3,5-diiodo-N-[2,6-bis(3,5-diethylphenyl)phenyl]salicylaldimine | 1538589-62-6

• 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: 3,5-diiodo-N-[2,6-bis(3,5-diethylphenyl)phenyl]salicylaldimine
• 英文别名: 2-[[2,6-Bis(3,5-diethylphenyl)phenyl]iminomethyl]-4,6-diiodophenol
• CAS: 1538589-62-6
• 化学式: C₃₃H₃₃I₂NO
• 分子量: 713.44
• InChiKey: JMGMDKXEUGBLSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吡啶 、 (N,N,N',N'-Tetramethylethylendiamin)(dimethyl)nickel(II) 、 3,5-diiodo-N-[2,6-bis(3,5-diethylphenyl)phenyl]salicylaldimine 以 苯 为溶剂， 反应 1.0h， 以78%的产率得到{3,5-diiodo-N-[2,6-bis(3,5-diethylphenyl)phenyl]salicylaldiminato-κ²-N,O}methylpyridine nickel(II)
  参考文献：
  名称：

  Monofunctional Hyperbranched Ethylene Oligomers

  摘要：

  The neutral kappa N-2,O-salicylaldiminato Ni(II) complexes [kappa N-2,O-{(2,6-(3',5'-R2C6H3)(2)C6H3-N=C(H)-(3,5-I-2-2-O-C6H2)}]NiCH3(pyridine)] (1a-pyr, R = Me; 1b-pyr, R = Et; 1c-pyr, R = iPr) convert ethylene to hyperbranched low-molecular-weight oligomers (M-n ca. 1000 g mol(-1)) with high productivities. While all three catalysts are capable of generating hyperbranched structures, branching densities decrease significantly with the nature of the remote substituent along Me > Et > iPr and oligomer molecular weights increase. Consequently, only 1a-pyr forms hyperbranched structures over a wide range of reaction conditions (ethylene pressure 5-30 atm and 20-70 degrees C). An in situ catalyst system achieves similar activities and identical highly branched oligomer microstructures, eliminating the bottleneck given by the preparation and isolation of Ni Me catalyst precursor species. Selective introduction of one primary carboxylic acid ester functional group per highly branched oligoethylene molecule was achieved by isomerizing ethoxycarbonylation and alternatively cross metathesis with ethyl acrylate followed by hydrogenation. The latter approach results in complete functionalization and no essential loss of branched oligomer material and molecular weight, as the reacting double bonds are close to a chain end. Reduction yielded a monoalcohol-functionalized oligomer. Introduction of one reactive epoxide group per branched oligomer occurs completely and selectively under mild conditions. All reaction steps involved in oligomerization and monofunctionalization are efficient and readily scalable.

  DOI：

  10.1021/ja411945n
• 作为产物：
  描述：

  1-溴-3,5-二乙基苯 在 正丁基锂 、 对甲苯磺酸 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 40.17h， 生成 3,5-diiodo-N-[2,6-bis(3,5-diethylphenyl)phenyl]salicylaldimine
  参考文献：
  名称：

  Monofunctional Hyperbranched Ethylene Oligomers

  摘要：

  The neutral kappa N-2,O-salicylaldiminato Ni(II) complexes [kappa N-2,O-{(2,6-(3',5'-R2C6H3)(2)C6H3-N=C(H)-(3,5-I-2-2-O-C6H2)}]NiCH3(pyridine)] (1a-pyr, R = Me; 1b-pyr, R = Et; 1c-pyr, R = iPr) convert ethylene to hyperbranched low-molecular-weight oligomers (M-n ca. 1000 g mol(-1)) with high productivities. While all three catalysts are capable of generating hyperbranched structures, branching densities decrease significantly with the nature of the remote substituent along Me > Et > iPr and oligomer molecular weights increase. Consequently, only 1a-pyr forms hyperbranched structures over a wide range of reaction conditions (ethylene pressure 5-30 atm and 20-70 degrees C). An in situ catalyst system achieves similar activities and identical highly branched oligomer microstructures, eliminating the bottleneck given by the preparation and isolation of Ni Me catalyst precursor species. Selective introduction of one primary carboxylic acid ester functional group per highly branched oligoethylene molecule was achieved by isomerizing ethoxycarbonylation and alternatively cross metathesis with ethyl acrylate followed by hydrogenation. The latter approach results in complete functionalization and no essential loss of branched oligomer material and molecular weight, as the reacting double bonds are close to a chain end. Reduction yielded a monoalcohol-functionalized oligomer. Introduction of one reactive epoxide group per branched oligomer occurs completely and selectively under mild conditions. All reaction steps involved in oligomerization and monofunctionalization are efficient and readily scalable.

  DOI：

  10.1021/ja411945n