Category: Dioxole

Enantioselective Aldehyde α-Nitroalkylation via Oxidative Organocatalysis was written by Wilson, Jonathan E.;Casarez, Anthony D.;MacMillan, David W. C.. And the article was included in Journal of the American Chemical Society in 2009.Related Products of 62563-07-9 This article mentions the following:

The first enantioselective organocatalytic α-nitroalkylation of aldehydes R¹CH₂CHO [R¹ = Me, n-Bu, cyclohexyl, PhCH₂O(CH₂)₃, PhCO₂(CH₂)₄, etc.] with silyl nitronates R²CH:N⁺(O^–)OSiR³₃ [R² = H, Me, Et, MeO₂CCH₂CH₂, cyclohexyl, etc.; SiR³₃ = SiMe₃, Si(i-Pr)₃, Si(t-Bu)Me₂, etc.] has been accomplished. The aforementioned process involves the oxidative coupling of an enamine intermediate, generated transiently via condensation of an amine catalyst with an aldehyde, with a silyl nitronate to produce a β-nitroaldehyde. Two methods, one that furnishes the syn β-nitroaldehyde and a second that provides access to the anti isomer, have been developed. Data are presented to support a hypothesis that explains this phenomenon in terms of a silyl group-controlled change in mechanism. Finally, a three-step procedure for the synthesis of both syn- and anti-α,β-disubstituted β-amino acids is presented. In the experiment, the researchers used many compounds, for example, 2-(3-Bromopropyl)-1,3-dioxolane (cas: 62563-07-9Related Products of 62563-07-9).

2-(3-Bromopropyl)-1,3-dioxolane (cas: 62563-07-9) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Related Products of 62563-07-9

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Asymmetric synthesis and structural assignment of (-)-α-conhydrine was written by Enders, Dieter;Nolte, Bert;Raabe, Gerhard;Runsink, Jan. And the article was included in Tetrahedron: Asymmetry in 2002.Application In Synthesis of 2-(3-Bromopropyl)-1,3-dioxolane This article mentions the following:

The first asym. synthesis of the conium alkaloid (-)-α-conhydrine (I) is reported. Starting from a protected glycol aldehyde hydrazone as chiral precursor, a short route based on our α-alkylation/1,2-addition methodol. has been developed. After cleavage of the auxiliary and simultaneous deprotection, the concluding ring closure is accomplished under reductive amination conditions. The title compound is obtained in moderate overall yield and in excellent diastereo- and enantiomeric excess (d.e., e.e. >96%). Single-crystal x-ray crystallog. as well as ¹H NMR NOE experiments confirm the expected relative and absolute (2R,7S)-configuration of the product. In the experiment, the researchers used many compounds, for example, 2-(3-Bromopropyl)-1,3-dioxolane (cas: 62563-07-9Application In Synthesis of 2-(3-Bromopropyl)-1,3-dioxolane).

2-(3-Bromopropyl)-1,3-dioxolane (cas: 62563-07-9) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Application In Synthesis of 2-(3-Bromopropyl)-1,3-dioxolane

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

1-(6-Amino-1,3-benzodioxol-5-yl)-3-(4-pyridyl)prop-2-en-1-one crystallizes with Z’ = 2: hydrogen-bonded supramolecular substructures in one and two dimensions, each containing only one type of molecule was written by Cuervo, Paola;Abonia, Rodrigo;Cobo, Justo;Low, John N.;Glidewell, Christopher. And the article was included in Acta Crystallographica, Section C: Crystal Structure Communications in 2007.Computed Properties of C9H9NO3 This article mentions the following:

1-(6-Amino-1,3-benzodioxol-5-yl)-3-(4-pyridyl)prop-2-en-1-one, C₁₅H₁₂N₂O₃, crystallizes with Z’ = 2 in the space group P1̅ and the intramol. dimensions show evidence for a polarized mol. electronic structure. Each of the 2 independent types of mol. forms its own H-bonded supramol. substructure, and these are entirely different from 1 another: 1 type of mol. forms a chain of edge-fused rings, while the other type forms sheets. Crystallog. data are given. In the experiment, the researchers used many compounds, for example, 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2Computed Properties of C9H9NO3).

