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Monosubstituted cobaltocene cationic derivative and high-efficiency preparation method

A cobaltocene and single-substitution technology, which is applied in chemical instruments and methods, metallocenes, organic chemistry, etc., can solve the problems of few reports on cobaltocene derivatives, achieve simple and fast post-treatment, high reaction efficiency, Simple and easy to operate effect

Inactive Publication Date: 2018-08-10
NORTHWESTERN POLYTECHNICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to synthetic challenges, monosubstituted cobaltocene derivatives have rarely been reported
In particular, there are almost no reports on cobaltocene derivatives substituted by various functional groups.

Method used

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  • Monosubstituted cobaltocene cationic derivative and high-efficiency preparation method
  • Monosubstituted cobaltocene cationic derivative and high-efficiency preparation method
  • Monosubstituted cobaltocene cationic derivative and high-efficiency preparation method

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0038] The preparation method of two kinds of compounds represented by general formula I, according to figure 1 The compound reacts according to the specified route to obtain one of the following general formulas:

[0039]

[0040] In the reaction, R=-C 12 h 25 ,-C 14 h 29 ,-C 16 h 33 ,-(CH 2 ) 11 OOC (C 5 h 5 ) 2 Fe,-(CH 2 ) 2 OH; R'=-CH 2 C(CH 2 Oh) 2 CH 2 -, -C 12 h 24 -, TMS means trimethylsilyl.

Embodiment 1

[0041] Embodiment 1: when R=-C 12 h 25 preparation of

[0042] Dissolve 2.32 mmol of trimethylsilyl-protected alkynyl cobaltocene cobalt hexafluorophosphate and 1.06 mmol of bis-azido-neopentyl glycol in 20 mL of anhydrous acetonitrile, and deoxygenate with nitrogen for 30 min; at the same time, in another round-bottomed flask Add 0.2mmol cuprous iodide (CuI) to the solution, pass nitrogen gas to remove oxygen for 30min; then transfer the acetonitrile solution to the flask of CuI under the protection of nitrogen, add 10.6mmol finely ground anhydrous potassium carbonate after 5min, and protect it under nitrogen at 40°C Under reaction 24h. The reacted suspension was filtered, rinsed with acetonitrile, and then concentrated by rotary evaporation. The concentrated solution was added dropwise to absolute ethanol, and the precipitate was collected and dried in a vacuum oven for 24 hours to obtain 81% of compound I-1.

[0043] 1 H NMR (d 6 -DMSO, δ / ppm) 3.28 (m, 4H), 4.54 (s, 4H...

Embodiment 2

[0049] Embodiment 2, the R=-C 14 h 29 When the preparation

[0050] Dissolve 3.262 mmol of trimethylsilyl-protected alkynyl cobaltocene cobalt hexafluorophosphate and 2.965 mmol of 1-azidodecane in 20 mL of anhydrous acetonitrile, and deoxygenate with nitrogen for 30 min; at the same time, in another round-bottomed flask Add 0.6mmol cuprous iodide (CuI), pass nitrogen gas to remove oxygen for 30min; then transfer the acetonitrile solution to the flask of CuI under nitrogen protection, add 29.6mmol finely ground anhydrous potassium carbonate after 5min, at 40°C under nitrogen protection Reaction 24h. After the reaction, the suspension was filtered, rinsed with acetonitrile, and then concentrated by rotary evaporation. The concentrated solution was added dropwise to anhydrous ether, and the precipitate was collected and dried in a vacuum oven for 24 hours to obtain 80% of compound I-2.

[0051] 1 H NMR (d 6 -DMSO,δ / ppm)0.86(t,3H),1.22(m,18),1.86(t,2H),4.42(t,2H),5.67(s,5H),...

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Abstract

The invention relates to a monosubstituted obaltocene cationic derivative and a high-efficiency preparation method. The preparation process is completed in one step by a one-pot method; an expensive catalyst is not needed; the operation is simple, easy and feasible; the reaction condition is mild; the reaction efficiency is high; the column separation is not needed; the post treatment is simple, convenient and quick, and the target monosubstituted obaltocene cationic derivative can be applied to the fields of novel surfactants, novel polyelectrolyte materials, antibacterial materials and fuel-cell diaphragms, and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, especially the technical field of organometallic chemistry, and relates to a monosubstituted cobaltocene cobalt cation derivative and a high-efficiency preparation method. Background technique [0002] Metallocene derivatives are widely used in electrochemical sensing, catalysts, biomedicine and other fields. Unlike conventional neutral ferrocenes, the most stable state of cobalt-ferrocenes is usually cobalt-ferrocene cations carrying a positive charge. However, monosubstituted cobaltocene derivatives have rarely been reported due to synthetic challenges. In particular, there are few reports on cobaltocene derivatives substituted by various functional groups. The ionic cobaltocene cation is easily adsorbed on silica gel, and its separation and purification has always been one of the difficult problems in this field. The present invention designs and synthesizes a series of derivatives containi...

Claims

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Application Information

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IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 闫毅颜静李学装张雪黄慧雅
Owner NORTHWESTERN POLYTECHNICAL UNIV
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