Category: Dioxole

Majumdar, Swapan published the artcileActivation Of 1,3-Dioxolane By A Protic Ionic Liquid In Aqueous Media: A Green Strategy For The Selective Hydrolytic Cleavage Of Acetals and Ketals, Safety of 1,4-Dioxaspiro[4.5]decane, the publication is RSC Advances (2014), 4(32), 16497-16502, database is CAplus.

A convenient method for the deprotection of acetals and ketals was achieved using an imidazolium based protic ionic liquid as a catalyst in aqueous medium via the dual activation of dioxolane. The protocol is highly efficient towards the deprotection of acyclic and cyclic acetals, ketals, benzylidene acetals and tetrahydropyranyl (THP) ethers, giving excellent yields. Functional groups such as tert-Bu ester, tert-Bu di-Me silyl (TBDMS), N-tert-butyloxycarbonyl (N-Boc), and double bond, mesyl, nitro, and glycosidic linkage were tolerated under the benign reaction conditions. Selective deprotection of the 5,6-isopropylidene moiety in 1,2:5,6-di-O-isopropylidene hexose and 3,5-cyclohexylidene moiety in pentose derivatives proceeded smoothly without affecting the 1,2-protected group. The attractive features of this new protocol are the use of mild reaction conditions, tolerance of a wide range of functional groups, use of relatively non-toxic solvent systems and recyclability of the ionic liquid catalyst.

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, Safety of 1,4-Dioxaspiro[4.5]decane.

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

Abouassali, Obada published the artcileIn vitro and in vivo cardiac toxicity of flavored electronic nicotine delivery systems, Recommanded Product: 2-Methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol, the publication is American Journal of Physiology (2021), 320(1), H133-H143, database is CAplus and MEDLINE.

The usage of flavored electronic nicotine delivery systems (ENDS) is popular, specifically in the teen and young adult age-groups. The possible cardiac toxicity of the flavoring aspect of ENDS is largely unknown. Vaping, a form of electronic nicotine delivery, uses “e-liquid” to generate “e-vapor,” an aerosolized mixture of nicotine and/or flavors. We report our investigation into the cardiotoxic effects of flavored e-liquids E-vapors containing flavoring aldehydes such as vanillin and cinnamaldehyde, as indicated by mass spectrometry, were more toxic in HL-1 cardiomyocytes than fruit-flavored e-vapor. Exposure of human induced pluripotent stem cell-derived cardiomyocytes to cinnamaldehyde or vanillin-flavored e-vapor affected the beating frequency and prolonged the field potential duration of these cells more than fruit-flavored e-vapor. In addition, vanillin aldehyde-flavored e-vapor reduced the human ether-a-go-go-related gene (hERG)-encoded potassium current in transfected human embryonic kidney cells. In mice, inhalation exposure to vanillin aldehyde-flavored e-vapor for 10 wk caused increased sympathetic predominance in heart rate variability measurements. In vivo inducible ventricular tachycardia was significantly longer, and in optical mapping, the magnitude of ventricular action potential duration alternans was significantly larger in the vanillin aldehyde-flavored e-vapor-exposed mice than in controls. We conclude that the widely popular flavored ENDS are not harm free, and they have a potential for cardiac harm. More studies are needed to further assess their cardiac safety profile and long-term health effects.

American Journal of Physiology 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, Recommanded Product: 2-Methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol.

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

Sun, Huan-Li published the artcileAsymmetric Hydrogenation of α-Purine Nucleobase-Substituted Acrylates with Rhodium Diphosphine Complexes: Access to Tenofovir Analogues, Related Products of dioxole, the publication is Organic Letters (2016), 18(9), 2260-2263, database is CAplus and MEDLINE.

The first asym. hydrogenation of α-purine nucleobase-substituted α,β-unsaturated esters, catalyzed by a chiral rhodium (R)-Synphos catalyst, has been developed. A wide range of mono- and disubstituted acrylates were successfully hydrogenated under very mild conditions in high yields with good to excellent enantioselectivities (up to 99% ee). This method provides a convenient approach to the synthesis of a new kind of optically pure acyclic nucleoside and Tenofovir analogs.