1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Computed Properties of C9H9NO3

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

2-Methylimidazol-1-yl-Substituted Analogs of Hexahydro-difenidol (HHD) and Hexahydro-sila-difenidol (HHSiD) as M₃ Receptor-Preferring Muscarinic Antagonists: A Study on C/Si Bioisosterism was written by Tacke, Reinhold;Handmann, Vera I.;Kreutzmann, Kai;Keim, Christine;Mutschler, Ernst;Lambrecht, Guenter. And the article was included in Organometallics in 2002.Formula: C12H14ClFO2 This article mentions the following:

The hexahydro-sila-difenidol (HHSiD, 1b) and p-fluoro-hexahydro-sila-difenidol (p-F-HHSiD, 2b) derivatives cyclohexyl[3-(2-methylimidazol-1-yl)propyl]phenylsilanol (4b) and cyclohexyl(4-fluorophenyl)[3-(2-methylimidazol-1-yl)propyl]silanol (5b) were synthesized in three-step syntheses, starting from (3-chloropropyl)cyclohexyldimethoxysilane. In addition, the corresponding carbon analogs 4a and 5a (→ Si/C replacement) were prepared in two-step syntheses, starting from 2-(3-chloropropyl)-2-phenyl-1,3-dioxolane and 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane, resp. The C/Si pairs 4a/4b and 5a/5b were studied for their affinities at recombinant human muscarinic M₁, M₂, M₃, M₄, and M₅ receptors stably expressed in CHO-K1 cells by evaluating their ability to inhibit the binding of the muscarinic antagonist [³H]N-methylscopolamine. These studies revealed that compounds 4a, 4b, 5a, and 5b behave as simple competitive antagonists at M₁-M₅ receptors. The exchange of the piperidin-1-yl group of the parent compounds HHD (1a), HHSiD (1b), p-F-HHD (2a), and p-F-HHSiD (2b) by a 2-methylimidazol-1-yl moiety resulted in a novel, potent, and M₃-preferring antimuscarinic agent, compound 4b. The affinities of compounds 4a, 5a, and 5b for muscarinic M₁ (pK_i = 7.74-7.93), M₂ (pK_i = 7.03-7.14), M₃ (pK_i = 8.04-8.11), M₄ (pK_i = 7.63-7.94), and M₅ receptors (pK_i = 7.29-7.52) were very similar at the individual receptor subtypes and in turn very similar to those of the parent compounds 1a, 2a, and 2b. In contrast, replacement of the piperidin-1-yl substituent of 1b by a 2-methylimidazol-1-yl group (→ 4b) increased the affinity for M₁-M₅ receptors up to 8.3-fold. The muscarinic receptor affinity profile of 4b was found to be M₃ (pK_i = 8.69) > M₁ (pK_i = 8.39) ≥ M₄ (pK_i = 8.32) > M₅ (pK_i = 8.02) > M₂ (pK_i = 7.43). Thus, compound 4b displayed a M₃ vs. M₂ receptor selectivity (18.2-fold). The receptor subtype affinities of the carbon compound 5a were very similar to those of the corresponding silicon analog 5b, whereas sila-substitution of 4a (→ 4b) increased the affinities for M₁-M₅ receptors, this increase being greatest at M₃ and M₅ receptors (4-fold). In the experiment, the researchers used many compounds, for example, 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9Formula: C12H14ClFO2).

