Category: Dioxole

Effect of N-alkylation on the affinities of analogs of spiperone for dopamine D₂ and serotonin 5-HT₂ receptors was written by Mach, Robert H.;Jackson, Joseph R.;Luedtke, Robert R.;Ivins, Kathryn J.;Molinoff, Perry B.;Ehrenkaufer, Richard L.. And the article was included in Journal of Medicinal Chemistry in 1992.Formula: C12H14ClFO2 This article mentions the following:

Two series of N-substituted spiperone analogs were prepared and evaluated in vitro to measure their affinities for dopamine D₂ and serotonin 5-HT₂ receptors. Substitution of the amide N with an alkyl group of 5 carbon units or less resulted in analogs displaying a low selectivity for D₂ compared to 5-HT₂ receptors. However, a moderate improvement in selectivity for D₂ receptors was observed with N-benzylspiperone. Substitution at either the ortho or para position of the benzyl group resulted in a further reduction in affinity for 5-HT₂ receptors and improvement in the selectivity ratio. Examination of N-substituted analogs of spiperone may provide insights into the topog. of the antagonist binding region of the 5-HT₂ receptor. The results also suggest that an ¹⁸F-labeled analog of N-(4-nitrobenzyl)spiperone may be a suitable tracer for studying D₂ receptors with positron emission tomog. since this compound displays a high selectivity for D₂ receptors relative to that of spiperone and N-methylspiperone. 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

Synthesis of cyclic carbonate-DOMA with CO₂ and GMA was written by Li, Xiang-long;Li, Ji-ming;Yan, Zhan-lei;Zhang, Xiao-lin. And the article was included in Jingxi Huagong Zhongjianti in 2013.Application In Synthesis of (2-Oxo-1,3-dioxolan-4-yl)methyl methacrylate This article mentions the following:

(2-Oxo-1,3-dioxolan-4-yl)methyl 2-methylprop-2-enoate (DOMA), which had cyclic carbonate structure and double bond structure, was synthesized from glycidyl methacrylate (GMA) and carbon dioxide as the raw materials in the presence of the solvent and catalyst under high pressure and high temperature In order to improve the yield of DOMA, the effects of factors were discussed such as catalyst, temperature, pressure and time. Crude product was obtained by means of washing, extraction and vacuum distillation, and the higher purity quotient of DOMA was refined by means of thin-layer chromatog. and column chromatog., and the yield of DOMA content was examined by high performance liquid chromatog. (HPLC) anal. Experiments showed that the yield of DOMA was up to 75.6% on the condition that the catalyst was tetra-butyl-ammonium bromide (TBAB) and ZnI₂, reaction temperature was 110°C, reaction pressure was 1.2 MPa and the reaction time was 4 h. The product after the reaction was characterized by means of Fourier transform IR spectroscopy (FTIR), NMR spectroscopy carbon spectrum (13C-NMR, 100 MHz, CDCl₃) and NMR spectroscopy hydrogen spectrum (¹H NMR, 400 MHz, CDCl₃), and the results proved that the functional groups and structure of the product were in accordance with DOMA. In the experiment, the researchers used many compounds, for example, (2-Oxo-1,3-dioxolan-4-yl)methyl methacrylate (cas: 13818-44-5Application In Synthesis of (2-Oxo-1,3-dioxolan-4-yl)methyl methacrylate).

(2-Oxo-1,3-dioxolan-4-yl)methyl methacrylate (cas: 13818-44-5) 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.Application In Synthesis of (2-Oxo-1,3-dioxolan-4-yl)methyl methacrylate

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

Organocatalytic one-pot asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones was written by Pan, Gao-Fei;Su, Li;Zhang, Yan-Lei;Guo, Shi-Huan;Wang, Yong-Qiang. And the article was included in RSC Advances in 2016.Application of 28657-75-2 This article mentions the following:

Highly efficient organocatalytic one-pot enantioselective synthesis of (R)-2-aryl-2,3-dihydro-4-quinolones from o-aminoacetophenones and aryl aldehydes were developed. The approach was characterized by being metal free, solvent free and protecting group free. Variety of 2-aryl-2,3-dihydro-4-quinolones could be obtained in good yields up to 99% ee. In the experiment, the researchers used many compounds, for example, 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2Application of 28657-75-2).

