Dioxole related

Jiang, Wei-hua published the artcileSynthesis of vanillin 1,2-propylene glycol acetal catalyzed by H₃PMo₁₂O₄₀, Recommanded Product: 2-Methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol, the publication is Huaxue Shiji (2009), 31(6), 457-460, database is CAplus.

A method for the synthesis of the title compound [i.e., 2-methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol, vanillin 1,2-propylene glycol acetal] is reported here. Vanillin 1,2-propylene glycol acetal was synthesized from vanillin [i.e., 4-hydroxy-3-methoxybenzaldehyde] and 1,2-propylene glycol using H₃PMo₁₂O₄₀ as the catalyst. Factors influencing the product formation, such as molar ratio of reactants, time, catalyst type and amount, and different water entrainment agents, were studied and optimized reaction conditions were determined Reaction conditions were found as follows: molar ratio of aldehyde/glycol = 1.0/1.3, catalyst dosage of 0.3%, a cyclohexane amount of 15 mL, and a reaction time of 4.5 h. The selectivity was above 98% and the product yield was 94.58%. The product structure was determined by IR, GC, NMR.

Huaxue Shiji 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

Yu, Bing published the artcileSynthesis of homoallylic alcohols via Lewis acid assisted enantioselective desymmetrization, Synthetic Route of 503538-69-0, the publication is Synthesis (2009), 853-859, database is CAplus.

A highly enantioselective allylic substitution of (Z)-but-2-ene-1,4-diol derivatives was developed using a Rh(I) catalyst and arylboronates as nucleophiles. The reaction yields versatile homoallylic alcs. from readily available linear bis-carbonates.

Synthesis 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 C9H5FO2, Synthetic Route of 503538-69-0.

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

Bucsi, I. published the artcileBronsted acid catalyzed formation of 1,3-dioxolanes from oxiranes and ketones, Application In Synthesis of 1193-11-9, the publication is Journal of Molecular Catalysis A: Chemical (2001), 168(1-2), 47-52, database is CAplus.

The catalytic effect of various acid catalysts (heteropoly acids, Nafion-H, K10 montmorillonite, trifluoroacetic acid, methanesulfonic acid) and the effect of the structure of the reactants were investigated on the formation of 1,3-dioxolanes from oxiranes and ketones. The yield of 1,3-dioxolanes strongly depends on competing reactions, mainly on the ratio of polymerization K10 montmorillonite was found to be the best catalyst resulting in the formation of 1,3-dioxolanes in 50-80% yield under optimal reaction conditions.

Journal of Molecular Catalysis A: Chemical 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, Application In Synthesis of 1193-11-9.

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

Braun, Manfred published the artcilePalladium-catalyzed diastereoselective and enantioselective allylic alkylations of ketone enolates, HPLC of Formula: 503538-69-0, the publication is Advanced Synthesis & Catalysis (2008), 350(2), 303-314, database is CAplus.

Lithium and magnesium enolates of cyclohexanone undergo palladium-catalyzed allylic alkylations under mild conditions. Diastereoselectivity and enantioselectivity are observed when the diphenyl- and dimethyl-substituted allylic substrates are reacted with cyclohexanone or Et mesityl ketone. The lithium enolates of cyclohexanone, cyclopentanone and α-tetralone lead to the alkylations products in an enantioselective manner. Axially chiral biphenyl- and binaphthyl-bisphosphanes provide high enantioselectivity and/or diastereoselectivity. In the case of the lithium enolates, the presence of lithium chloride is also crucial to reactivity and stereoselectivity. The stereochem. outcome of the allylic alkylation of cyclohexanone and acetophenone has been investigated by the palladium-catalyzed reaction of their lithium enolates with the cis/trans isomeric alkenes. It turns out that the preformed, non-stabilized enolates attack π-allyl-palladium complexes generated in situ from the face opposite to the noble metal thus following the stereochem. pathway of soft, stabilized carbanions.

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, HPLC of Formula: 503538-69-0.

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

Tahara, Satoshi published the artcileNaturally occurring antidotes against benzimidazole fungicides, Synthetic Route of 110204-45-0, the publication is Zeitschrift fuer Naturforschung, C: Journal of Biosciences (1993), 48(9-10), 757-65, database is CAplus.

TLC bioautog. using precoated glass thin-layer plates impregnated with benomyl or carbendazim (MBC), and Cladosporium herbarum as a test fungus, was evaluated as a facile way to detect plant secondary metabolites antidoting against benzimidazole fungicides. In addition to emodin and α-tocopherol from Polygonum sachalinense, three phenolics, 3,5-dihydroxy-4-methylstilbene and 5-methoxy-6,7-methylenedioxyflavone from P. lapathifolium and 2,6-dimethoxybenzoquinone from P. thunbergii, were isolated and characterized as new benzimidazole antidotes. Emodin exhibited the antidoting activity not only against benomyl but also against MBC, thiabendazole, thiophanate-Me and nocodazole. Furthermore, emodin showed antidoting activity against MBC in the wild-type Neurospora crassa and against diethofencarb in the mutant of N. crassa resistant to benzimidazole fungicides but highly susceptible to diethofencarb.

Zeitschrift fuer Naturforschung, C: Journal of Biosciences 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 C10H18O, Synthetic Route of 110204-45-0.

