1-(2-nitrophenylamino)ferrocene | 1075257-01-0

• 英文名称: 1-(2-nitrophenylamino)ferrocene
• CAS: 1075257-01-0
• 化学式: C₁₆H₁₄FeN₂O₂
• 分子量: 322.146
• InChiKey: RBNXNAPFZXJEER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  甲酸 、 1-(2-nitrophenylamino)ferrocene 在 NaHCO₂ 、 Pd/C 作用下， 以 formic acid 为溶剂， 以93%的产率得到
  参考文献：
  名称：

  Redox-Active N-Heterocyclic Carbenes: Design, Synthesis, and Evaluation of Their Electronic Properties

  摘要：

  To investigate effects of redox-active functional groups on the coordination chemistry and electronic properties of N-heterocyclic carbenes (NHCs), we prepared a series of complexes comprising 1,3-diferrocenylimidazolylidene and -benzimidazolylidene (1 and 2, respectively), 1-ferrocenyl-3-methyl- and 1, 3-diphenyl-5-ferrocenylbenzimidazolylidene (3 and 4, respectively), N,N'-diisobutyldiaminocarbene[3]ferrocenophane (FcDAC), and 1,3-dimesitylnaphthoquinoimidazolylidene (NqMes) ligands and coordinated [Ir(COD)Cl] (COD = 1,5-cyclooctadiene), [Ir-(CO)(2)Cl], and [M(CO)(5)] (M = Cr, Mo, W) units. The coordination chemistry of the aforementioned NHCs was investigated by X-ray crystallography, and their electronic properties were studied by NMR and IR spectroscopy, as well as electrochemistry. No significant variation in nu(CO) was observed among metal carbonyl complexes supported by 2-4 and FcDAC, indicating that the number (one vs two) or redox-active groups, the location (N atom vs backbone) of the redox-active group, and carbene ring identities (strained six-membered, nonaromatic vs five-membered, heteroaromatic) did not have a significant effect on ligand electron-donating ability. Because the shifts in nu(CO) upon oxidation of 1-3 and FcDAC were similar in magnitude but opposite in sign to NqMes, we conclude that the enhancement or attenuation of ligand donating is primarily Coulombic in origin (i.e., due to the molecule acquiring a positive or negative charge).

  DOI：

  10.1021/om900698x
• 作为产物：
  描述：

  aminoferrocene 、 1-氟-2-硝基苯 在 NaHCO₃ 作用下， 以 dimethylsulfoxide 为溶剂， 以92%的产率得到1-(2-nitrophenylamino)ferrocene
  参考文献：
  名称：

  Redox-Active N-Heterocyclic Carbenes: Design, Synthesis, and Evaluation of Their Electronic Properties

  摘要：

  To investigate effects of redox-active functional groups on the coordination chemistry and electronic properties of N-heterocyclic carbenes (NHCs), we prepared a series of complexes comprising 1,3-diferrocenylimidazolylidene and -benzimidazolylidene (1 and 2, respectively), 1-ferrocenyl-3-methyl- and 1, 3-diphenyl-5-ferrocenylbenzimidazolylidene (3 and 4, respectively), N,N'-diisobutyldiaminocarbene[3]ferrocenophane (FcDAC), and 1,3-dimesitylnaphthoquinoimidazolylidene (NqMes) ligands and coordinated [Ir(COD)Cl] (COD = 1,5-cyclooctadiene), [Ir-(CO)(2)Cl], and [M(CO)(5)] (M = Cr, Mo, W) units. The coordination chemistry of the aforementioned NHCs was investigated by X-ray crystallography, and their electronic properties were studied by NMR and IR spectroscopy, as well as electrochemistry. No significant variation in nu(CO) was observed among metal carbonyl complexes supported by 2-4 and FcDAC, indicating that the number (one vs two) or redox-active groups, the location (N atom vs backbone) of the redox-active group, and carbene ring identities (strained six-membered, nonaromatic vs five-membered, heteroaromatic) did not have a significant effect on ligand electron-donating ability. Because the shifts in nu(CO) upon oxidation of 1-3 and FcDAC were similar in magnitude but opposite in sign to NqMes, we conclude that the enhancement or attenuation of ligand donating is primarily Coulombic in origin (i.e., due to the molecule acquiring a positive or negative charge).

  DOI：

  10.1021/om900698x

文献信息

• Convenient synthesis of ferrocene amines via Cu-catalyzed coupling reaction
  作者：Jinsheng Wu、Xiaolong Li、Mingyu Yang、Yujie Gao、Qianru Lv、Baohua Chen

  DOI：10.1139/v08-096

  日期：2008.9.1

  An efficient copper-catalyzed Ullmann-type cross-coupling reaction without ligand of iodo-ferrocene with amines has been reported. In this process, a range of ferrocenyl amine compounds have been prepared in moderate to good yields.Key words: amines, iodo-ferrocene, cross-coupling, copper, Ullmann coupling.

  据报道，碘二茂铁与胺在无配体的情况下发生了高效的铜催化乌尔曼型交叉偶联反应。在此过程中，制备了一系列二茂铁胺化合物，产率从中等到良好。