2,5-diferrocenylbenzo-1,4-quinone | 738580-53-5

• 英文名称: 2,5-diferrocenylbenzo-1,4-quinone
• 英文别名: 2,5-diferrocenylquinone
• CAS: 738580-53-5
• 化学式: C₂₆H₂₀Fe₂O₂
• 分子量: 476.138
• InChiKey: HRJNWNDHCPCHHQ-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

• 作为产物：
  描述：

  二茂铁乙炔 、 一氧化碳 以 正己烷 为溶剂， 以53%的产率得到2,5-diferrocenylbenzo-1,4-quinone
  参考文献：
  名称：

  Photochemical Reactions of Fe(CO)₅ with Monometal Alkynyls and Free Alkynes:  Synthesis and Characterization of [(η⁵-C₅Me₅)Fe₂Mo(CO)₇{μ₃-η¹:η⁴:η²- C(H)C(Ph)C(Ph)C}] and Diferrocenylquinones

  摘要：

  Photolysis of a benzene solution containing Fe(CO)(5) and [(eta(5)-C5R5)Mo(CO)(3)(Cequivalent toCPh)] yielded mixed-metal clusters [(eta(5)-C5R5)Fe2Mo(CO)(8)(mu(3)-eta(1):eta(2)-CCPh)] (R = H, 1; Me, 2) and [(eta(5)-C5H5)Fe3Mo(CO)(11)(mu(4)-eta(1):eta(1):eta(2):eta(1)-CCPh)] (3). When a mixture of [(eta(5)-C5Me5)Mo(CO)(3)(Cequivalent toCPh)], Fe(CO)(5), and phenylacetylene was photolyzed, coupling of the acetylide and acetylene was observed and the mixed-metal cluster [(eta(5)-C5Me5)Fe2Mo(CO)(7)(mu(3)-eta(1):eta(4):eta(2)-C(H)C(Ph)C(Ph)C)] (4) was obtained. Interestingly, use of a bulky substituent on the free acetylene in the reaction mixture did not produce analogues of 4. Reaction of Fe(CO)(5) with ferrocenylacetylene produced three different compounds, tetracarbonyl(2-ferrocenylmaleoyl)iron (5), 2,5-diferrocenylquinone (6), and 2,6-diferrocenylquinone (7). All new compounds were characterized by IR and H-1 and C-13 NMR spectroscopy. Structures of 2-7 were established crystallographically.

  DOI：

  10.1021/om049739y

文献信息

• One pot synthesis of maleimide and hydantoin by Fe(CO)5 catalyzed [2 + 2 + 1] co-cyclization of acetylene, isocyanate and CO
  作者：Pradeep Mathur、Raj Kumar Joshi、Dhirendra Kumar Rai、Badrinath Jha、Shaikh M. Mobin

  DOI：10.1039/c2dt11942k

  日期：——

  In the presence of a catalytic amount of Fe(CO)5, terminal acetylenes, isocyanates and CO undergo [2 + 2 + 1] cyclization to form substituted maleimides and hydantoins; when internal alkynes are used, exclusive maleimide formation is observed. While the maleimides can be obtained as the major products, in up to 90% yield, when the reaction is carried out in CO atmosphere, in absence of CO, the hydantoins are formed in up to 87% yield. Formation of maleimides has been shown to occur via the formation of a ferrole intermediate, whereas the hydantoins are proposed to form through successive insertion of isocyanate into the iron–acetylide bond. All compounds were characterized by spectroscopic methods and molecular structures of some compounds were established by single crystal X-ray diffraction method.

  在催化量的Fe(CO)5存在下，末端炔烃、异氰酸酯和CO发生[2 + 2 + 1]环化反应形成取代的马来酰亚胺和氢腺嘌呤；当使用内烯炔时，观察到只形成马来酰亚胺。虽然在CO气氛中进行反应时，马来酰亚胺可以作为主要产物获得，产率高达90%，但在没有CO的情况下，氢腺嘌呤的产率可达87%。已显示马来酰亚胺的形成通过形成铁酰基中间体进行，而氢腺嘌呤则被提议通过异氰酸酯逐步插入到铁-炔基键中形成。所有化合物均通过光谱方法进行表征，部分化合物的分子结构通过单晶X射线衍射方法建立。
• Photochemical reactions of 1-ferrocenyl-4-phenyl-1,3-butadiyne with Fe(CO)5 and CO
  作者：Pradeep Mathur、Radhe Shyam Ji、Sathyanarayana Boodida、Amrendra K. Singh、Shaikh M. Mobin

  DOI：10.1016/j.jorganchem.2010.05.004

  日期：2010.8

  products: [Fe(CO)2η2:η2-PhCCCC(Fc)C(CCPh)C(Fc)Fe(CO)3}-μ-CO] (1), [Fe2(CO)6μ-η1:η1:η2:η2-PhCCCC(Fc)–C(O)–C(Fc)CCCPh}] (2), [Fe2(CO)6μ-η1:η1:η2:η2-FcCC(CC Ph)–C(O)–C(Fc)CCCPh}] (3), [Fe2(CO)6μ-η1:η1:η2:η2-FcCCCC(Fc)–C(O)–C(Fc)CCCPh}] (4), [Fe(CO)3μ-η2: η2-[FcCC(CCPh)C(CCPh)C(Fc)}CO] (5) and [Fe(CO)3μ-η2: η2-[FcCC(CCPh)C(CCPh)C(Fc)}CO] (6) formed by coupling of acetylenic moieties with CO insertion

