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Alkyne ketene compound and preparation method thereof

A compound, the technology of alkyne enone, which is applied in the field of alkyne enone compound and its preparation, can solve environmental hazards and other problems, and achieve the effects of reducing pollution, simple preparation process, and fast and effective preparation method

Inactive Publication Date: 2010-12-01
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] (3) A large number of by-products such as halides, triphenylphosphine, etc. are generated during the reaction, causing great harm to the environment

Method used

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  • Alkyne ketene compound and preparation method thereof
  • Alkyne ketene compound and preparation method thereof
  • Alkyne ketene compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1～7

[0027] Add catalyzer in the Schlenk tube of 35ml according to the proportioning of table 1, DDQ and propargyl ether compound (II), mix and stir, after the reaction condition reaction is completed according to table 1, filter, sample mixing, column chromatography (washing Removing agent is sherwood oil: ethyl acetate is 20: 1) purification obtains corresponding alkyne enone product, and reaction process is as shown in the following formula:

[0028]

[0029] Table 1

[0030]

[0031] Wherein, T in the above table is the reaction temperature, and t is the reaction time.

[0032] The preparation method of above-mentioned propargyl ether compound (II) is:

[0033] (1) Preparation of propargyl alcohol compound:

[0034] R 1 When =H, propargyl alcohol compound is 3-phenyl propargyl alcohol, and preparation method is as follows: in 100ml there-necked flask, add iodobenzene (60mmol), 2-propargyl alcohol (60mmol), diethylamine ( 50ml), dichlorobis(triphenylphosphine) palladiu...

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PUM

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Abstract

The invention discloses an alkyne ketene compound, wherein the structure of the alkyne ketene compound is disclosed as formula (I), wherein R1 is H, methyl group or halogen atom. The invention also discloses a preparation method of the alkyne ketene compound, which comprises the following steps: adding catalyst, DDQ and propargyl ether compound into an organic solvent, and completely reacting while stirring, wherein the catalyst is Lewis acid, the structural formula of the propargyl ether compound is disclosed as formula (II), and R1 in formula (I) is H, methyl group or halogen atom. The alkyne ketene compound is an important intermediate. The preparation method uses the accessible Lewis acid as the catalyst, thereby reducing environmental pollution and unnecessary raw material waste. Thus, the whole preparation process is simple, and the product yield is high.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to an alkyne enone compound and a preparation method thereof. Background technique [0002] Alkyne enone compounds widely exist in natural products, and these compounds are important synthetic intermediates. In recent years, due to the application in medicinal chemistry and their unique biological activities, the synthesis methods of such compounds have attracted the interest of a large number of synthetic researchers. Many new synthetic reactions are based on the design of such compounds. There are several methods for synthesizing alkyne enone compounds at present: Gary A.Molander et al. Compounds; Tuyet Jeffery et al. (Tuyet Jeffery.Synthesis.1987, 1, 70-71) synthesize alkyne enones via the Heck reaction of alkynyl halides; Vito Fiandanese et al. (Vito Fiandanese; Daniela Bottalico; Giuseppe Marchese; Angela Punzi .Tetrahedron 2006,62,5126-5132) by Sonogashira reaction synthesi...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C45/00
Inventor 张玉红谢永居
Owner ZHEJIANG UNIV
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