2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Formula: C12H14ClFO2

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

High Performance Liquid Chromatography versus Stacking-Micellar Electrokinetic Chromatography for the Determination of Potentially Toxic Alkenylbenzenes in Food Flavouring Ingredients was written by Dang, Huynh N. P.;Quirino, Joselito P.. And the article was included in Molecules in 2022.Name: 6-Allyl-4-methoxybenzo[d][1,3]dioxole This article mentions the following:

Alkenylbenzenes, including eugenol, methyleugenol, myristicin, safrole, and estragole, are potentially toxic phytochems., which are commonly found in foods. Occurrence data in foods depends on the quality of the anal. methodologies available. Here, we developed and compared modern reversed-phase high performance liquid chromatog. (HPLC) and stacking-micellar electrokinetic chromatog. (MEKC) methods for the determination of the above alkenylbenzenes in food flavouring ingredients. The anal. performance of HPLC was found better than the stacking-MEKC method. Compared to other HPLC methods found in the literature, our method was faster (total run time with conditioning of 15 min) and able to sep. more alkenylbenzenes. In addition, the anal. methodol. combining an optimized methanol extraction and proposed HPLC was then applied to actual food flavouring ingredients. This methodol. should be applicable to actual food samples, and thus will be vital to future studies in the determination of alkenylbenzenes in food. In the experiment, the researchers used many compounds, for example, 6-Allyl-4-methoxybenzo[d][1,3]dioxole (cas: 607-91-0Name: 6-Allyl-4-methoxybenzo[d][1,3]dioxole).

6-Allyl-4-methoxybenzo[d][1,3]dioxole (cas: 607-91-0) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Name: 6-Allyl-4-methoxybenzo[d][1,3]dioxole

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Severe Acute Respiratory Syndrome Coronavirus Papain-like Novel Protease Inhibitors: Design, Synthesis, Protein-Ligand X-ray Structure and Biological Evaluation was written by Ghosh, Arun K.;Takayama, Jun;Rao, Kalapala Venkateswara;Ratia, Kiira;Chaudhuri, Rima;Mulhearn, Debbie C.;Lee, Hyun;Nichols, Daniel B.;Baliji, Surendranath;Baker, Susan C.;Johnson, Michael E.;Mesecar, Andrew D.. And the article was included in Journal of Medicinal Chemistry in 2010.Application In Synthesis of 2-Bromomethyl-1,3-dioxolane This article mentions the following:

The design, synthesis, X-ray crystal structure, mol. modeling, and biol. evaluation of a series of new generation SARS-CoV PLpro inhibitors are described. A new lead compound 3 (6577871) was identified via high-throughput screening of a diverse chem. library. Subsequently, we carried out lead optimization and structure-activity studies to provide a series of improved inhibitors that show potent PLpro inhibition and antiviral activity against SARS-CoV infected Vero E6 cells. Interestingly, the (S)-Me inhibitor 15h (enzyme IC₅₀ = 0.56 μM; antiviral EC₅₀ = 9.1 μM) and the corresponding (R)-Me 15g (IC₅₀ = 0.32 μM; antiviral EC₅₀ = 9.1 μM) are the most potent compounds in this series, with nearly equivalent enzymic inhibition and antiviral activity. A protein-ligand X-ray structure of 15g-bound SARS-CoV PLpro and a corresponding model of 15h docked to PLpro provide intriguing mol. insight into the ligand-binding site interactions. In the experiment, the researchers used many compounds, for example, 2-Bromomethyl-1,3-dioxolane (cas: 4360-63-8Application In Synthesis of 2-Bromomethyl-1,3-dioxolane).

2-Bromomethyl-1,3-dioxolane (cas: 4360-63-8) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Application In Synthesis of 2-Bromomethyl-1,3-dioxolane

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Phytochemical components and biological activities of essential oils from three selected medicinal plants was written by Zhang, Lanyue;Ye, Mao;Shi, Yaohui;Zhu, Haiping;Chi, Lejing;Pan, Chunxing;Xu, Yani;Zheng, Xi;Xiang, Hongping;Li, Chunlian. And the article was included in Industrial Crops and Products in 2021.Application In Synthesis of 6-Allyl-4-methoxybenzo[d][1,3]dioxole This article mentions the following:

