Dioxole related

Rondestvedt, Christian S. Jr. published the artcileNew rearrangement. Catalytic isomerization of m- dioxanes to β-alkoxy aldehydes. II. Scope and limitations, Related Products of dioxole, the publication is Journal of the American Chemical Society (1962), 3307-19, database is CAplus.

cf. CA 55, 10311b. Rearrangement of m-dioxanes to β-alkoxy aldehydes is effected by pumice or certain forms of silica at 250550°. Yields and conversions are generally good. The m-dioxanes from simple aliphatic aldehydes and ketones rearrange cleanly at about 400° on pumice; silica is active at 250-350°, but yields are slightly lower. Formals (R¹ = R² = H) are much more sluggish than other acetals and ketals. An acrolein acetal (R¹ = CH₂:CH; R² = H) is inert to pumice but is rearranged smoothly by silica. A benzal (R¹ = Ph, R² = H) is isomerized with astonishing facility, but ring substituents (p-Cl, p-MeO, m-O₂N, p-Me₂N) generally retard strongly the rearrangement. Even p-alkyl groups are slightly inhibitory. The aryl acetals on silica are converted in part also to the aromatic aldehyde and to the substituted toluene. An ether oxygen in the substituents R¹-R⁴ retards rearrangement. If R³ = R⁴ = H, rearrangement occurs, but the product is cleaved to acrolein and an alc. Acetals with 5- and 7-membered rings do not undergo the rearrangement, but rather are cleaved. Diacetals are inert to hot pumice, but some of them are converted to diether-dialdehydes in fair yields by silica.

Journal of the American Chemical Society 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, Related Products of dioxole.

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

Gundekari, Sreedhar published the artcileSelective preparation of renewable ketals from biomass-based carbonyl compounds with polyols using β-zeolite catalyst, Quality Control of 177-10-6, the publication is Molecular Catalysis (2022), 112269, database is CAplus.

The preparation of ketals from biomass-based carbonyl compounds and polyols was demonstrated. The emphasis is on levulinate-based ketals using Et levulinate (EL) with ethylene glycol (EG) or glycerol (Gly) as polyols. Among the catalysts screened, Na-β zeolite resulted in 99% conversion of EL with 100% selectivity for the corresponding ketal within 1 h, when used in conjunction with azeotropic distillation in cyclohexane medium. Using Gly as the polyol, a similar yield and selectivity was obtained, albeit after a longer reaction time (4 h). The authors explored the reaction scope by using a multitude of biomass-based ketones and polyols as reactants, which showed excellent selectivity for the ketals. Slight deactivation of the catalyst was observed after reaction, owing to the deposition of organic carbon on the catalyst, which was identified using anal. tools. The deactivated catalyst was regenerated on calcination. This strategy was successfully demonstrated for ketal preparation using crude glycerol with EL.

Molecular Catalysis 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

Tindall, Daniel J. published the artcileSelective and Scalable Synthesis of Sugar Alcohols by Homogeneous Asymmetric Hydrogenation of Unprotected Ketoses, Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Angewandte Chemie, International Edition (2021), 60(2), 721-725, database is CAplus and MEDLINE.

Sugar alcs. are of great importance for the food industry and are promising building blocks for bio-based polymers. Industrially, they are produced by heterogeneous hydrogenation of sugars with H₂, usually with none to low stereoselectivities. Now, we present a homogeneous system based on com. available components, which not only increases the overall yield, but also allows a wide range of unprotected ketoses to be diastereoselectively hydrogenated. Furthermore, the system is reliable on a multi-gram scale allowing sugar alcs. to be isolated in large quantities at high atom economy.

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 C5H5BrN2, Recommanded Product: (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

Wang, Jian-Ping published the artcileTwo Strandberg-type organophosphomolybdates: synthesis, crystal structures and catalytic properties, Related Products of dioxole, the publication is Dalton Transactions (2014), 43(45), 17172-17176, database is CAplus and MEDLINE.

