Category: 5455-94-7

Harper, Kaid C.; Vilardi, Sarah C.; Sigman, Matthew S. published the artcile< Prediction of Catalyst and Substrate Performance in the Enantioselective Propargylation of Aliphatic Ketones by a Multidimensional Model of Steric Effects>, Product Details of C8H14O2, the main research area is catalyst substrate performance enantioselective propargylation aliphatic ketone steric effect.

The effectiveness of a new asym. catalytic methodol. is often weighed by the number of diverse substrates that undergo reaction with high enantioselectivity. Here we report a study that correlates substrate and ligand steric effects to enantioselectivity for the propargylation of aliphatic ketones. The math. model is shown to be highly predictive when applied to substrate/catalyst combinations outside the training set.

Journal of the American Chemical Society published new progress about Aliphatic ketones Role: RCT (Reactant), RACT (Reactant or Reagent). 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, Product Details of C8H14O2.

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

Ando, Wataru; Kumamoto, Yorio; Tokito, Norihiro published the artcile< Photolysis of a sterically protected bicyclic 1,2,3-selenadiazole>, Recommanded Product: 2,2,5,5-Tetramethyldihydrofuran-3(2H)-one, the main research area is selenadiazole sterically protected photolysis olefin; regioselective photochem cyclocondensation selenadiazole olefin; zwitterionic intermediate photolysis selenadiazole.

The photolysis of sterically protected 1,2,3-selenadiazole I in the presence of olefin (e.g. CH2:CHCN, CH2:CHCO2Me, cyclopentadiene) was studied. The regioselective cycloadducts e.g. II (R = CO2Me, cyano) were obtained via the initially formed zwitterionic intermediate.

Tetrahedron Letters published new progress about Photocyclocondensation 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

Yates, Peter; Burke, Patrick Michael published the artcile< Keto ethers. IV. Products formed on reaction of dihydro-2,2,5,5-tetramethyl-3(2H)-furanone with strong acids>, Synthetic Route of 5455-94-7, the main research area is tetramethylfuranone rearrangement acid; furanone tetramethyl rearrangement acid.

Reaction of furanone I with 96 or ca. 100% sulfuric acid or hot polyphosphoric acid followed by aqueous quenching gave the following products: 2-hydroxy-2,5-dimethyl-4-hexen-3-one, 2,4,4-trimethyl-2-cyclopenten-1-one, 3,5,5-trimethyl-2-cyclopenten-1-one, tetrahydro-3,4,5,5-tetramethylfuran-2,3-diol, 2,5-dihydro-3,5,5-trimethyl-2-methylenefuran and its dimer, 2,5-dihydro-2,3,5,5-tetramethyl-2-furanol, 4-hydroxy-2,4-dimethyl-2-pentenoic acid γ-lactone, 2,3,5-trimethyl-2-cyclopenten-1-one (II), and tetramethylfuran (III). In 96% sulfuric acid the products arise by ring opening, ring opening followed by reclosure to carbocyclic products, Me migration from C-2 to C-3 to give rearranged furan derivatives, and oxidation In ca. 100% sulfuric acid or hot polyphosphoric acid further Me migrations can occur to give II and III.

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

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

Saimoto, Hiroyuki; Hiyama, Tamejiro; Nozaki, Hitosi published the artcile< Regiocontrolled formation of 4,5-dihydro-3(2H)-furanones from 2-butyne-1,4-diol derivatives. Synthesis of bullatenone and geiparvarin>, Recommanded Product: 2,2,5,5-Tetramethyldihydrofuran-3(2H)-one, the main research area is furanone dihydro; butynediol cyclization; bullatenone; geiparvarin.

Two new methods for selective hydration of 1,1,4-trisubstituted 2-butyne-1,4-diols (I) gave 4,5-dihydro-3(2H)-furanones. The first involves selective monoacetylation of the less hindered OH followed by Ag(I)-catalyzed rearrangement and cyclization. to give 3-acetoxy-2,2,5-trisubstituted 2,5-dihydrofurans (II) which on hydrolysis gave 2,2,5-trisubstituted 4,5-dihydro-3(2H)-furanones. Oxidation of II with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone gave 3(2H)-furanones. This method gave naturally occurring 3(2H)-furanones, e.g., bullatenone and geiparvarin. The second approach gave the opposite regioisomer, 2,5,5-trisubstituted 4,5-dihydro-3(2H)-furanones, from diols I by treating the diols with Hg/Nafion-H.

