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Novel method for preparing allene by cesium hydroxide catalysis

A cesium hydroxide and allene technology, applied in the field of green catalytic synthesis, achieves the effects of wide source of raw materials, high reaction selectivity and yield, and simple experimental operation

Inactive Publication Date: 2015-10-14
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are no published documents and patent applications about the preparation of allenes by cesium hydroxide catalysis at home and abroad.

Method used

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  • Novel method for preparing allene by cesium hydroxide catalysis
  • Novel method for preparing allene by cesium hydroxide catalysis

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0017] P-nitrophenyl propargyl ether was added to a 10 mL reaction tube, cesium hydroxide (0.2 eq) was added, and 1 mL of acetonitrile was added dropwise, and the reaction was carried out at 20° C. for 0.5 h. After the reaction, the target compound was separated by column chromatography to obtain a yellow solid with a yield of 97%.

preparation example 2

[0019] Phenyl propargyl ether was added to a 10 mL reaction tube, cesium hydroxide (0.4 eq) was added, 1 mL of tetrahydrofuran was added dropwise, and the reaction was carried out at 40° C. for 1 h. After the reaction, the target compound was separated by column chromatography to obtain a colorless liquid with a yield of 94%.

preparation example 3

[0021] P-methoxyphenyl propargyl ether was added to a 10 mL reaction tube, cesium hydroxide (0.2 eq) was added, and 1 mL of acetonitrile was added dropwise, and the reaction was carried out at 30° C. for 3 h. After the reaction, the target compound was separated by column chromatography to obtain a colorless liquid with a yield of 98%.

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Abstract

A compound containing an allene group is an important component in organic chemistry research and some compounds containing allene groups are important component units of drugs. Functionalized allene has wide antibacterial properties, cytotoxicity and enzyme inhibition activity. The method utilizes cesium hydroxide as a catalyst, utilizes an oxygen-containing nitrogenous terminal alkyne compound as a reaction raw material, is free of a nitrogen atmosphere and can realize high-yield reaction of a series of allene compounds in the presence of a polar solvent. The method has the advantages of low cost, simple processes and no pollution and has a certain feasibility in industrial production. The method provides a cheap and green approach for allene preparation.

Description

【Technical field】 [0001] The invention belongs to the field of catalytic organic synthesis, in particular to a green catalytic synthesis method using cesium hydroxide as a catalyst. The method uses nitrogen-containing and oxygen-containing terminal alkynes as raw materials, and the reaction can obtain allene compounds with higher yields in an organic solvent. 【Background technique】 [0002] Allene refers to a class of compounds containing 1,2-propadiene functional groups. Among the three carbon atoms of the allene functional group, the two terminal sp 2 The remaining unhybridized p-orbital of the hybridized carbon atom overlaps with the two mutually perpendicular p-orbitals of the sp hybridized carbon atom in the middle to form two mutually perpendicular π-orbitals, which makes the three carbon atoms have different electron cloud densities. When different functional groups are attached to the allene, under the influence of substituent group steric hindrance, electronic ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B35/08C07C205/37C07C201/12C07C43/205C07C41/32C07C43/225C07C47/575C07C45/67C07C43/20C07D209/08C07D209/30C07C233/07C07C233/15C07C231/14
Inventor 邱仁华李游许新华陈锦杨王勰龙进国
Owner HUNAN UNIV
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