1-(6-(1-(4-bromo-2,6-dimethylphenylimino)ethyl)pyridin-2-yl)ethanone | 896712-63-3

• 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-(4-bromo-2,6-dimethylphenylimino)ethyl)pyridin-2-yl)ethanone
• 英文别名: 2-acetyl-6-[1-(4-bromo-2,6-dimethylphenyl)iminoethyl]pyridine；1-[6-[N-(4-bromo-2,6-dimethylphenyl)-C-methylcarbonimidoyl]pyridin-2-yl]ethanone
• CAS: 896712-63-3
• 化学式: C₁₇H₁₇BrN₂O
• 分子量: 345.239
• InChiKey: POTKJTBKANKIQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  42.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(6-(1-(4-bromo-2,6-dimethylphenylimino)ethyl)pyridin-2-yl)ethanone 、 4-氨基苯硼酸频哪醇酯 以 甲苯 为溶剂， 以73%的产率得到(4-bromo-2,6-dimethylphenyl)[1-(6-(1-(4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenylimino)ethyl)pyridin-2-yl)ethylidene]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
• 作为产物：
  描述：

  2,6-二乙酰基吡啶 、 4-溴-2,6-二甲基苯胺 在 甲酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以93%的产率得到1-(6-(1-(4-bromo-2,6-dimethylphenylimino)ethyl)pyridin-2-yl)ethanone
  参考文献：
  名称：

  二核和三核铁/钛和铁/锆配合物与杂环配体作为乙烯聚合的催化剂

  摘要：

  摘要聚烯烃树脂的性能很大程度上取决于其分子量，侧链支链的数量和分子量分布。仅在一个反应​​步骤中获得这种定制产物的一种方法是应用具有不同活性位点的不对称多核催化剂。由于每个活性位点都在产生自己的聚合物，因此产生了“分子共混”。为了达到这个目的，已经合成并表征了铁，钛和锆的各种单，双和三核络合物，其中包含2，6-双（芳基乙基）吡啶和苯氧基亚胺。碘化功能化的反应2 通过Sonogashira交叉偶联反应与炔烃官能化的苯氧基亚胺化合物形成的6-双（芳基-乙基）吡啶衍生物可生成可为两种不同金属提供配位点的配体前体。具有Ti / Fe和Zr / Fe组合的三核络合物（每个分子在两个2，6-双（芳基乙基）吡啶单元中包含两个铁原子）提供了最佳的乙烯聚合结果。由于快速的配体交换反应，不能从单（苯氧基亚胺）钛配合物和偶联的双（螯合物）配体前体的反应中分离出双核铁/钛配合物。由于金属中心在不同的聚合温度下表现出最佳性能，因此成分（因此，

  DOI：

  10.1016/j.poly.2016.07.033

文献信息

• Di- and trinuclear iron/titanium and iron/zirconium complexes with heterocyclic ligands as catalysts for ethylene polymerization
  作者：Christian Görl、Eva Betthausen、Helmut G. Alt

  DOI：10.1016/j.poly.2016.07.033

  日期：2016.11

  for two different metals. Trinuclear complexes with the combinations Ti/Fe and Zr/Fe, each molecule containing two iron atoms in two 2,6-bis(aryliminoethyl)pyridine units, gave the best ethylene polymerization results. Due to fast ligand exchange reactions, dinuclear iron/titanium complexes could not be isolated from reactions of mono(phenoxyimine) titanium complexes and the coupled bis(chelate) ligand

  摘要聚烯烃树脂的性能很大程度上取决于其分子量，侧链支链的数量和分子量分布。仅在一个反应​​步骤中获得这种定制产物的一种方法是应用具有不同活性位点的不对称多核催化剂。由于每个活性位点都在产生自己的聚合物，因此产生了“分子共混”。为了达到这个目的，已经合成并表征了铁，钛和锆的各种单，双和三核络合物，其中包含2，6-双（芳基乙基）吡啶和苯氧基亚胺。碘化功能化的反应2 通过Sonogashira交叉偶联反应与炔烃官能化的苯氧基亚胺化合物形成的6-双（芳基-乙基）吡啶衍生物可生成可为两种不同金属提供配位点的配体前体。具有Ti / Fe和Zr / Fe组合的三核络合物（每个分子在两个2，6-双（芳基乙基）吡啶单元中包含两个铁原子）提供了最佳的乙烯聚合结果。由于快速的配体交换反应，不能从单（苯氧基亚胺）钛配合物和偶联的双（螯合物）配体前体的反应中分离出双核铁/钛配合物。由于金属中心在不同的聚合温度下表现出最佳性能，因此成分（因此，
• Modification of Iron(II) Tridentate Bis(imino)pyridine Complexes by a Boryl Group for the Production of α-Olefins at High Temperature
  作者：Alex S. Ionkin、William J. Marshall、Douglas J. Adelman、Barbara Bobik Fones、Brian M. Fish、Matthew F. Schiffhauer

  DOI：10.1021/om800036b

  日期：2008.4.1

  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.