Category: Dioxole

Du, Ya published the artcileSn-catalyzed synthesis of propylene carbonate from propylene glycol and CO₂ under supercritical conditions, Related Products of dioxole, the publication is Journal of Molecular Catalysis A: Chemical (2005), 241(1-2), 233-237, database is CAplus.

Dibutyltin oxide or dibutyltin dimethoxide was first used as a remarkable selective catalyst for the synthesis of propylene carbonate from propylene glycol and carbon dioxide. The effects of the reaction parameters, such as reaction time, temperature and CO₂ pressure on the amount of propylene carbonate were also exptl. studied. Under the optimized conditions, the amount of propylene carbonate was nearly proportional to PG concentration The use of N,N-dimethylformamide as a co-solvent in this study significantly enhanced the catalytic activity, and the ketals as dehydrating agents greatly improved the yield of PC, which can be limited by the equilibrium A postulated mechanism for the dibutyltin oxide-catalyzed carboxylation of propylene glycol was also discussed.

Journal of Molecular Catalysis A: Chemical published new progress about 1193-11-9. 1193-11-9 belongs to dioxole, auxiliary class Dioxolanes, name is 2,2,4-Trimethyl-1,3-dioxolane, and the molecular formula is C6H12O2, Related Products of dioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Dikusar, E. A. published the artcileSynthesis of New 1-Adamantanecarboxylic Acid Derivatives, Category: dioxole, the publication is Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) (2004), 40(3), 346-352, database is CAplus.

Reactions of 1-adamantanecarbonyl chloride with functionally substituted alcs., phenols, amines, thiols, and ketone oximes gave hitherto unknown 1-adamantanecarboxylic acid esters, amides, and thio esters, including those containing a peroxide group.

Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) published new progress about 68527-74-2. 68527-74-2 belongs to dioxole, auxiliary class Dioxolane,Benzene,Phenol,Ether, name is 2-Methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol, and the molecular formula is C11H14O4, Category: dioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Linton, Elizabeth C. published the artcileCatalytic Enantioselective Meerwein-Eschenmoser Claisen Rearrangement: Asymmetric Synthesis of Allyl Oxindoles, Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Journal of the American Chemical Society (2008), 130(48), 16162-16163, database is CAplus and MEDLINE.

The first catalytic, enantioselective Meerwein-Eschenmoser Claisen rearrangement has been achieved. Palladium(II) BINAP or phosphinooxazoline catalysts were employed to generate oxindole products, e.g. I, with 100% conversion and up to 92% ee.

Journal of the American Chemical Society published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Cho, Chang-Woo published the artcileα-Hydroxy Esters via Enantioselective Hydrogen-Mediated C-C Coupling: Regiocontrolled Reactions of Silyl-Substituted 1,3-Diynes, COA of Formula: C38H24F4O4P2, the publication is Organic Letters (2006), 8(17), 3873-3876, database is CAplus and MEDLINE.

Rhodium-catalyzed asym. reductive coupling of Et glyoxalate and 1,3-diynes in the presence of mol. hydrogen afforded α-hydroxy-β,γ-enynoates with high regio- and enantioselectivity. Reaction of R¹CCCCR³ with OHCCOOR² and H₂ in the presence of Rh-(R)-Cl,MeO-BIPHEP [(1R)-5,5′-dichloro-6,6′-dimethoxy-1,1′-biphenyl-2,2′-bis(diphenylphosphine)] gave (2R)-R³CCCH:CR¹CH(OH)COOR² (1c, R¹ = R³ = Ph, R² = Et; 4c–9c, R¹ = Me₃Si, Me₂^tBuSi; R² = Et; R³ = Ph, Me, cyclopropylmethyl, Me₂^tBuSiOCH₂) with alkyne regioselectivity of >99% and ee values of 89-94%. Notably, for trialkylsilyl-substituted 1,3-diynes, C-C coupling occurs exclusively at the carbon atom bearing silyl group. π-Back-bonding from low valent rhodium as described by the Dewar-Chatt-Duncanson model appears to direct the regiochem. of C-C coupling, as corroborated by calculations of the diyne LUMO coefficients

Organic Letters published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, COA of Formula: C38H24F4O4P2.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Mahungu, Symon M. published the artcileVolatile compounds in heated oleic acid-esterified propoxylated glycerol, SDS of cas: 1193-11-9, the publication is Journal of the American Oil Chemists’ Society (1998), 75(6), 683-690, database is CAplus.

