[1-(6-(1-(3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenylimino)ethyl)pyridin-2-yl)ethylidene](2,4,6-trimethylphenyl)amine | 1020072-01-8

• 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: [1-(6-(1-(3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenylimino)ethyl)pyridin-2-yl)ethylidene](2,4,6-trimethylphenyl)amine
• 英文别名: 1-[6-[C-methyl-N-(2,4,6-trimethylphenyl)carbonimidoyl]pyridin-2-yl]-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanimine
• CAS: 1020072-01-8
• 化学式: C₃₀H₃₆BN₃O₂
• 分子量: 481.446
• InChiKey: ORTAEOGFGCWENT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  56.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [1-(6-(1-(3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenylimino)ethyl)pyridin-2-yl)ethylidene](2,4,6-trimethylphenyl)amine 、 iron(II) chloride 以 四氢呋喃 为溶剂， 以68%的产率得到[1-(6-(1-(3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenylimino)ethyl)pyridin-2-yl)ethylidene](2,4,6-trimethylphenyl)amineiron(II) chloride
  参考文献：
  名称：

  Modification of Iron(II) Tridentate Bis(imino)pyridine Complexes by a Boryl Group for the Production of α-Olefins at High Temperature

  摘要：

  A new series of boryl-substituted bis(imino)pyridine ligands [o-PinacoIB-Ph-N=C(Me)-Py-C(Me)=N- Ph-o-BPinaeoll, Pinacol = (-O-(Me)(2)C-C(Me)(2)-O-) (6), [2,4,6-tri-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-o-BPinacol] (11), [4-bromo-2,6-di-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-o-BPinacol] (12), [2,4,6-tri-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-m-BPinacol] (14), [2,4,6-tri-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-p-BPinacol] (17), and [4-Bromo-2,6-di-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-p-BPinacol] (18), and their corresponding Fe(II) complexes [o-PinacolB-Ph-N=C(Me)-Py-C(Me) N-Ph-o-BPinacol)FeCl2] (3), [{2,4,6-tri-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-o-BPinaco}FeCl2] (19), [{4-bromo-2,6-di-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-o-BPinacol} FeCl2] (20), [2,4,6-tri-Me-Ph-N=C (Me)-Py-C(Me)=N-Ph-m-BPinacol}- FeCl2] (21), [2,4,6-tri-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-p-BPinacol) FeCl2] (22), and [(4-bromo-2,6-di-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-p-BPinacol)FeCl2] (23) were synthesized. According to X-ray analysis, the introduction of boryl groups in the ortho-positions of the complex as in 3 caused the shortening of the axial Fe-N bond lengths (up to 0.02 angstrom) vs the analogous Fe(II) complex with ortho-methyl groups [{o-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-o-Me)FeCl2], 1. The comparisons of the axial bond lengths in ortho-boryl-substituted isomer 19 with para-boryl -substituted 22 revealed that these bonds are shorter in the ortho-isomer (2.201(11) angstrom) than in the para-isomer (2.232(2) angstrom). An interesting structural feature of 3 is that it exists in the unexpected "up-up" conformer in the solid state, despite reasonable bulkiness of dioxaboranyl substituents in ortho-positions. Complexes 21-23 afforded very productive catalysts for the production of alpha-olefins with a more linear Schultz-Flory distribution and with the least amounts of the heavier insoluble fractions of a-olefins than the parent methyl-substituted Fe(II) complex 1.

  DOI：

  10.1021/om800036b
• 作为产物：
  描述：

  2-acetyl-6-(1-((2,4,6-trimethylphenyl)imino)ethyl)pyridine 、 3-氨基苯硼酸频哪醇酯 以 甲苯 为溶剂， 以88%的产率得到[1-(6-(1-(3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenylimino)ethyl)pyridin-2-yl)ethylidene](2,4,6-trimethylphenyl)amine
  参考文献：
  名称：

  Modification of Iron(II) Tridentate Bis(imino)pyridine Complexes by a Boryl Group for the Production of α-Olefins at High Temperature

  摘要：

  A new series of boryl-substituted bis(imino)pyridine ligands [o-PinacoIB-Ph-N=C(Me)-Py-C(Me)=N- Ph-o-BPinaeoll, Pinacol = (-O-(Me)(2)C-C(Me)(2)-O-) (6), [2,4,6-tri-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-o-BPinacol] (11), [4-bromo-2,6-di-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-o-BPinacol] (12), [2,4,6-tri-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-m-BPinacol] (14), [2,4,6-tri-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-p-BPinacol] (17), and [4-Bromo-2,6-di-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-p-BPinacol] (18), and their corresponding Fe(II) complexes [o-PinacolB-Ph-N=C(Me)-Py-C(Me) N-Ph-o-BPinacol)FeCl2] (3), [{2,4,6-tri-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-o-BPinaco}FeCl2] (19), [{4-bromo-2,6-di-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-o-BPinacol} FeCl2] (20), [2,4,6-tri-Me-Ph-N=C (Me)-Py-C(Me)=N-Ph-m-BPinacol}- FeCl2] (21), [2,4,6-tri-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-p-BPinacol) FeCl2] (22), and [(4-bromo-2,6-di-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-p-BPinacol)FeCl2] (23) were synthesized. According to X-ray analysis, the introduction of boryl groups in the ortho-positions of the complex as in 3 caused the shortening of the axial Fe-N bond lengths (up to 0.02 angstrom) vs the analogous Fe(II) complex with ortho-methyl groups [{o-Me-Ph-N=C(Me)-Py-C(Me)=N-Ph-o-Me)FeCl2], 1. The comparisons of the axial bond lengths in ortho-boryl-substituted isomer 19 with para-boryl -substituted 22 revealed that these bonds are shorter in the ortho-isomer (2.201(11) angstrom) than in the para-isomer (2.232(2) angstrom). An interesting structural feature of 3 is that it exists in the unexpected "up-up" conformer in the solid state, despite reasonable bulkiness of dioxaboranyl substituents in ortho-positions. Complexes 21-23 afforded very productive catalysts for the production of alpha-olefins with a more linear Schultz-Flory distribution and with the least amounts of the heavier insoluble fractions of a-olefins than the parent methyl-substituted Fe(II) complex 1.

  DOI：

  10.1021/om800036b