Category: 5455-94-7

Barclay, Lawrence R. C.; Young, Robert Hayworth; Adams, Keir Leigh; Foote, Helen M. published the artcile< o-Diquaternary aromatic compounds. IV. Acid-catalyzed rearrangements of poly(alkyltetralones) and related ketones>, Related Products of 5455-94-7, the main research area is tetralone polymethyl rearrangement; methyltetralone rearrangement; acetylindan derivative; indan acetyl methyl.

The ketones 1,1,4,4-tetramethyl-2-tetralone (I), 1,1,4,4,7-pentamethyl-2-tetralone (II), and 1,1,4,4,6-pentamethyl-2-tetralone (III) undergo rearrangement on heating with aluminum chloride or ferric chloride in tetrachloroethane or nitromethane into mixtures of their resp. isomeric ketones, 1-acetyl-1,3,3-trimethylindan and 2,2,4,4-tetramethyl-1-tetralone from I, 1-acetyl-1,3,3,6-tetramethylindan and 2,2,4,4,7-pentamethyl-1-tetralone from II, and 1-acetyl-1,3,3,5-tetramethylindan and 2,2,4,4,6-pentamethyl-1-tetralone from III. A quant. study using g.l.c. of the distribution of the ketones with time shows that the sequence of the rearrangement is: A methyl group homologously para to the carbonyl (in III) accelerates the rearrangement. The same kind of rearrangement takes place during Friedel-Crafts cycloalkylation with 2,2,5,5-tetramethyltetrahydrofuranone. A unifying reaction mechanism is postulated to account for the rearrangements. This mechanism also accounts for the rearrangement and fragmentation products from treatment of 1,1,4,4-tetramethyl-2,3-dioxotetralin (IV) with aluminum chloride or sulfuric-acetic acids. The products from IV include 1-acetyl-1,3,3-trimethyl-2-indanone, 1,1,3-trimethyl-2-indanone, and, from the aluminum chloride-catalyzed rearrangement, 5(or 6)-acetyl-1,1,3-trimethyl-2-indanone.

Canadian Journal of Chemistry published new progress about Alkylation. 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, Related Products of 5455-94-7.

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Nazarski, Ryszard; Skolimowski, Janusz; Skowronski, Romuald published the artcile< Sterically crowded five-membered heterocyclic systems. Part I. Synthesis of acetylene derivatives of azolidyne and oxolane>, Product Details of C8H14O2, the main research area is ethynylation Favorskii pyrrolidinone tetramethyl; alkynylation tetrahydrofuranone tetramethyl; alkynylpyrrolidinol tetramethyl; alkynylfuranol tetrahydrotetramethyl.

Alkynyl 5-membered heterocyclic compounds I (R = H, Ph; X = O, NH) were prepared by alkynylation of the heterocyclic ketones II by the Favorskii alkynylation (KOH, alkyne, THF) or Grignard-Iotsitch method (EtMgBr, alkyne). Favorskii ethynylation of II (X = NH) gave 44% I (R = H; X = NH), whereas Favorskii ethynylation of II (X = O) gave no ethynylation product which indicated that the amino group in II (X = NH) acts as a catalyst in the ethynylation.

Polish Journal of Chemistry published new progress about 5455-94-7. 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, Product Details of C8H14O2.

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Jasiobedzki, Wieslaw; Wozniak-Kornacka, Janina published the artcile< Electron spectra and synthesis of some α-tetrahydrofurandiones and -diols with phenyl and tert-butyl substituents in 2,5 positions>, Reference of 5455-94-7, the main research area is hydration tetrahydrofurandione UV; tetrahydrofuranone UV hydration; furandiol tetrahydro UV.

The effect of hydration on the UV spectra of α-diones I (R = R1 = R2 = R3 = Me; R = R2 = Ph, R1 = R3 = Me3C; R = R1 = R2 = Ph, R3 = CMe3; R = R1 = R2 = R3 = Ph) was compared to that on similarly structured tetrahydrofuranones, e.g., II. The UV spectrum of 3,4-tetrahydrofurandiols and 3-tetrahydrofuranols were determined

Bulletin de l’Academie Polonaise des Sciences, Serie des Sciences Chimiques published new progress about Hydration reaction. 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, Reference of 5455-94-7.

