺序反应可以合成高密度官能化的氟化结构单元。
• Nickel-Catalyzed Selective Defluorination to Generate Partially Fluorinated Biaryls
  作者：Alex D. Sun、Jennifer A. Love

  DOI：10.1021/ol200860t

  日期：2011.5.20

  A Ni-catalyzed, chemoselective cross-coupling reaction of polyfluoroarenes under mild reaction conditions is reported. A variety of fluorine-containing blaryls are synthesized in good-to-excellent yields. A wide range of substitution patterns and functional groups are tolerated.
• Cyclometalated Platinum(II) Compounds with Fluorinated Iminic Ligands: Synthesis and Reactivity Tuning. Crystal Structures of the Compounds [PtMe(RCH:NCH2C6H5)(PPh3)] (R = 2,3,4-C6HF3 and 2,3-C6H2F2)
  作者：Margarita Crespo、Xavier Solans、Merce Font-Bardia

  DOI：10.1021/om00001a051

  日期：1995.1

  [Pt(2)Me(4)(mu-SMe(2))(2)] (1) reacts with fluorinated imines ArCH=NCH2C6H5 (2; Ar = 2,3,4-C6H2F3, 2,4,5-C6H2F3, 2,3-C6H3F2) to yield the C,N-cyclometalated platinum(II) compounds [PtMe(RCH=NCH2C6H5)(SMe(2))] (3) by ortho metalation with loss of methane. Complexes 3 react with triphenylphosphine to give cyclometalated compounds [PtMe(RCH=N-CH2C6H5)(PPh(3))] (4). For R = 2,4,5-C6HF3, an excess of PPh(3) produces metallacycle cleavage, and [PtMe(RCH=NCH2C6H5)(PPh(3))(2)] (5) is formed with the imine acting as a [C-] unidentate ligand. Similarly, reactions of the previously reported compounds [PtMeRCH=NCH2(2-C6H4Cl)}(SMe(2))] (R = 3,5-C6H2F2, 2-C6H3F, 5-C6H3F) with PPh(3) produce the cyclometalated compounds 4. When an excess of PPh(3) is used, compounds 5 are obtained only if there is a fluorine atom adjacent to platinum (F-5). 3-5 were characterized by elemental analyses and NMR spectroscopy, and [PtMe(2,3,4-C6HF3CH=NCH2C6H5)(PPh(3))] (4a) and [PtMe(2,3-C6H2F2CH=NCH2C6H5)(PPh(3))] (4c) were characterized crystallographically. 4a crystallizes in the monoclinic space group P2(1)/c, with a = 12.475(3) Angstrom, b = 21.642(5) Angstrom, c = 10.497(2) Angstrom, 12.031(2) Angstrom, beta = 96.92(2)degrees, and Z = 4. 4c crystallizes in the triclinic space group P ($) over bar 1, with a = 13.757(2) Angstrom, c = 9.768(2) Angstrom, alpha = 72.91(2)degrees, beta = 114.91(1)degrees, gamma = 104.20(2)degrees, and Z = 2. Structural and NMR parameters for compounds 4 are discussed in relation to the observed reactivity of these compounds.