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

Kan, S. B. Jennifer published the artcileCatalytic direct-type substitution reaction of α-alkyl enolates: a Pd/Bronsted base-catalyzed approach to the decarboxylative allylation of sulfonylimidates, Synthetic Route of 503538-69-0, the publication is Chemical Communications (Cambridge, United Kingdom) (2008), 6354-6356, database is CAplus and MEDLINE.

A mild and efficient process for the direct-type catalytic allylation of sulfonylimidates has been developed; this reaction represents the first example of Bronsted base-catalyzed, in situ generation and use of α-alkyl enolates in substitution reactions; the success of this methodol. stems from the tunable α-proton acidity and nucleophilicity of sulfonylimidates, which could be harnessed in the realization of a broader range of catalytic direct-type reactions using ester equivalent as nucleophiles.

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, Synthetic Route of 503538-69-0.

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

Kokubo, Ken published the artcileSynthesis and characterization of new acetalized [60]fullerenes, Safety of 1,4-Dioxaspiro[4.5]decane, the publication is Tetrahedron Letters (2013), 54(27), 3510-3513, database is CAplus.

Acetalized [60]fullerenes were synthesized from cyclohexanone-fused [60]fullerene, which was facilely prepared by Diels-Alder reaction of C₆₀ with 2-trimethylsilyloxy-1,3-butadiene, on treatment of various aliphatic alcs. under TiCl₄ catalyst. The spiro-cyclic acetalized [60]fullerenes having five, six, and seven-membered rings were also synthesized by using the corresponding diols under the same condition. The slightly raised reduction potentials E^red (∼0.04 V) relative to those of PCBM were observed by cyclic voltammetry measurement, depending on the identity of alkyl group/chain. The noncyclic acetalized [60]fullerenes showed lower thermal stability up to 200°, while the cyclic ones exhibited the drastically improved thermal stability up to 350° under nitrogen atm. The acid-catalyzed hydrolysis easily removed the acetal moiety quant., resulting in a considerable change of solvent solubility of the fullerene.

Tetrahedron Letters 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

Simon, Marc-Olivier published the artcileRuthenium-catalyzed C-H bond activation of Michael acceptors: an unusual reactivity leading to allylsilanes, Name: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Advanced Synthesis & Catalysis (2009), 351(1+2), 153-157, database is CAplus.

The authors report here an improved catalyst for the functionalization of Michael acceptors, involving C-C bond formation via C-H bond activation, using an in situ generated Ru active species. On some particular substrates, the C-H functionalization resulted unexpectedly in the formation of allylsilanes rather than in the expected conjugated adducts, affording a new straightforward methodol. to access useful stereodefined trisubstituted allylsilanes via C-H bond activation. Preliminary results showed that they were reactive in the allylation of aldehydes, providing an access to alcs. bearing a quaternary C center.

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 C8H5IO, 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

Navarre, Laure published the artcileAccess to enantioenriched α-amino esters via rhodium-catalyzed 1,4-addition/enantioselective protonation, COA of Formula: C38H24F4O4P2, the publication is Journal of the American Chemical Society (2008), 130(19), 6159-6169, database is CAplus and MEDLINE.

Conjugate addition of potassium trifluoro(organo)borates to dehydroalanine derivatives, mediated by a chiral rhodium catalyst and in situ enantioselective protonation, afforded straightforward access to a variety of protected α-amino esters with high yields and enantiomeric excesses up to 95%. Among the tested chiral ligands and proton sources, Binap, in combination with guaiacol (2-methoxyphenol), an inexpensive and nontoxic phenol, afforded the highest asym. inductions. Organostannanes have also shown to participate in this reaction. By a fine-tuning of the ester moiety, and using Difluorophos as chiral ligand, increased levels of enantioselectivity, generally close to 95%, were achieved. Deuterium labeling experiments revealed, and DFT calculation supported, an unusual mechanism involving a hydride transfer from the amido substituent to the α carbon explaining the high levels of enantioselectivity attained in controlling this α chiral center.

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, COA of Formula: C38H24F4O4P2.

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

Ling, Johanne published the artcileCopper(I)-Catalyzed Dearomative (3 + 2) Cycloaddition of 3-Nitroindoles with Propargylic Nucleophiles: An Access to Cyclopenta[b]indolines, Application In Synthesis of 503538-69-0, the publication is Journal of Organic Chemistry (2020), 85(5), 3838-3848, database is CAplus and MEDLINE.

The copper(I)-catalyzed dearomatization of 3-nitroindoles I [R¹ = 4-Me, 5-Cl, 7-CO₂Me, etc.; R² = Ac, Bz, (4-methylphenyl)sulfonyl, etc.] and 3-nitro-1-benzofuran-5-yl acetate with propargylic nucleophiles CHCCH₂R³ (R³ = 1,3-dimethoxy-1,3-dioxopropan-2-yl, 1,3-bis(benzyloxy)-1,3-dioxopropan-2-yl, 4-methylbenzene-1-sulfonamidyl, etc.) is described. In mild reaction conditions, this original dearomative (3+2) cycloaddition process gives access to a wide variety of cyclopenta[b]indolines e.g., II in good to excellent yields, with high functional group tolerance. The proof of concept that an enantioselective version of this reaction is accessible by employing chiral phosphorus ligands was obtained. A mechanism proposal is given based on kinetic studies.

Journal of Organic Chemistry 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 In Synthesis of 503538-69-0.

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