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Method for synthesizing sulfonyl-substituted pyran type compound

A sulfonyl and compound technology, applied in the field of organic synthesis and catalysis, can solve the problems of high reaction cost, harsh reaction conditions, long reaction time, etc., and achieve the effects of simple and convenient operation, low price and single product

Inactive Publication Date: 2018-06-29
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods have some problems to varying degrees, including harsh reaction conditions (high temperature, toxic solvents), the use of a large amount of transition metal catalysts, and the addition of some ligands, the reaction time is longer, the yield is lower, and not all All elements participate in the reaction, there is waste of elements, etc. These factors lead to high reaction costs and heavy pollution, which do not conform to the concept of green environmental protection and atomic economics, and are not suitable for industrial production.

Method used

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  • Method for synthesizing sulfonyl-substituted pyran type compound
  • Method for synthesizing sulfonyl-substituted pyran type compound
  • Method for synthesizing sulfonyl-substituted pyran type compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Weigh 45.6 mg (0.24 mmol) of p-toluenesulfonyl chloride, Ir(dtbbpy)(ppy) 2 PF 6 2.0 mg (0.002 mmol) was put into a reaction flask, added to 2 mL of acetonitrile solution, and 3-((3-methylbut-2-en-1-yl)oxy)prop-1-yn-1 was measured. - base) benzene 42.3 ul (0.20 mmol), water 36 ul (2.00 mmol), in N 2 Placed under the condition of 23 W fluorescent lamp under the irradiation of room temperature stirring reaction, TLC detected the progress of the reaction, after about 24h, the detection reaction was complete, separated and purified (petroleum ether: ethyl acetate=20:1) by column chromatography to obtain a white solid, record As product 1, yield: 87%.

[0019] The structural characterization of product 1 is as follows:

[0020]

[0021] white solid; melting point: 124 - 126 o C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.53–7.39 (m, 1H), 7.26 ( J = 8.0 Hz, 2H), 7.13 ( J = 8.0 Hz, 3H), 7.01 ( J = 8.0 Hz, 2H), 6.47(brs, 1H), 4.83 (d, J = 17.6 Hz, 1H), 4.68 (d, J = 12.0 ...

Embodiment 2

[0047] Using the same method and reaction conditions of Example 1, when 3-methyl-1-(propyl-2-ynyl-1-oxyl)-2-butene is a different substituent, the following different target products are obtained .

[0048] The structure of product 2 is characterized as follows:

[0049]

[0050] Reddish-brown solid; melting point: 164 - 166 o C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.26 (dd, J =8.7, 3.4 Hz, 2H), 7.22 (d, J = 8.2 Hz, 2H), 7.05 (d, J = 8.0 Hz, 2H), 6.96–6.91 (m, 1H), 4.84 (d, J = 18.1 Hz, 1H), 4.69–4.52 (m, 2H), 3.51 (dd, J =12.0, 3.1 Hz, 1H), 2.59 (s, 1H), 2.33 (s, 3H), 1.63 (s, 4H), 1.28 (s, 3H); 13 CNMR (CDCl 3 , 150 MHz): 143.8, 143.2, 140.1, 139.0, 137.2, 132.2, 129.0, 128.2, 127.2, 126.7, 73.8, 66.7, 66.4, 54.6, 33.4, 30.6, 21.56; IR (neat) n = 2927,1605, 1460, 1383, 1307, 1149, 1092, 846, 805, 717cm -1 ; HRMS (ESI) theoretically calculated value [C 19 H 21 S 2 O 3 ClNa] + [M+Na] + : 419.0518, actual measured value: 419.0528, in order to further determ...

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Abstract

The invention discloses a method for synthesizing a paratoluensulfonyl chloride substituted pyran type compound. The method comprises the following steps: adding paratoluensulfonyl chloride, 3-methyl-1-(propyl-2-alkynyl-1-oxy)-2-butene with different substituted groups, water and a photocatalyst to a solvent, performing reaction at room temperature under an illumination condition, performing a TLCmonitoring reaction process, and after the reaction is completed, performing column chromatography separation and purification to obtain the product. The method adopts novel light-catalyzed reactionand has the advantages of mild reaction conditions, simple operation, convenient subsequent treatment and the like, and the structure of the prepared product is characterized and analyzed through IR (Infrared Ray), 1H NMR (Nuclear Magnetic Resonance), 13C NMR, X-Ray single crystal diffraction and high resolution mass spectrum.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and catalysis, and particularly relates to a convenient method for synthesizing sulfonyl-substituted pyran compounds. Background technique [0002] The six-membered carbon-oxygen heterocyclic compound is a pyran compound, and the oxygen atom in the pyran has a strong basicity and can form a salt with strong stability. Some important natural substances such as sugars, antibiotics and alkaloids contain pyran or pyran salt structures, such as pyranose (a six-membered hemiacetal structure formed by a five-carbon sugar or a six-membered sugar). Drugs containing sulfonyl groups occupy a considerable proportion in clinical treatment drugs, because sulfonyl groups have their special physical and chemical properties, the introduction of sulfonyl groups can change the solubility of drugs, and can also provide two hydrogen bond receptors, thereby enhancing the drug's effect. biological activity an...

Claims

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Application Information

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IPC IPC(8): C07D309/28C07D409/04
CPCC07D309/28C07D409/04
Inventor 侯虹李恒学许月
Owner YANGZHOU UNIV
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