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.Application of 28657-75-2

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

Hafnium-doped silica nanotubes for the upgrading of glycerol into solketal: Enhanced performances and in-depth structure-activity correlation was written by Soumoy, Loraine;Celis, Chloe;Debecker, Damien P.;Armandi, Marco;Fiorilli, Sonia;Aprile, Carmela. And the article was included in Journal of Catalysis in 2022.Name: (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol This article mentions the following:

An unprecedented type of Hf-doped silica nanotubes was synthesized using a straightforward one-pot sol-gel procedure. The well-defined nanotubes with a diameter of 14-20 nm exhibited high sp. surface area and a widely open texture. The method – involving a key pH adjustment step – allowed a quant. insertion of hafnium in the materials (Si/Hf = 74) and favored the insertion of Hf as dispersed species. Depending on the synthesis parameters, the chem. environment around Hf was modified, as evidenced by XPS, NH₃-TPD and NH₃-IR. Hf-doped silica nanotubes showed excellent activity in the conversion of glycerol to solketal, a reaction of high relevance in the context of biorefineries. Importantly, the turnover frequency and the acidity were unambiguously correlated with the insertion of Hf in the silica matrix. The best catalyst was proven to be stable and recyclable, and this sustainable reaction was also amenable to further catalytic enhancement upon optimized reaction conditions. In the experiment, the researchers used many compounds, for example, (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol (cas: 100-79-8Name: (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol).

(2,2-Dimethyl-1,3-dioxolan-4-yl)methanol (cas: 100-79-8) 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. Although benzodioxole is not particularly important, many related compounds containing the methylenedioxyphenyl group are bioactive, and thus are found in pesticides and pharmaceuticals.Name: (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol

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

Aroma quality evaluation of Dianhong black tea infusions by the combination of rapid gas phase electronic nose and multivariate statistical analysis was written by Chen, Jiayu;Yang, Yanqin;Deng, Yuliang;Liu, Zhengquan;Xie, Jialing;Shen, Shuai;Yuan, Haibo;Jiang, Yongwen. And the article was included in LWT–Food Science and Technology in 2022.Application of 607-91-0 This article mentions the following:

Aroma is one of the most important quality attributes of black tea infusions. In this study, the aroma quality of 44 Dianhong black tea (DBT) infusions were investigated by rapid gas phase electronic nose (GC-E-Nose) combined with multivariate statistical anal. for the first time. Among 61 volatile compounds identified, the most abundant ones were aldehydes. Both partial least squares discriminant anal. (PLS-DA) and Fisher discriminant anal. (FDA) could effectively classify the aroma quality of DBT infusions. The prediction accuracy of FDA (95.2%) was higher than that of PLS-DA (78.6%). Moreover, stepwise multiple linear regression was shown to accurately predict the quality score of DBT infusions, and the Rp value of the sensory score of the predicted model was 0.94. Furan, Me acetate, 2,3-pentanedione, limonene, and linalool were found pos. correlated with the aroma quality of DBT infusions, while 3-ethylpentane, 1-pentene, (E)-2-hexene, and Me eugenol were neg. correlated with the aroma quality of DBT infusions. These results contribute to understand that rapid GC-E-Nose technol. is a supplement to the objective sensory evaluation, and provide a new tech. method for the quality evaluation and control of tea infusions. In the experiment, the researchers used many compounds, for example, 6-Allyl-4-methoxybenzo[d][1,3]dioxole (cas: 607-91-0Application of 607-91-0).

