Month: November 2022

Chan, Vincent S. published the artcileDevelopment of ruthenium catalysts for the enantioselective synthesis of P-stereogenic phosphines via nucleophilic phosphido intermediates, Safety of (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 (2009), 131(16), 6021-6032, database is CAplus and MEDLINE.

Ruthenium chiral diphosphine complexes [L₂RuH][BPh₄] or [(L¹)(dmpe)RuH][BPh₄] [L, L¹ = chiral diphosphines, dmpe = 1,2-bis(dimethylphosphino)ethane] catalyze base-promoted low-temperature asym. alkylation of secondary phosphine PhMePH by benzyl halides, yielding chiral PhMe(ArCH₂)P (Ar = Ph, 4-ClC₆H₄, 4-MeC₆H₄, 4-MeOC₆H₄, 2-MeC₆H₄, 1-naphthyl, 2-pyridinyl, 2-furanyl) or diphosphines PhMePCH₂Ar¹CH₂PMePh (Ar¹ = 1,3-phenylene, 1,2-phenylene, 1,3-pyridinediyl) with up to 80% ee [L = 4-ⁱPr-2-(C₆H₄PPh₂-2)oxazoline (ⁱPr-PHOX) or L¹ = MeO-BiPHEP, SEGPHOS]. The optimized base for the reaction was found to be sodium tert-amylate, which prevents the occurrence of background non-catalytic alkylation by deprotonation of uncoordinated PhMePH. The reactions proceed through the intermediacy of nucleophilic phosphido species, which have low barriers to pyramidal inversion; this allows for a dynamic kinetic asym. alkylation. The initially discovered [((R)-ⁱPr-PHOX)₂Ru(H)][BPh₄] (6) catalyst was found to be effective in the reaction with benzylic chlorides; moreover, the alkylation displayed an unusual temperature dependence. However, the limited scope of alkylation of 6 motivated further studies which led to the development of two complementary chiral mixed ligand Ru(II) catalysts of type [L¹L²Ru(H)]⁺. These catalysts were derived from a combination of one chiral and one achiral ligand, where a synergistic interaction of the two ligands creates an effective asym. environment around the ruthenium center. The (R)-MeO-BiPHEP catalyst [((R)-MeO-BiPHEP)(dmpe)RuH][BPh₄] (10) was found to be effective for the asym. alkylation by benzyl chlorides, while the (R)-DIFLUORPHOS catalyst [[(R)-DIFLUORPHOS](dmpe)RuH][BPh₄] (11) was optimal for the nucleophilic substitution of less activated alkyl bromides; the scope of the resp. catalysts was also explored.

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, 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

Ye, Zhi-Shi published the artcileIridium-catalyzed asymmetric hydrogenation of pyridinium salts, 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 (2012), 51(40), 10181-10184, S10181/1-S10181/62, database is CAplus and MEDLINE.

A highly efficient iridium-catalyzed asym. hydrogenation of 2-substituted pyridinium salts is developed. A series of chiral 2-substituted piperidines were obtained in good to excellent yields and up to 93% ee.

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 C9H22OSi, 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

Yang, Zhi-Wang published the artcileBaeyer-Villiger oxidation and acetalization of cyclic ketones on SO^2-₄/SnO₂-Fe₂O₃ solid acid catalysts, Formula: C8H14O2, the publication is Wuli Huaxue Xuebao (2012), 28(9), 2148-2154, database is CAplus.

Fe-doped SO^2-₄/SnO₂ (STF) solid acid catalysts with different amounts of iron were prepared via co-condensation, followed by sulfation and calcination. These materials were characterized by Fourier transform IR (FTIR) spectroscopy, x-ray powder diffraction (XRD), N₂ adsorption-desorption anal. (BET), thermogravimetric (TG) anal., and SEM. The Fe-doped catalysts exhibited more activity than undoped catalysts in acetalization reactions of 4-tert-butylcyclohexanone and diols. The catalytic acetalization of several ketones and 1,2-diols with the SO^2-₄/SnO₂-Fe₂O₃ catalysts (with the Fe/Sn molar ratio of 0.5) were studied. The influence of the reaction time and the amount of the catalysts on the acetalization were also investigated. In addition, the high performance of this Fe-modified catalyst was demonstrated in the Baeyer-Villiger oxidation of cyclic ketones. The catalyst can be recycled several times without any significant loss in catalytic activity.

Wuli Huaxue Xuebao 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 C12H23N3S, Formula: C8H14O2.

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

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

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

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

Seiser, Tobias published the artcileEnantioselective construction of indanones from cyclobutanols using a rhodium-catalyzed C-C/C-H/C-C bond activation process, Safety of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Synlett (2010), 1699-1703, database is CAplus.

Enantioselective rhodium(I)-catalyzed reactions of tert-cyclobutanols, e.g. I, lead to indanones with quaternary stereogenic centers, e.g. II, via consecutive C-C/C-H/C-C bond activations.

Synlett 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 C23H43NP2, 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

Azzena, Ugo published the artcileCyclopentyl methyl ether-NH₄X: a novel solvent/catalyst system for low impact acetalization reactions, Computed Properties of 177-10-6, the publication is Green Chemistry (2015), 17(6), 3281-3284, database is CAplus.

Cyclopentyl Me ether, a low impact ether forming a pos. azeotrope with water, was successfully employed as a solvent in the synthesis of 1,3-dioxanes and 1,3-dioxolanes carried out under Dean-Stark conditions by the acetalization of aliphatic and aromatic aldehydes or ketones, employing ammonium salts as environmentally friendly acidic catalysts.

Green 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, Computed Properties of 177-10-6.

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

Du, Jing published the artcileSynthesis and catalytic activities of two new extended Preyssler-type tungstophosphates with different cavity centers, Synthetic Route of 177-10-6, the publication is Inorganic Chemistry Communications (2016), 119-123, database is CAplus.

Two new extended Preyssler-type polyoxometalates (POMs) constructed by Fe(III), 2,2′-biimidazole and Preyssler-type tungstophosphate anions with Na and Ag cavity centers, resp., {(H₄biim)₅H[Fe(H₂biim)(H₂O)₂(ZP₅W₃₀O₁₁₀)]·17H₂O}_n (Z = Na, 1; Z = Ag, 2; H₂biim = 2,2′-biimidazole), were designed and synthesized under hydrothermal conditions, and were systematically characterized by physicochem. and spectroscopic methods. The two compounds are isostructural coordination polymers. In compound 1 or 2, there exists interesting infinite 1-dimensional chains composed of Preyssler-type [ZP₅W₃₀O₁₁₀]^14- (abbreviated as {ZP₅W₃₀}) polyanions bridged by Fe(III)-complex fragments, and these chains further formed 3-dimensional supramol. frameworks via extensive H-bonding interactions. For 2, two types of transition metals, i.e. one Ag⁺ ion as a center in the inner cavity and two Fe³⁺ ions as modified cations on the outer surface of one {ZP₅W₃₀} unit, exist in the same compound Also, the electrochem. behaviors and acid catalytic activities of 1 and 2 were studied.

Inorganic Chemistry 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, Synthetic Route of 177-10-6.

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