Bulletin of the Chemical Society of Japan published new progress about Cyclization. 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

Wasacz, J. P.; Badding, V. G. published the artcile< A hydration of an alkyne illustrating steam and vacuum distillation>, HPLC of Formula: 5455-94-7, the main research area is laboratory experiment alkyne hydration; steam distillation laboratory experiment.

An experiment involving the conversion of 2,5-dimethyl-3-hexyne-2,5-diol to 2,2,5,5-tetramethyltetrahydrofuran-3-one, suitable for an early organic chem. laboratory course and using aqueous mercuric sulfate without the use of acid, is described. The experiment demonstrated several principles and techniques: hydration of an alkyne; steam distillation; vacuum distillation (optimal); drying of an organic liquid; stereochem.; synthesis of a ketone; keto-enol tautomerism; synthesis of a cyclic ether; and salting out techniques (optional).

Journal of Chemical Education published new progress about Alkynes Role: MSC (Miscellaneous). 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, HPLC of Formula: 5455-94-7.

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

Hirai, Hajime; Ueda, Kenzo; Matsui, Masanao published the artcile< Studies on chrysanthemic acid. Part XXV. Alternative synthesis of chrysanthemic acid via tetrahydrofuran derivatives>, Application of C8H14O2, the main research area is chrysanthemic acid insecticide; chloromethylchloroisopropylhexanoic acid ester.

The olefination reaction between 2,2,5,5-tetramethyltetrahydrofuran-3-one and (EtO)2P(:O)CH2CO2Et afforded an isomeric mixture of the normal α,β-unsaturated ester (I) and the endocyclic β,γ-unsaturated ester (II). Catalytic hydrogenation and subsequent hydrolysis of the mixture gave 2,2,5,5-tetramethyltetrahydrofuryl-3-acetic acid III. III was treated with SOCl2 in the presence of ZnCl2 to give Me2CClCH(CH2CO2Et)CH2CClMe2, from which trans-chrysanthemic acid was obtained by a known method. Pyrocin was also obtained in good yield by heating III with BF3-etherate.

Agricultural and Biological Chemistry published new progress about Insecticides. 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, Application of C8H14O2.

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

Jurutka, Peter W.; Kaneko, Ichiro; Yang, Joanna; Bhogal, Jaskaran S.; Swierski, Johnathon C.; Tabacaru, Christa R.; Montano, Luis A.; Huynh, Chanh C.; Jama, Rabia A.; Mahelona, Ryan D.; Sarnowski, Joseph T.; Marcus, Lisa M.; Quezada, Alexis; Lemming, Brittney; Tedesco, Maria A.; Fischer, Audra J.; Mohamed, Said A.; Ziller, Joseph W.; Ma, Ning; Gray, Geoffrey M.; van der Vaart, Arjan; Marshall, Pamela A.; Wagner, Carl E. published the artcile< Modeling, Synthesis, and Biological Evaluation of Potential Retinoid X Receptor (RXR) Selective Agonists: Novel Analogues of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl|benzoic Acid (Bexarotene) and (E)-3-(3-(1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalen-7-yl)-4-hydroxyphenyl)acrylic Acid (CD3254)>, Electric Literature of 5455-94-7, the main research area is bexarotene methylnaphthylhydroxyphenylacrylic acid preparation retinoic X receptor agonist; structure bexarotene methylnaphthylhydroxyphenylacrylate analog retinoid X receptor agonist activity; mutagenicity vitamin D3 receptor agonism apoptosis bexarotene analog; antitumor activity bexarotene methylnaphthylhydroxyphenylacrylic acid RXR agonist analog; methylnaphthylcyclopropyl pyrimidinecarboxylic acid mol crystal structure.

Analogs of the retinoid X receptor (RXR) agonists bexarotene I (X = CH) and of pentamethylnaphthylhydroxyphenylacrylic acid II such as I (X = N) were prepared as potential antitumor agents and tested for their abilities to act as RXR agonists, to initiate apoptosis in human cancer cells, to modulate transcription mediated by the vitamin D3 receptor, and their mutagenicity in Saccharomyces cerevisiae. Seven of the compounds including I (X = N) stimulate RXR-regulated transcription in mammalian two-hybrid and RXRE-mediated assays, possessed comparable or elevated biol. activity based on EC50 profiles, and retained similar or improved apoptotic activity in CTCL assays compared to bexarotene. The novel compounds demonstrated selectivity for RXR and minimal crossover onto the retinoic acid receptor (RAR) compared to all-trans-retinoic acid, with select analogs also reducing inhibition of other RXR-dependent pathways (e.g., VDR-RXR). The structure of a pentamethylnaphthylcyclopropyl pyrimidinecarboxylic acid RXR agonist was determined by X-ray crystallog.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, Electric Literature of 5455-94-7.

