711-79-5

Usage

Uses

Used in Chemical Synthesis:
1'-HYDROXY-2'-ACETONAPHTHONE is used as a key intermediate in the synthesis of various complex organic compounds. Its unique structure allows for the formation of naphtho[1,2-e]-1,3-oxazines, naphtho[2,1-e]-1,3-oxazines, or their spiro dimers, which can be further utilized in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
1'-HYDROXY-2'-ACETONAPHTHONE is used as a building block for the development of novel pharmaceutical compounds. Its ability to form diverse chemical structures makes it a valuable asset in the design and synthesis of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
1'-HYDROXY-2'-ACETONAPHTHONE is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its unique chemical properties enable the development of innovative and effective products for agricultural applications.
Used in Specialty Chemicals:
1'-HYDROXY-2'-ACETONAPHTHONE is used as a raw material in the production of specialty chemicals, such as dyes, pigments, and fragrances. Its versatility in forming various chemical structures allows for the creation of unique and high-quality products in these industries.

InChI:InChI=1/C12H10O2/c1-8(13)10-7-6-9-4-2-3-5-11(9)12(10)14/h2-7,14H,1H3

Upstream product

• 141-82-2 malonic acid 
• 90-15-3 α-naphthol 
• 830-81-9 1-naphthyl acetate 
• 79-03-8 propionyl chloride 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 19455-84-6 3,4-dihydronaphthalen-1-yl acetate 
• 129589-46-4 2-acetyl-1-allyloxynaphthalene 
• 51783-45-0 1-hydroxy-2-acetonaphthone 
• 136811-77-3 2-acetyl-1-(3-methylbut-2-enyloxy)naphthalene 
• 917-54-4 methyllithium 
• 86-48-6 1-hydroxy-2-naphthoic acid 
• 1888-33-1 N-acetyl-(4-methylbenzene)sulfonamide 

Downstream Products

• 125574-07-4 1t-(3-hydroxy-4-methoxy-phenyl)-3-(1-hydroxy-naphthyl-⁽²⁾)-propen-⁽¹⁾-one-⁽³⁾ 
• 273926-67-3 1-(1-ethoxy-[2]naphthyl)-ethanone 
• 861353-04-0 4-methyl-3-phenyl-benzo[h]chromen-2-one 
• 30159-69-4 2-ethyl-1-naphthol 
• 679833-22-8 2-ethyl-1,2,3,4-tetrahydro-[1]naphthol 
• 52220-64-1 1-(4-bromo-1-hydroxynaphthalen-2-yl)ethanone 
• 99414-69-4 2-[1-(2-phenylhydrazono)ethyl]naphthalen-1-ol 
• 51864-09-6 1-(1-hydroxynaphthalen-2-yl)ethan-1-one oxime 
• 530740-47-7 1-(4-chloro-1-hydroxy-2-naphthyl)ethanone 
• 80309-01-9 ω,4-dibromo-2-acetyl-1-naphthol 
• 104397-06-0 bis-(3-acetyl-4-hydroxy-[1]naphthyl)-phenyl-methane 
• 125574-10-9 3',4'-benzo-2',4-dihydroxychalcone 
• 934163-66-3 2-acetylnaphthalen-1-yl 4-methoxybenzoate 
• 57822-39-6 3',4'-benzo-2',3-dihydroxychalcone 

Relevant academic research and scientific papers

Lanthanide bis(trifluoromethanesulfonyl)amides, synthesis, characterization and catalytic activity

The synthesis of lanthanum, neodymium and ytterbium bis(trifluoromethanesulfonyl)amides, named triflimidates, from acetates, carbonates and oxides is investigated. When the synthesis is performed in water, all the salts contain one molecule of water and the lanthanum and neodymium salts synthesized from the acetates also contain one molecule of acetic acid. After removal of the water and acetic acid in refluxing ethanol, the salts are obtained anhydrous but associated for lanthanum and neodymium, whereas the ytterbium salt is monomeric and volatile. When the synthesis is performed directly in ethanol, the neodymium salt contains two molecules of coordinated ethanol. In non-hazardous solvents, these triflimidates are better catalysts than the analogous triflates toward either Friedel-Crafts acylations, or Fries transpositions or Baeyer-Villiger oxidations. Unexpectedly, the cerium(IV) triflimidate catalyzes the oxidation of aromatic ketones to give the corresponding acids.

Manganese triacetate oxidation of methyl 1-hydroxy-2-naphthalene carboxylates

Manganese-triacetate mediated oxidation of 1-hydroxy-2-napthalene carboxylates in benzene under anhydrous conditions delivers the dimerized product. However, acetoxylation on the ortho- or para-position, or oxidation to quinones occurs on the 1-hydroxy-3-substituted 2-napthalene carboxylates depending on the nature of the substituents when the reaction is carried out in a mixture of acetic acid/acetonitrile.

A novel fluorescent probe based on 7,8-benzochromone-3-carbaldehyde-(rhodamine B carbonyl) hydrazone for detection of trivalent cations and Zn2+ in different systems

In this article, a new fluorescence probe 7,8-benzochromone-3-carbaldehyde- (rhodamine B carbonyl) hydrazone (L) was synthesized, which had been explored to detect Zn2+ and trivalent metal ions M3+ (Al3+, Cr3+ and Fe3+). When the excitation wavelength was 490 nm, L showed high selectivity and high sensitivity to M3+ which was superior to monovalent and divalent metal cations in methanol solution. In EtOH/H2O (15/1, V/V), L showed selective fluorescence response to Zn2+, when the excitation wavelength was set to 425 nm. Furthermore, the detection limits of L for Fe3+, Al3+ and Cr3+ were 2.46 × 10?9 M, 2.54 × 10-9 M and 4.23 × 10-8 M, respectively. And the detection limit of L for Zn2+ was calculated to be 1.45 × 10-7 M. The coordination ratio between L and M3+ was determined from the Job's plot (fluorescent spectrum) to be 2:1 and the coordination ratio of L and Zn2+ was 1:1. Additionally, L might be used as a colorimetric probe of Cu2+ in EtOH/H2O (15/1, V/V) solution., which could be observed with the naked eye from colorless to red in the presence of Cu2+.

