Acetylenic ketone compounds and preparing method thereof

A technology of aldehyde compounds and compounds, which is applied in the field of acetylenic compounds and their preparation, can solve the problems of low yield, complicated process, and harsh preparation conditions of acetylenic compounds, etc., and achieves reduced production costs, simple process, and smooth reaction process. Safe and controllable effect

Inactive Publication Date: 2015-01-07
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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Problems solved by technology

[0004] The purpose of the present invention is to overcome the above-mentioned deficiencies in the prior art, provide a kind of acetylene compound and its preparation method, to overcome the technical problems such as harsh preparation conditions, low yield and complex process of the existing acetylene compound

Method used

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  • Acetylenic ketone compounds and preparing method thereof
  • Acetylenic ketone compounds and preparing method thereof
  • Acetylenic ketone compounds and preparing method thereof

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preparation example Construction

[0069] Correspondingly, the embodiment of the present invention also provides a preparation method of the acetylenic compound of the general formula (I) above. The method comprises the steps of:

[0070] S01: respectively provide aldehyde compound A and hypervalent iodine compound B represented by the following structural formula:

[0071]

[0072] S02: adding the aldehyde compound A and the hypervalent iodine compound B into a reaction system containing a copper / gold salt catalyst, a secondary amine catalyst, a ligand catalyst and an oxidant to react at a temperature of -20-200°C, Obtain the following structural general formula as the acetylenic compound shown in (I),

[0073]

[0074] Specifically, in the above step S01, R in the molecular structural formula of aldehyde compound A 1 The represented group is as R in the general formula (I) of the acetylenic compound molecular structure above 1 The groups represented are the same. R in the molecular structure formula...

Embodiment 1

[0095] 4-Phenyl-1-triisopropylsilyl-1-yne-3-butanone and its preparation method. The structural formula of the 4-phenyl-1-triisopropylsilyl-1-yne-3-butanone is shown in the following molecular structural formula I1:

[0096]

[0097] Its preparation steps are as follows:

[0098] In a dry 10mL schlenk bottle, add 3.0mg (0.01mmol) of gold trichloride, 3.6mg (0.02mmol) of 4,5-diazofluoren-9-one, and triisopropylsilylethynylphenyliodoyl ketone ( TIPS-EBX) 51.3mg (0.12mmol), 5.0mL anhydrous Et 2 O, replaced with oxygen three times, added 0.1mmol phenylpropanal, 8.2uL pyrrolidine (0.1mmol, 1.0eq), and stirred at 40°C for 10h after sealing the reaction bottle. After the reaction was completed, the reaction solution was filtered through a glass dropper containing silica gel, rinsed with ether, the filtrate was spin-dried, and separated by column chromatography to obtain the target product, a pale yellow oily liquid, with a yield of 72%.

[0099] The product I1 of preparation is...

Embodiment 2

[0101] 4-(4-Bromophenyl)-1-triisopropylsilyl-1-yne-3-butanone and its preparation method. The structural formula of the 4-(4-bromophenyl)-1-triisopropylsilyl-1-yne-3-butanone is shown in molecular structural formula I2 below:

[0102]

[0103] Its preparation method refers to the preparation method of 4-phenyl-1-triisopropylsilyl-1-yne-3-butanone in Example 1, the difference is that 4-bromophenylpropanal (0.1mmol) is used instead of benzene Propionaldehyde, the secondary amine compound catalyst is pyrrolidine (0.1mol). After the reaction was completed, the reaction solution was filtered through a glass dropper containing silica gel, rinsed with ether, the filtrate was spin-dried, and separated by column chromatography to obtain the target product, a light yellow oily liquid, with a yield of 73%.

[0104] The product I2 of preparation is carried out proton nuclear magnetic resonance spectrum (H NMR) analysis, and the result is: 1 H NMR (400MHz, CDCl 3 )δ7.46(d, J=8.2Hz, 2...

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Abstract

Acetylenic ketone compounds and a preparing method thereof are disclosed. The general formula of the acetylenic ketone compounds is shown as a formula (I) in the specification. The preparing method includes adding an aldehyde compound A and a high-valence iodoalkyne compound B into a reaction system comprising a copper/gold salt catalyst, a secondary amine catalyst, a ligand catalyst and an oxidant and reacting at a temperature ranging from -20 DEG C to 200 DEG C. The acetylenic ketone compounds have a typical acetylenic ketone structure, have similarity with other acetylenic ketone compounds, and can be used for development of medicine intermediates and preparation of functional materials. The preparing method is simple in process, low in reaction condition requirements, safe and controllable in reaction procedures, high in atom utilization rate, high in production efficiency, and low in environment pollution stress, and obviously reduces the production cost of the acetylenic ketone compounds provided by the invention.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a acetylene compound and a preparation method thereof. Background technique [0002] Alkyne ketones are important building blocks for the synthesis of pharmaceutical intermediates and the preparation of functional materials. The classic methods for the synthesis of acetylenones include the nucleophilic attack of carbonyl compounds by alkynyl Grignard reagents or lithium reagents, and transition metal-catalyzed coupling reactions. But there are many shortcomings in these methods, such as 1) harsh reaction conditions, narrow substrate range; 2) complex operation, high temperature and high pressure; 3) low yield, poor selectivity, many by-products; 4) lengthy steps, long reaction time, low efficiency. [0003] Therefore, we urgently need a new method for preparing acetylenic compounds to overcome the above-mentioned defects in the prior art. Conten...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C07F7/10C07F7/18
Inventor 汪兆丰黄湧
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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