Essential oils extracted from herbs have been utilized in food and medicine on the account of their increasing physicochem. characteristics. This present study aimed to investigate the phytochem. components, anti-inflammatory, cytotoxic, anti-microbial and anti-oxidant activities of essential oils from Pogostemon cablin (P. cablin), Angelica dahurica (A. dahurica) and Myristica fragrans (M. fragrans), all belong to”medicine food homol. “herbs. Approx. 107 components were identified by gas chromatog. mass spectrometry (GC-MS) from these essential oils. The main compounds of P. cablin essential oils (PCEOs) were patchouli alc. (27.72%),α -buaiacene (17.94%) and α -guaiene (14.15%); in A. dahurica essential oils (ADEOs) were anethole (24.91%) and cinnamaldehyde (18.35%); and in M. fragrans essential oils (MFEOs) were (1S)-(-)-α -pinene (23.39%), α ;-terpineol (18.60%) and caryophyllene (10.34%). These essential oils were found to have strong anti-inflammatory activities through decreasing the production of cyclooxygenase-2 (COX-2), interleukin-6 (IL-6), nuclear factor-kappa B p65 (P65) and tumor necrosis factor-α (TNF-α). These essential oils also had significant anti-bacterial activities against both Gram-neg. and Gram-pos. strains and anti-fungal activities. Moreover, effective anti-oxidant properties of three essential oils were estimated (0.001962%-0.19%). The study also explored the effect of these essential oils on the survival of Brain microglia (BV2) microglial cells (IC₅₀ = 145.50-281.52μg/mL). Based on these bioactivities, these essential oils could be used as food additives, fragrances, cosmetics and health products. In the experiment, the researchers used many compounds, for example, 6-Allyl-4-methoxybenzo[d][1,3]dioxole (cas: 607-91-0Application In Synthesis of 6-Allyl-4-methoxybenzo[d][1,3]dioxole).

6-Allyl-4-methoxybenzo[d][1,3]dioxole (cas: 607-91-0) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Application In Synthesis of 6-Allyl-4-methoxybenzo[d][1,3]dioxole

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Synthesis of partially protected 3-deoxy-oct-2-ulosonic acid was written by Zheng, Shan-shan;Huang, Jia-sheng;Gao, Liang;Yang, Jin-song. And the article was included in Huaxue Yanjiu Yu Yingyong in 2014.Formula: C12H20O6 This article mentions the following:

α, β-Octenoate was prepared by Wittig reaction of D-mannose, then was turned to the corresponding diol cyclic sulfite. By β-elimination and in situ trapping (DBU/TMSCl) into enol silyl ether, α-oxocarboxylic acid ester was obtained. With total eight steps yielding 36.3%, the synthesis of Et 4, 5:7, 8-di-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosonate was completed. In the experiment, the researchers used many compounds, for example, (3aS,4S,6R,6aS)-6-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol (cas: 14131-84-1Formula: C12H20O6).

(3aS,4S,6R,6aS)-6-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol (cas: 14131-84-1) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Although benzodioxole is not particularly important, many related compounds containing the methylenedioxyphenyl group are bioactive, and thus are found in pesticides and pharmaceuticals.Formula: C12H20O6

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Conformationally constrained butyrophenones with mixed dopaminergic (D₂) and serotoninergic (5-HT_2A, 5-HT_2C) affinities: synthesis, pharmacology, 3D-QSAR, and molecular modeling of (aminoalkyl)benzo- and -thienocycloalkanones as putative atypical antipsychotics was written by Ravina, Enrique;Negreira, Jesus;Cid, Jose;Masaguer, Christian F.;Rosa, Elizabeth;Rivas, M. Emilia;Fontenla, Jose A.;Loza, M. Isabel;Tristan, Helena;Cadavid, M. Isabel;Sanz, Ferran;Lozoya, Estrella;Carotti, Angelo;Carrieri, Antonio. And the article was included in Journal of Medicinal Chemistry in 1999.Formula: C12H14ClFO2 This article mentions the following:

