57960-31-3

Usage

InChI:InChI=1/C22H30O3/c1-2-3-4-5-6-7-8-9-10-11-16-19-20(23)17-14-12-13-15-18(17)21(24)22(19)25/h12-15,25H,2-11,16H2,1H3

Upstream product

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 56038-98-3 dilauroyl peroxide 
• 1785-67-7 1,2,4-triacetyloxynaphthalene 
• 130-15-4 [1,4]naphthoquinone 
• 64-17-5 ethanol 
• 64955-12-0 3-chloro-2-n-dodecyl-1,4-naphthoquinone 
• 112-53-8 1-dodecyl alcohol 
• 64955-08-4 2-n-dodecyl-1-naphthol-4-sulfonic acid 
• 64955-09-5 2-Dodecyl-[1]naphthol 

Downstream Products

• 125110-78-3 2-(1-methylaminododecyl)-3-hydroxy-1,4-naphthoquinone 
• 57960-19-7 acequinocyl 

Relevant academic research and scientific papers

Naphthoquinone compounds and preparation and acaricidal and bactericidal application thereof

The invention relates to naphthoquinone compounds as well as a preparation and acaricidal and bactericidal application thereof, and relates to 15 kinds of 2, 3-substituted naphthoquinone derivatives as well as a preparation method and acaricidal and bactericidal application thereof. The preparation method comprises the following steps: carrying out addition reaction on 2-hydroxy-1, 4 naphthoquinone with different aldehydes to obtain compounds 1-6, and carrying out condensation reaction with different acyl chlorides or sulfonyl chlorides under the catalysis of alkali to obtain compounds 7-15. The compounds can be used as acaricides for preventing and treating crop mites, and can also be used as bactericides for preventing and treating botrytis cinerea, valsa mali, fusarium oxysporum and gaeumannomyces graminis.

Preparation method of 2-dodecyl-3-hydroxy-1,4-naphthoquinone

The invention discloses a preparation method of 2-dodecyl-3-hydroxy-1,4-naphthoquinone. The 2-dodecyl-3-hydroxy-1,4-naphthoquinone is obtained by one-step reduction reaction of 2-(1-dodecanecarbenyl)-3-hydroxy-1,4-naphthoquinone, and the one-step reduction reaction is carried out in the presence of magnesium ribbons and methanol, wherein the molar ratio of the 2-(1-dodecanecarbenyl)-3-hydroxy-1,4-naphthoquinone to the magnesium ribbons is (1:1)-(1:3), the weight ratio of the 2-(1-dodecanecarbenyl)-3-hydroxy-1,4-naphthoquinone to the methanol is (1:3)-(1:10), the temperature of the one-step reduction reaction is 25-70 DEG C, and the time of the one-step reduction reaction is 1-5h. The preparation method disclosed by the invention adopts a reduction system containing the magnesium ribbons and methanol to reduce the 2-(1-dodecanecarbenyl)-3-hydroxy-1,4-naphthoquinone to prepare the 2-dodecyl-3-hydroxy-1,4-naphthoquinone, and the reduction system can selectively hydrogenate double bonds under certain conditions, so that a target product can be obtained by only one-step reaction.

Synthesis and biological evaluation of lipophilic 1,4-naphthoquinone derivatives against human cancer cell lines

To examine the effect of hydrophobicity on the anticancer activity of 1,4-naphthoquinone derivatives, a series of compounds bearing a 2-O-alkyl-, 3-C-alkyl- or 2/3-N-morpholinoalkyl group were synthesized and evaluated for their anticancer activity against five human cancer cell lines in vitro. The cytotoxicity of these derivatives was assayed against HT-29, SW480, HepG2, MCF-7 and HL-60 cells by the MTT assay. Among them, 2-hydroxy-3-farnesyl-1,4-naphthoquinone (11a) was found to be the most cytotoxic against these cell lines. Our results showed that the effectiveness of compound 11a may be attributed to its suppression of the survival of HT-29. Secondly, in the Hoechst 33258 staining test, compound 11a-treated cells exhibited nuclear condensation typical of apoptosis. Additionally, cell cycle analysis by flow cytometry indicated that compound 11a arrested HT-29 cells in the S phase. Furthermore, cell death detected by Annexin V-FITC/propidium iodide staining showed that compound 11a efficiently induced apoptosis of HT-29 in a concentration-dependent manner. Taken together, compound 11a effectively inhibits colon cancer cell proliferation and may be a potent anticancer agent.

2-(1-alkylaminoalkyl)-3-hydroxy-1,4-naphthoquinone

A 2-(1-alkylaminoalkyl)-3-hydroxy-1,4-naphthoquinone of the formula: STR1 wherein R1 is an alkyl group or a cycloalkyl group, and R2 is an alkyl group having at least 2 carbon atoms. The compounds are used in the preparation of a 2-(1-alkenyl)-3-hydroxy-1,4-naphthoquinone having insecticidal and fungicidal activity and a 2-alkyl-3-acyloxy-1,4-naphthoquinone having insecticidal and fungicidal activity and a 2-alkyl-3-acyloxy-1,4-naphthoquinone having miticidal activity.

Miticidal ethers

Naphthoquinone ethers are useful as miticides having improved knockdown characteristics.

2-Alkyl-1-naphthol-4-sulfonic acids

Compounds of the formula STR1 wherein R is alkyl of 11 to 14 carbon atoms, and X is --SO3 H, --NO2 or --SO2 Cl Are useful intermediates in the preparation of naphthoquinone miticides.