cyclopenta-1,3-diene;2-[2-(1,3-dioxan-2-yl)-3-ethynylcyclopenta-1,4-dien-1-yl]-1,3-dioxane;iron(2+) | 827343-03-3

• 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: cyclopenta-1,3-diene;2-[2-(1,3-dioxan-2-yl)-3-ethynylcyclopenta-1,4-dien-1-yl]-1,3-dioxane;iron(2+)
• CAS: 827343-03-3
• 化学式: C₂₀H₂₂FeO₄
• 分子量: 382.239
• InChiKey: URUBVPZHVABCTK-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

• 作为反应物：
  描述：

  cyclopenta-1,3-diene;2-[2-(1,3-dioxan-2-yl)-3-ethynylcyclopenta-1,4-dien-1-yl]-1,3-dioxane;iron(2+) 、 4-碘甲苯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 作用下， 以 further solvent(s) 为溶剂， 以99%的产率得到cyclopenta-1,3-diene;2-[2-(1,3-dioxan-2-yl)-3-[2-(4-methylphenyl)ethynyl]cyclopenta-1,4-dien-1-yl]-1,3-dioxane;iron(2+)
  参考文献：
  名称：

  Synthesis of the first pentaethynylferrocene derivatives

  摘要：

  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.

  DOI：

  10.1016/j.jorganchem.2004.05.006
• 作为产物：
  描述：

  2,3-bis(1,3-dioxan-2-yl)cyclopenta-2,4-diene-1-carbaldehyde;cyclopenta-1,3-diene;iron(2+) 、 (1-重氮基-2-氧代丙基)膦酸二甲酯 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以86%的产率得到cyclopenta-1,3-diene;2-[2-(1,3-dioxan-2-yl)-3-ethynylcyclopenta-1,4-dien-1-yl]-1,3-dioxane;iron(2+)
  参考文献：
  名称：

  Synthesis of the first pentaethynylferrocene derivatives

  摘要：

  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.

  DOI：

  10.1016/j.jorganchem.2004.05.006