64449-33-8

Basic information

• Product Name: 2-Allyl-3-methyl-1,4-naphthoquinone
• Synonyms: 2-Allyl-3-methyl-1,4-naphthoquinone;2-Methyl-3-(2-propenyl)-1,4-naphthalenedione
• CAS NO: 64449-33-8
• Molecular Formula: C14H12O2
• Molecular Weight: 212.24
• Mol File: 64449-33-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Allyl-3-methyl-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Allyl-3-methyl-1,4-naphthoquinone(64449-33-8)
• EPA Substance Registry System: 2-Allyl-3-methyl-1,4-naphthoquinone(64449-33-8)

Safety Data

• Hazardous Substances Data: 64449-33-8(Hazardous Substances Data)

Upstream product

• 71573-68-7 2‐allyl‐1,4‐dimethoxy‐3‐methylnaphthalene 
• 58-27-5 menadione 
• 762-72-1 allyl-trimethyl-silane 
• 106-95-6 allyl bromide 
• 614-45-9 tert-Butyl peroxybenzoate 
• 65593-24-0 3-(propen-3-yl)-1,4-naphthoquinone 
• 18330-27-3 2-ethylidene-pent-4-enoic acid methyl ester 
• 27613-27-0 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile 
• 1431987-65-3 C₁₉H₁₈O₂ 
• 53772-33-1 2-bromo-3-methyl-1,4-dimethoxynaphthalene 
• 24850-33-7 allyltributylstanane 
• 66557-16-2 2,3-benzo-1-allyl-1-hydroxy-6-methylcyclohexa-2,4-dien-4-one 

Relevant articles and documents

Bioinspired Photoredox Benzylation of Quinones

3-Benzylmenadiones were obtained in good yield by using a blue-light-induced photoredox process in the presence of Fe(III), oxygen, and γ-terpinene acting as a hydrogen-atom transfer agent. This methodology is compatible with a wide variety of diversely substituted 1,4-naphthoquinones as well as various cheap, readily available benzyl bromides with excellent functional group tolerance. The benzylation mechanism was investigated and supports a three-step radical cascade with the key involvement of the photogenerated superoxide anion radical.

Bismuth-catalyzed methylation and alkylation of quinone derivatives with tert-butyl peroxybenzoate as an oxidant

A bismuth-catalyzed methylation of quinones in the presence of tert-butyl peroxybenzoate (TBPB) was developed via a radical reaction mechanism. Particularly, TBPB was used not only as an efficient oxidant, but also as a green methyl source in such transformation. Moreover, this method could also be efficiently extended to the alkylation of quinones. This reaction tolerated a series of functional groups and prepared a series of derivatives of vitamin K3 and benzoquinone. Notably, antimalarial parvaquone was synthesized by the reaction.

Synthesis of Vitamin K and Related Naphthoquinones via Demethoxycarbonylative Annulations and a Retro-Wittig Rearrangement

Anionic annulations of 3-nucleofugal phthalides with α-alkyl(aryl)acrylates involving a demethoxycarbonylation provide a succinct synthesis of vitamin K and related naphthoquinones. Also reported is a new cascade reaction stemming from a Cope-retro-Wittig rearrangement. This cascade leads to direct formation of 1-hydroxy-4-prenyloxynaphthalene-2-carboxylates from the corresponding α-prenyl acrylate acceptors.

QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS FOR OPHTHALMIC USE

The present invention relates to novel nitric oxide donor compounds for the use in the treatment and/or prophylaxis of hypertensive glaucoma, normotensive glaucoma and ocular hypertension.

QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS

The present invention relates to nitric oxide donor compounds having a quinone based structure, to processes for their preparation and to their use in the treatment of pathological conditions where a deficit of NO plays an important role in their pathogenesis.