Synthesis and supramolecular structure of 2-acetyl-1-naphthol

2-Acetyl-1-naphthol with the molecular formula C12H10O2, is stabilized by intramolecular O2-H2...O1 hydrogen bond forming a six-membered ring, nearly planar with the naphthone ring and the distances from C1 atom of acetyl group to mean plane of the three six-membered ring is 0.112(3) ?. Moreover, the structure is stabilized by intermolecular C-H...p and p-p stacking interactions.

Synthesis and structure-activity relationship studies of α-naphthoflavone derivatives as CYP1B1 inhibitors

Cytochrome P450 1B1(CYP1B1) has been recognized as an important target for cancer prevention and drug resistance reversal. In order to obtain potent and selective CYP1B1 inhibitors, a series of forty-one α-naphthoflavone (ANF) derivatives were synthesized, characterized, and evaluated for CYP1B1, CYP1A1 and CYP1A2 inhibitory activities. A closure look into the structure-activity relationship for the inhibitory effects on CYP1B1 indicated that modification of the C ring of ANF would decrease the CYP1B1 inhibitory potency, while incorporation of substituent(s) into the different positions of the B ring yielded analogues with varying CYP1B1 inhibitory capacity. Among these derivatives, compounds 9e and 9j were identified as the most potent two selective CYP1B1 inhibitors with IC50 values of 0.49 and 0.52 nM, respectively, which were 10-fold more potent than the lead compound ANF. In addition, molecular docking and a reasonable 3D-QSAR (three-dimensional quantitative structure-activity relationship) study were performed to provide a better understanding of the key structural features influencing the CYP1B1 inhibitory activity. The results achieved in this study would lay a foundation for future development of selective, potent, low-toxic and water-soluble CYP1B1 inhibitors.

Benzoflavone derivatives as potent antihyperuricemic agents

Two series of benzoflavone derivatives were rationally designed, synthesized and evaluated for their xanthine oxidase (XO) inhibitory potential. Among both series, eight compounds (NF-2, NF-4, NF-9, NF-12, NF-16, NF-25, NF-28, and NF-32) were found to exert significant XO inhibition with IC50 values lower than 10 μM. Enzyme kinetic studies revealed that the most potent benzoflavone derivatives (NF-4 and NF-28) are mixed type inhibitors of the XO enzyme. Molecular modeling studies were also performed to investigate the binding interactions of these molecules (NF-4 and NF-28) with the amino acid residues present in the active site of the enzyme. Docking results confirmed that their favorable binding conformations in the active site of XO can completely block the catalytic activity of the enzyme. Benzoflavone derivatives exhibiting potent XO enzyme inhibition also showed promising results in a hyperuricemic mice model when tested in vivo.

Directed Hydroxylation of sp2 and sp3 C-H Bonds Using Stoichiometric Amounts of Cu and H2O2

The use of copper for C-H bond functionalization, compared to other metals, is relatively unexplored. Herein, we report a synthetic protocol for the regioselective hydroxylation of sp2 and sp3 C-H bonds using a directing group, stoichiometric amounts of Cu and H2O2. A wide array of aromatic ketones and aldehydes are oxidized in the carbonyl γ-position with remarkable yields. We also expanded this methodology to hydroxylate the β-position of alkylic ketones. Spectroscopic characterization, kinetics, and density functional theory calculations point toward the involvement of a mononuclear LCuII(OOH) species, which oxidizes the aromatic sp2 C-H bonds via a concerted heterolytic O-O bond cleavage with concomitant electrophilic attack on the arene system.

ATF3 INDUCTION COMPOUNDS

Provided are compounds for treating and/or preventing obesity and obesity-related disorders. Particularly, provided are chromanone derivatives used as ATF3 inducer and for treating and/or preventing obesity and obesity-related disorders such as heart disease, hypertension, hyperlipidemia and diabetes.

Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies

A library of forty 7,8-benzoflavone derivatives was synthesized and evaluated for their inhibitory potential against cholesterol esterase (CEase). Among all the synthesized compounds seven benzoflavone derivatives (A-7, A-8, A-10, A-11, A-12, A-13, A-15) exhibited significant inhibition against CEase in in vitro enzymatic assay. Compound A-12 showed the most promising activity with IC50value of 0.78?nM against cholesterol esterase. Enzyme kinetic studies carried out for A-12, revealed its mixed-type inhibition approach. Molecular protein–ligand docking studies were also performed to figure out the key binding interactions of A-12 with the amino acid residues of the enzyme's active site. The A-12 fits well at the catalytic site and is stabilized by hydrophobic interactions. It completely blocks the catalytic assembly of CEase and prevents it to participate in ester hydrolysis mechanism. The favorable binding conformation of A-12 suggests its prevailing role as CEase inhibitor.

Lithiation of a silyl ether: Formation of an ortho-fries hydroxyketone

A hydroxy-directed alkylation of an N,N-diethylarylamide using CIPE-assisted α-silyl carbanions (CIPE=complex-induced proximity effect) has been developed using a simple reagent combination of LDA (lithium diisopropylamide) and chlorosilane. A study of the mechanism, and the application of the procedure to an anionic Snieckus-Fries rearrangement for a highly efficient synthesis of the potent phosphatidylinositol 3-kinase (PI3K) inhibitor LY294002, are reported.