Day: November 25, 2022

Liao, Xuebin published the artcileEnantioselective α-Arylation of Ketones with Aryl Triflates Catalyzed by Difluorphos Complexes of Palladium and Nickel, 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 (2008), 130(1), 195-200, database is CAplus and MEDLINE.

The asym. α-arylation of ketones with aryl triflates is described, and the use of this electrophile with nickel and palladium catalysts containing a segphos derivative increases substantially the scope of highly enantioselective arylations of ketone enolates. The combination of aryl triflates as reactant, difluorphos as ligand, palladium catalysts for reactions of electron-neutral or electron-rich aryl triflates, and nickel catalysts for reactions of electron-poor aryl triflates led to a series of α-arylations of tetralone, indanone, cyclopentanone, and cyclohexanone derivatives Enantioselectivities ranged from 70% to 98% with 10 examples over 90%. Systematic studies on these α-arylations have revealed a number of factors that affect enantioselectivity. Ligands containing biaryl backbones with smaller dihedral angles generate catalysts that react with higher enantioselectivity than related ligands with larger dihedral angles. In addition, faster rates for reactions of aryl triflates vs. those for reactions of aryl bromides allow the α-arylations of aryl triflates to be conducted at lower temperatures, and this lower temperature improves enantioselectivity. Finally, studies that compare the enantioselectivities of catalytic reactions to those of stoichiometric reactions of isolated [(segphos)Pd(Ar)(Br)], [(segphos)Pd(Ar)(I)], and [(segphos)Ni(C₆H₄CN-4)Br] suggest that catalyst decomposition affects enantioselectivity.

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

Zhang, Du published the artcileReuse of waste catalytic-cracking catalyst: fine performance in acetalization, Synthetic Route of 177-10-6, the publication is Journal of Material Cycles and Waste Management (2020), 22(1), 22-29, database is CAplus.

Equilibrium fluid-catalytic-cracking catalyst (E-cat), a waste catalyst from fluid-catalytic cracking in petroleum refining, was used to catalyze acetalization of aldehydes (ketones) with diols. Although the activity of E-cat in catalytic cracking has decreased, it still presented fine catalytic performance in the acetalization. The ketal was stoichiometrically formed in the reaction of cyclohexanone with ethanediol, conversion of the ketone reached to 99.7% and selectivity of the ketal maintained 100% in the optimum conditions. It was revealed that E-cat can be provided with the wide adaptability in acetalization from the syntheses of different kinds of acetals or ketals. Moreover, E-cat appeared a superreusability through filtration from the reaction flask. It was an attracted example for decrement from the bulk waste catalyst in petroleum refining.

Journal of Material Cycles and Waste Management 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 C38H74Cl2N2O4, Synthetic Route of 177-10-6.

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

Lu, Yao published the artcileCharacterization of a bio-oil from pyrolysis of rice husk by detailed compositional analysis and structural investigation of lignin, Category: dioxole, the publication is Bioresource Technology (2012), 114-119, database is CAplus and MEDLINE.

Detailed compositional anal. of a bio-oil (BO) from pyrolysis of rice husk was carried out. The BO was extracted sequentially with n-hexane, CCl₄, CS₂, benzene and CH₂Cl₂. In total, 167 organic species were identified with GC/MS in the extracts and classified into alkanes, alcs., hydroxybenzenes, alkoxybenzenes, dioxolanes, aldehydes, ketones, carboxylic acids, esters, nitrogen-containing organic compounds and other species. The benzene ring-containing species (BRCCs) were attributed to the degradation of lignin while most of the rests were derived from the degradation of cellulose and hemicellulose. Along with guaiacyl and p-hydroxyphenyl units as the main components, a new type of linkage was suggested, i.e., C_ar-CH₂-C_ar in 4,4′-methylenebis(2,6-dimethoxyphenol). Based on the species identified, a possible macromol. structure of the lignin and the mechanism for its pyrolysis are proposed. The BO was also extracted with petroleum ether in ca. 17.8% of the extract yield and about 82.1% of the extracted components are BRCCs.

Bioresource Technology 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, Category: dioxole.