Static headspace and capillary gas chromatog., in combination with IR and mass spectrometry, were used to collect, sep., identify, and quantitate the oxidative and thermal decomposition products in two heated model compound triacylglycerols, oleic acid-esterified propoxylated glycerol (EPG-08 oleate) and triolein. The EPG-08 oleate and triolein were each heated in a deep-fat fryer at 192 ± 8°C for 12 h each day until the oil contained ≥20% polymeric material. Most of the volatile compounds identified in heated triolein and EPG-08 oleate were associated with the oxidative and thermal decomposition of oleates, such as short-chain alkanes, aldehydes, and alcs. The major volatile compounds (concentration >20 ppm) in heated EPG-08 oleate and triolein were heptane, octane, heptanal, octanal, trans-2-decenal, nonanal, and trans-2-undecenal. However, a few minor volatile compounds, not previously found in heated fats and oils, were identified in the heated EPG-08 oleate samples. These compounds included 1,2-propanediol, 1-hydroxy-2-propanone (hydroxyacetone), 1-acetoxy-2-propanone (acetoxyacetone), 2-ethyl-4-methyl-1,3-dioxolane, 2,2,4-trimethyl-1,3-dioxolane, 2-heptyl-4-methyl-1,3-dioxolane, and 4-methyl-2-octyl-1,3-dioxolanes. Alkyl-substituted dioxolanes have been found in heated Me linoleate.

Journal of the American Oil Chemists’ Society published new progress about 1193-11-9. 1193-11-9 belongs to dioxole, auxiliary class Dioxolanes, name is 2,2,4-Trimethyl-1,3-dioxolane, and the molecular formula is C6H12O2, SDS of cas: 1193-11-9.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Woelfel, Keith published the artcileMass spectrometry of the acetal derivatives of selected generally recognized as safe listed aldehydes with ethanol, 1,2-propylene glycol and glycerol, Name: 2-Methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol, the publication is ACS Symposium Series (1998), 193-210, database is CAplus.

The FEMA-GRAS list offers flavor chemists a repertoire of nearly 2000 chems. for use in compounding natural and synthetic flavors for the U.S. marketplace. Aldehydes constitute an important class of these potential flavorants and are widely utilized to impart specific nuances. Alcs. such as ethanol, 1,2-propylene glycol and glycerol are commonly employed as solvents in compounded flavor systems due to their low odor and miscibility in a wide range of aqueous and organic matrixes. However, alcs. and aldehydes react rapidly under anhydrous conditions to form acetal derivatives which often possess different sensory properties. This well known reaction is reversible and its equilibrium is influenced by time, temperature, pH and moisture content. Mass spectra of acetals are currently under represented in com. databases and few literature references are available. Our investigation involved a systematic mass spectrometric study of the acetal derivatives of selected GRAS aldehydes reacted with ethanol, 1,2-propylene glycol and glycerol. Aldehydes from different chem. classes representing saturated and unsaturated aliphatics, aromatics, heterocyclics, terpenoids and others were included for characterization. The corresponding acetals were synthesized, analyzed by GC-MS in electron ionization mode and their retention indexes on a non-polar (polydimethylsiloxane) capillary column were determined A database of mass spectra was produced which includes many previously unreported species. In total, over 60 individual mass spectra were recorded. The characteristic mass spectral fragmentation pathways for each class of acetal are described.