A series of novel conformationally restricted butyrophenones (2-(aminoethyl)- and 3-(aminomethyl)thieno- or benzocycloalkanones bearing (6-fluorobenzisoxazolyl)piperidine, (p-fluorobenzoyl)piperidine, (o-methoxyphenyl)piperazine, or linear butyrophenone fragments) were prepared and evaluated as atypical antipsychotic agents by in vitro assays of affinity for dopamine receptors (D₁, D₂) and serotonin receptors (5-HT_2A, 5-HT_2C) and by in vivo assays of antipsychotic potential and the risk of inducing extra pyramidal side effects. Potency and selectivity depended mainly on the amine fragment connected to the cycloalkanone structure. As a group, compounds with a benzisoxazolyl fragment had the highest 5-HT_2A activities, followed by the benzoylpiperidine derivatives; in general, α-substituted cycloalkanone derivatives were more active than the corresponding β-substituted congeners. CoMFA (comparative mol. field anal.) and docking studies showed electrostatic, steric, and lipophilic determinants of 5-HT_2A and D₂ affinities and 5-HT_2A/D₂ selectivity. The in vitro and in vivo pharmacol. profiles of N-[(4-oxo-4H-5,6-dihydrocyclopenta[b]thiophene-5-yl)ethyl]-4-(6-fluorobenzisoxazol-3-yl)piperidine (QF 0510B), N-[(4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-yl)ethyl]-4-(6-fluorobenzisoxazol-3-yl)piperidine (QF 0610B), and N-[(7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-6-yl)ethyl]-4-(6-fluorobenzisoxazol-3-yl)piperidine (QF 0902B) suggest that they may be effective antipsychotic drugs with low propensity to induce extra pyramidal side effects. In the experiment, the researchers used many compounds, for example, 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9Formula: C12H14ClFO2).

2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Formula: C12H14ClFO2

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Self-assembly synthesis of a high-content sulfonic acid group functionalized ordered mesoporous polymer-based solid as a stable and highly active acid catalyst was written by Wang, Wei;Zhuang, Xin;Zhao, Qingfei;Wan, Ying. And the article was included in Journal of Materials Chemistry in 2012.Application of 177-10-6 This article mentions the following:

A stable and highly active ordered mesoporous polymer-based acid catalyst has been prepared via a ethylene oxide-propylene oxide triblock copolymer surfactant templating of a formaldehyde-3-mercaptopropyltrimethoxysilane-phenol-tetraethoxysilane copolymer and oxidation of the HS to SO₃H. The composition and nanostructure are characterized by XRD, NMR, XPS, TEM, nitrogen sorption, elemental and chem. anal. The sulfonic acid groups have been anchored within the well-arranged channels of the polymer-based matrix. Even with a high SO₃H group loading (up to about 27.4 wt%) on the mesoporous polymer-based material, the ordered mesostructure and high surface area (∼400 m² g^-1) can be retained and the functional moieties are highly chem. accessible. With the large number of acid sites (0.93-2.38 H⁺ mmol g^-1 determined by acid-base titration) and the hydrophobic character, the mesoporous polymer-based solid exhibits catalytic performance in acid-catalyzed reactions such as condensation and acetalization, not only high activity (per site yield of bisphenol A is over 45 in the condensation of phenol and acetone) but also excellent stability. Loss in acidic loading and activity is negligible even after the catalyst is reused 20 times in the acetalization of butanediol and aldehyde. The stability is most likely attributed to the hydrophobic nature of the mesoporous polymer-based solids, which favors the diffusion of water and thereby inhibits the poisoning of acidic sites caused by water generating in the reaction. Moreover, with large mesopores, the diffusion of reactants and products can be promoted and hence the catalytic activity can be further increased. In the experiment, the researchers used many compounds, for example, 1,4-Dioxaspiro[4.5]decane (cas: 177-10-6Application of 177-10-6).

1,4-Dioxaspiro[4.5]decane (cas: 177-10-6) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Application of 177-10-6

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem