2670-18-0

Usage

InChI:InChI=1/C12H14O2/c1-7-5-9-10(6-8(7)2)12(14)4-3-11(9)13/h3-4,9-10H,5-6H2,1-2H3

Upstream product

• 123-31-9 hydroquinone 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 106-51-4 p-benzoquinone 

Downstream Products

• 6944-78-1 2-amino-3-bromo-6,7-dimethyl-1,4-naphthoquinone 
• 41791-77-9 2,3-dibromo-6,7-dimethyl-1,4-naphthoquinone 
• 52280-69-0 6,7-Dimethyl-2-hydroxy-1,4-naphthochinon 
• 7475-96-9 6,7-dimetil-5,8-dihidro-1,4-naftohidroquinona 
• 170751-93-6 3-mesitil-6,7-dimetilnafto<2,3-d>isoxazol-4,9-diona 
• 2202-79-1 6,7-dimethyl-1,4-naphthoquinone 

Relevant academic research and scientific papers

Synthesis of cage [4.4.2]propellanes and D3 -trishomocubanes bearing spiro linkage

Abstract: The synthesis of substituted cage [4.4.2]propellanes and D3-trishomocubanes bearing spiro linkage have been assembled with the aid of Diels–Alder reaction and ring-rearrangement as key steps. Here, readily available 1,4-hydroquinone, isoprene, spiro[2.4]hepta-4,6-diene and spiro[4.4]nona-1,3-diene were used as starting materials. The unusual rearrangement of cage propellanes with zinc/acetic acid produced D3-trishomocubanes in good yields. Graphical Abstract: Several cage [4.4.2]propellanes and D3-trishomocubanes have been assembled by Diels–Alder reaction (DA), [2+2] photocycloaddition, and acid-promoted rearrangement. Ring-rearrangement was observed in cage [4.4.2]propellane framework during the acid catalyzed reaction. Rearrangement approach provide new opportunities to construct unusual polycycles.[Figure not available: see fulltext.]

Ruthenium(II)-Catalyzed Double Annulation of Quinones: Step-Economical Access to Valuable Bioactive Compounds

Double ruthenium(II)-catalyzed alkyne annulations of quinones were accomplished. Thus, a strategy is reported that provides step-economical access to valuable quinones with a wide range of applications. C?H/N?H activations for alkyne annulations of naphthoquinones provided challenging polycyclic quinoidal compounds by forming four new bonds in one step. The singular power of the thus-obtained compounds was reflected by their antileukemic activity.

Porous Crystalline Olefin-Linked Covalent Organic Frameworks

The first unsubstituted olefin-linked covalent organic framework, termed COF-701, was made by linking 2,4,6-trimethyl-1,3,5-triazine (TMT) and 4,4′-biphenyldicarbaldehyde (BPDA) through Aldol condensation. Formation of the unsubstituted olefin (-CHa?CH-)

Organocatalytic double arylation of 3-isothiocyanato oxindoles: Stereocontrolled synthesis of complex spirooxindoles

Quinones, precursors of aromatic structures, were firstly employed as the electrophiles for the organocatalytic Michael addition/cyclization cascade reaction with versatile 3-isothiocyanato oxindoles. Chiral bifunctional organocatalyst was appropriate for this enantioselective transformation to afford a variety of novel spirooxindoles, possessing a spirocyclic stereocenter adjacent to the aromatic ring, via asymmetric double arylation. These synthesized spirooxindoles are very difficult to access by the reported methods and were obtained in excellent chemical yields with excellent enantioselectivities.

Ruthenium-catalyzed C-H oxygenation of quinones by weak O-coordination for potent trypanocidal agents

Ruthenium-catalysis enabled the C-5 selective C-H oxygenation of naphthoquinones, and also sets the stage for the site-selective introduction of a hydroxyl group into anthraquinones. A-ring modified naphthoquinoidal compounds represent an important class of bioactive quinones for which the present study encompasses the first C-H oxygenation strategy by weak O-coordination.

