5697-00-7

Usage

InChI:InChI=1/C14H12O4/c1-9(15)17-13-7-8-14(18-10(2)16)12-6-4-3-5-11(12)13/h3-8H,1-2H3

Upstream product

• 58851-76-6 4-acetyloxy-5,8-dihydronaphthalen-1-yl acetate 
• 571-60-8 1,4-Dihydroxynaphthalene 
• 3408-13-7 2,2'-binaphthoquinone 
• 108-24-7 acetic anhydride 
• 35889-53-3 1',4'-dihydroxy-2,2'-binaphthyl-1,4-quinone 
• 91-20-3 naphthalene 
• 638-39-1 tin(II) acetate 
• 130-15-4 [1,4]naphthoquinone 
• 75-36-5 acetyl chloride 
• 127-09-3 sodium acetate 
• 30432-51-0 1,4-bis(trimethylsiloxy)-naphthalene 
• 1515-76-0 1-acetoxy-1,3-butadiene 
• 106-51-4 p-benzoquinone 
• 75-15-0 carbon disulfide 

Downstream Products

• 7475-24-3 5,6,7,8-tetrahydronaphthalene-1,4-diacetate 
• 288074-67-9 1-(4-ethoxy-1-hydroxynaphthalen-2-yl)ethan-1-one 
• 1452153-58-0 1-(5-hydroxy-2-methyl-2-phenyl-2,3-dihydronaphtho[1,2-b]-furan-4-yl)ethanone 
• 1452153-59-1 1-(5-hydroxy-2-(4-methoxyphenyl)-2,3-dihydronaphtho[1,2-b]-furan-4-yl)ethanone 
• 5813-57-0 2-acetyl-1,4-naphthoquinone 
• 130-15-4 [1,4]naphthoquinone 
• 41426-37-3 4-isopropyloxynaphth-1-ol 
• 352200-69-2 (R)-(-)-1-benzyloxy-4-(oxiranylmethoxy)naphthalene 
• 352200-70-5 (S)-(+)-1-benzyloxy-4-(oxiranylmethoxy)naphthalene 
• 352200-67-0 acetic acid 4-benzyloxy-naphthalen-1-yl ester 
• 133024-37-0 (+/-)-1-benzyloxy-4-(oxiranylmethoxy)naphthalene 
• 73661-06-0 1-Benzyloxy-4-hydroxynaphthalene 
• 40420-47-1 3-acetyl-4-hydroxynaphthalen-1-yl acetate 
• 40420-48-2 2-acetylnaphthalene-1,4-diol 

Relevant academic research and scientific papers

Stereospecific synthesis of highly substituted novel carbasugar as carbonic anhydrase inhibitors: Decahydronaphthalene-1,2,3,4,5,6,7-heptol

Decahydronaphthalene-1,2,3,4,5,6,7-heptol, a new polycyclitol, was synthesized starting from p-benzoquinone. An endo selective Diels-Alder cycloaddition between p-benzoquinone and 1-acetoxybutadiene followed by stereoselective reduction with NaBH4/CeCl3·7H 2O led to the formation of an allylic cis-diol. The formed diol was converted into its acetate with Ac2O/pyridine, in a transformation that required inert atmosphere conditions to suppress a competing aromatization. Controlled oxidation by OsO4 of two olefinic bonds followed by acetylation yielded the heptaacetate whose structure was established unequivocally via application of X-ray crystallographic methods. Removal of the acetate groups by NH3 provided the target heptol. In addition, the carbonic anhydrase inhibitory potency of the title compound was investigated and it was shown to be a potent inhibitor compared to the standard CA inhibitors.

