Synthetic method of beta-iodo-alkenyl sulfone compound

The technology of an iodoalkenyl sulfone and a synthesis method is applied in the field of synthesizing β-iodoalkenyl sulfones, which can solve the problems of potential safety hazards, lack of environmental friendliness, etc. Adaptability, mild effect of reaction conditions

Active Publication Date: 2018-12-14
GUANGZHOU YUEWANG AGRI CO LTD
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  • Claims
  • Application Information

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Problems solved by technology

Although the synthesis methods of β-iodoalkenyl sulfone have made great progress, most of these methods involve the use of strong peroxides, which have great safety hazards and are not environmentally friendly. Therefore, the development of new β- - Iodoalkenyl sulfone synthesis method is particularly important

Method used

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  • Synthetic method of beta-iodo-alkenyl sulfone compound
  • Synthetic method of beta-iodo-alkenyl sulfone compound
  • Synthetic method of beta-iodo-alkenyl sulfone compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]

[0043] 4-Chlorophenylacetylene (68mg, 0.5mmol), p-toluenesulfonyl hydrazide (93mg, 0.5mmol), diiodine pentoxide (167mg, 0.5mmol) and solvent 1,4-dioxane 2mL were added to In a 10 mL sealed tube, heat and stir in an oil bath at 80°C for 8 h, stop heating after the reaction, cool the sealed tube to room temperature, and separate the crude product by column chromatography (the eluent is petroleum ether / ethyl acetate volume ratio 15:1 mixture), the product (E)-1-chloro-4-(1-iodo-2-p-toluenesulfonylvinyl)benzene (compound 1) 117.18 mg (yield 56%) was obtained.

[0044] Product characterization: white solid; mp=143-144°C; 1 H NMR (500MHz, CDCl 3) δ7.50(d, J=8.1Hz, 2H), 7.34(s, 1H), 7.29–7.22(m, 4H), 7.18(d, J=8.3Hz, 2H), 2.41(s,3H). 13 C NMR (125 MHz, CDCl 3 ) δ 144.88, 141.72, 138.06, 137.11, 135.87, 129.78, 129.09, 128.19, 127.85, 112.03, 21.65.

Embodiment 2

[0046]

[0047] 4-n-pentyloxyphenylacetylene (94mg, 0.5mmol), p-toluenesulfonyl hydrazide (186mg, 1.0mmol), diiodine pentoxide (167mg, 0.5mmol) and solvent 1,4-dioxane Add 2 mL into a 10 mL sealed tube, heat and stir in an oil bath at 80°C for 6 h, stop heating after the reaction, cool the sealed tube to room temperature, and separate the crude product by column chromatography (eluent is petroleum ether / ethyl acetate ester volume ratio of 15:1 mixture), to obtain the product (E)-1-n-pentyloxy-4-(1-iodo-2-p-toluenesulfonylvinyl)benzene (compound 2) 166.85 mg (yield 71%).

[0048] Product characterization: brown liquid; 1 H NMR (500MHz, CDCl 3) δ7.50 (d, J = 8.2Hz, 1H), 7.46–7.34 (m, 1H), 7.30–7.17 (m, 4H), 7.03 (d, J = 8.7Hz, 1H ),6.87–6.66(m,3H),3.95(dt,J=11.5,6.4Hz,2H),2.39(s,3H),1.78(dt,J=10.7,6.0Hz,2H),1.46–1.37( m, 4H), 0.94 (t, J = 7.1 Hz, 3H). 13 C NMR (126 MHz, CDCl 3 ) δ 160.46, 140.16, 137.53, 134.64, 131.56, 129.98, 129.63, 127.83, 113.69, 94.36, 68.14, 28.84, 2...

Embodiment 3

[0050]

[0051] Add 1-heptyne (48 mg, 0.5 mmol), p-toluenesulfonyl hydrazide (186 mg, 1.0 mmol), diiodine pentoxide (267 mg, 0.8 mmol) and 2 mL of solvent dimethyl sulfoxide into a 10 mL sealed tube, Heat and stir in an oil bath at 80°C for 6 hours, stop heating after the reaction is over, seal the tube and cool to room temperature, and separate the crude product by column chromatography (the eluent is a mixture of petroleum ether / ethyl acetate with a volume ratio of 15:1) liquid) to obtain 49.14 mg of product (E)-1-p-toluenesulfonyl-2-iodo-n-heptene (compound 3) (yield 26%).

[0052] Product characterization: brown liquid; 1 H NMR (500MHz, CDCl3) δ7.47 (d, J = 7.8Hz, 2H), 7.36 (s, 1H), 7.09 (d, J = 7.6Hz, 2H), 2.65-2.58 (m, 2H), 2.40 (s,3H), 1.69-1.61(m,2H), 1.38(s,4H), 0.94(s,3H). 13 C NMR (125MHz, CDCl3) δ 144.42, 140.94, 136.91, 129.56, 127.90, 114.96, 35.82, 31.53, 30.98, 22.55, 21.64, 14.06.

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Abstract

The invention discloses a synthetic method of a beta-iodo-alkenyl sulfone compound. The synthesis method comprises the following steps: mixing an alkyne derivative, a sulfonyl hydrazine derivative, iodine pentoxide and a solvent to obtain a mixed solution, carrying out stirring for a reaction, carrying out cooling after the reaction is finished, and carrying out column chromatography separation toobtain the beta-iodo-alkenyl sulfone compound represented by a formula III. According to the synthesis method, the iodine pentoxide is used as an iodine source and an initiator, the raw materials arecheap and are simple and easy to obtain, the application range of alkyne and sulfonhydrazide compounds is wide, reaction conditions are mild, post-treatment is simple, and the product yield is high.In addition, use of peroxides is avoided, so that the method is safe and is friendly to the environment, and reaction toxicity is low.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of β-iodoalkenyl sulfone compounds. Background technique [0002] Functionalized olefin compounds are important organic intermediates in organic chemistry, and their functional group structures can be further transformed into other useful chemical products. Addition reactions via alkynes are one of the important routes to prepare functionalized alkenes. In recent years, the 1,2-difunctionalization reaction of alkynes has attracted great attention of chemists because of the advantages of one-step introduction of two functional groups, high selectivity and simple post-treatment. Among them, β-iodoalkenyl sulfone, as a multi-substituted olefin compound, has attracted great attention because of its rich conversion properties between iodine atom and sulfone functional group, and various chemical reactions can occur. [0003] Generally, β-iodo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/00C07D213/34C07D333/18C07C317/14C07C317/18C07B45/00
CPCC07B45/00C07C315/00C07D213/34C07D333/18C07C317/14C07C317/18
Inventor 唐裕才申有名刘学文
Owner GUANGZHOU YUEWANG AGRI CO LTD
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