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Peijnenburg, W. J. G. M.; Buck, H. M. published the artcile< The effects of substituents and solvent polarity on photochemical [1,3] sigmatropic shifts. Experimental evidence in favor of the occurrence of sudden polarization in acyclic alkenes>, Name: 2,2,5,5-Tetramethyldihydrofuran-3(2H)-one, the main research area is photorearrangement ethylidenenaphthalenol mechanism.

On direct irradiation of I in various solvents, fast E-Z isomerization around the exocyclic double bond was observed This led to the formation of a 50:50 mixture of E/Z isomers. Further irradiation of this mixture resulted in the clean formation of II, the product derived from a photochem. [1,3]-OH shift in I or its geometric isomer. The yield of II decreases going from a highly apolar solvent to the most polar solvent, n-hexane-autonitrile. This result is a clear support in favor of the sudden polarization mode 1.

Tetrahedron published new progress about Photorearrangement. 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, Name: 2,2,5,5-Tetramethyldihydrofuran-3(2H)-one.

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Hagens, Graham; Wasacz, John P.; Joullie, Madeleine; Yates, Peter published the artcile< Photolysis of 2,2,5,5-tetramethyldihydro-3-furanone>, SDS of cas: 5455-94-7, the main research area is furanones photolysis; photolysis furanones.

The photolysis of 2,2,5,5-tetramethyldihydro-3(2H)-furanone in MeOH gives Me 3-isopropoxy-3-methylbutanoate, Me 3-methyl-2-butenoate, iso-Pr 3-methyl-2-butenoate, Me 3-methyl-3-butenoate, and iso-PrOH. These products are all considered to arise via the ketene formed by Norrish type I cleavage of the dihydrofuranone followed by intramol. H abstraction. Corroboration for this view is that photolysis of 2,2,5,5-tetramethyldihydro-3(2H)-furanone-4-d2 in MeOH gives Me 3-(isopropoxy-2-d)-3-methylbutanoate and Me 3-methyl-2-butenoate-2-d.

Journal of Organic Chemistry published new progress about Photolysis. 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, SDS of cas: 5455-94-7.

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Brown, David W.; Mahon, Mary F.; Ninan, Aleyamma; Sainsbury, Malcolm published the artcile< Synthesis and oxidative behavior of reduced indeno[1,2-b]quinoxalines and benzo[b]phenazines>, Formula: C8H14O2, the main research area is quinoxaline tetracyclic preparation oxidation.

New routes to tetracyclic quinoxalines have been explored and their oxidative behavior has been examined Only if such compounds are devoid of benzylic hydrogen atoms are the corresponding cation radicals stable. Attempts to prepare certain polymethylated quinoxalines failed because of steric problems, and evidence is presented to show that in the case of some monohydrochloride salts proton migration between two nitrogen atoms is discernable through 1H NMR spectroscopy.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry published new progress about Heterocyclization. 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, Formula: C8H14O2.

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Burke, Patrick M.; Reynolds, William F.; Tam, Janet C. L.; Yates, Peter published the artcile< The assignment of proton and carbon-13 chemical shifts for dihydro-3(2H)-furanone derivatives by means of specific deuterium labeling experiments and 13C{1H} decoupling experiments>, Product Details of C8H14O2, the main research area is PMR hydrotetramethylfuranone; furanone dihydrotetramethyl carbon NMR; ring cleavage methyldihydrofuranone acid.

The PMR of I(R=Me,R2=H)(II) in 80% H2SO4 shows a time-dependent decrease in the intensity of the lower-field gem-di-Me signal relative to the upper-field gem-di-Me signal. Due to the reversible opening of II to 2-hydroxy-2,5-dimethyl-4-hexen-3-one which results in D exchange at the C-5 Me groups of II. The lower-field gem-di-Me signal of II in this medium is therefore assigned to these Me groups. A similar relation between the Me proton signals of II in organic solvents is demonstrated by synthesis of I(R=CD3, R1=D), comparison of the PMR and its 2,2- and 5,5-di-Me analogs. and observation of long range coupling in the spectrum of II. Assignment of 13C chem. shifts for II are made based on proton-coupled spectra, showing that the signal of the C-5 Me carbons appears at ∼4 ppm towards lower field than that of the C-2 Me carbons. Both the 1H and 13C chem. shift assignments for II are confirmed from 13C{1H} spectra using low power single frequency 1H decoupling.