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 C11H21BO2Si, Related Products of dioxole.

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

Yang, Fan published the artcilePalladium/Lewis Acid Co-catalyzed Divergent Asymmetric Ring-Opening Reactions of Azabenzonorbornadienes with Alcohols, Name: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Organic Letters (2016), 18(19), 4832-4835, database is CAplus and MEDLINE.

By fine tuning the combinations of chiral palladium catalysts and Lewis acids, both the addnl. and reductive asym. ring-opening reactions of azabenzonorbornadienes with alcs. were accomplished with good chemoselectivity, regioselectivity, and enantioselectivity. It was proven that the reductive ring-opening products were generated through a transfer hydrogenation process with alcs. as hydrogen source.

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 C4H5BN2O2, 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

Alikarami, Mohammad published the artcileOxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers, acetals and ketals with N,N’-dibenzyl-1,4-diazoniabicyclo[2.2.2]octane peroxodisulfate under non-aqueous conditions, Name: 1,4-Dioxaspiro[4.5]decane, the publication is Organic Chemistry: An Indian Journal (2013), 9(11), 463-468, database is CAplus.

An efficient and convenient conversion of trimethylsilyl and tetrahydropyranyl ethers, acetals and ketals to the corresponding carbonyl compounds with N,N’-dibenzyl-1,4-diazoniabicyclo[2.2.2]octane peroxodisulfate under non-aqueous conditions is described.

Organic Chemistry: An Indian Journal 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, Name: 1,4-Dioxaspiro[4.5]decane.

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

Anteunis, M. published the artcileNuclear magnetic resonance experiments on ketals. III. Proton magnetic resonance (P.M.R.) spectrum and conformations of the glycol ketal of 1,2-propanediol with acetone and acetaldehyde, Safety of 2,2,4-Trimethyl-1,3-dioxolane, the publication is Bulletin des Societes Chimiques Belges (1964), 73(11-12), 889-97, database is CAplus.

cf. CA 61, 10570h. The H N.M.R. (P.M.R.) spectra of 2,2,4-trimethyl-1,3-dioxolane (I) and cis- and trans-2,4-dimethyl-1,3-dioxolane (II) were determined and analyzed. The chem. shifts are in accordance with a half-chair conformation. The 1,3-H-Me interaction causes an upfield shift of ∼0.15 ppm. when the 2 are cis to one another. A similar shift of 0.05 ppm. was noted for a cis-1,3-Me-Me interaction. In I and cis-II, long-range coupling between the 4-Me and the methylene H cis to it is observed. I (b. 100°) was prepared from Me₂C(OMe)₂ (0.3 moles), propanediol (III) (0.2 moles), and H₂SO₄ catalyst. II was prepared by slow distillation of MeCH0 from acidified paraldehyde into III. Separation of the product by gas-liquid chromatography gave cis-II, b. 91.8°, n²⁵ 1.3945, d_23.6 0.92786, m. 55-60°; and trans-II, b. 89.5°, n²⁵ 1.3928; d_23.0 0.91570. meso4,5-Dimethyl-1,3-dioxolane (b. 104°) was prepared by azeotropic H₂O removal with C₆H₆ from a mixture of monobutanediol and (HCHO)_x. The HCHO ketal of 4,5-trimethylene-1,3-dioxolane prepared similarly b. 80°/18 mm.

Bulletin des Societes Chimiques Belges 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

Langlois, Jean-Baptiste published the artcileCopper-catalyzed asymmetric allylic alkylation of racemic cyclic substrates: Application of dynamic kinetic asymmetric transformation (DYKAT), Quality Control of 503538-69-0, the publication is Advanced Synthesis & Catalysis (2010), 352(2+3), 447-457, database is CAplus.

