2,3-bis(1,3-dioxan-2-yl)cyclopenta-2,4-diene-1-carbaldehyde;cyclopenta-1,3-diene;iron(2+) | 372963-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2,3-bis(1,3-dioxan-2-yl)cyclopenta-2,4-diene-1-carbaldehyde;cyclopenta-1,3-diene;iron(2+)
• CAS: 372963-88-7
• 化学式: C₁₉H₂₂FeO₅
• 分子量: 386.228
• InChiKey: JTIGFTKQWTZBEG-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：
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反应信息

• 作为反应物：
  描述：

  2,3-bis(1,3-dioxan-2-yl)cyclopenta-2,4-diene-1-carbaldehyde;cyclopenta-1,3-diene;iron(2+) 在 p-toluenesulfonic acid 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到1,2,3-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 、 在 sec-BuLi 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到2,3-bis(1,3-dioxan-2-yl)cyclopenta-2,4-diene-1-carbaldehyde;cyclopenta-1,3-diene;iron(2+)
  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

文献信息

• Synthesis of the first pentaethynylferrocene derivatives
  作者：Winfried Steffen、Matthew Laskoski、Jason G.M. Morton、Uwe H.F. Bunz

  DOI：10.1016/j.jorganchem.2004.05.006

  日期：2004.11

  Starting from a bisprotected ferrocene-1,2,3-triscarbaldehyde, Ohira-alkynylation and Pd-catalyzed protection of the free alkyne with 4-iodotoluene leads to a ferrocene in which one Cp-ring is 1,2,3-substituted by two acetal rings (1,2-position) and all internal alkyne. Metalation of the ferrocene nucleus with sec-BuLi, workup with DMF and reduction with LiAlH4 leads to a 1,2,3,4-tetra-substituted ferrocene carrying a hydroxymethyl group. The acetal groups are removed by para-toluenesulfonic acid and the aldehyde groups are converted into arylalkynes. A second metalation followed by workup with DMF furnishes a 1,2,3,4,5-pentasubstituted ferrocenecarbaidehyde. The aldehyde is transformed into an alkyne by the Ohira method and converted to an internal alkyne by Pd-catalyzed reaction with 4-iodotoluene. The sequence gives a 1,2,3,4,5-pentasubstituted ferrocene derivative with four alkyne groups and one hydroxymethyl group. Airless Marko oxidation of the alcohol is followed by another Ohira alkynylation. Pd-catalyzed arylation finishes the reaction sequence to give the symmetrical 1,2,3,4,5-pentakis(4'-tolylethynyl)ferrocene, the first pentaethynylferrocene derivative. A second, similar route was explored that furnished 1,2,3,4,5-pentakis(4'-butylphenylethynyl)ferrocene and its butadiyne-bridged dimer. (C) 2004 Elsevier B.V. All rights reserved.