6345-56-8Relevant academic research and scientific papers
IMPROVED PROCESS FOR THE PREPARATION OF A BENZENE COMPOUND
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Page/Page column 12; 13, (2016/07/05)
A benzene compound is prepared in a process, which comprises (i) reacting a furan compound of formula (I): wherein R1 and R2 are the same or different and independently selected from the group consisting of hydrogen, alkyl, aralkyl, -CHO, -CH2OR3, -CH(OR4 )(OR5), -COOR6, wherein R3, R4 and R5 are the same or different and are independently selected from the group consisting of hydrogen, alkyl, aryl, alkaryl, aralkyl, alkylcarbonyl and arylcarbonyl, or wherein R4 and R5 together form an alkylene group, and wherein R6 is selected from the group consisting of hydrogen, alkyl and aryl, with an olefin of the formula (II): R7-CH=CH-R8; wherein R7 and R8 are the same or different and are independently selected from the group consisting of hydrogen, sulfonate, -CN, -CHO, and -COOR9, wherein R9 is selected from the group consisting of hydrogen, and an alkyl group, or R7 and R8 together form a –C(O)-O-(O)C- group or a –C(O)-NR10-C(O)- group, wherein R10 represents hydrogen, an aliphatic or an aromatic group, to produce an unsaturated bicyclic ether having an unsaturated carbon-carbon bond; (ii) hydrogenating the unsaturated carbon-carbon bond in the unsaturated bicyclic ether to produce a saturated bicyclic ether; and (iii) dehydrating and aromatizing the saturated bicyclic ether to produce the benzene compound.
Substituted Phthalic Anhydrides from Biobased Furanics: A New Approach to Renewable Aromatics
Thiyagarajan, Shanmugam,Genuino, Homer C.,?liwa, Micha?,Van Der Waal, Jan C.,De Jong, Ed,Van Haveren, Jacco,Weckhuysen, Bert M.,Bruijnincx, Pieter C. A.,Van Es, Daan S.
, p. 3052 - 3056 (2015/09/28)
A novel route for the production of renewable aromatic chemicals, particularly substituted phthalic acid anhydrides, is presented. The classical two-step approach to furanics-derived aromatics via Diels-Alder (DA) aromatization has been modified into a three-step procedure to address the general issue of the reversible nature of the intermediate DA addition step. The new sequence involves DA addition, followed by a mild hydrogenation step to obtain a stable oxanorbornane intermediate in high yield and purity. Subsequent one-pot, liquid-phase dehydration and dehydrogenation of the hydrogenated adduct using a physical mixture of acidic zeolites or resins in combination with metal on a carbon support then allows aromatization with yields as high as 84 % of total aromatics under relatively mild conditions. The mechanism of the final aromatization reaction step unexpectedly involves a lactone as primary intermediate.
Total synthesis of neo-tanshinlactones through a cascade benzannulation-lactonization as the key step
Ghosh, Ketaki,Karmakar, Raju,Mal, Dipakranjan
, p. 4037 - 4046 (2013/07/19)
The cascade annulation-lactonization of phthalides with α-carboxyfurylacrylates in the presence of lithium hexamethyldisilazide (LiHMDS) provides both convergent and semiconvergent regioselective syntheses of neo-tanshinlactones in moderate yields. This methodology also offers an avenue for the direct syntheses of hitherto unreported 6-alkoxycarbonyl-substituted neo-tanshinlactones and their heterocyclic analogues. A new synthesis of 4-alkyl phthalides was developed on the basis of a combination of a Duff reaction and Fuerstner cross-coupling. The cascade benzannulation-lactonization of phthalides with α-carboxyfurylacrylates was employed as the key reaction for the concise synthesis of neo-tanshinlactone. Copyright
From Spanish fly to room-temperature ionic liquids (RTILs): Synthesis, thermal stability and inhibition of dynamin 1 GTPase by a novel class of RTILs
Zhang, Jie,Lawrance, Geoffrey A.,Chau, Ngoc,Robinson, Phillip J.,McCluskey, Adam
, p. 28 - 36 (2008/03/30)
In a series of simple synthetic manipulations the active component of the aphrodisiac Spanish fly has resulted in the generation of a new family of room-temperature ionic liquids (RTILs). These RTILs are synthesized in high yield from readily attainable starting materials and can be generated in either meso or chiral forms dependant on the starting furan analogue. Substituted furans (2-methyl and 2-ethyl) afford chiral RTILs, furan affords a family of meso RTILs. In all cases the counterion was crucial, with CH3SO 3- consistently displaying the lowest melting points. Of the RTILs synthesized, TGA plots showed most to be stable up to at least 250°C. We had sought to use these RTILs in a series of dynamic combinatorial chemistry (DCC) assembly reactions via solubulisation of dynamin GTPases pleckstrin homology (PH) domain, as such all analogues were screened as potential inhibitors. Screening reveals that these RTILs display varying levels of dynamin GTPase inhibition with a number amongst the most potent inhibitors of dynamin GTPase yet discovered, e.g.13 IC50 = 2.3 ± 0.3 μM (4-(N,N-dimethyl-N-octadecyl-N-ethyl)-4-aza-10-oxatricyclo[5.2.1]decane-3, 5-dione bromide. Accordingly these RTILs have limited utility for DCC assembly with dynamin GTPase, but may be of use with other proteins or in other fields of study. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
