4-Methyl-2-(6-naphthalen-1-ylpyridin-2-yl)-6-(2-phenylpropan-2-yl)phenol | 1419184-34-1

• 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: 4-Methyl-2-(6-naphthalen-1-ylpyridin-2-yl)-6-(2-phenylpropan-2-yl)phenol
• 英文别名: 4-methyl-2-(6-naphthalen-1-ylpyridin-2-yl)-6-(2-phenylpropan-2-yl)phenol
• CAS: 1419184-34-1
• 化学式: C₃₁H₂₇NO
• 分子量: 429.561
• InChiKey: JXZOSLVYCQMUSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Methyl-2-(6-naphthalen-1-ylpyridin-2-yl)-6-(2-phenylpropan-2-yl)phenol 、 tetrabenzyl titanium 以 乙醚 、 正戊烷 为溶剂， 反应 13.0h， 以27%的产率得到
  参考文献：
  名称：

  Olefin Polymerization Behavior of Titanium(IV) Pyridine-2-phenolate-6-(σ-aryl) Catalysts: Impact of “py-Adjacent” and Phenolate Substituents

  摘要：

  A series of Ti(IV) post-metallocene bis(benzyl) precatalysts supported by tridentate pyridine-2-phenolate-6-(sigma-aryl) [O,N,C] ligands, featuring various substituents on the sigma-aryl (directly adjacent to the pyridine ring: fluoro, trifluoromethyl, benzo [C4H4]) and phenolate groups (tert-butyl, trifluoromethyl, cumyl, 1,1-diphenylethyl), have been prepared. Multinuclear (including H-1, C-13, and F-19) NMR characterizations of the complexes have been performed. The principal purpose of this study was to investigate the impact of these substituents upon ethylene polymerization reactivity and polymer properties. The cumyl-phenolate sigma-naphthyl Ti precatalyst, in conjunction with [Ph3C][B(C6F5)(4)], displays good activity and produces polyethylene with exceptionally high (M-n = 4 x 10(6)) and an M-w/M-n value (2.5) approaching single-site character at 50 degrees C, but multisite behavior is apparent for other catalysts. DFT calculations have been performed to probe the polymerization behavior and the role of the py-adjacent substituent. These studies revealed the possibility of two distinct polymerization reactions, namely conventional and ethylene-assimilated (comprising initial ethylene insertion into the Ti-C(sigma-aryl) bond) chain propagation, and found that the latter is kinetically preferred. Furthermore, the viability of another kinetically competitive pathway, namely the isomerization of the ethylene-assimilated [Ti-CH2CH2-aryl] species via beta-H elimination and 2,1-reinsertion, was also indicated.

  DOI：

  10.1021/om300832q
• 作为产物：
  描述：

  2-(ethoxymethoxy)-1-iodo-5-methyl-3-(2-phenylpropan-2-yl)benzene 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 64.0h， 生成 4-Methyl-2-(6-naphthalen-1-ylpyridin-2-yl)-6-(2-phenylpropan-2-yl)phenol
  参考文献：
  名称：

  Olefin Polymerization Behavior of Titanium(IV) Pyridine-2-phenolate-6-(σ-aryl) Catalysts: Impact of “py-Adjacent” and Phenolate Substituents

  摘要：

  A series of Ti(IV) post-metallocene bis(benzyl) precatalysts supported by tridentate pyridine-2-phenolate-6-(sigma-aryl) [O,N,C] ligands, featuring various substituents on the sigma-aryl (directly adjacent to the pyridine ring: fluoro, trifluoromethyl, benzo [C4H4]) and phenolate groups (tert-butyl, trifluoromethyl, cumyl, 1,1-diphenylethyl), have been prepared. Multinuclear (including H-1, C-13, and F-19) NMR characterizations of the complexes have been performed. The principal purpose of this study was to investigate the impact of these substituents upon ethylene polymerization reactivity and polymer properties. The cumyl-phenolate sigma-naphthyl Ti precatalyst, in conjunction with [Ph3C][B(C6F5)(4)], displays good activity and produces polyethylene with exceptionally high (M-n = 4 x 10(6)) and an M-w/M-n value (2.5) approaching single-site character at 50 degrees C, but multisite behavior is apparent for other catalysts. DFT calculations have been performed to probe the polymerization behavior and the role of the py-adjacent substituent. These studies revealed the possibility of two distinct polymerization reactions, namely conventional and ethylene-assimilated (comprising initial ethylene insertion into the Ti-C(sigma-aryl) bond) chain propagation, and found that the latter is kinetically preferred. Furthermore, the viability of another kinetically competitive pathway, namely the isomerization of the ethylene-assimilated [Ti-CH2CH2-aryl] species via beta-H elimination and 2,1-reinsertion, was also indicated.

  DOI：

  10.1021/om300832q

文献信息

• Olefin Polymerization Behavior of Titanium(IV) Pyridine-2-phenolate-6-(σ-aryl) Catalysts: Impact of “py-Adjacent” and Phenolate Substituents
  作者：Jerry C. Y. Lo、Michael C. W. Chan、Po-Kam Lo、Kai-Chung Lau、Takashi Ochiai、Haruyuki Makio

  DOI：10.1021/om300832q

  日期：2013.1.28

  A series of Ti(IV) post-metallocene bis(benzyl) precatalysts supported by tridentate pyridine-2-phenolate-6-(sigma-aryl) [O,N,C] ligands, featuring various substituents on the sigma-aryl (directly adjacent to the pyridine ring: fluoro, trifluoromethyl, benzo [C4H4]) and phenolate groups (tert-butyl, trifluoromethyl, cumyl, 1,1-diphenylethyl), have been prepared. Multinuclear (including H-1, C-13, and F-19) NMR characterizations of the complexes have been performed. The principal purpose of this study was to investigate the impact of these substituents upon ethylene polymerization reactivity and polymer properties. The cumyl-phenolate sigma-naphthyl Ti precatalyst, in conjunction with [Ph3C][B(C6F5)(4)], displays good activity and produces polyethylene with exceptionally high (M-n = 4 x 10(6)) and an M-w/M-n value (2.5) approaching single-site character at 50 degrees C, but multisite behavior is apparent for other catalysts. DFT calculations have been performed to probe the polymerization behavior and the role of the py-adjacent substituent. These studies revealed the possibility of two distinct polymerization reactions, namely conventional and ethylene-assimilated (comprising initial ethylene insertion into the Ti-C(sigma-aryl) bond) chain propagation, and found that the latter is kinetically preferred. Furthermore, the viability of another kinetically competitive pathway, namely the isomerization of the ethylene-assimilated [Ti-CH2CH2-aryl] species via beta-H elimination and 2,1-reinsertion, was also indicated.