ACS Symposium Series published new progress about 68527-74-2. 68527-74-2 belongs to dioxole, auxiliary class Dioxolane,Benzene,Phenol,Ether, name is 2-Methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol, and the molecular formula is C14H14, Name: 2-Methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Ge, Shaozhong published the artcileNickel-Catalyzed Asymmetric α-Arylation and Heteroarylation of Ketones with Chloroarenes: Effect of Halide on Selectivity, Oxidation State, and Room-Temperature Reactions, Quality Control of 503538-69-0, the publication is Journal of the American Chemical Society (2011), 133(41), 16330-16333, database is CAplus and MEDLINE.

We report the α-arylation of ketones with a range of aryl chlorides with enantioselectivities from 90 to 99% ee catalyzed by the combination of Ni(COD)₂ and (R)-BINAP and the coupling of ketones with a range of heteroaryl chlorides with enantioselectivities up to 99% ee catalyzed by Ni(COD)₂ and (R)-DIFLUORPHOS. The analogous reactions of bromoarenes occur with much lower enantioselectivities. Mechanistic studies showed that the difference in the rates of decomposition of the arylnickel(II) halide intermediates to {[(R)-BINAP]NiX}₂ likely accounts for the difference in the enantioselectivities of the reactions of bromoarenes and chloroarenes. This catalyst decomposition can be overcome by conducting the reactions with [(R)-BINAP]Ni(η²-NC-Ph) (4), which undergoes oxidative addition to haloarenes at room temperature

Journal of the American Chemical Society published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Quality Control of 503538-69-0.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Islam, Tofazzal Md. published the artcileInterruption of the homing events of phytopathogenic Aphanomyces cochlioides zoospores by secondary metabolites from nonhost Amaranthus gangeticus, Name: 9-Hydroxy-6-phenyl-8H-[1,3]dioxolo[4,5-g]chromen-8-one, the publication is Journal of Pesticide Science (Tokyo, Japan) (2004), 29(1), 6-14, database is CAplus.

On the screening of 200 nonhost plants, an Amaranthus gangeticus extract was found to attract and subsequently inhibit the motility of Aphanomyces cochlioides zoospores. The attractant was identified as N-trans-feruloyl-4-O-methyldopamine (I) and the motility inhibitor as nicotinamide (II) using bioassay-guided fractionation and spectroscopic methods. Also isolated were cochliophilin A and chondrillasterol 3-O-β-D-glucopyranoside. I had no inhibitory effect on zoospore motility whereas II immediately halted the motility and caused encystment in a dose-dependent manner (MIC, 5 × 10^-8 M). The cystospores produced by II regenerated zoospores instead of germinating. Concomitant application of I and II produced cystospores that germinated to give hyphae. TLC examinations revealed that A. gangeticus seedling exuded sufficient amounts of II from the roots. Exudation of II from A. gangeticus might be involved in its resistance against the soilborne oomycete phytopathogen A. cochlioides.

Journal of Pesticide Science (Tokyo, Japan) published new progress about 110204-45-0. 110204-45-0 belongs to dioxole, auxiliary class Flavonoids, name is 9-Hydroxy-6-phenyl-8H-[1,3]dioxolo[4,5-g]chromen-8-one, and the molecular formula is C16H10O5, Name: 9-Hydroxy-6-phenyl-8H-[1,3]dioxolo[4,5-g]chromen-8-one.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Berkelhamer, Sara K. published the artcileIn vitro consequences of electronic-cigarette flavoring exposure on the immature lung, COA of Formula: C11H14O4, the publication is International Journal of Environmental Research and Public Health (2019), 16(19), 3635, database is CAplus and MEDLINE.

