(N-tert-butylcarbamoyl)ferrocene | 143226-92-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (N-tert-butylcarbamoyl)ferrocene
• 英文别名: N-tert-butylferrocenecarboxamide；N-tert-butylcyclopenta-1,3-diene-1-carboxamide;cyclopenta-1,3-diene;iron(2+)
• CAS: 143226-92-0
• 化学式: C₁₅H₁₉FeNO
• 分子量: 285.169
• InChiKey: CTUOILZKZJFGOV-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

• 作为产物：
  描述：

  环戊二烯锂 、 iron(II) chloride 、 叔丁基异氰酸酯 以 四氢呋喃 为溶剂， 以1%的产率得到(N-tert-butylcarbamoyl)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

• Reaction of ferrocenecarboxylic acid with N,N′-disubstituted carbodiimides: synthesis, spectroscopic and X-ray crystallographic analysis of N,N′-disubstituted N-ferrocenoylureas and identification of a one-pot coupling reagent for the formation of ferrocenecarboxamides in a non-aqueous solvent
  作者：Bernd Schetter、Bernd Speiser

  DOI：10.1016/j.jorganchem.2003.12.045

  日期：2004.5

  N,N'-dicyclohexyl-N-ferrocenoylurea 2, N,N-diisopropyl-N-ferrocenoylurea 3, N,N'-di-p-tolyl-N-ferrocenoylurea 4 and N,N'-ditert-butyl-N-ferrocenoylurea 5 were obtained by reaction of ferrocenecarboxylic acid I with N,N'-dicyclohexylcarbodiimide (DCC), N,N'-diisopropylcarbodiimide (DIC), N,N'-di-p-tolylcarbodiimide 10 and N,N-di-tert-butylcarbodiimide 11, respectively. Both N-tert-butyl-N'-ethyl-N-ferrocenoylurea 6 and N'-tert-butyl-N-ethyl-N-ferrocenoylurea 7 were obtained by reaction of 1 with N-tert-butyl-N'-ethylcarbodiimide 12. In all cases a small amount of ferrocenecarboxylic anhydride 8 was formed as a by-product. All compounds were characterized by H-1 NMR, C-13 NMR, IR and MS. Single crystal X-ray structural analyses were made of 2, 3 and 4. From the consistent results, the reaction products of 1 with carbodiimides appear different from those proposed by some earlier workers. With N-(3-dimethylaminopropyl)-N'-ethylcarbodiimidehydrochloride 9 ferrocenoylurea, was not isolated, but the main product was rather 8. The suitability of 8 as acylation reagent was applied by using 9 to obtain N-(3-triethoxysilyl)-propylferrocenecarboxamide in a one-pot reaction from 1 and 3-(triethoxysilyi)-propylamine. (C) 2004 Elsevier B.V. All rights reserved.