(1E,2E)-N¹,N²-dicyclohexyl-1,2-diphenylethane-1,2-diimine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1E,2E)-N¹,N²-dicyclohexyl-1,2-diphenylethane-1,2-diimine
• 化学式: C₂₆H₃₂N₂
• 分子量: 372.553
• InChiKey: MZIJKOWHDWZHSK-NBHCHVEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.63
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  24.72
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  异氰环已烷 、 四苯基铅 在 palladium diacetate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以47%的产率得到环己胺,N-(二苯亚甲基)-
  参考文献：
  名称：

  Palladium-Catalyzed Diarylation of Isocyanides with Tetraarylleads for the Selective Synthesis of Imines and α-Diimines

  摘要：

  Using tetraaryllead compounds (PbAr4) as arylating reagents, isocyanides undergo selective diarylation in the presence of palladium catalysts such as Pd(OAc)(2) or Pd(PPh3)(4) to afford imines and/or alpha-diimines based on the isocyanide employed. With aliphatic isocyanides, imines are obtained preferentially, whereas alpha-diimines are formed in the case of electron-rich aromatic isocyanides. The differences in imine/alpha-diimine selectivity can be attributed to the stability of imidoylpalladium intermediates formed in this catalytic reaction. Compared with other arylating reagents, tetraaryllead compounds are excellent candidates for use in the selective transformations to imines and/or alpha-diimines, especially in terms of inhibiting the oligomerization of isocyanides, which results in a lower product selectivity in many transition-metal-catalyzed reactions of isocyanides.

  DOI：

  10.1021/acs.joc.9b01639

文献信息

• [EN] IMPROVED CARBONYLATION PROCESS<br/>[FR] PROCÉDÉ DE CARBONYLATION AMÉLIORÉ
  申请人：EASTMAN CHEM CO

  公开号：WO2009123675A1

  公开（公告）日：2009-10-08

  Disclosed is an improved carbonylation process for the production of carboxylic acids, carboxylic acid esters, and/or carboxylic acid anhydrides wherein a carbonylation feedstock compound selected from one or more organic oxygenates such as alcohols, ethers, and esters is contacted with carbon monoxide in the presence of a carbonylation catalyst and one or more onium compounds. The carbonylation process differs from known carbonylation processes in that a halide compound, other than the onium salt, such as a hydrogen halide (typically, hydrogen iodide) and/or an alkyl halide (typically, methyl iodide), extraneous or exogenous to the carbonylation process is not fed or supplied to the process. The process can be improved by using a bidentate ligand comprising two functional groups selected from tertiary amines and tertiary phosphines, such as 2,2'-bipyridine and diphosphine derivatives.
• Palladium-Catalyzed Diarylation of Isocyanides with Tetraarylleads for the Selective Synthesis of Imines and α-Diimines
  作者：Cong Chi Tran、Shin-ichi Kawaguchi、Yohsuke Kobiki、Hitomi Matsubara、Dat Phuc Tran、Shintaro Kodama、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1021/acs.joc.9b01639

  日期：2019.9.20

  Using tetraaryllead compounds (PbAr4) as arylating reagents, isocyanides undergo selective diarylation in the presence of palladium catalysts such as Pd(OAc)(2) or Pd(PPh3)(4) to afford imines and/or alpha-diimines based on the isocyanide employed. With aliphatic isocyanides, imines are obtained preferentially, whereas alpha-diimines are formed in the case of electron-rich aromatic isocyanides. The differences in imine/alpha-diimine selectivity can be attributed to the stability of imidoylpalladium intermediates formed in this catalytic reaction. Compared with other arylating reagents, tetraaryllead compounds are excellent candidates for use in the selective transformations to imines and/or alpha-diimines, especially in terms of inhibiting the oligomerization of isocyanides, which results in a lower product selectivity in many transition-metal-catalyzed reactions of isocyanides.