1,1'-bis(propanoyl)ferrocene | 1274-01-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1'-bis(propanoyl)ferrocene
• 英文别名: 1,1'-dipropionylferrocene；1,1'-dipropanoylferrocene；1-cyclopenta-1,4-dien-1-ylpropan-1-one;iron(2+)
• CAS: 1274-01-7
• 化学式: C₁₆H₁₈FeO₂
• 分子量: 298.165
• InChiKey: HBGDLPSHKMBSQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1'-bis(propanoyl)ferrocene 生成 1,1'-bis(hydroxypropyl)ferrocene
  参考文献：
  名称：

  外消旋 2,2'-二烷基-Sila[1]二茂铁的聚合：使用模型化合物通过 29Si NMR 光谱进行 DFT 辅助聚合物分析

  摘要：

  所描述的研究旨在制备外消旋的、C 2对称的硅[1]二茂铁，其2,2'-位上带有烷基，以补充其已知的对映体纯对应物。作为合成方法，选择众所周知的Ugi 胺化学将平面手性引入二茂铁骨架中。该多步骤过程中的挑战是通过 LiAlH 4或 NaBH 4还原 1,1'-二烷酰基二茂铁获得的外消旋和内消旋二醇混合物的分离。在三个测试的烷酰基中，只有一个导致显着过量的外消旋二醇，其可以通过结晶分离并转化为外消旋-2,2'-二异丁基-二甲基硅[1]二茂铁。这种新单体的热开环聚合产生了由两种类型的二元组组成的聚（二茂铁基硅烷），如其29 Si NMR 谱中以 -5.66 和 -7.74 ppm 为中心的两组峰所示。29 Si NMR 化学位移可以通过平面手性双（二茂铁基）二甲基硅烷的密度泛函理论（DFT）方法来预测，该方法用于模拟聚合物的这些内消旋和外消旋二元组。这些计算真实地预测外消旋二元组的硅原子比内消旋

  DOI：

  10.1021/acs.organomet.3c00351
• 作为产物：
  描述：

  二茂铁 、 丙酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到1,1'-bis(propanoyl)ferrocene
  参考文献：
  名称：

  A convenient synthesis of E-alkenylferrocenes

  摘要：

  Alkenylferrocenes, FcCHCHR [R = (CH2)(n)CH3, n = 0-4], and 1,1 ' -bisalkenylferrocenes, Fc(CHCHR)(2) (R = CH3, CH2CH3) were synthesized by elimination reaction from the corresponding alpha -hydroxyferrocenylalkanes using methanesulfonylchloride and triethylamine. (C) 2001 Elsevier science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00862-2

文献信息

• Synthesis of ferrocene-based phosphine ligands via Cu-catalyzed reductive coupling of ferrocenyl ketone-derived tosylhydrazones and H -phosphorus oxides
  作者：Li Ling、Jianfeng Hu、Yanhong Huo、Hao Zhang

  DOI：10.1016/j.tet.2016.11.054

  日期：2017.1

  Ferrocene-based phosphine oxides with various substituents at phosphorous atoms were synthesized by Cu-catalyzed reductive coupling of ferrocenyl ketone-derived tosylhydrazones and H-phosphorus oxides. Followed by the reduction of ferrocene-based phosphine oxides, 1-substituted ferrocene-based phosphine ligand 7 and 1,1'-disubstituted ferrocene-based phosphine ligand 9 were obtained. Josiphos type ligand 8 were produced after ortho-lithiation of 7 and trapping with chlorodiphenyl phosphine or chlorodicyclohexylphosphine. (C) 2016 Elsevier Ltd. All rights reserved.
• Efficient Synthesis of Ferrocenylquinolines via the Friedländer Reaction
  作者：Yuhua Long、Haifeng Zhang、Dingqiao Yang

  DOI：10.1080/00397911.2010.519090

  日期：2013.1.1

  Acylferrocenes 2a-c reacted with ortho-aminoarylaldehydes 1a-e via the Friedlander condensation reaction to afford the corresponding ferrocenylquinolines 3a-o in moderate yields in the presence of sodium ethoxide (30 mmol%) under mild reaction conditions. Under the same reaction conditions, 1,1'-diacetylferrocene 2d and 1,1'-dipropionylferrocene 2e reacted with ortho-aminoaldehydes 1a-e to afford the corresponding 1,1'-bis(substituted quinolin-2-yl) ferrocene derivatives 3p-t. The structures of compounds 3a-t were determined and characterized by infrared, H-1 NMR, mass spectrometry, and elemental analysis. The crystal structures of 3e and 3q were determined by x-ray crystallography.
• Improvement of ferrocene acylation. Conventional vs. microwave heating for scandium-catalyzed reaction in alkylmethylimidazolium-based ionic liquids
  作者：Serena Berardi、Valeria Conte、Giulia Fiorani、Barbara Floris、Pierluca Galloni

  DOI：10.1016/j.jorganchem.2008.06.022

  日期：2008.9

  Acylation of ferrocene-catalyzed by scandium triflate was thoroughly investigated. Reaction time and temperature are important parameters, in that prolonged treatment causes substrate decomposition and/or catalyst deactivation. Hydrophobic alkylmethylimidazolium-based solvents gave best results, in particular 1-butyl-3-methylimidazolium bis(trifluorometansulfonyl) imide. Anhydrides behave as superior acylating reagents with respect to acyl chlorides. MW irradiation allowed to quantitatively acylate ferrocene within minutes. (C) 2008 Elsevier B. V. All rights reserved.
• A convenient synthesis of E-alkenylferrocenes
  作者：Walther G Jary、Arnulf-Kai Mahler、Thomas Purkathofer、Judith Baumgartner

  DOI：10.1016/s0022-328x(01)00862-2

  日期：2001.6

  Alkenylferrocenes, FcCHCHR [R = (CH2)(n)CH3, n = 0-4], and 1,1 ' -bisalkenylferrocenes, Fc(CHCHR)(2) (R = CH3, CH2CH3) were synthesized by elimination reaction from the corresponding alpha -hydroxyferrocenylalkanes using methanesulfonylchloride and triethylamine. (C) 2001 Elsevier science B.V. All rights reserved.