cyclopenta-1,3-diene;iron(2+);[2,3,4,5-tetrakis[2-(4-methylphenyl)ethynyl]cyclopenta-1,3-dien-1-yl]methanol | 827343-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cyclopenta-1,3-diene;iron(2+);[2,3,4,5-tetrakis[2-(4-methylphenyl)ethynyl]cyclopenta-1,3-dien-1-yl]methanol
• CAS: 827343-16-8
• 化学式: C₄₇H₃₆FeO
• 分子量: 672.649
• InChiKey: DSFSPCPOMBUBJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.13
• 重原子数：
  49
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyclopenta-1,3-diene;iron(2+);[2,3,4,5-tetrakis[2-(4-methylphenyl)ethynyl]cyclopenta-1,3-dien-1-yl]methanol 、 (1-重氮基-2-氧代丙基)膦酸二甲酯 在 1,10-菲罗啉 、 偶氮二甲酸二叔丁酯 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以62%的产率得到cyclopenta-1,3-diene;1-[2-[2-ethynyl-3,4,5-tris[2-(4-methylphenyl)ethynyl]cyclopenta-1,4-dien-1-yl]ethynyl]-4-methylbenzene;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：

  cyclopenta-1,3-diene;[2-ethynyl-3,4,5-tris[2-(4-methylphenyl)ethynyl]cyclopenta-1,4-dien-1-yl]methanol;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94%的产率得到cyclopenta-1,3-diene;iron(2+);[2,3,4,5-tetrakis[2-(4-methylphenyl)ethynyl]cyclopenta-1,3-dien-1-yl]methanol
  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