Month: November 2022

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

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

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

Mita, Tsuyoshi published the artcileCo-Catalyzed Direct Addition of Allylic C(sp³)-H Bonds to Ketones, Computed Properties of 503538-69-0, the publication is Organic Letters (2017), 19(21), 5876-5879, database is CAplus and MEDLINE.

By using Co(acac)₂/Xantphos with AlMe₃, the C(sp³)-H bonds of allylarene derivatives were cleaved for reaction with various ketones, affording the homoallylic alcs. in moderate to good yields. The branch/linear selectivity depended on the steric and electronic factors of the ketone electrophiles. The intermediate in this reaction is thought to be a low-valent allylcobalt(I) species, which exhibits high nucleophilicity toward ketones.

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, Computed Properties of 503538-69-0.

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

Xu, Xiaofeng published the artcile2,7-Carbazole-1,4-phenylene Copolymers with Polar Side Chains for Cathode Modifications in Polymer Light-Emitting Diodes, Safety of 9-(6-Bromohexyl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, the publication is Macromolecules (Washington, DC, United States) (2011), 44(11), 4204-4212, database is CAplus.

Alc.-soluble 2,7-carbazole-1,4-phenylene copolymers PCP-NOH and PCP-EP, comprising surfactant-like diethanolamino and phosphonate end groups on the side chains, resp., were synthesized and utilized as electron injection layer (EIL) in combination with high work function Al electrode in polymer light-emitting diodes (PLEDs). The UV-vis absorption and photoluminescence properties of the PCP-NOH and PCP-EP are mainly determined by the conjugated 2,7-carbazole-1,4-phenylene main chain. The PCP-NOH and PCP-EP possess comparable HOMO levels of -5.20 eV and LUMO levels around -2.35 eV. Multilayer PLEDs with a device configuration of ITO/PEDOT:PSS (40 nm)/emissive layer (70 nm)/EIL (15 nm)/Al (100 nm) were successfully fabricated. With fluorescent PFO-DBT15 as the emissive layer, the PLEDs using the PCP-NOH and PCP-EP as the EIL displayed luminous efficiency (LE) of 1.01 and 0.88 cd/A, resp., all obviously higher than 0.015 cd/A for sole Al cathode and 0.58 cd/A for the well-known Ba/Al cathode. With a phosphorescent Ir(mppy)₃-doped polymer blend (PVK:PBD:Ir(mppy)₃ = 100:30:1) as the emissive layer, the PLEDs with the EIL showed high maximum LE of 39.3 cd/A for PCP-NOH and 42.5 cd/A for PCP-EP, in comparison to 0.35 cd/A for sole Al cathode and 32.2 cd/A for the Ba/Al cathode. Particularly, the PLED with PCP-EP as EIL exhibited an excellent LE of 33.3 cd/A at a c.d. of 61.1 mA/cm² (luminance = 20 300 cd/cm²), showing weak roll-off of efficiency at high c.d. Inserting the polar alc.-soluble polymers as interlayer can significantly increase built-in potentials in the PLEDs, from which electron injection barrier from the Al electrode is decreased. The results indicate that the PCP-NOH and PCP-EP are excellent electron injection polymers for high-performance PLEDs with high work function Al electrode.

Macromolecules (Washington, DC, United States) published new progress about 1268162-40-8. 1268162-40-8 belongs to dioxole, auxiliary class Boronic acid and ester,Boronic acid and ester,Bromide, name is 9-(6-Bromohexyl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, and the molecular formula is C14H22BNO4S, Safety of 9-(6-Bromohexyl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole.

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

Lin, Sen published the artcileCatalytic activities of dialkyltin compounds containing silicon to the condensation reaction of acetal (ketal)-alcohol, Quality Control of 177-10-6, the publication is Yingyong Huaxue (2013), 30(3), 271-275, database is CAplus.

The catalytic activities of ten dialkyltin compounds containing silicon were investigated through the condensation reaction of acetal (ketal)-alc. Factors such as amount of catalyst, reaction time, molar ratio of aldehyde (ketone) to alc. and solvent kind were studied toward the yield of reaction. The results show that, except one catalyst, nine compounds are good in catalytic activities for the acetalization and ketalization. The yield reached 92% and 86% under optimal compounds: catalyst dosage was 1.4% based on the mass of the reactants, the molar ratio of the aldehyde to glycol was 1:1.3, ketone to glycol was 1:1.9, cyclohexane was used as the water carrying agent, and the reaction was refluxed for 3 h.