Molecular and crystal structure of 1,4-diacetoxynaphthalene: Structural analysis of methyl substituted 1,4-diacetoxynaphthalenes

Methyl substituted 1,4-diacetoxynaphthalenes have been synthesized and analyzed by means of ultraviolet and 1H-nmr.Positional effects of the methyl substitution on the spectroscopic parameters have been rationalized. 6,7-Dimethyl-1,4-diacetoxynaphthalene, V, has been analyzed by X-ray diffraction techniques.Crystals are monoclinic P21, a = 8.816(1), b = 26.676(7), c = 6.189(1) Angstroem, β = 103.9(2) deg and four molecules in the unit cell.

Exponential Molecular Amplification by H2O2-Mediated Autocatalytic Deprotection of Boronic Ester Probes to Redox Cyclers

Herein, a new molecular autocatalytic reaction scheme based on a H2O2-mediated deprotection of a boronate ester probe into a redox cycling compound is described, generating an exponential signal gain in the presence of O2 and a reducing agent or enzyme. For such a purpose, new chemosensing probes built around a naphthoquinone/naphthohydroquinone redox-active core, masked by a self-immolative boronic ester protecting group, were designed. With these probes, typical autocatalytic kinetic traces with characteristic lags and exponential phases were obtained by using either UV/Visible or fluorescence optical detection, or by using electrochemical monitoring. Detection of concentrations as low as 0.5 μm H2O2 and 0.5 nm of a naphthoquinone derivative were achieved in a relatively short time (2O2 or redox cycling compounds, or for use as a new building block in the development of more complex chemical reaction networks.

Efficient Syntheses of Diverse, Medicinally Relevant Targets Planned by Computer and Executed in the Laboratory

The Chematica program was used to autonomously design synthetic pathways to eight structurally diverse targets, including seven commercially valuable bioactive substances and one natural product. All of these computer-planned routes were successfully executed in the laboratory and offer significant yield improvements and cost savings over previous approaches, provide alternatives to patented routes, or produce targets that were not synthesized previously. Although computers have demonstrated the ability to challenge humans in various games of strategy, their use in the automated planning of organic syntheses remains unprecedented. As a result of the impact that such a tool could have on the synthetic community, the past half century has seen numerous attempts to create in silico chemical intelligence. However, there has not been a successful demonstration of a synthetic route designed by machine and then executed in the laboratory. Here, we describe an experiment where the software program Chematica designed syntheses leading to eight commercially valuable and/or medicinally relevant targets; in each case tested, Chematica significantly improved on previous approaches or identified efficient routes to targets for which previous synthetic attempts had failed. These results indicate that now and in the future, chemists can finally benefit from having an “in silico colleague” that constantly learns, never forgets, and will never retire. Multistep synthetic routes to eight structurally diverse and medicinally relevant targets were planned autonomously by the Chematica computer program, which combines expert chemical knowledge with network-search and artificial-intelligence algorithms. All of the proposed syntheses were successfully executed in the laboratory and offer substantial yield improvements and cost savings over previous approaches or provide the first documented route to a given target. These results provide the long-awaited validation of a computer program in practically relevant synthetic design.

Photooxygenation of oxygen-substituted naphthalenes

The reaction of oxygen-substituted naphthalenes with singlet oxygen (1O2) has been investigated, and labile endoperoxides have been isolated and characterized at –78°C for the first time. Low-temperature kinetics by UV spectroscopy revealed that alkoxy and silyloxy substituents remarkably increase the rate of photooxygenations compared to 1,4-dimethylnaphthalene, whereas acyloxy-substituted acenes are inert towards 1O2. The reactivities nicely correlate with HOMO energies and free activation energies, which we determined by density functional theory calculations. The lability of the isolated endoperoxides is due to their very fast back reaction to the corresponding naphthalenes even at –20°C under release of 1O2, making them to superior sources of this reactive species under very mild conditions. Finally, a carbohydrate-substituted naphthalene has been synthesized, which reacts reversibly with 1O2 and might be applied for enantioselective oxidations in future work.

