1,1',2-triformylferrocene | 372963-86-5

• 英文名称: 1,1',2-triformylferrocene
• CAS: 372963-86-5
• 化学式: C₁₃H₁₀FeO₃
• 分子量: 270.068
• InChiKey: WMNABKXMJJQKOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  1,1',2-triformylferrocene 、 甲基三苯基溴化膦 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 24.67h， 以72%的产率得到1,1',2-trivinylferrocene
  参考文献：
  名称：

  Multi-functionalized ferrocenes: –Synthesis and characterization –

  摘要：

  Ferrocenes with up to four formyl functionalities have been synthesized by selective one-or two-fold ortho-lithiation of 1,1'-di(1,3-dioxan-2-yl)ferrocene followed by the reaction with dimethylformamide. Subsequent deprotection afforded tri- and tetraformyl-ferrocene in good yields. Wittig reactions convert the aldehydes to tri-and tetravinyl-ferrocene. The structures of three formyl-ferrocenes in the solid-state have been determined by single crystal X-ray diffraction. In two of the structures the ferrocene moieties form 1D chains by parallel displaced p-interactions with Cp center dot center dot center dot Cp distances as short as 3.21 angstrom. Electrochemical measurements (CV) demonstrated an irreversible behavior of the electron-poor multi-formyl ferrocenes. Reducing the measurement temperature down to -40 degrees C and the usage of [(NBu4)-Bu-n][B(C6F5)(4)] prevents side reactions and hence reversible redox-processes could be obtained. It was found that the number of formyl functionalities correlates with the ferrocenyl's redox potential in a strictly linear fashion. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.12.027
• 作为产物：
  描述：

  1,2'-diformylferrocene 在 p-toluenesulfonic acid 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到1,1',2-triformylferrocene
  参考文献：
  名称：

  Triformylferrocenes, novel modules for organometallic scaffolds

  摘要：

  Protection of formylferrocene with propanediol under acidic conditions furnishes its acetal. Metalation of the acetal occurs mainly in the ortho position at the same ring. Reaction with N-formylpiperidine leads to the semiprotected 1,2-diformylferrocene, and the monoacetal of 1,1',2-triformylferrocene, which can be obtained upon acidic deacetalization. Further protection of the semiprotected 1,2-diformylferrocene with propanediol results in the corresponding bisacetal, which is metalated to give the title compound 1,2,3-triformylferrocene after quenching of the anion with N-formylpiperidine and acidic deprotection. The 1,1',2-triformylferrocene undergoes an interesting solid-state reaction at 170 degreesC under cross-linking to yield a novel organometallic polycondensate, while 1,2,3-triformylferrocene melts undecomposed. 1,2-Diformylferrocene was transformed into 1,2-bisbutadiynylferrocene by treatment with Taber's reagent, followed by coupling of 1,2-diethynylferrocene to bromo-triisopropylsilylethyne under Cadiot-Chodkiewicz conditions in an overall 40% yield starting from diformylferrocene. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00893-2