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Vanillin derivative containing dithioacetals, preparation method and purpose thereof

A technology of dithioacetal and vanillin, which is applied in the chemical field, can solve the problem of anti-plant virus that has not been reported, achieve good therapeutic and protective effects, and improve the effect of reaction yield

Active Publication Date: 2017-03-01
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In summary, vanillin derivatives have various biological activities such as antibacterial, anticancer, and antioxidative. However, their anti-plant virus has not been reported.

Method used

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  • Vanillin derivative containing dithioacetals, preparation method and purpose thereof
  • Vanillin derivative containing dithioacetals, preparation method and purpose thereof
  • Vanillin derivative containing dithioacetals, preparation method and purpose thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0027] ((((4-phenyl) oxygen)-3-methoxyphenyl) methylene) two (4-chlorophenyl) dithioacetal synthetic (compound number is a), comprising the following steps:

[0028] (1) Synthesis of 4-(benzyloxy)-3-methoxybenzaldehyde:

[0029] Add vanillin (1.52 g, 10 mmol) and benzyl chloride (1.26 g, 10 mmol) into a 100 mL three-neck flask and add 40 mL of acetonitrile to dissolve the solid, add anhydrous K 2 CO 3 (2.76 g, 20 mmol), the reaction system is light yellow turbidity (K 2 CO 3 undissolved), refluxed and stirred, followed the reaction process by TLC (the developing solvent was petroleum ether:ethyl acetate=3:1, V / V), after the raw material point disappeared, the reaction was stopped, the solvent was spin-dried, and 50 mL H 2 O was stirred at room temperature to separate out a white solid, and recrystallized from ethanol to obtain a white solid;

[0030] (2) ((((4-phenyl) oxygen)-3-methoxyphenyl) methylene) two (4-chlorophenyl) dithioacetal synthesis:

[0031] Add 4-(benzylox...

Embodiment 2

[0033] ((4-((3-methylphenyl) oxygen)-3-methoxyphenyl) methylene) two (4-chlorophenyl) dithioacetal synthesis (compound number is b), including The following steps:

[0034] (1) Synthesis of 4-((3-methylphenyl) oxygen)-3-methoxybenzaldehyde:

[0035] Synthesize as embodiment 1 (1) method and condition, difference is that 3-methyl benzyl chloride is raw material;

[0036] (2) ((4-((3-methylphenyl) oxygen)-3-methoxyphenyl) methylene) two (4-chlorophenyl) dithioacetal synthesis:

[0037] Synthesize as in Example 1(2) method and conditions, the difference is that 4-((3-methylphenyl)oxy)-3-methoxybenzaldehyde is the raw material.

Embodiment 3

[0039] Synthesis of ((4-((4-methylphenyl)oxy)-3-methoxyphenyl)methylene)bis(4-chlorophenyl)dithioacetal (compound number c), including The following steps:

[0040] (1) Synthesis of 4-((4-methylphenyl) oxygen)-3-methoxybenzaldehyde:

[0041] Synthesize as embodiment 1 (1) method and condition, difference is that 4-methyl benzyl chloride is raw material;

[0042] (2) ((4-((4-methylphenyl) oxygen)-3-methoxyphenyl) methylene) two (4-chlorophenyl) dithioacetal synthesis:

[0043] Synthesize as in Example 1 (2) method and conditions, the difference is that 4-((4-methylphenyl)oxy)-3-methoxybenzaldehyde is the raw material.

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Abstract

The invention discloses a vanillin derivative containing dithioacetals, a preparation method and a purpose thereof. A structural general formula of the derivative is shown in a specification, wherein, R1 is a substituted aromatic ring, heterocycle or 1,1-dichloroethylene; a methyl atom, a nitro atom or a halogen atom is contained on an o-position, a meta-position and a para-position of the aromatic ring, the halogen atom can be fluorine, chlorine, or bromine; the heterocycle is five-membered or six-membered heterocycle, and one halogen atom is contained on the heterocycle. R2 is substituted aromatic ring, 1-propanol or heterocycle; fluorine or chlorine is contained on para-position of the aromatic ring, and the heterocycle is furan ring. The compound can inhibit plant virus such as tobacco mosaic virus, cucumber mosaic virus and potato y potyvirus.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a dithioacetal-containing vanillin derivative, and also to a preparation method of the dithioacetal-containing vanillin derivative, as well as to the preparation of anti-cucumber mosaic virus disease, tobacco mosaic virus disease, potato Y virus, southern rice black-streaked dwarf virus disease and rice stripe virus pesticide. Background technique [0002] Vanillin, also known as vanillin, is an important natural product that exists in beet, vanilla bean, benzoin gum, Peru balsam, tolu balsam, etc. Vanillin has a wide range of applications in foreign countries. It is widely used in the production of pharmaceutical intermediates, and is also used in plant growth promoters, fungicides, lubricant defoamers, electroplating brighteners, and conductive agents for printed circuit board production. Domestic vanillin is mainly used as a food additive. In recent years, its appli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C323/16C07D213/61C07D277/32A01N43/40A01N35/02A01P1/00
CPCA01N35/02A01N43/40C07C319/14C07D213/61C07D277/32C07C323/16
Inventor 宋宝安张建胡德禹薛伟吴增雪赵磊张国平潘建科陈瑾
Owner GUIZHOU UNIV
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