[(η5-C5H5)Fe(η5-C5H4(p-C6H4-O-(tetrahydropyranyl)))] | 1385024-05-4

• 英文名称: [(η5-C5H5)Fe(η5-C5H4(p-C6H4-O-(tetrahydropyranyl)))]
• 英文别名: Fc-COCHC(OH)(p-C6H4-O-THP)
• CAS: 1385024-05-4
• 化学式: C₂₄H₂₄FeO₄
• 分子量: 432.299
• InChiKey: FRYBEHNKGUDUPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 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：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  [(η5-C5H5)Fe(η5-C5H4(p-C6H4-O-(tetrahydropyranyl)))] 、 水 在 aq. HCl 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到[(η5-C5H5)Fe(η5-C5H4-COCHC(OH)(p-C6H4OH))]
  参考文献：
  名称：

  Stepwise construction of a 4-hydroxyphenyl functionalized O,N,N-tridentate ferrocene-containing enaminone: Spectral, analytical and structural studies

  摘要：

  Tetrahydropyranylation of methyl-4-hydroxybenzoate proceeds with formation of its corresponding THP aromatic ether THP-O-p-C6H4CO2CH3 (1; THP = tetrahydropyranyl, C5H9O). Reaction with in situ generated carbanion of acetylferrocene gave the protected organometallic complex Fc-C(=O) CH=C(OH) (p-C6H4-O-THP) (2, Fc=(eta(5)-C5H5)Fe(eta(5)-C5H4)) featuring keto-enol functionality; subsequent acidic treatment of 2 afforded the 4-hydroxyphenyl substituted counterpart Fc-C(=O) CH=C(OH)(p-C6H4OH) (3) that exists as a 73/27 mixture of keto-enol/beta-diketone tautomers in DMSO solution. The functionalized tridentate metalloligand Fc-C(=O) CH=C(p-C6H4OH) N(H)CH2CH2NH2 (4) incorporating O,N,N-donors is readily obtained upon Schiff base condensation of 3 with 1,2-diaminoethane. Complex 4 exists exclusively as its ferrocenyl-enaminone tautomer in solution and in the solid state. Compounds 1-4 were characterized by NMR (H-1, C-13) and IR spectroscopy as well as by elemental analysis and single-crystal X-ray diffraction. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.04.028
• 作为产物：
  描述：

  乙酰基二茂铁 、 potassium tert-butylate 、 methyl 4-((tetrahydro-2H-pyran-2-yl)oxy)benzoate 在 aq. HCl 作用下， 以 四氢呋喃 为溶剂， 以51%的产率得到[(η5-C5H5)Fe(η5-C5H4(p-C6H4-O-(tetrahydropyranyl)))]
  参考文献：
  名称：

  Stepwise construction of a 4-hydroxyphenyl functionalized O,N,N-tridentate ferrocene-containing enaminone: Spectral, analytical and structural studies

  摘要：

  Tetrahydropyranylation of methyl-4-hydroxybenzoate proceeds with formation of its corresponding THP aromatic ether THP-O-p-C6H4CO2CH3 (1; THP = tetrahydropyranyl, C5H9O). Reaction with in situ generated carbanion of acetylferrocene gave the protected organometallic complex Fc-C(=O) CH=C(OH) (p-C6H4-O-THP) (2, Fc=(eta(5)-C5H5)Fe(eta(5)-C5H4)) featuring keto-enol functionality; subsequent acidic treatment of 2 afforded the 4-hydroxyphenyl substituted counterpart Fc-C(=O) CH=C(OH)(p-C6H4OH) (3) that exists as a 73/27 mixture of keto-enol/beta-diketone tautomers in DMSO solution. The functionalized tridentate metalloligand Fc-C(=O) CH=C(p-C6H4OH) N(H)CH2CH2NH2 (4) incorporating O,N,N-donors is readily obtained upon Schiff base condensation of 3 with 1,2-diaminoethane. Complex 4 exists exclusively as its ferrocenyl-enaminone tautomer in solution and in the solid state. Compounds 1-4 were characterized by NMR (H-1, C-13) and IR spectroscopy as well as by elemental analysis and single-crystal X-ray diffraction. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.04.028