  的[Fe（CO）：含有ironpentacarbonyl，1-二茂铁基-4-苯基-1,3-丁二炔在低温下的产率六个新产品的己烷溶液光解2 η 2：η 2 -PhC CCC（FC）C（C CPH）C（Fc）的铁（CO）3 }-μ-CO] （1） ，的[Fe 2（CO）6 μ-η 1：η 1：η 2：η 2 -PhC CCC（FC）-C （O）-C（Fc）的CC器CPh}]（2），的[Fe 2（CO）6 μ-η 1：η 1：η 2：η 2 -FcCC（C ℃pH值）-C（O） -碳（Fc）CC器CPh}]（3），的[Fe 2（CO）6 μ-η 1：η 1：η 2：η 2 -FCC CCC（FC）-C（O）-C（Fc）的CC器CPh}]（4），的[Fe（CO）3 μ-η 2：η 2 - [FCCC（C器CPh）C（C CPH）C（Fc）的} CO]（5）和[铁（CO）3 μ-η 2：η
• Photochemical reactions of Fe(CO)5 with FcCCH in the presence of S-powder and CS2: Synthesis and characterization of [{μ-SC(H)C(Fc)S}(CO)6Fe2], [μ-SC(O)C(H)C(Fc)S}(CO)6Fe2]; cis-[μ-η1:η2:η1:η1-{C(Fc)C(H)CS2C(H)C(Fc)}(CO)6Fe2] and trans -[μ-η1:η2:η1:η1-{C(Fc)C(H)CS2C(Fc)C(H)}(CO)6Fe2]
  作者：Pradeep Mathur、Vinay K. Singh、Amrendra K. Singh、Shaikh M. Mobin、Carsten Thöne

  DOI：10.1016/j.jorganchem.2006.04.016

  日期：2006.7

  ferrocenylacetylene and S-powder under argon at −30 °C led to the formation of two different products: [μ-SC(H)C(Fc)S}(CO)6Fe2] (1) and [μ-SC(O)C(H)C(Fc)S}(CO)6Fe2] (2) featuring new C–S, C–C, Fe–Fe and Fe–S bond formations. In presence of CS2, formation of cis-[μ-η1:η2:η1:η1-C(Fc)C(H)CS2C(H)C(Fc)}(CO)6Fe2] (5) and trans-[μ-η1:η2:η1:η1-C(Fc)C(H)CS2C(Fc)C(H)}(CO)6Fe2] (6) was observed, along with 1. All

  含Fe（CO）5，二茂铁乙炔和S-粉末的己烷溶液在氩气下在-30°C下光解导致形成两种不同的产物：[μ-SC（H）C（Fc）S}（CO）6 Fe 2 ]（1）和[μ-SC（O）C（H）C（Fc）S}（CO）6 Fe 2 ]（2）具有新的C–S，CC–，Fe–Fe和Fe-S键的形成。在CS的存在2，的形成顺式- [μ-η 1：η 2：η 1：η 1 - C（Fc）的C（H）CS 2 C（H）C（FC）}（CO）6的Fe 2 ]（5）和反- [μ-η 1：η 2：η 1：η 1 - （FC）（H）CS C C 2 C（Fc）的C（H）}（CO）6的Fe 2 ]（6中观察到的），沿与1。所有新化合物均通过IR和1 H和13 C NMR光谱进行表征。的结构1，2，5和6进行了结晶学确定。
• Synthesis, structure and electrochemistry of CO incorporated diruthenium metallacyclic compounds [Ru2(CO)6{μ-η1:η1:η2:η2-1,4-Fc2C5H2O}] and [Ru2(CO)6{μ-η1:η1:η2:η2-1,5-Fc2C5H2O}]
  作者：Pradeep Mathur、Saurav Chatterjee、Atanu Das、Goutam K. Lahiri、Somnath Maji、Shaikh M. Mobin

  DOI：10.1016/j.jorganchem.2006.12.017

  日期：2007.3

  Ferrocenyl substituted ruthenium metallacyclic compounds, [Ru-2(CO)(6)mu-eta(1) :eta(1)eta(2):eta(2)-1,4-Fc(2)C(5)H(2)O}] (1) and [Ru-2(CO)(6)-mu-eta(1):eta(1):eta(2):eta(2)-1,5-Fc(2) C5H2O}] (2) have been synthesized and structurally characterized. Electrochemical studies for 1 and 2 and the respective quinone derivatives 3 and 4 show weak to no electrochemical coupling at the mixed-valent intermediate state which is dependent on the complex frameworks. (c) 2006 Elsevier B.V. All rights reserved.