Anti-tyrosinase, antioxidant, and antibacterial activities of novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2- b ]furans

Novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans (7a-k) were synthesized using ceric ammonium nitrate (CAN)-catalyzed formal [3 + 2] cycloaddition. Synthesized compounds were evaluated for their tyrosinase inhibitory, antioxidant, and antibacterial activities. A modified spectrophotometric method using l-DOPA as substrate was used to determine tyrosinase inhibitory activities, and a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay was used to evaluate antioxidant properties. Antibacterial activities against gram-negative Escherichia coli (KCTC-1924) and gram-positive Staphylococcus aureus (KCTC-1916) were evaluated using the disc diffusion technique. Of the synthesized compounds, 7b with a 4-acetyl and an electron-enriched dihydronaphthofuran ring showed the highest tyrosinase-inhibition activity (IC50 Combining double low line 8.91 μg/mL), which was comparable with that of standard kojic acid (IC50 Combining double low line 10.16 μg/mL), potent antioxidant activity (IC50 Combining double low line 3.33 μg/mL), which was comparable with that of BHT (IC50 Combining double low line 34.67 μg/mL), and excellent antibacterial activities (MICs: 0.50 μg/mL against E. coli and S. aureus strains). A mechanistic analysis of 7b demonstrated that its tyrosinase inhibitory activity was reversible and competitive. Compounds 7c and 7d showed potent antioxidant activities (IC50: 6.30 and 5.01 μg/mL), and compound 7d also exhibited potent inhibitory activity against E. coli with a MIC of 0.5 μg/mL. Furthermore, compounds 7a, 7e, 7f, and 7i showed potent antibacterial activities against S. aureus with MICs of 0.5 μg/mL, which was comparable to that of ampicillin (MIC Combining double low line 0.5 μg/mL).

Stereospecific synthesis of highly substituted novel carbasugar as carbonic anhydrase inhibitors: Decahydronaphthalene-1,2,3,4,5,6,7-heptol

Decahydronaphthalene-1,2,3,4,5,6,7-heptol, a new polycyclitol, was synthesized starting from p-benzoquinone. An endo selective Diels-Alder cycloaddition between p-benzoquinone and 1-acetoxybutadiene followed by stereoselective reduction with NaBH4/CeCl3·7H2O led to the formation of an allylic cis-diol. The formed diol was converted into its acetate with Ac2O/pyridine, in a transformation that required inert atmosphere conditions to suppress a competing aromatization. Controlled oxidation by OsO4of two olefinic bonds followed by acetylation yielded the heptaacetate whose structure was established unequivocally via application of X-ray crystallographic methods. Removal of the acetate groups by NH3provided the target heptol. In addition, the carbonic anhydrase inhibitory potency of the title compound was investigated and it was shown to be a potent inhibitor compared to the standard CA inhibitors.

Efficient access to naphthoquinon-1,3-dithioles: Formal cycloaddition and oxidation of quinones and amines with CS2

An efficient strategy for one-pot synthesis of a variety of naphthoquinon-1,3-dithiole derivatives has been developed. The combined action of the formal cycloaddition and oxidation reaction of quinones and amines in the presence of CS2 without additional oxidant produced naphthoquinon-1,3-dithiole derivatives in good yields.

CONTROLLED RELEASE SYSTEM

The invention provides a molecule comprising a linker moiety attached to a functional moiety via an electrochemically transformable link. The addition of an electrical potential allows the release of the functional moiety. The invention allows the controlled release of, for example, biologically active agents, antidotes, fragrances or detectable agents.

A facile synthesis of naturally occurring binaphthoquinones: Efficient oxidative dimerization of 4-alkoxy-1-naphthols using silver(II) oxide-40% nitric acid

Oxidation of 4-alkoxy-1-naphthols with AgO-40% HNO3 occurred along with a dimerization to give the corresponding bi-1,4-naphthoquinones. The oxidative dimerization required one hydroxyl group and took place at its ortho position. This reaction was applicable to syntheses of naturally occurring binaphthoquinones, bivitamin K3 and 3,3′-bijuglone.