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Styrenic quaternary carbon compound and preparation method thereof

A technology of styrene and carbon compounds, which is applied in the preparation of organic compounds, the production of hydrocarbons from oxygen-containing organic compounds, and the production of hydrocarbons from halogen-containing organic compounds, etc. problems such as poor adaptability to animals, to achieve the effects of low price, good adaptability and mild conditions

Active Publication Date: 2017-04-26
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the high activity of R-MX, the storage and reaction conditions are harsh (anhydrous, oxygen-free and low temperature), prone to side reactions (such as β-hydrogen elimination), and poor substrate adaptability (such as raw materials containing 2-position OR groups difficult to prepare), which greatly limits its practicality

Method used

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  • Styrenic quaternary carbon compound and preparation method thereof
  • Styrenic quaternary carbon compound and preparation method thereof
  • Styrenic quaternary carbon compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0019] Example 1: 1-(4,4-Dimethyloctyl-1-en-2-yl)-4-(trifluoromethyl)benzene

[0020] 1-(4,4-dimethyloct-1-en-2-yl)-4-(trifluoromethyl)benzene

[0021]

[0022] Add Zn powder (0.9mmol, 300%), ligand 2,6-bis-(4-isopropyl-4,5-dihydrooxazol-2-yl) in a dry Schlenk reaction flask equipped with magnetons Pyridine (iPr-box, 0.045mmol, 15%), MgCl 2 (0.3 mmol, 100%). Cover the rubber stopper and repeatedly evacuate and flush nitrogen three times, then add nickel bromide ethylene glycol dimethyl ether (NiBr 2 .Glyme, 0.03mmol, 10%), then inject solvent N, N-dimethylacetamide (DMA, 1ml), carbonic acid 2-(4-substituted phenyl) allyl methyl ester (methyl(1-(4 -(trifluoromethyl)phenyl)vinyl)carbonate, liquid, 0.6mmol, 200%), tertiary halogenated hydrocarbon (2-bromo-2-methylhexane, liquid, 0.3mmol, 100%), pyridine (0.09mmol, 30%) . The reaction was stirred at 20-25 °C for 8-12 h under the protection of nitrogen. After the reaction, the target product (63.0mg, 0.222mmol, 74% yield) ...

example 2

[0024] Example 2: (4,4-Dimethyloctyl-1-en-2-yl)benzene

[0025] (4,4-dimethyloct-1-en-2-yl)benzene

[0026]

[0027] Add Zn powder (0.9mmol, 300%), ligand 2,6-bis-(4-isopropyl-4,5-dihydrooxazol-2-yl) into a Schlenk reaction bottle equipped with magneton drying Pyridine (iPr-box, 0.045mmol, 15%), MgCl 2 (0.3 mmol, 100%). Cover the rubber stopper and repeatedly evacuate and flush nitrogen three times, then add nickel bromide ethylene glycol dimethyl ether (NiBr 2 .Glyme, 0.03mmol, 10%), inject solvent DMA (1ml) then, carbonic acid 2-(4-substituted phenyl) allyl methyl ester (methyl(1-phenylvinyl)carbonate, liquid, 0.6mmol, 200%) , tertiary haloalkane (2-bromo-2-methylhexane, liquid, 0.3mmol, 100%), pyridine (0.09mmol, 30%). The reaction was stirred at 20-25 °C for 8-12 h under the protection of nitrogen. After the reaction, the target product (55.1 mg, 0.255 mmol, 85% yield) was directly obtained by column chromatography.

[0028] The product is a colorless oily liquid....

example 3

[0029] Example 3: 3,3-Dimethyl-5-phenylhexyl-5-en-1-ylbenzoate

[0030] 3,3-dimethyl-5-phenylhex-5-en-1-yl benzoate

[0031]

[0032] Add Zn powder (0.9mmol, 300%), ligand 2,6-bis-(4-isopropyl-4,5-dihydrooxazol-2-yl) into a Schlenk reaction bottle equipped with magneton drying Pyridine (iPr-box, 0.045mmol, 15%), MgCl 2 (0.3 mmol, 100%). Cover the rubber stopper and repeatedly evacuate and flush nitrogen three times, then add nickel bromide ethylene glycol dimethyl ether (NiBr 2 .Glyme, 0.03mmol, 10%), then inject solvent DMA (1ml), carbonic acid 2-(4-substituted phenyl) allyl methyl ester (methyl(1-phenylvinyl)carbonate, 0.6mmol, liquid, 200%) , Tertiary halogenated alkanes (3-bromo-3-methylbutyl benzoate, liquid, 100%), pyridine (0.09mmol, 30%). The reaction was stirred at 20-25 °C for 8-12 h under the protection of nitrogen. After the reaction, the target product (78.5mg, 0.255mmol, 85% yield) was directly separated by column chromatography.

[0033] The product is ...

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Abstract

The invention relates to a styrenic quaternary carbon compound and a preparation method thereof. The general structural formula of the styrenic quaternary carbon compound is (img file='dest_path_image002. TIF'wi='86'he='122' / ), wherein R1 is C1-C8 alkyl chain or aromatic group and R2 is the substituent group of OMe and CF3. The reaction of the styrenic quaternary carbon compound and the preparation method thereof is the catalytic-reduction coupled reaction of metallic nickel, wherein the reducing agent is the environmentally friendly Zn powder and the catalyst is nickel bromide glycol dimethyl ether (NiBr2. glyme) which has the advantage of low cost and stable valence. The reaction condition has the advantages of being mild, being simple to operate, having good acceptability for functional groups and higher productivity as well as producing no-isomerized by-products of tertiary halogenated substrates.

Description

technical field [0001] The invention relates to a styrene quaternary carbon compound and a preparation method thereof, in particular to a nickel-catalyzed tertiary halogenated alkane reductive coupling to construct a C(sp 3 )-C(sp 3 ) Quaternary carbon compounds and preparation methods thereof. Background technique [0002] Carbon-carbon bond is the most basic chemical bond in chemistry. The development of carbon-carbon bond formation methods promotes the development of organic synthetic chemistry. Therefore, how to efficiently construct new carbon-carbon bonds is particularly important, and more importantly, It has attracted the attention of countless scientific researchers. The discovery and application of a series of classic carbon-carbon bond formation reactions such as Wittig reaction, Diels-Alder reaction and Grignard reaction have played a pivotal role in organic synthesis. In recent decades, with the vigorous development of transition metal-catalyzed organic react...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/293C07C41/30C07C69/78C07C43/215C07C17/263C07C22/08C07C1/26C07C1/20C07C15/50
CPCC07B2200/07C07C1/20C07C1/26C07C15/50C07C17/263C07C22/08C07C41/30C07C43/215C07C67/293C07C69/78Y02P30/20Y02P30/40
Inventor 钱群虞盈盈贾霄龚和贵王洪宇
Owner SHANGHAI UNIV
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