1,2'-diformylferrocene | 372963-82-1

• 英文名称: 1,2'-diformylferrocene
• CAS: 372963-82-1
• 化学式: C₁₆H₁₆FeO₄
• 分子量: 328.148
• InChiKey: SCBZHHCJBPANNI-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：
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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：
  None

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  哌啶-1-甲醛 、 2-ferrocenyl-1,3-dioxane 在 sec-BuLi 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到[(η5-C5H5)Fe(1-(CHO)-2-(C(H)O(CH2)3O)-η5-C5H3)]
  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