Canadian Journal of Chemistry published new progress about Exchange reaction. 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, Product Details of C8H14O2.

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Smejkal, Tomas; Gopalsamuthiram, Vijayagopal; Ghorai, Sujit K.; Jawalekar, Anup M.; Pagar, Dinesh; Sawant, Krishna; Subramanian, Srinivas; Dallimore, Jonathan; Willetts, Nigel; Scutt, James N.; Whalley, Louisa; Hotson, Matthew; Hogan, Anne-Marie; Hodges, George published the artcile< Optimization of Manganese Coupling Reaction for Kilogram-Scale Preparation of Two Aryl-1,3-dione Building Blocks>, Recommanded Product: 2,2,5,5-Tetramethyldihydrofuran-3(2H)-one, the main research area is manganese catalysis coupling reaction aryl dione building block preparation.

Aryl-1,3-diones represent a promising new class of herbicidal acetyl-CoA carboxylase (ACCase) inhibitors. The original synthesis of this structural motif employed in the research phase involved a selenium oxide mediated oxidation, the use of diazoacetate and aryl lead reagents, and a low temperature oxidation of an aryl lithium intermediate, so it was not well suited to large scale synthesis. For kilogram scale synthesis of the two aryl-1,3-dione building blocks I [R = Me, Et], we developed an alternative route which employs a manganese or manganese-copper catalyzed alkyl Grignard coupling and a semi-pinacol rearrangement of an epoxide as the key steps. The optimized conditions could be of general interest as scalable methods for the synthesis of 2-alkyl substituted benzaldehydes and of 2-aryl-1,3-diones.

Organic Process Research & Development published new progress about Coupling reaction. 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, Recommanded Product: 2,2,5,5-Tetramethyldihydrofuran-3(2H)-one.

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Galkina, Olesia S.; Maas, Gerhard; Rodina, Liudmila L.; Nikolaev, Valerij A. published the artcile< Eco-Friendly Approach to Tetrasubstituted Diazodihydrofuranones: Valuable Precursors of Oxetane Derivatives and Other Heterocyclic Compounds>, COA of Formula: C8H14O2, the main research area is diazodihydrofuranone tetrasubstituted green preparation crystal structure.

Eco-friendly routes to 2,2,5,5-tetrasubstituted 4-diazodihydrofuran-3(2H)-ones were developed. In this manner, useful precursors to oxetane derivatives, potential NSAIDs, and other biol. active pharmaceuticals can be prepared without use of toxic reagents and solvents.

Synthesis published new progress about Crystal structure. 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, COA of Formula: C8H14O2.

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Kiani, Salma; Staples, Richard J.; Ted Treves, S.; Packard, Alan B. published the artcile< Synthesis and characterization of a tetramethyl furanone functionalized diiminedioxime, a potential ligand for 64Cu radiopharmaceuticals, and its copper(II) and nickel(II) complexes>, Recommanded Product: 2,2,5,5-Tetramethyldihydrofuran-3(2H)-one, the main research area is copper nickel furanone functionalized imineoxime preparation structure; crystal structure copper nickel furanone functionalized imineoxime; furanone functionalized imineoxime preparation potential radiopharmaceutical imaging ligand.

As part of the authors’ on-going effort to develop 64Cu-based radiopharmaceuticals for PET (positron emission tomog.) imaging of multidrug resistance in cancer, the authors prepared a tetramethylfuranone-functionalized diiminedioxime ligand, TMFPreH (TMFPreH = 4-[3-(4-hydroxyimino-2,2,5,5-dimethyl-dihydro-furan-3-ylideneamino)-propylimino]-2,2,5,5-tetramethyl-dihydrofuran-3(2H)-one oxime) and its Cu(II) and Ni(II) complexes. When the Cu(II) complex was prepared from Cu(ClO4)2 in EtOH, it was isolated as a Cu(II)-bridged dimer, but when it was prepared from Cu(OAc)2 and heated in acetone, an unusual example of an acetone adduct of the ligand is formed by reduction of one of the imine double bonds by the solvent. The Ni(II) complex is square planar with the perchlorate counterion not bonded.

Polyhedron published new progress about Crystal structure. 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, Recommanded Product: 2,2,5,5-Tetramethyldihydrofuran-3(2H)-one.

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem