N,N'-dicyclohexyl-1,2-diphenylethane-1,2-diimine | 20586-41-8

• 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: N,N'-dicyclohexyl-1,2-diphenylethane-1,2-diimine
• 英文别名: Cy-N=C(Ph)-C(Ph)=N-Cy；Benzil-bis-cyclohexylimid；Benzil-bis-cyclohexylimin
• CAS: 20586-41-8
• 化学式: C₂₆H₃₂N₂
• 分子量: 372.553
• InChiKey: MZIJKOWHDWZHSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-dicyclohexyl-1,2-diphenylethane-1,2-diimine 、 三氯化铁 以 二氯甲烷 为溶剂， 生成 [Cy-N=C(Ph)-C(Ph)=N-Cy]FeCl3
  参考文献：
  名称：

  Correlation of Metal Spin-State in α-Diimine Iron Catalysts with Polymerization Mechanism

  摘要：

  The alpha-diimine iron complexes, (R',R '')[N,N]FeCl2 ((R',R '')[N,N] = R'-N=CR"-CR ''=N-R', where R' = tert-butyl (tBu), cyclohexyl (Cy) and R '' = phenyl (Ph), para-fluorophenyl (F-Ph), para-bromophenyl (Br-Ph), para-methylphenyl (Me-Ph), or para-methoxyphenyl (MeO-Ph)), are found to polymerize styrene through a catalytic chain transfer (CCT) mechanism. Magnetic moment measurements indicate that Fe(III) complexes containing these ligands possess intermediate (S = 3/2) spin-state iron centers. In contrast, Fe(III) complexes bearing proton (R '' = H) and paradimethylaminophenyl (R '' = NMe2-Ph) substituents are high-spin and are efficient atom transfer radical polymerization (ATRP) catalysts. Hammett plots show a linear correlation of the substituent constant, sigma, with polymerization rate and polymer molecular weight, respectively.

  DOI：

  10.1021/ic701500y
• 作为产物：
  描述：

  异氰环已烷 、 三苯基铋 在 palladium diacetate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以82%的产率得到N,N'-dicyclohexyl-1,2-diphenylethane-1,2-diimine
  参考文献：
  名称：

  Palladium-Catalyzed Synthesis of α-Diimines from Triarylbismuthines and Isocyanides

  摘要：

  In this study, we report a highly selective coupling reaction between triarylbismuthines and isocyanides using palladium diacetate as the catalyst, affording alpha-diimines, with the formation of three C-C bonds. Among several aryl sources,(Ar-YLn : Y = B, Sn, Pb, Sb, Bi, I), only triarylbismuthines successfully undergo coupling with isocyanides to selectively afford alpha-diimines. The coupling reaction exhibits the advantages of high atom economy and convenient operation, with no need for any additive.

  DOI：

  10.1021/acs.orglett.5b01566

文献信息

• Palladium-Catalyzed Synthesis of α-Diimines from Triarylbismuthines and Isocyanides
  作者：Yohsuke Kobiki、Shin-ichi Kawaguchi、Akiya Ogawa

  DOI：10.1021/acs.orglett.5b01566

  日期：2015.7.17

  In this study, we report a highly selective coupling reaction between triarylbismuthines and isocyanides using palladium diacetate as the catalyst, affording alpha-diimines, with the formation of three C-C bonds. Among several aryl sources,(Ar-YLn : Y = B, Sn, Pb, Sb, Bi, I), only triarylbismuthines successfully undergo coupling with isocyanides to selectively afford alpha-diimines. The coupling reaction exhibits the advantages of high atom economy and convenient operation, with no need for any additive.
• Correlation of Metal Spin-State in α-Diimine Iron Catalysts with Polymerization Mechanism
  作者：Laura E. N. Allan、Michael P. Shaver、Andrew J. P. White、Vernon C. Gibson

  DOI：10.1021/ic701500y

  日期：2007.10.1

  The alpha-diimine iron complexes, (R',R '')[N,N]FeCl2 ((R',R '')[N,N] = R'-N=CR"-CR ''=N-R', where R' = tert-butyl (tBu), cyclohexyl (Cy) and R '' = phenyl (Ph), para-fluorophenyl (F-Ph), para-bromophenyl (Br-Ph), para-methylphenyl (Me-Ph), or para-methoxyphenyl (MeO-Ph)), are found to polymerize styrene through a catalytic chain transfer (CCT) mechanism. Magnetic moment measurements indicate that Fe(III) complexes containing these ligands possess intermediate (S = 3/2) spin-state iron centers. In contrast, Fe(III) complexes bearing proton (R '' = H) and paradimethylaminophenyl (R '' = NMe2-Ph) substituents are high-spin and are efficient atom transfer radical polymerization (ATRP) catalysts. Hammett plots show a linear correlation of the substituent constant, sigma, with polymerization rate and polymer molecular weight, respectively.