The copper-catalyzed asym. allylic alkylation (AAA) is of great interest in organic synthesis. This reaction was extensively studied using a broad range of substrates, ligands and organometallic reagents. However, the use of racemic substrates was still limited. Although some processes of kinetic resolution are reported in the literature, no examples of quant. deracemization are described as is the case for the Pd-catalyzed allylic alkylation. The development and results of the copper-catalyzed AAA is reported. High enantioselectivities, scope of the reaction and mechanistic considerations are reported herein.

Advanced Synthesis & Catalysis 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

Hargrave, Jonathan D. published the artcileCatalytic Enantioselective Dieckmann-Type Annulation: Synthesis of Pyrrolidines with Quaternary Stereogenic Centers, 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 (2010), 49(10), 1825-1829, S1825/1-S1825/70, database is CAplus and MEDLINE.

A Dieckmann-type cyclization coupled to an arylation reaction was used to synthesize the title compounds, e.g., I, with up to 96% ee from amine-tethered ester-substituted acrylates. The presence of a coordinating functionality in the substrate, e.g., II, induces a competition between cyclization and elimination pathways that is influenced by the nature of the chiral ligand. A mechanistic rationale is proposed to account for these observations.

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, 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

Potowski, Marco published the artcileCatalytic asymmetric exo-selective [6+3] cycloaddition of iminoesters with fulvenes, COA of Formula: C38H24F4O4P2, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(71), 7800-7802, database is CAplus and MEDLINE.

A novel exo-selective [6+3] cycloaddition approach for the highly enantioselective synthesis of polysubstituted piperidines was developed. The developed methodol. was applied in a one-pot [6+3]-[4+2] dicycloaddn., allowing the construction of structurally and stereochem. rich polycyclic compounds from simple building blocks.

Chemical Communications (Cambridge, United Kingdom) 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

Bygd, Madison D. published the artcileUnexpected mechanism of biodegradation and defluorination of 2,2-difluoro-1,3-benzodioxole by Pseudomonas putida F1, Computed Properties of 503538-69-0, the publication is mBio (2021), 12(6), e03001, database is CAplus and MEDLINE.

Perfluorinated carbon atoms in a diether linkage are common in com. anesthetics, drugs, fungicides, and insecticides. An important chem. group comprising perfluorodiethers is the 2,2-fluoro-1,3-benzodioxole (DFBD) moiety. The fluorine atoms stabilize the mol. by mitigating against metabolism by humans and microbes, as used in drugs and pesticides, resp. Pseudomonas putida F1 catalyzed defluorination of DFBD at an initial rate of 2,100 nmol/h per mg cellular protein. This is orders of magnitude higher than previously reported microbial defluorination rates with multiply fluorinated carbon atoms. Defluorination rates declined after several hours, and the medium darkened. Significant defluorination activity was observed with cells grown on toluene but not l-arginine. Defluorination required only toluene dioxygenase. Pseudomonas and recombinant Escherichia coli cells expressing toluene dioxygenase oxidized DFBD to DFBD-4,5-dihydrodiol. The dihydrodiol could be oxidized to 4,5-dihydroxy-DFBD via the dihydrodiol dehydrogenase from P. putida F1. The dihydrodiol dehydrated with acid to yield a mixture of 4-hydroxy-DFBD and 5-hydroxy-DFBD. All those metabolites retained the difluoromethylene group; no fluoride or dark color was observed The major route of DFBD-4,5-dihydrodiol decomposition produced fluoride and 1,2,3-trihydroxybenzene, or pyrogallol, and that was shown to be the source of the dark colors in the medium. A mechanism for DFBD-4,5-dihydrodiol transformation to two fluoride ions and pyrogallol is proposed. The Pseudomonas genome database and other databases revealed hundreds of bacteria with enzymes sharing high amino acid sequence identity to toluene dioxygenase from P. putida F1, suggesting the mechanism revealed here may apply to the defluorination of DFBD-containing compounds in the environment.

mBio 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