Two novel Strandberg-type organophosphomolybdate hybrid compounds [(Cu(H₂O))₂(μ-bipy)₂(C₆H₅PO₃)₂Mo₅O₁₅]_n (1) and [(Cu(H₂O)₂)₂(μ-bipy)(C₆H₅PO₃)₂Mo₅O₁₅]_n (2) (bipy = 4,4′-bipyridyl) were prepared under mild hydrothermal conditions and structurally characterized by physicochem. and spectroscopic methods. Single crystal x-ray diffraction anal. reveals that compounds 1 and 2 are polyoxometalate-based Cu-coordination polymers with a three-dimensional framework. In 1, the Cu²⁺ ions not only link [(C₆H₅PO₃)₂Mo₅O₁₅]^4- (abbreviated as {(C₆H₅P)₂Mo₅}) polyanions, but also act as connectors of bipy ligands to produce two sym. 1-dimensional chains, and all 1-dimensional chains are further held together by polyanions to generate a 3-dimensional network. In 2, each {(C₆H₅P)₂Mo₅} polyanion acting as a hexadentate ligand links four Cu(II)-bipy/H₂O units, forming 2-dimensional plane structures, which are further bridged by Cu(II)-bipy-Cu(II) fragments to generate a 3-dimensional network. Their fluorescence properties and catalytic properties for the synthesis of cyclohexanone ethylene ketal were also studied.

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 C19H14N2, Related Products of dioxole.

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

Melhado, Asa D. published the artcileAu(I)-catalyzed enantioselective 1,3-dipolar cycloadditions of munchnones with electron-deficient alkenes, Formula: C38H24F4O4P2, the publication is Journal of the American Chemical Society (2007), 129(42), 12638-12639, database is CAplus and MEDLINE.

The catalytic enantioselective 1,3-dipolar cycloaddition of munchnone dipoles with electron-deficient alkenes is described. The reaction is catalyzed by chiral bis(phosphine)gold(I) benzoate complexes and provides Δ¹-pyrrolines, e.g., I, with excellent regio-, diastereo-, and enantioselectivity. The reaction is proposed to proceed through a 1,3-dipole generated by deprotonation of a gold(I)-activated azlactone.

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

Liu, Fei published the artcileSynthesis of vanillin propylene glycol acetal catalyzed by solid superacid, Synthetic Route of 68527-74-2, the publication is Jingxi Huagong (2010), 27(2), 155-159, database is CAplus.

The synthesis of vanillin propylene glycol acetal catalyzed by solid superacid was investigated. A series of solid superacids were prepared and used to synthesize vanillin propylene glycol acetal. Solid superacids excelled phosphoric acid and citric acid, and SO₄^2-/ZrO₂ was the best catalyst. The optimum conditions using SO₄^2-/ZrO₂ were as follows: when vanillin was 0.05 mol, n(vanillin):n(1,2-propylene glycol)=1:2.4, the water-carrying agent was toluene (20 mL); the amount of catalyst was 0.25% of the weight of vanillin; and the reaction time 1.0 h. Under these conditions, the yield of vanillin propylene glycol acetal was 95.1%. The total yield was 90.5% and the relative mass fraction was 99.5% after vacuum distillation The structure of the product was identified by IR and GC-MS. The yield could still achieve 91.1% when the catalyst was calcined 20 days later. The reaction time was short and the catalyst was efficient and stable. The post-processing was simple in this process.

Jingxi Huagong 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, Synthetic Route of 68527-74-2.

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

Liu, Xiaoxia published the artcileA simple approach to the preparation of H₆P₂W₁₈O₆₂/Cu₃(BTC)₂ (BTC = 1,3,5-benzenetricarboxylate) and its catalytic performance in the synthesis of acetals/ketals, Category: dioxole, the publication is Reaction Kinetics, Mechanisms and Catalysis (2015), 116(1), 159-171, database is CAplus.