Bi(OTf)3-catalyzed allylation of quinones with allyltrimethylsilane

p-Quinones react smoothly with allyltrimethylsilane in the presence of 2 mol% of Bi(OTf)3 under mild reaction conditions to afford the corresponding allyl substituted benzene derivatives, p-allylquinols and allyl substituted 1,4-naphthoquinones in excellent yields with high regioselectivity. This method is very useful for the direct introduction of an allyl functionality onto a quinone moiety.

Allylation of quinones bu allylic indium reagents

Allylation of a variety of quinones by allylic indium sesquihalides was studied.Reactions of unsubstituted p-benzoquinone with allylindium, prenylindium, and geranylindium reagents gave, after oxidation with silver oxide, the corresponding allylated quinones in good yields.These reactions appear to proceed via 1,2-addition of the allylic indium reagents at the γ-carbon followed by sigmatropic rearrangement.Substituted quinones reacted with allylindium reagent giving excellent yields of allylquinols, whereas with prenylindium and geranylindium reagents, trisubstituted quinones gave diprenylcyclohexene-1,4-diones and 2,3-disubstituted quinones gave mixtures of prnylhydroquinones and diprenylcyclohexene-1,4-diones.In the prenylation of haloquinones, 1,2-addition, sigmatropic rearrangement, and elimination of indium(III) halide occurred in sequence yielding prenylquinones. 2-Hydroxy- and 2-methoxy-1,4-naphthoquinones gave α-addition products with prenylindium and cinnamylindium reagents.

Allylation of Quinones via Photoinduced Electron-Transfer Reactions from Allylstannanes

Photochemical reactions of quinones with allylstannanes provided four types of products: adducts of allyl group to the carbonyl oxygens of quinones, adducts of allyl group to the olefinic carbons, adducts of allyl group to the carbonyl carbons, and hydroquinones.An electron-transfer mechanism was confirmed by 1H-CIDNP (Chemically Induced Dynamic Nuclear Polarization) method.This study suggests that a) photoinduced electron transfer from allylstannanes to quinones produces the corresponding quinone anion radicals and tin cation radicals, b) the tin cation radicals cleave to give allyl radicals as well as tin cation, and c) the allyl radicals attack the quinone anion radicals resulting in the formation of final products, allylated quinones.

SYNTHESIS OF UBIQUINONE AND MENAQUINONE ANALOGUES BY OXIDATIVE DEMETHYLATION OF ALKENYLHYDROQUINONE ETHERS WITH ARGENTIC OXIDE OR CERIC AMMONIUM NITRATE IN THE PRESENCE OF 2,4,6-PYRIDINE-TRICARBOXYLIC ACID

It was found that alkenylhydroquinone ethers demethylated with argentic oxide or ceric ammonium nitrate in the presence of 2,4,6-pyridinetricarboxylic acid as a catalyst and afforded ubiquinone-2, menaquinone-2 and their analogs in yields of 53 to 89 percent.The new approach to the synthesis of starting alkenylhydroquinone ethers as well as 2,4,6-pyridinetricarboxylic acid and its derivatives has been reported.

Reactions of Complex Ligands, XVII. Regiospecific Reaction of 1,4-Enynes with Pentacarbonyl(methoxyphenylcarbene)chromium(0): Preparation of Allyl-substituted 1-Naphthol- and 1,4-Naphthoquinone Derivatives

Pentacarbonyl(methoxyphenylcarbene)chromium(0) (1) and the enynes 2-5 react on warming in di-n-butyl ether to give the tricarbonyl(2(or 3)-alkyl-3(or 2)-allyl-4-methoxy-1-naphthol)chromium(0) complexes 6-9.Chromatography of these compounds on silica gel under atmospheric conditions results in decomplexation and formation of a naphthol- (9 -> 11) or a 1,4-naphthoquinone derivative (8 -> 10).Oxidation of 6-9 with silver(1) oxide leads exclusively to the quinones 12-14 and their tricarbonylchromium complexes 15-17.The products are characterized by spectroscopic methods.