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

Wang, Cong-Shuai published the artcileAsymmetric Synthesis of Axially Chiral Naphthyl-C3-indoles via a Palladium-Catalyzed Cacchi Reaction, Formula: C38H24F4O4P2, the publication is Organic Letters (2021), 23(19), 7401-7406, database is CAplus and MEDLINE.

Atropoisomeric biaryl motifs are widely found in natural products and bioactive compounds as well as chiral catalysts and ligands. Various efficient approaches have been disclosed for the construction of chiral six-six biaryl skeletons. In contrast, the enantioselective synthesis of axially chiral arylindoles through the strategy of de novo construction, other than the asym. functionalization of indoles, remain a challenging task. Herein authors report an efficient Pd(0)/(S)-Segphos-catalyzed atroposelective Cacchi reaction of 2-alkynylanilines with sterically congested naphthyl halides, which afforded an array of naphthyl-C3-indoles in high yields with good to excellent atroposelectivities. The addition of water and the modulation of the manipulation procedure by premixing the palladium complex and the naphthyl halide were the keys to success. The conformational stability of the obtained axially chiral naphthyl-C3-indole containing a synthetically more-valuable free NH moiety is revealed through kinetic experiments

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 C6H5F4NO3S, Formula: C38H24F4O4P2.

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

Zhu, Zai-ming published the artcileSynthesis of cyclohexanone ethylene ketal catalyzed by Keggin-type Ni/Cu/2,2′-H₂ biim-tungstosilicates, Application of 1,4-Dioxaspiro[4.5]decane, the publication is Yingyong Huagong (2015), 44(5), 882-886, 889, database is CAplus.

A series of Keggin-type Ni/Cu/H₂biim-tungstosilicates (H₂ biim = 2,2′-biimidazole) were synthesized with the parent tungstosilicic acid as a reactant and H₂ biim, Ni²⁺/Cu²⁺ and their complexes as raw materials by a direct precipitation method. They were characterized by single crystal XRD, IR and elemental anal. The acid-catalyzed synthesis of cyclohexanone ethylene ketal by the reaction of cyclohexanone with ethylene glycol was selected as a model reaction. The catalytic activities of these tungstosilicates were investigated. The results show that the introduction of large cation reduced the POM’s solubility, and the catalysts can be recycled and reused, so that their utilization can be improved. Moreover, the catalytic activities of these heterogeneous catalysts were almost unchanged after three cycles.

Yingyong Huagong 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 C15H23BO2, Application of 1,4-Dioxaspiro[4.5]decane.

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

Li, Zi-Liang published the artcileThree molybdophosphates based on Strandberg-type anions and Zn(II)-H₂biim/H₂O subunits: syntheses, structures and catalytic properties, Recommanded Product: 1,4-Dioxaspiro[4.5]decane, the publication is Dalton Transactions (2014), 43(15), 5840-5846, database is CAplus and MEDLINE.

Three new inorganic-organic hybrid compounds based on Strandberg-type anions and Zn(II)-H₂biim/H₂O subunits, namely {H₄(H₂biim)₃}[Zn(H₂biim)(H₃biim)(H₂O)(HP₂Mo₅O₂₃)]₂·3H₂O (1), {H₉(H₂biim)₇}[(μ-biim){(Zn(H₂O)₂)_0.5(HP₂Mo₅O₂₃)}₂]·7H₂O (2) and {H₇(H₂biim)₇}[Zn(H₂biim)(H₂O)₂(HP₂Mo₅O₂₃)][H₂P₂Mo₅O₂₃]·8H₂O (3) (H₂biim = 2,2′-biimidazole), have been synthesized in aqueous solutions and characterized. They were also used as efficient and reusable catalysts for the protection of carbonyl compounds Their fascinating structural features are that mono Zn(II)-supporting biphosphopentamolybdate ({P₂Mo₅}) clusters exist in their crystal structures, and the nitrogen donor ligand H₂biim exhibits three different coordination modes in these three compounds, resp.: for 1, two 2,2′-biimidazole mols., as mono- and bidentate ligands coordinate to the same Zn(II) ion; for 2, one bi-neg. tetradentate ligand μ-biim bridges two Zn(II) ions, while for 3, one neutral bidentate H₂biim ligand links one Zn(II) ion. Most importantly, compounds 1–3 represent the first example where Strandberg-type POMs are used as acid-catalysts in an organic reaction.

Dalton Transactions 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, Recommanded Product: 1,4-Dioxaspiro[4.5]decane.

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

Yang, Qingjing published the artcileKinetic Resolution and Dynamic Kinetic Resolution of Chromene by Rhodium-Catalyzed Asymmetric Hydroarylation, Application of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Angewandte Chemie, International Edition (2019), 58(16), 5343-5347, database is CAplus and MEDLINE.

A highly efficient kinetic resolution and dynamic kinetic resolution of chromene was reported for the first time and they proceeded by a rhodium-catalyzed asym. hydroarylation pathway. This new approach offered versatile access to various chiral 2,3-diaryl-chromanes containing vicinal stereogenic centers, as well as the recovered chiral flavenes, in high yields with excellent ee values (s factor up to 532). Particularly noteworthy was that this strategy could be further extended to the establishment of a dynamic version of the kinetic resolution of chromene acetals and allowed complete access to chiral isoflavanes and α-aryl hydrocoumarins.

Angewandte Chemie, International Edition 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 C39H35N5O8, 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

Zhang, Shi-Meng published the artcileChemical Constituents of the Seeds of Celosia cristata, Category: dioxole, the publication is Chemistry of Natural Compounds (2016), 52(5), 827-829, database is CAplus.

Phytochem. investigation of the seeds of Celosia cristata led to the isolation of a new phenolic compound, celosialdehyde (10, I), together with 21 known compounds including seven phenolic compounds, four flavonoids, three fatty acids, three saponins, two glycerides, one steroid, and one triterpenoid. The structures of these compounds were characterized and identified by spectral analyses. To the best of our knowledge compounds 2, 7-10, 13, and 15-22 were isolated from this plant for the first time.

Chemistry of Natural Compounds 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 C12H9N3O4, Category: dioxole.

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

Huang, Shi-jie published the artcileQuality control of tobacco flavor by GC-MS combined with clustering analysis, COA of Formula: C11H14O4, the publication is Anhui Nongye Kexue (2009), 37(14), 6344-6346, database is CAplus.

[Objective] The research aimed to establish the GC-MS fingerprint of tobacco flavor A# and provide new methods for the quality control of tobacco flavor. [Method] Eight batches of tobacco flavor A# were determined by GC-MS combined with clustering anal. [Result] The fingerprints of tobacco flavor A#, including 23 mutual peaks were developed after determination of 6 batches of flavor according to the clustering anal. [Conclusion] The separation effect of peaks in fingerprints is better and the characteristic is also obvious. The RSD values of precision and reproducibility are less than 3%. This method can be used for the quality control of tobacco flavor.

Anhui Nongye Kexue 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

Praetorius, Jeremy M. published the artcileBenzimidazoles as Ligands in the Ruthenium-Catalyzed Enantioselective Bifunctional Hydrogenation of Ketones, Category: dioxole, the publication is Organometallics (2010), 29(3), 554-561, database is CAplus.

A series of Cl₂Ru(diphosphane)L₂ (II) complexes in which L = N1-alkylated benzimidazoles, bonding to the metal through nitrogen, have been synthesized and characterized. In the case of 1-methylbenzimidazole, the resulting complexes exist as statistical mixtures of all possible conformational isomers. When the size of the substituent on the benzimidazole was increased to trityl, complexes could be prepared that exist as a single diastereomer. All complexes possessing benzimidazole ligands bound to the ruthenium center are active for the mild and chemoselective hydrogenation of ketones in the presence of alkenes. Catalysts that exist as a single diastereomer, prepared with enantiomerically pure diphosphanes, catalyze the hydrogenation of prochiral ketones with moderate levels of enantioselectivity that are significantly improved relative to catalysts existing in several conformations.

Organometallics 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, Category: dioxole.

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