Photosensitization of Fluorofuroxans and Its Application to the Development of Visible Light-Triggered Nitric Oxide Donor

Nitric oxide (NO) is an endogenous signaling molecule used in multiple biochemical processes. The development of switchable NO donors that deliver an NO payload under spatiotemporal control harbors many medicinal benefits. Previously, 4-fluorofuroxans were found to function as a UV light-induced NO donor under physiological conditions based on the photoinduced isomerization mechanism; however, the isomerization of fluorofuroxans with longer wavelength light is desired for further application into living systems. Herein, we report the use of photosensitizers in the photochemical isomerization of fluorofuroxan, enabling the use of visible light to induce isomerization. Among the tried photosensitizers, anthraquinone derivatives showed a good sensitizing ability to isomerize 4-fluorofuroxan to 3-fluorofuroxan using visible light. This new phenomenon was applied to the synthesis of a water-soluble anthraquinone-fluorofuroxan all-in-one molecule, which demonstrated promising NO-releasing ability using 400-500 nm irradiation. A high level of control is displayed with "on" and "off" NO-release functionality suggesting that photosensitizer-furoxan hybrids would make valuable donors. Furthermore, unlike most furoxans, NO is released in the absence of thiol cofactor.

Pentacenequinone-stabilized silver nanoparticles: A reusable catalyst for the diels-alder [4 + 2] cycloaddition reactions

Silver nanoparticles (AgNPs) stabilized by aggregates of derivative 4 have been used as catalyst for the construction of synthetically and biologically important [4 + 2] cycloadducts at room temperature.

Trinuclear Mn(ii) complex with paramagnetic bridging 1,2,3-dithiazolyl ligands

The first metal coordination complex of a radical ligand based on the 1,2,3-dithiazolyl heterocycle is reported. 6,7-Dimethyl-1,4-dioxo-naphtho[2,3-d] [1,2,3]dithiazolyl acts as a bridging ligand in the volatile trinuclear Mn(hfac)2-Rad-Mn(hfac)2-Rad-Mn(hfac)2 complex (hfac = 1,1,1,5,5,5-hexafluoroacetylacetonato-). The Mn(ii) and radical ligand spins are coupled anti-ferromagnetically (AF) resulting in an ST = 13/2 spin ground state.

Regioselective cyclopolymerization of 1,7-octadiynes

The regioselective cyclopolymerization of two structurally different 1,7-octadiynes, i.e. of 1,4-dihexyloxy-2,3-dipropargylbenzene (M1) and (R,R)/(S,S)-4,5-bis(trimethylsilyloxy)-1,7-octadiyne (M2) has been achieved with the modified Grubbs-Hoveyda-type metathesis initiator Ru(NCO) 2(IMesH2)(=CH-(2-(2-PrO)C6H4)) (I1, IMesH2 = 1,3-dimesitylimidazolidin-2-ylidene) and with a series of Schrock initiators in the presence of quinuclidine, yielding conjugated polymers consisting virtually exclusively of 1,2-cyclohex-1-enylenvinylene units. In contrast to I1, Mo(N-2,6-(2-Pr)2C6H3) (CHCMe2Ph)(OCHMe2)2 (I3) allows for establishing a living polymerization with M2 in the presence of quinuclidine. The structure of the polymers, which represent highly soluble and stable poly(acetylene) analogues, was confirmed by comparing the 13C NMR shifts of model compounds with those of the corresponding polymer. Poly(ene)s that are virtually solely based on six-membered repeat units show a bathochromic shift in UV-absorption compared to poly(ene)s based on six- and seven-membered rings.

A Tin-tungsten mixed oxide as an efficient heterogeneous catalyst for C-C Bond Bond-Forming reactions

The tin-tungsten mixed oxide prepared by the calcination of the tin-tungsten hydroxide precursor with a Sn/W molar ratio of 2 at 800 °C (SnW2-800) acts as an effective and reusable solid catalyst for C-C bond-forming reactions, such as the cyclization of citronellal, the Diels-Alder reaction, and the cyanosilylation of carbonyl compounds with trimethylsilyl cyanide (TMSCN). Various kinds of structurally diverse aliphatic, aromatic, and unsaturated, heteroatom-containing substrates could be converted into the desired products in high to excellent yields. The observed catalyses for these reactions were truly heterogeneous and the recovered catalyst could be reused several times without an appreciable loss of its high catalytic performance. The Bronsted acid sites generated on the aggregated polytungstate species on SnW2-800 likely play an important role in the C-C bond-forming reactions.