The developing lung is uniquely susceptible and may be at increased risk of injury with exposure to e-cigarette constituents. We hypothesize that cellular toxicity and airway and vascular responses with exposure to flavored refill solutions may be altered in the immature lung. Fetal, neonatal, and adult ovine pulmonary artery smooth muscle cells (PASMC) were exposed to popular flavored nicotine-free e-cigarette refill solutions (menthol, strawberry, tobacco, and vanilla) and unflavored solvents: propylene glycol (PG) or vegetable glycerin (VG). Viability was assessed by lactate dehydrogenase assay. Brochodilation and vasoreactivity were determined on isolated ovine bronchial rings (BR) and pulmonary arteries (PA). Neither PG or VG impacted viability of immature or adult cells; however, exposure to menthol and strawberry flavored solutions increased cell death. Neonatal cells were uniquely susceptible to menthol flavoring-induced toxicity, and all four flavorings demonstrated lower LDs (LD50) in immature PASMC. Exposure to flavored solutions induced bronchodilation of neonatal BR, while only menthol induced airway relaxation in adults. In contrast, PG/VG and flavored solutions did not impact vasoreactivity with the exception of menthol-induced relaxation of adult PAs. The immature lung is uniquely susceptible to cellular toxicity and altered airway responses with exposure to common flavored e-cigarette solutions

International Journal of Environmental Research and Public Health published new progress about 68527-74-2. 68527-74-2 belongs to dioxole, auxiliary class Dioxolane,Benzene,Phenol,Ether, name is 2-Methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol, and the molecular formula is C11H14O4, COA of Formula: C11H14O4.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Maj, Anna M. published the artcileFirst catalytic asymmetric hydrogenation of quinoxaline-2-carboxylates, Synthetic Route of 503538-69-0, the publication is Tetrahedron (2016), 72(10), 1375-1380, database is CAplus.

For the first time, the asym. hydrogenation of quinoxaline-2-carboxylates was performed successfully. The best catalysts are based on iridium complexes modified by chiral phosphorous ligands. Accelerated examination of ligands and catalysts has been undertaken by using a Chemspeed workstation (automated instrument) workstation enables carrying out, in parallel, eight independent catalytic reactions at the laboratory scale. Tetrahydroquinoxaline-2-carboxylates could be obtained with high yields and up to 74% ee. The synthesis of the target compounds was achieved using chiral ligands, such as (11aR)-10,11,12,13-tetrahydro-N,N-dimethyldiindeno[7,1-de:1′,7′-fg][1,3,2]dioxaphosphocin-5-amine [i/e/. (R)-siphos], 1,1′-[(1S)-6,6′-dimethoxy[1,1′-biphenyl]-2,2′-diyl]bis[1,1-diphenylphosphine] [i.e., (S)-MeO-BIPHEP], (R)-Cl-MeO-BIPHEP, (R)-difluorphos, (R)-GARPHOS, (R)-P-PHOS, (S)-C3-TUNEPHOS [i.e., 1,1′-[(13aS)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin-1,13-diyl]bis[1,1-diphenylphosphine]], (S)-SEGPHOS, (S)-Xyl-SolPhos, CATASium T3, N-[(1R)-2-[(11bR)-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yloxy]-1-methylethyl]-N‘-phenylurea [i.e., ureaphos], SL-J404-1, SL-J006-1, SL-J002-1, SL-J003-1, SL-J009-1, SL-T002-1, SL-W006-1. Pre-catalysts included bis(acetato-κO,κO‘)[(4R)-1,1′-[4,4′-bi-1,3-benzodioxole]-5,5′-diylbis[1,1-diphenylphosphine-κP]]ruthenium [i.e., Ru(OAc)₂[(R)-segphos]], [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium [i.e., RuCl[(R,R)-TsDPEN][p-cymene]] and [1,1′-(1S)-[4,4′-bi-1,3-benzodioxole]-5,5′-diylbis[1,1-diphenylphosphine-κP]][4-cyano-3-nitrobenzenecarboxylato(2-)-κC⁶,κO¹](η³-2-propen-1-yl)iridium.

Tetrahedron published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Synthetic Route of 503538-69-0.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem