Day: November 28, 2022

Liao, Xuebin published the artcileEnantioselective Total Syntheses of (-)-Taiwaniaquinone H and (-)-Taiwaniaquinol B by Iridium-Catalyzed Borylation and Palladium-Catalyzed Asymmetric α-Arylation, Category: dioxole, the publication is Journal of the American Chemical Society (2011), 133(7), 2088-2091, database is CAplus and MEDLINE.

We report a concise, enantioselective total synthesis of (-)-taiwaniaquinone H (I) and the first enantioselective total synthesis of (-)-taiwaniaquinol B (II) by a route that includes asym. palladium-catalyzed α-arylation of a ketone with an aryl bromide that was generated by sterically controlled halogenation via iridium-catalyzed C-H borylation. This asym. α-arylation creates the benzylic quaternary stereogenic center present in the taiwaniaquinoids. The synthesis was completed efficiently by developing a Lewis acid-promoted cascade to construct the [6,5,6] tricyclic core of an intermediate common to the synthesis of a number of taiwaniaquinoids. Through the preparation of these compounds, we demonstrate the utility of constructing benzylic quaternary stereogenic centers, even those lacking a carbonyl group in the α-position, by asym. α-arylation.

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, Category: dioxole.

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

Gerten, Anthony L. published the artcileEnantioselective dearomative [3 + 2] cycloadditions of indoles with azomethine ylides derived from alanine imino esters, Related Products of dioxole, the publication is Organic Chemistry Frontiers (2016), 3(3), 339-343, database is CAplus.

Catalytic, enantioselective [3 + 2] cycloadditions of azomethine ylides derived from alanine imino esters with 3-nitroindoles were reported. The dearomative cycloaddition reactions occurred in the presence of a catalyst generated in situ from Cu(OTf)₂ and (R)-Difluorphos to form exo’-pyrroloindoline cycloadducts and established four contiguous stereogenic centers, two of which were fully substituted. The exo’-pyrroloindoline products were formed in moderate-to-good yields (39-85%) with high diastereoselectivities (up to 98 : 1 : 1 dr) and enantioselectivities (up to 96% ee).

Organic Chemistry Frontiers 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, Related Products of dioxole.

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

Berthet, Matheo published the artcileCatalytic Alkynylation of Cyclic Acetals and Ketals Enabled by Synergistic Gold(I)/Trimethylsilyl Catalysis, Quality Control of 177-10-6, the publication is Journal of Organic Chemistry (2017), 82(18), 9916-9922, database is CAplus and MEDLINE.

A completely regioselective and challenging gold(I)-catalyzed ring-opening of cyclic 1,3-dioxolanes and dioxanes by trimethylsilyl alkynes to set diol-derived propargyl trimethylsilyl bis-ethers is reported. This unprecedented and not trivial transformation does not operate with the catalytic methodologies recently reported for catalytic alkynylation of acyclic acetals/ketals, and is uniquely enabled by the application of a recently introduced synergistic gold(I)-silicon catalysis concept capable of producing simultaneously catalytic amounts of two key players, a silicon-based Lewis superacid and a nucleophilic gold acetylide.

Journal of Organic Chemistry 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

Li, Ruiyun published the artcileEfficient and reusable SBA-15-immobilized Bronsted acidic ionic liquid for the ketalization of cyclohexanone with glycol, Synthetic Route of 177-10-6, the publication is RSC Advances (2018), 8(13), 7179-7185, database is CAplus and MEDLINE.

Ketalization of cyclohexanone with glycol has been carried out using mol. sieve SBA-15 immobilized Bronsted acidic ionic liquid catalyst. The properties of the heterogeneous catalysts were characterized by elemental anal., Fourier transform IR spectra, SEM, thermogravimetry/differential scanning calorimetry, and N₂ adsorption-desorption. The results suggested that Bronsted acidic ionic liquid [BSmim][HSO₄] had been successfully immobilized on the surface of SBA-15 and the catalytic performance evaluation demonstrated that the catalyst BAIL@SBA-15 exhibited excellent catalytic activities in the ketalization of cyclohexanone with glycol. In addition, the effects of reaction temperature, catalyst loading, reaction time, and reactant molar ratio have also been investigated in detail, and a general reaction mechanism for the ketalization of cyclohexanone with glycol was given. The SBA-15 immobilized ionic liquid can be recovered easily and after reusing for 5 times in the ketalization reaction, the catalyst could still give satisfactory catalytic activity.

RSC Advances 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, Synthetic Route of 177-10-6.

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

Partridge, Benjamin M. published the artcileIridium-catalyzed arylative cyclization of alkynones by 1,4-iridium migration, Safety of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Angewandte Chemie, International Edition (2014), 53(25), 6523-6527, database is CAplus and MEDLINE.

1,4-Metal migrations enable the remote functionalization of C-H bonds, and were utilized in a wide variety of valuable synthetic methods. The vast majority of existing examples involve the 1,4-migration of Pd or Rh. Herein, the stereoselective synthesis of complex polycycles by the Ir-catalyzed arylative cyclization of alkynones with arylboronic acids is described.

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 C38H24F4O4P2, Safety 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

Bennet, Andrew J. published the artcileOxygen-18 and secondary deuterium kinetic isotope effects confirm the existence of two pathways for acid-catalyzed hydrolyses of α-arabinofuranosides, Safety of 2,2,4-Trimethyl-1,3-dioxolane, the publication is Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) (1985), 1233-6, database is CAplus.

The ¹⁸O kinetic isotope effects observed in the HClO₄-catalyzed hydrolysis of 4-nitrophenyl and iso-Pr α-arabinofuranoside-1–¹⁸O and the secondary D effect observed in the hydrolysis of propan-2-yl-2–d α-arabinofuranoside suggest that the nitrophenyl glycoside reacts with exocyclic C-O cleavage and the propan-2-yl glycoside by endocyclic C-O cleavage.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) 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, Safety of 2,2,4-Trimethyl-1,3-dioxolane.

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

Chandrasekhar, Sosale published the artcileChloral Hydrate as a Water Carrier for the Efficient Deprotection of Acetals, Dithioacetals, and Tetrahydropyranyl Ethers in Organic Solvents, SDS of cas: 177-10-6, the publication is Synthetic Communications (2014), 44(13), 1904-1913, database is CAplus.

The efficient deprotection of several acetals, dithioacetals, and tetrahydropyranyl (THP) ethers under ambient conditions, using chloral hydrate in hexane, is described. Excellent yields were realized for a wide range of both aliphatic and aromatic substrates. The method is characterized by mild conditions (room temperatures or below), simple workup, and the ready availability of chloral hydrate. High chemoselectivity was also observed in the deprotection, acetonides, esters, and amides being unaffected under the reaction conditions. Products were generally purified chromatog. and identified spectrally. These results constitute a novel addition to current methodol. involving a widely employed deprotection tactic in organic synthesis. It seems likely that the mechanism of the reaction involves adsorption of the substrate on the surface of the sparingly soluble chloral hydrate.

Synthetic Communications 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, SDS of cas: 177-10-6.

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

Yu, Xiao-Qiang published the artcileRhodium-catalyzed 1,4-addition of lithium 2-furyltriolborates to unsaturated ketones and esters for enantioselective synthesis of γ-oxo-carboxylic acids by oxidation of the furyl ring with ozone, Synthetic Route of 503538-69-0, the publication is Chemistry – An Asian Journal (2011), 6(3), 932-937, database is CAplus and MEDLINE.

Rhodium-catalyzed 1,4-addition of lithium 5-methyl-2-furyltriolborate ([ArB(OCH₂)₃CCH₃]Li, Ar=5-methyl-2-furyl) to unsaturated ketones to give β-furyl ketones was followed by ozonolysis of the furyl ring for enantioselective synthesis of γ-oxo-carboxylic acids. [Rh(nbd)₂]BF₄ (nbd=2,5-norbornadiene) chelated with 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (binap) or 2,3-bis(diphenylphosphino)butane (chiraphos) gave high yields and high selectivities in a range of 91-99 % ee at 30 °C in a basic dioxane/water solution The corresponding reaction of unsaturated esters, such as Me crotonate, had strong resistance under analogous conditions, but the 1,4-adduct was obtained in 70 % yield and with 94 % ee when more electron-deficient Ph crotonate was used as the substrate.

Chemistry – An Asian 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 C10H11N3O3S, Synthetic Route of 503538-69-0.

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

Ishida, Naoki published the artcile1,5-Rhodium Shift in Rearrangement of N-Arenesulfonylazetidin-3-ols into Benzosultams, Formula: C38H24F4O4P2, the publication is Journal of the American Chemical Society (2013), 135(51), 19103-19106, database is CAplus and MEDLINE.

In the presence of [Rh(COD)(OH)]₂ and the nonracemic bibenzodioxolediphosphine (R)-difluorphos, 1-arylsulfonyl-3-aryl-3-azetidinols such as I (R = Ph, 4-MeOC₆H₄, 4-F₃CC₆H₄; Ts = 4-MeC₆H₄SO₂) underwent enantioselective rearrangement to give fused thiazinediones such as II (R = Ph, 4-MeOC₆H₄, 4-F₃CC₆H₄) in 90-95% yields and in 91:9-93:7 er. Stereoselective rearrangement of nonracemic amino acid-derived 1-arylsulfonyl-3-aryl-3-azetidinols such as III (R¹ = Ph, 4-MeOC₆H₄, 4-F₃CC₆H₄; R² = Me, Me₂CH, MeSCH₂CH₂; R³ = H, Me, MeO, F₃C; R⁴ = H, Me) in the presence of racemic 2,2′-bis{bis(3,5-xylyl)phosphino}-1,1′-binaphthyl yielded fused dihydrohydroxythiazinediones such as IV (R¹ = Ph, 4-MeOC₆H₄, 4-F₃CC₆H₄; R² = Me, Me₂CH, MeSCH₂CH₂; R³ = H, Me, MeO, F₃C; R⁴ = H, Me) as single diastereomers and enantiomers in 97-99% yields. Rearrangement of I (R = Ph) with a perdeuterated tosyl group yielded a deuterated product monolabeled at the N-Me group; a mechanism for the rearrangement is proposed. The structure of IV (R¹ = Ph; R² = Me; R³ = Me; R⁴ = H) was determined by X-ray crystallog.

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, Formula: C38H24F4O4P2.

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

Sakihama, Yasuko published the artcileA photoaffinity probe designed for host-specific signal flavonoid receptors in phytopathogenic Peronosporomycete zoospores of Aphanomyces cochlioides, Related Products of dioxole, the publication is Archives of Biochemistry and Biophysics (2004), 432(2), 145-151, database is CAplus and MEDLINE.

Aphanomyces cochlioides zoospores show chemotaxis to cochliophilin A (5-hydroxy-6,7-methylenedioxyflavone, 1), a host derived attractant, and also respond to 5,7-dihydroxyflavone (2) known as an equivalent chemoattractant. To investigate the chemotactic receptors in the zoospores, we designed photoaffinity probes 4′-azido-5,7-dihydroxyflavone (3) and 4′-azido-7-O-biotinyl-5-hydroxyflavone (4) considering chem. structure of 2. Both 3 and 4 had zoospore attractant activity which was competitive with that of 1. When zoospores were treated with the biotinylated photoaffinity probe followed by UV irradiation and streptavidin-gold or peroxidase-conjugated streptavidin, probe-labeled proteins were detected on the cell membrane. This result indicated that the 1-specific-binding proteins, a candidate for hypothetical cochliophilin A receptor, were localized on the cell membrane of the zoospores. This is the first exptl. evidence of flavonoid-binding proteins being present in zoospores, using chem. synthesized azidoflavone as photoaffinity-labeling reagent.

Archives of Biochemistry and Biophysics 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, Related Products of dioxole.

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