Diaryl iodide salt compound as well as preparation method and application thereof

A technology of diaryliodonium and compound, applied in the field of diaryliodonium salt compound and preparation thereof, can solve the problems of few research reports on the application of antibacterial agents, no preparation method and application of diaryliodonium salt compound are involved, and the like. The effect of high yield, simple synthesis, and antibacterial property promotion

Active Publication Date: 2018-12-21
上海邦高化学有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The current reports of diaryliodonium salts are mostly based on their unique arylation reagents, but there are few reports on the application of antibacterial agents.
[0004] In summary, the prior art does not relate to diaryliodonium salt compounds as shown in the present invention and its preparation method and application

Method used

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  • Diaryl iodide salt compound as well as preparation method and application thereof
  • Diaryl iodide salt compound as well as preparation method and application thereof
  • Diaryl iodide salt compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The preparation of diaryliodonium salt compound Ia:

[0037]

[0038] Place o-iodophenol (5mmol, 1equiv) in a 250mL round-bottomed flask, dissolve it in 100mL of dichloromethane (DCM), and add 1.25 equivalents of diisopropylethylamine and 1.25 equivalents of trifluoromethane in sequence at -78°C Sulfonic anhydride, reacted for 10 minutes and continued to react at room temperature for 2 hours to obtain compound 2a. Dissolve compound 2a in 40 mL of DCM, add 1.1 equivalents of m-chloroperoxybenzoic acid and 2.5 equivalents of boron trifluoride ether, react at room temperature for 1 hour, cool to 0°C, add 1.1 equivalents of 4-fluorophenylboronic acid and stir for 10 minutes, The reaction system was raised to room temperature and reacted for 30 minutes, 1.2 equivalents of trifluoromethanesulfonic acid was added at 0°C, raised to room temperature and reacted for 15 minutes, diaryliodonium salt compound Ia (80%) was obtained by recrystallization from ether.

[0039] Ia.M.p...

Embodiment 2

[0041] The preparation of diaryliodonium salt compound Ib:

[0042]

[0043]Place o-iodophenol (5mmol, 1equiv) in a 250mL round-bottomed flask, dissolve in 100mL DCM, add 1.25 equivalents of diisopropylethylamine and 1.25 equivalents of trifluoromethanesulfonic anhydride successively at -78°C, and react 10 After 2 minutes, the reaction was continued at room temperature for 2 hours to obtain compound 2a. Dissolve compound 2a in 40 mL of DCM, add 1.1 equivalents of m-chloroperoxybenzoic acid and 2.5 equivalents of boron trifluoride ether, react at room temperature for 1 hour, cool to 0°C, add 1.1 equivalents of 3-chlorophenylboronic acid and stir for 10 minutes, The reaction system was raised to room temperature and reacted for 30 minutes, 1.2 equivalents of trifluoromethanesulfonic acid was added at 0° C., raised to room temperature and reacted for 15 minutes, diaryliodonium salt compound Ib (70%) was obtained by diethyl ether recrystallization.

[0044] Ib. White solid, M....

Embodiment 3

[0046] Preparation of diaryliodonium salt compound Ic:

[0047]

[0048] Place o-iodophenol (5mmol, 1equiv) in a 250mL round-bottomed flask, dissolve in 100mL DCM, add 1.25 equivalents of diisopropylethylamine and 1.25 equivalents of trifluoromethanesulfonic anhydride successively at -78°C, and react 10 After 2 minutes, the reaction was continued at room temperature for 2 hours to obtain compound 2a. Dissolve compound 2a in 40 mL of DCM, add 1.1 equivalents of m-chloroperoxybenzoic acid and 2.5 equivalents of boron trifluoride ether, react at room temperature for 1 hour, cool to 0°C, add 1.1 equivalents of 4-chlorophenylboronic acid and stir for 10 minutes, The reaction system was raised to room temperature and reacted for 30 minutes, 1.2 equivalents of trifluoromethanesulfonic acid was added at 0° C., raised to room temperature and reacted for 15 minutes, diaryliodonium salt compound Ic (71%) was obtained by recrystallization from ether.

[0049] Ic. White solid, M.p.: 18...

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PUM

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Abstract

The invention discloses a diaryl iodide salt compound, as shown in Formula I which is shown in the specification: wherein R1 and R2 are independently selected from hydrogen, halogen, alkyl, alkoxy, halogen-substituted alkyl, halogen-substituted alkoxy. The diaryl iodide salt compound designed and prepared by the invention as an antibacterial agent is simple in synthesis and high in yield, comparedwith commercially available isothiazolinone, has a relatively antibacterial property against escherichia coli, and has obvious advantage of antibacterial property against staphylococcus aureus.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a diaryliodonium salt compound and its preparation method and application. Background technique [0002] Since the first case of organic hypervalent iodide PhICl in 1886 2 Since it was synthesized, more than 1,000 organic hypervalent iodine compounds have been discovered. These compounds containing pentavalent (Ⅴ) iodine and trivalent (Ⅲ) iodine have attracted widespread attention because of their mildness and non-toxicity. Among them, diaryliodonium salts are a representative class of trivalent iodide salts, because of the high electron deficiency of iodide cations and the relatively easy leaving property of iodobenzene, it can be used in transition metal-catalyzed C-H bond activation / aromatic It has been widely used in alkylation reaction, α-arylation of carbonyl compounds and asymmetric cascade cyclization. [0003] The current reports of diaryliodoniu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/28C07C303/30C07C303/32C07C309/06C07C309/65A61P31/04A01P1/00
CPCA61P31/04C07C303/28C07C303/30C07C303/32C07C309/06C07C309/65Y02A50/30
Inventor 王利民崔丽媛车飞陈煌冠马静怡韩建伟田禾
Owner 上海邦高化学有限公司
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