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

Lauer, Matthew G.; Henderson, William H.; Awad, Amneh; Stambuli, James P. published the artcile< Palladium-Catalyzed Reactions of Enol Ethers: Access to Enals, Furans, and Dihydrofurans>, Recommanded Product: 2,2,5,5-Tetramethyldihydrofuran-3(2H)-one, the main research area is palladium catalyzed oxidation alkyl enol ether enal furan hydrofuran.

The palladium-catalyzed oxidation of alkyl enol ethers to enals, which employs low loadings of a palladium catalyst, is described. The mild oxidation conditions tolerate a diverse array of functional groups, while allowing the formation of di-, tri-, and tetrasubstituted olefins. The application of this methodol. to intramol. reactions of alkyl enol ethers containing pendant alcs. provides furan and 2,5-dihydrofuran products.

Organic Letters published new progress about Acetalization. 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

Kuronen, Pirjo; Laitalainen, Tarja published the artcile< Crystal and molecular structure and spectra of 2',2',5,5,5',5',7,7-octamethyl-2',5,5',7-tetrahydrofuro[3,4-d]-1-oxa-3,4-diselenin-2-spiro-3'-furan-4'(3'H)-one from selenium dioxide oxidation of 2,2,5,5-tetramethyltetrahydrofuran-3-one. A novel six-membered heterocyclic ring system in the chalcogen series>, Synthetic Route of 5455-94-7, the main research area is tetramethyltetrahydrofuranone oxidation selenium dioxide; tetrahydrofurandione tetramethyl; crystal structure octamethyltetrahydrofurooxadiseleninspirofuranone; spirofuranone octamethyltetrahydrofurooxadiselenin crystal mol structure; furanone octamethyltetrahydrofurooxadiseleninspiro crystal mol structure; mol structure octamethyltetrahydrofurooxadiseleninspirofuranone.

When 2,2,5,5-tetramethyltetrahydrofuran-3-one 1 was oxidized with selenium dioxide in ethanol, the title heterocycle I was formed along with 2,2,5,5-tetramethyltetrahydro-3,4-furandione 2. The diselenide I represents a novel six-membered heterocycle in the chalcogen series.

Journal of Heterocyclic Chemistry published new progress about Crystal structure. 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, Synthetic Route of 5455-94-7.

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

Rodina, Liudmila L.; Galkina, Olesia S.; Maas, Gerhard; Platz, Matthew S.; Nikolaev, Valerij A. published the artcile< A New Method for C-H Functionalization of Aliphatic Compounds by an Unusual Photochemical Reaction of Diazoketones without Elimination of Nitrogen>, Category: tetrahydrofurans, the main research area is diazotetrahydrofuranone aliphatic compound Wolff rearrangement photochem; hydrazone diazotetrahydrofuranyl preparation; aliphatic compound diazotetrahydrofuranone Wolff rearrangement photochem; bisfuranylhydrazonoethane preparation.

Benzophenone-sensitized reactions of 4-diazotetrahydrofuran-3(2H)-ones with H-donors such as THF, 1,4-dioxane, cyclohexane and di-Et ether, occur without elimination of nitrogen and give rise to the corresponding N-substituted hydrazones or bis-hydrazonoethanes due to a formal insertion of the terminal N atom of diazo group into α-C-H bonds of ethers and aliphatic hydrocarbons, with yields of up to 78 %. Long-wavelength UV irradiation (λ>310 nm) was most suitable for this process, whereas oxygen mols. adequately quench the triplet excited state of the diazoketone and reduce the preparative yields of C-H-insertion products. Hence this photochem. reaction of diazoketones could be used for C-H functionalization of different aliphatic compounds

Asian Journal of Organic Chemistry published new progress about Aliphatic hydrocarbons Role: RCT (Reactant), RACT (Reactant or Reagent). 5455-94-7 belongs to class tetrahydrofurans, and the molecular formula is C8H14O2, Category: tetrahydrofurans.

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