H₆P₂W₁₈O₆₂/Cu₃(BTC)₂ (BTC = 1,3,5-benzenetricarboxylate) as a new catalyst was prepared by the impregnation method and used to synthesize cyclohexanone ethylene ketal as a probe reaction, which has shown its favorable catalytic activity. FT-IR, XRD, SEM, N₂ adsorption-desorption isotherms and TG/DTA were used to characterize its composition, structure, morphol., stability and toleration for thermal in order to further prepare the catalyst with effective performance. Moreover, we have also explored the optimized conditions of carrying out the probe reaction by orthogonal experiments The optimized conditions were as follows: fixing cyclohexanone consumption was 0.02 mol, n(cyclohexanone):n(ethylene glycol) = 1:1.3, the mass ratio of the catalyst to total reactant was 0.2 %, cyclohexane dosage was 4 mL, and the reaction time was 75 min. The yield of the acetals and ketones could reach 54.9 ∼ 83.5 % under the optimum conditions. In addition, H₆P₂W₁₈O₆₂/Cu₃(BTC)₂ exhibited good reusability and the approaches above may enable rational design of advanced and environmental-friendly MOF-based catalysts.

Reaction Kinetics, Mechanisms and Catalysis 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, Category: dioxole.

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

Wu, Yue published the artcileDetermination of key amino acids and reducing sugars contributing to cocoa flavor by Plackett-Burman design, Recommanded Product: 2,2,4-Trimethyl-1,3-dioxolane, the publication is Shipin Kexue (Beijing, China) (2007), 28(11), 75-80, database is CAplus.

The Plackett-Burnam design was applied to screen out the key factors from the following eleven components of amino acids and reducing sugars, which would affect cocoa flavor. Statistical analyses were performed. It was found that phenylalanine, serine, leucine, glutamic acid, arginine and glycine were significant factors for contributing to cocoa flavor but not the two reducing sugars, after the mixtures of five amino acids and two reducing sugars were selected to react for cocoa flavor. Then these reacting products were analyzed by organoleptic investigation and GC-MS, and 52 compounds were identified.

Shipin Kexue (Beijing, China) 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 C24H26ClNO4, Recommanded Product: 2,2,4-Trimethyl-1,3-dioxolane.

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

Liu, Li-jun published the artcileReusable heterogeneous catalyst for acetal/ketal formation of 8-hydroxy-2-methylquinoline modified H₄SiW₁₂O₄₀, Related Products of dioxole, the publication is RSC Advances (2018), 8(46), 26180-26187, database is CAplus and MEDLINE.

A heteropoly acid based organic hybrid heterogeneous catalyst, HMQ-STW, was prepared by combining 8-hydroxy-2-methylquinoline (HMQ) with Keggin-structured H₄SiW₁₂O₄₀ (STW). The catalyst was characterized via elemental anal., X-ray diffractometry (XRD), Fourier transform IR spectroscopy (FT-IR), SEM (SEM), thermogravimetric anal. (TG) and potentiometric titration anal. The catalytic performance of the catalyst was assessed in the ketalization of ketones with glycol or 1,2-propylene glycol. Various reaction parameters, such as the glycol to cyclohexanone molar ratio, catalyst dosage, reaction temperature and time, were systematically examined HMQ-STW exhibited a relatively high yield of corresponding ketal, with 100% selectivity under the optimized reaction conditions. Moreover, catalytic recycling tests demonstrated that the heterogeneous catalyst exhibited high potential for reusability, and it was revealed that the organic modifier HMQ plays an important role in the formation of a heterogeneous system and the improvement of structural stability. These results indicated that the HMQ-STW catalyst is a promising new type of heterogeneous acid catalyst for the ketalization of ketones.

RSC Advances 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, Related Products of dioxole.

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

Hu, Jian published the artcileHighly active catalysts of bisphosphine oxides for asymmetric Heck reaction, Name: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(82), 9425-9427, database is CAplus and MEDLINE.

Bisphosphine oxides formed highly active asym. Heck catalysts, which were applied in asym. synthesis of pharmacol. active azacycles. E.g., reaction of 2-naphthyl triflate with cyclopentene in the presence of 2.5% Pd(dba)₂ and 3% of chiral ligand, (R)-7-bis(m-xylyl)phosphino-7′-bis(3,5-dimethylphenyl)phosphinyl-1,1′-spirobiindane, in 1,4-dioxane with N-ethyldiisopropylamine at 50° to give 95% yield of (S)-3-(2-naphthyl)cyclopentene. Olefin insertion proceeded via cis pathways, different from P,N-ligands.

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, 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