40420-47-1

Upstream product

• 571-60-8 1,4-Dihydroxynaphthalene 
• 64-19-7 acetic acid 
• 5697-00-7 1,4-diacetoxynaphthalene 
• 7446-70-0 aluminium trichloride 
• 98-95-3 nitrobenzene 

Downstream Products

• 5813-57-0 2-acetyl-1,4-naphthoquinone 
• 155379-65-0 3-acetyl-2-allyl-1-benzyloxy-4-methoxynaphthalene 
• 155379-66-1 2-allyl-1-benzyloxy-3-(1-hydroxyethyl)-4-methoxynaphthalene 

Relevant academic research and scientific papers

Antifungal activity of 1,4-dialkoxynaphthalen-2-acyl imidazolium salts by inducing apoptosis of pathogenic candida spp.

Even though Candida spp. are staying commonly on human skin, it is also an opportunistic pathogenic fungus that can cause candidiasis. The emergence of resistant Candida strains and the toxicity of antifungal agents have encouraged the development of new classes of potent antifungal agents. Novel naphthalen-2-acyl imidazolium salts (NAIMSs), especially 1,4-dialkoxy-NAIMS from 1,4-dihydroxynaphthalene, were prepared and evaluated for antifungal activity. Those derivatives showed prominent anti-Candida activity with a minimum inhibitory concentration (MIC) of 3.125 to 6.26 μg/mL in 24 h based on microdilution antifungal susceptibility test. Among the tested com-pounds, NAIMS 7c showed strongest antifungal activity with 3.125 μg/mL MIC value compared with miconazole which showed 12.5 μg/mL MIC value against Candida spp., and more importantly >100 μg/mL MIC value against C. auris. The production of reactive oxygen species (ROS) was increased and JC-1 staining showed the loss of mitochondrial membrane potential in C. albicans by treatment with NAIMS 7c. The increased release of ultraviolet (UV) absorbing materials suggested that NAIMS 7c could cause cell busting. The expression of apoptosis-related genes was induced in C. albicans by NAIMS 7c treatment. Taken together, the synthetic NAIMSs are of high interest as novel antifungal agents given further in vivo examination.

Bismuth triflate-catalyzed fries rearrangement of aryl acetates

Bismuth triflate was found to be an efficient catalyst in the Fries rearrangement of phenyl or 1-naphthyl acetates. Both reactions proceeded smoothly with a catalytic amount of bismuth triflate (10 mol%) to afford the corresponding hydroxyaryl ketone in moderate to good yields in most cases.

Synthetic Utility and Mechanistic Implications of the Fries Rearrangement of Hydroquinone Diesters in Boron Trifluoride Complexes

Reactions of boron trifluoride methyl and ethyl etherate complexes with hydroquinone diesters yield monomethyl and monoethyl derivatives of acetylhydroquinones. The use of sterically hindered boron trifluoride etherate complexes results in acetylhydroquinone derivatives. This procedure represents a one-step synthesis of acetylhydroquinone derivatives, important building blocks for a variety of synthetic applications.

Photo-Fries Rearrangement in Some Acetoxynaphthalene Derivatives

Photo-Fries migration of 1,4-diacetoxynaphthalene, 1,2,4-triacetoxynaphthalene, 1,5-diacetoxynaphthalene and 1,4-diacetoxy-2-methylnaphthalene gives 4-acetoxy-2-acetyl-1-naphthol, 2-acetyl-3,4-diacetoxy-1-naphthol, 5-acetoxy-2-acetyl-1-naphthol and 4-acetoxy-2-acetyl-3-methyl-1-naphthol respectively.