Yingyong Huaxue published new progress about 177-10-6. 177-10-6 belongs to dioxole, auxiliary class Dioxolane,Spiro, name is 1,4-Dioxaspiro[4.5]decane, and the molecular formula is C8H14O2, Quality Control of 177-10-6.

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

Nguyen, Qui-Hien published the artcileIntermolecular Palladium(0)-Catalyzed Atropo-enantioselective C-H Arylation of Heteroarenes, Name: (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 (2020), 142(5), 2161-2167, database is CAplus and MEDLINE.

Atropisomeric (hetero)biaryls are motifs with increasing significance in ligands, natural products, and biol. active mols. The straightforward construction of the stereogenic axis by efficient C-H functionalization methods is extremely rare and challenging. An intermol. and highly enantioselective C-H arylation of relevant heteroarenes providing an efficient access to atropisomeric (hetero)biaryls is reported. The use of a Pd(0) complex equipped with H₈-BINAPO as a chiral ligand enables the direct functionalization of a broad range of 1,2,3-triazoles and pyrazoles in excellent yields and selectivities of up to 97.5:2.5 er. The method also allows for an atroposelective double C-H arylation for the construction of two stereogenic axes with >99.5:0.5 er.

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, Name: (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

Liu, Wenzhu published the artcileSulfuric Acid Immobilized on Activated Carbon Aminated with Ethylenediamine: An Efficient Reusable Catalyst for the Synthesis of Acetals (Ketals), Product Details of C8H14O2, the publication is Nanomaterials (2022), 12(9), 1462, database is CAplus and MEDLINE.

Through the amination of oxidized activated carbon with ethylenediamine and then the adsorption of sulfuric acid, a strong carbon-based solid acid catalyst with hydrogen sulfate (denoted as AC-N-SO₄H) was prepared, of which the surface acid d. was 0.85 mmol/g. The acetalization of benzaldehyde with ethylene glycol catalyzed by AC-N-SO₄H was investigated. The optimized catalyst dosage accounted for 5 weight% of the benzaldehyde mass, and the molar ratio of glycol to benzaldehyde was 1.75. After reacting such mixture at 80 °C for 5 h, the benzaldehyde was almost quant. converted into acetal; the conversion yield was up to 99.4%, and no byproduct was detected. It is surprising that the catalyst could be easily recovered and reused ten times without significant deactivation, with the conversion yield remaining above 99%. The catalyst also exhibited good substrate suitability for the acetalization of aliphatic aldehydes and the ketalization of ketones with different 1,2-diols.

Nanomaterials published new progress about 177-10-6. 177-10-6 belongs to dioxole, auxiliary class Dioxolane,Spiro, name is 1,4-Dioxaspiro[4.5]decane, and the molecular formula is C8H14O2, Product Details of C8H14O2.

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

Cai, Xian-Feng published the artcileSynthesis of chiral exocyclic amines by asymmetric hydrogenation of aromatic quinolin-3-amines, Application of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Chemistry – A European Journal (2014), 20(24), 7245-7248, database is CAplus and MEDLINE.

Asym. hydrogenation of aromatic quinolin-3-amines was successfully developed with up to 94 % enantiomeric excess (ee). Introduction of the phthaloyl moiety to the amino group is crucial to eliminate the inhibition effect caused by the substrate and product, to activate the aromatic ring, and to improve the diastereoselectivity. This new methodol. provides direct and facile access to chiral exocyclic amines. Notably, this report is the first on the highly enantioselective hydrogenation of aromatic amines. The structures and absolute configuration of the compounds were confirmed by the single crystal x-ray diffraction anal. of 4-methyl-N-((2S,3S)-2-phenyl-1,2,3,4-tetrahydroquinolin-3-yl)benzenesulfonamide and its crystallog. data were deposited at the Cambridge Crystallog. Data Center as supplementary publication number CCDC 962689.

Chemistry – A European Journal 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, Application of (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

Chen, Xiaomei published the artcileSynthesis of acetals and ketals catalyzed by task-specific acidic ionic liquid, Formula: C6H12O2, the publication is Yingyong Huagong (2006), 35(2), 96-98, database is CAplus.

In the absence of any organic solvents, the acetalization of aldehydes or ketones with diols was investigated, which catalyzed by task-specific acidic ionic liquid (IL) under mild conditions. The influences of other conditions including the amount of catalyst, reaction time and temperature on yield of products were also discussed. Results showed the optimal reaction conditions were 353 K, the mole ratio of aldehydes or ketones to IL was 5:1, and the yield of acetals achieved 93.8%. It was unnecessary to remove water produced during the reaction process; the catalyst can be reused for five times without any apparent loss of catalytic activity.

Yingyong Huagong 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, Formula: C6H12O2.

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