1,1'-bis(N'-butyl carboxamido) ferrocene | 52202-09-2

• 英文名称: 1,1'-bis(N'-butyl carboxamido) ferrocene
• 英文别名: 1,1'-bis(n-butylcarbamido)ferrocene；1,1'-bis(N-n-butylcarbamoyl)ferrocene；1,1'-bis(n-butylcarbamido)ferrocen
• CAS: 52202-09-2
• 化学式: C₂₀H₂₈FeN₂O₂
• 分子量: 384.302
• InChiKey: CDOZQXBTYBIMBK-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：

  1,1'-bis(N'-butyl carboxamido) ferrocene 、 lithium aluminium tetrahydride 以 not given 为溶剂， 以73%的产率得到1,1′-bis((N-(n-butyl)amino)methyl)ferrocene
  参考文献：
  名称：

  Zur reaktion von 1,1′-bis(alkylaminomethylen)ferrocenen mit benzoylisothiocyanat

  摘要：

  The reaction of 1,1'-bis((n)butylaminomethylene)ferrocene with two equivalents of benzoyl isothiocyanate yields 1,1'-ferrocenediyl-bis(N-methylene-N-(n)butyl-N'-benzoyl thiourea). In contrast, the respective reaction with 1,1'-bis(ethylaminomethylene)ferrocene leads to 2-N-ethylammonium-[3]-1,1'-ferrocenophane thiocyanate. Both compounds are characterized by X-ray structure determination. A possible reaction mechanism is discussed.

  DOI：

  10.1016/s0022-328x(96)06502-3
• 作为产物：
  描述：

  环戊二烯锂 、 异氰酸正丁酯 、 iron(II) chloride 以 四氢呋喃 为溶剂， 以24%的产率得到((butylamino)carbonyl)ferrocene
  参考文献：
  名称：

  The Isocyanate Route to Cyclopentadienyl-Carboxamide- and Cyclopentadienyl-Amino Ester-Substituted Metallocene Complexes

  摘要：

  Lithium cyclopentadienide adds to a variety of isocyanates [R-N=C=O, R = tert-butyl (a), n-butyl (b), cyclohexyl (c), phenyl (d), 3-pyridyl (e), 2-tetrahydropyranyl (f), adamantyl (g)] to yield the monocarbamoyl-substituted cyclopentadienides C(5)H(4)CONHR(-) 3 admired with varying amounts of the respective 1,2-dicarbamoyl-substituted C5H3(CONHR)(2)(-) systems 4 and a corresponding quantity of the C5H5- Starting material. Subsequent treatment of these reaction mixtures with anhydrous FeCl2 gave the 1,1'-dicarbamoylferrocenes 6 and the corresponding monocarbamoylferrocenes 5, which were easily separated by chromatography. The carbamoylferrocenes 5b, 5c, and 6d were characterized by X-ray crystal structure analyses. The (N-phenyl- and (N-adamantylcarbamoyl)cyclopentadienides were treated with CpTiCl(3) to give the carboxamide-substituted titanocene dichloride complexes [CP(C(5)H(4)CONHR)TiCl2] 8a (R = Ph) and Sh (R = adamantyl), respectively. Complex 8b was also characterized by X-ray diffraction. The valine ester-derived isocyanate reacts with lithium cyclopentadienide to give the N-valinyl-substituted carbamoylcyclopentadienide 3h. Subsequent treatment with FeCl2 or FeCl2/CpLi, respectively, produces the 1,1'-difunctionalized ferrocene 6h or the monofunctionalized ferrocene 5h. Both complexes were characterized by X-ray crystal structure analyses.

  DOI：

  10.1021/om960234k

文献信息

• Formation of intramolecular hydrogen bonds in heterodisubstituted ferrocene diamides with a secondary and a tertiary amido group: X-ray structure of 1′-(N′-butyl-carbamoyl)-morpholino ferrocenecarboxamide
  作者：Árpád Kuik、Rita Skoda-Földes、Attila C. Bényei、Gábor Rangits、László Kollár

  DOI：10.1016/j.jorganchem.2006.03.013

  日期：2006.6

  bearing a secondary and a tertiary amido group are explained by the formation of an internal hydrogen bond between the substituents. Addition of chloride ions (as a tetrabutylammonium salt) into the solutions of these compounds results in spectroscopic changes due to the formation of intermolecular hydrogen bonds between the ferrocene diamide and the anion. The solid state structure of 1′-(N′-butyl-

  从1，1′-二碘二茂铁开始，通过均相催化羰基化合成了各种不对称取代的二茂铁1，1′-二酰胺。带有仲和叔酰胺基的化合物在1 H NMR和IR光谱中观察到的独特特征是通过在取代基之间形成内部氢键来解释的。由于二茂铁二酰胺和阴离子之间形成了分子间氢键，因此将氯离子（四丁基铵盐）加到这些化合物的溶液中会导致光谱变化。1'-（N'-丁基-氨基甲酰基）-吗啉代二茂铁羧酰胺（1a）也已通过X射线晶体学测定。观察到N'-丁基-氨基甲酰基部分的NH基团和叔酰胺基的CO之间的强分子内H键。