1-(diphenylphosphino)-1′-{[(2-(trimethylazonia)ethyl)amino]carbonyl}ferrocene chloride | 1433996-50-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(diphenylphosphino)-1′-{[(2-(trimethylazonia)ethyl)amino]carbonyl}ferrocene chloride
• 英文别名: [Ph2PfcCONHCH2CH2NMe3]Cl*CH2Cl2；[Ph2PfcCONHCH2CH2NMe3]Cl；2-(cyclopenta-2,4-diene-1-carbonylamino)ethyl-trimethylazanium;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+);chloride
• CAS: 1433996-50-9
• 化学式: C₂₈H₃₂FeN₂OP*Cl
• 分子量: 534.849
• InChiKey: CQECCXAGRSMAPJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(diphenylphosphinothioyl)-1′-{[(2-(trimethylazonia)ethyl)amino]carbonyl}ferrocene iodide 、 sodium chloride 在 Raney nickel 作用下， 以 乙腈 、 二氯甲烷 、 水 为溶剂， 生成 1-(diphenylphosphino)-1′-{[(2-(trimethylazonia)ethyl)amino]carbonyl}ferrocene chloride 、 1-(diphenylphosphino)-1′-{[(2-(trimethylazonia)ethyl)amino]carbonyl}ferrocene iodide
  参考文献：
  名称：

  Synthesis, Coordination Properties, and Catalytic Use of Phosphinoferrocene Carboxamides Bearing Donor-Functionalized Amide Substituents

  摘要：

  Phosphinoferrocene carboxamides bearing donor-functionalized substituents at the amide nitrogen, Ph(2)PfcCONH(CH2)(n)Y (Y/n = NMe2/2 (1), NMe2/3 (2), PPh2/2 (3), and PPh2/3 (4); fc = ferrocene-1,1'-diyl), were obtained by amide coupling reactions of 1'-(diphenylphosphino)ferrocene-1-carboxylic acid (Hdpf) with the respective amines and structurally characterized. Amide 1 was further converted to the corresponding omega-azoniaalkyl amidophosphine [Ph(2)PfcCONHCH(2)CH(2)NMe(3)]X (7; X = Cl/I). Amides 1 and 3, possessing the shorter ethane-1,2-diyl linker, reacted smoothly with [PdCl2(cod)] (cod = cyclocta-1,5-diene) to give the respective trans-chelate complexes, trans-[PdCl2(L-kappa P-2,Y)] (8: L = 1; 9: L = 3). The homologous donors 2 and 4 showed more complicated coordination behavior, affording mixtures of several Pd(II) complexes under similar conditions. Compounds 1, 3, and 7 were further evaluated as ligands for Pd-catalyzed Suzuki-Miyaura cross-coupling using 4-bromoacetophenone and phenylboronic acid as model substrates. In dioxane, the yields of the coupling product decreased in the order 3 > 1 > 7, presumably due to different donor ability of these ligands (type of donor atoms; PP > PN > PN+). The catalytic performance in pure water was different: The yields were generally lower and the order of ligands changed to 3 > 7 > 1.

  DOI：

  10.1021/om400282z