Chain polyacetylene compound and preparation method and application thereof

A compound and chain-like technology, applied in the fields of organic chemistry and metalorganic chemistry, to achieve the effects of controllable structure, efficient acquisition, and simple synthesis method

Active Publication Date: 2017-01-04
XIAMEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the problem of directly synthesizing metal heterocondensed ring compounds by pincer ligands, the present inventio

Method used

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  • Chain polyacetylene compound and preparation method and application thereof
  • Chain polyacetylene compound and preparation method and application thereof
  • Chain polyacetylene compound and preparation method and application thereof

Examples

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preparation example Construction

[0070] According to the second aspect of the present invention, the present invention provides the preparation method of above-mentioned chain polyyne compound, when R 3 For hydrogen, the method includes:

[0071] Compound shown in formula II and organometallic reagent RM 1 and / or RM 2 Z carries out the metal exchange reaction in the aprotic solvent, and the obtained reaction mixture is contacted with the compound shown in the formula III to obtain the chain polyyne compound protected by the Y group shown in the formula IV; then the compound shown in the formula IV The chain-like polyyne compound of the Y group protection shown carries out deprotection group treatment, obtains the chain-like polyyne compound shown in formula I:

[0072]

[0073] in,

[0074] Y is a protecting group used to protect an alkynyl group, and Y can be any one of TMS (trimethylsilyl), TES (triethylsilyl) and TIPS (triisopropylsilyl). X, R 1 , m and n are the same as above.

[0075] The organo...

Embodiment 1

[0098] This example is used to prepare the chain polyyne compound provided by the present invention.

[0099]

[0100] Among them, TMS stands for trimethylsilyl. EtMgBr is ethylmagnesium bromide (purchased from Bailingwei Technology Co., Ltd., trade name is 248474), (Trimethylsilylpropynaldehyde, purchased from Bailingwei Technology Co., Ltd., the trade name is 2975-46-4), (n-Bu) 4 NF (tetra-n-butylammonium fluoride, purchased from Bailingwei Technology Co., Ltd., the trade name is A10588).

[0101] (1) Preparation of compound 1

[0102] Under nitrogen atmosphere, under magnetic stirring, 1,6-heptadiyne (5.0mL, 4.02g, 43.63mmol, purchased from Aladdin Reagents (Shanghai) Co., Ltd., trade name H102744-25mL) was dissolved in 100mL THF , cooled to 0°C, added ethylmagnesium bromide solution (1.0M tetrahydrofuran solution, 43.6mL, containing 43.60mmol ethylmagnesium bromide) dropwise, added within 1h, reacted at room temperature for 1h and then cooled to 0 ℃, quickly added ...

Embodiment 2

[0110] This example is used to prepare the chain polyyne compound provided by the present invention.

[0111]

[0112] Wherein, n-BuLi is n-butyllithium (purchased from Bailingwei Technology Co., Ltd., the trade name is 913796).

[0113] (1) Preparation of Compound 3

[0114] Under nitrogen atmosphere, under magnetic stirring, 2,2-dimethyl propargylmalonate (5.00g, 24.0mmol, synthesized according to the document J.Am.Chem.Soc.2013,135,8133.) Dissolve in 200mL tetrahydrofuran, cool to -78°C, add n-butyllithium (2.2M tetrahydrofuran solution, 10.90mL, containing 24.0mmol n-butyllithium) dropwise, add within 1h, react at -78°C for 15min , added trimethylsilylpropynal (3.52mL, 24.0mmol) dropwise, and continued the reaction for 2h. After the reaction, quenched with saturated ammonium chloride solution, extracted with ether, combined the organic phases, dried over anhydrous magnesium sulfate, and filtered , concentrated, and silica gel column chromatography (eluent: n-hexane / et...

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Abstract

The invention relates to the fields of organic chemistry and metal organic chemistry, and discloses a chain polyacetylene compound, a preparation method of the compound, and an application of the compound to prepare a metal fused heterocyclic compound. The provided chain polyacetylene compound has the structure shown in the formula I. The invention further discloses a preparation method of the chain polyacetylene compound and an application of the chain polyacetylene compound to synthesize the metal fused heterocyclic compound. The chain polyacetylene compound contains multiple functional groups, is controllable in structure, and can be directly used to synthesize the metal fused heterocyclic compound with high efficiency. The chain polyacetylene compound is simple in synthetic method and can be fast effectively obtained.

Description

technical field [0001] The invention relates to the fields of organic chemistry and organometallic chemistry, in particular to a chain polyyne compound, its preparation method and its application in the preparation of metal heterocondensed ring compounds. Background technique [0002] Pincer ligands refer to a class of compounds with a structure similar to ECE (E, C are any atoms that can coordinate with metals). This concept was first proposed in the 1970s. Due to the good stability, reactivity and stereoselectivity of the chelate formed by the coordination of pincer ligands and metals, it is widely used in the fields of coordination chemistry, organic synthesis, homogeneous catalysis and material chemistry (Angew. Chem. Int. Ed. 2001, 40, 3750-3781). In recent years, pincer ligands and metal complexes have not only played an important role in C-C coupling reactions, activation of inert chemical bonds, etc., but also have important applications in optoelectronic materials,...

Claims

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Application Information

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IPC IPC(8): C07D333/24C07F7/08C07F15/00C07C215/24C07C247/08C07C29/00C07C33/04C07C67/317C07C69/732C07C41/18C07C43/178C07C41/26C07C67/31C07C303/40C07C311/17
CPCC07D333/24C07C29/00C07C33/04C07C67/317C07C69/732C07C41/18C07C43/178C07C43/1782C07C41/26C07C67/31C07C303/40C07C311/17
Inventor 夏海平卓庆德林剑锋周小茜陈志昕邵一凡张弘何旭敏
Owner XIAMEN UNIV
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