33982-92-2

Upstream product

• 106-51-4 p-benzoquinone 
• 78-79-5 isoprene 
• 123-31-9 hydroquinone 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 2622-21-1 1-vinylcyclohexene 
• 3943-91-7 ethyl 2,5-dihydroxybenzoate 

Downstream Products

• 81402-06-4 6-(hydroxymethyl)naphthalene-1,4-dione 

Relevant academic research and scientific papers

AN ANTHRAQUINONE FROM HEDYOTIS DIFFUSA

A new anthraquinone, 2,3-dimethoxy-6-methylanthraquinone, has been isolated from Hedyotis diffusa.

Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized D3-Trishomocubanes via the Rearrangement Approach

A new synthetic route to D3-trishomocubanone and oxa- D3-trishomocubane derivatives has been established by the rearrangement approach. A remotely located methyl substituent in the six-membered ring contributed to the acid-catalyzed rearrangement of the cage dione in an unusual fashion. This rearrangement approach provided an attractive route to extended D3-trishomocubanes, which are not accessible by the conventional multistep synthetic sequence. For the first time, two phenyl groups were incorporated from the solvent into the strained trishomocubane skeleton in an unprecedented manner via carbocation-mediated rearrangement with the aid of BF3·OEt2. Interestingly, an oxa-bridged trishomocubane skeleton was also formed during acid-promoted rearrangement.

Synthesis of six-membered functionalized carbocyclic compounds by one-pot reaction of hydroquinone derivatives and dienes

A general method for one-pot reaction of hydroquinone derivatives and dienes has been developed. The system of Pb3O4 in tetrahydrofuran- trifluoroacetic acid was found to play dual roles as oxidant for the generation of quinones in situ and as catalyst for the Diels-Alder cycloaddition, which makes the one-pot reaction efficient and easy to carry out. Using this method, a variety of six-membered functionalized carbocyclic compounds can be easily prepared in medium to excellent yields at room temperature. Copyright

6-Substituted 1,4-naphthoquinone oxime derivatives (I): synthesis and evaluation of their cytotoxic activity

Abstract: A series of 6-substituted 1,4-naphthoquinone oxime derivatives were synthesized and evaluated for their in vitro cytotoxicity against four cancer cell lines and one normal cell line. Some compounds exhibited moderate to good cytotoxicity towards cancer cells and meanwhile all the synthesized compounds displayed no apparent cytotoxic activity against normal cells (IC50?>?100?μM). Among these oxime derivatives, three compounds showed more potent cytotoxicity against human colon cancer cell lines (HCT-15) than adriamycin and 5-fluorouracil, with an IC50 value of 2.52, 1.96, and 2.27?μM, respectively. Additionally, structure–activity relationship studies revealed that cytotoxic effects of these oxime derivatives were not only largely dependent upon the size of alkyl chain R1, but also upon substituents R2 of the branch chain, indicating that the strong cytotoxicity of these compounds was ascribed to their appropriate lipophilicity. Collectively, this study could provide available strategy for design and synthesis of 6-substituted 1,4-naphthoquinone oxime derivatives as potential anticancer agents. Graphical abstract: [Figure not available: see fulltext.].

Non-covalent allosteric regulation of capsule catalysis

Allosteric regulation is an essential biological process that allows enzymes to modulate their active site properties by binding a control molecule at the protein exterior. Here we show the first example of capsule catalysis in which activity is changed by exotopic binding. This study utilizes a simple Pd2L4 capsule that can partition substrates and external effectors with high fidelity. We also present a detailed, quantitative understanding of how effector interactions alter both substrate and transition state binding. Unlike other allosteric host systems, perturbations are not a consequence of large mechanical changes, rather subtle electronic effects resulting from weak, non-covalent binding to the exterior surface. This investigation paves the way to more sophisticated allosteric systems.

High Activity and Efficient Turnover by a Simple, Self-Assembled "artificial Diels-Alderase"

The Diels-Alder (DA) reaction is a cornerstone of synthesis, yet Nature does not use catalysts for intermolecular [4+2] cycloadditions. Attempts to create artificial "Diels-Alderases" have also met with limited success, plagued by product inhibition. Using a simple Pd2L4 capsule we now show DA catalysis that combines efficient turnover alongside enzyme-like hallmarks. This includes excellent activity (kcat/kuncat > 103), selective transition-state stabilization comparable to the most proficient DA catalytic antibodies, and control over regio- and chemoselectivity that would otherwise be difficult to achieve using small-molecule catalysts. Unlike other catalytic approaches that use synthetic capsules, this method is not defined by entropic effects; instead multiple H-bonding interactions modulate reactivity, reminiscent of enzymatic action.

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.]

Catalytic Electrophilic Alkylation of p-Quinones through a Redox Chain Reaction

Allylation and benzylation of p-quinones was achieved through an unusual redox chain reaction. Mechanistic studies suggest that the existence of trace hydroquinone initiates a redox chain reaction that consists of a Lewis acid catalyzed Friedel–Crafts alkylation and a subsequent redox equilibrium that regenerates hydroquinone. The electrophiles could be various allylic and benzylic esters. The addition of Hantzsch ester as an initiator improves the efficiency of the reaction.

Hydrogen-bond-rich ionic liquids as effective organocatalysts for Diels-Alder reactions

The synthesis and characterisation of new hydrogen-bond-rich ionic liquids and studies of their catalytic performance in Diels-Alder reactions are described. d-Glucose and chloroalcohols were used as the raw materials and as the sources of hydroxyl groups for the synthesis of ionic-liquid cations, whereas weakly coordinating bis(trifluoromethylsulfonyl)imide was used as the anion. The new ionic liquids were analysed by 1H and 13C NMR spectroscopy and by ESI-MS experiments, which confirmed their structures. In addition, the thermal data of the studied ionic liquids measured by differential scanning calorimetry and thermogravimetric analysis showed that these compounds tend to form a glass at temperatures in the range of -29°C to -16°C and are thermally stable from ambient temperature to at least 430°C, most likely because of the presence of bis(trifluoromethylsulfonyl) imide anions. The performance of the ionic liquids in the model reaction of cyclopentadiene with diethyl maleate or methyl acrylate was investigated. The studied ionic liquids showed high activity even when present in catalytic amounts (4 mol% with respect to the dienophile). An increase in the number of hydroxyl groups present in the ionic liquid structure resulted in higher reaction rates. This journal is the Partner Organisations 2014.

Recyclable organotungsten Lewis acid and microwave assisted Diels-Alder reactions in water and in ionic liquids

The water-soluble, organotungsten Lewis acid, [OP(2-py)3W(CO) (NO)2](BF4)2 (1), was synthesized and characterized. A series of 1-catalyzed Diels-Alder reactions were investigated under conventional heating or microwave heating conditions. The cycloaddition reactions were efficiently conducted in either water or in an ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate. The ionic liquid acts as a powerful medium not only for rate- and selectivity enhancements but also for facilitating catalyst recycling. Dramatic rate acceleration via microwave flash heating as compared to thermal heating was observed. Graphical Abstract