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 of 607-91-0

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

Antagonism of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane stimulus with a newly identified 5-HT_2- versus 5-HT_1C-selective antagonist was written by Ismaiel, Abd M.;De Los Angeles, Joseph;Teitler, Milt;Ingher, Stacy;Glennon, Richard A.. And the article was included in Journal of Medicinal Chemistry in 1993.Synthetic Route of C12H14ClFO2 This article mentions the following:

DOM [i.e., 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane] is a 5-HT_1C/2 serotonin agonist that exerts stimulus control of behavior in animals. In order to determine if the discriminative stimulus effect of DOM is 5-HT_1C– or 5-HT₂-mediated, it would be informative to conduct tests of stimulus antagonism with a 5-HT_1C or 5-HT₂-selective antagonist. To date, no such agents exist. Although the neuroleptic agent spiperone binds at D2 dopamine receptors and 5-HT_1A serotonin receptors, (a) it displays about a 1000-fold selectivity for 5-HT₂ vs. 5-HT_1C sites and (b) it has been used as a “5-HT₂-selective” antagonist. Because spiperone is a behaviorally disruptive agent, it is not suitable for use in drug-discrimination studies. Using the spiperone mol. as a starting point, a limited structure-affinity investigation was conducted in order to identify a suitable antagonist with high affinity and selectivity for 5-HT₂ receptors, and yet an antagonist that might lack the disruptive actions of spiperone. Various modifications of the spiperone mol. were examined, but most resulted in decreased 5-HT₂ affinity or in loss of selectivity. One compound, 8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (I), was shown to bind at 5-HT₂ sites with high affinity (K_i = 2 nM) and >2,000-fold selectivity vs. 5-HT_1C sites. In tests of stimulus antagonism using rats trained to discriminate 1 mg/kg of DOM from saline vehicle, I behaved as a potent antagonist (ED₅₀ = 0/003 mg/kg) and lacked the disruptive effects associated with spiperone. As such, (a) it would appear that the DOM stimulus is primarily a 5-HT₂-mediated, and not 5-HT_1C-mediated, phenomenon, and (b) compound I may find application in other pharmacol. investigations where spiperone may not be a suitable antagonist. In the experiment, the researchers used many compounds, for example, 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9Synthetic Route of 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.Synthetic Route of C12H14ClFO2

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

A nitrilase-mediated entry to 4-carboxymethyl-β-lactams from chemically prepared 4-(cyanomethyl)azetidin-2-ones was written by Decuyper, Lena;Piens, Nicola;Mincke, Jens;Bomon, Jeroen;De Schrijver, Bert;Mollet, Karen;De Winter, Karel;Desmet, Tom;D’hooghe, Matthias. And the article was included in RSC Advances in 2016.Computed Properties of C6H10O3 This article mentions the following:

The compounds (3R,4S)-3-Alkoxy/aryloxy-4-(cyanomethyl)azetidin-2-ones I (R¹ = i-Pr, n-Bu; R² = Me, Bn, Ph; R³ = CN) were efficiently prepared from readily available 1,2:5,6-di-O-isopropylidene-D-mannitol by means of a classical organic synthesis approach via 4-hydroxymethyl-β-lactams I (R³ = OH) as key intermediates. The corresponding 4-carboxymethyl-β-lactams I (R³ = CO₂H) were subsequently obtained after selective hydrolysis of the nitrile functionality by means of a nitrilase enzyme without affecting the sensitive four-membered ring system, hence overcoming the difficulties associated with the chem. hydrolysis approach. Thus, the implementation of a biocatalytic step allows a convenient synthetic route to new 4-carboxymethyl-β-lactams I (R³ = CO₂H) as versatile building blocks for further elaboration. In the experiment, the researchers used many compounds, for example, (R)-2,2-Dimethyl-1,3-dioxolane-4-carbaldehyde (cas: 15186-48-8Computed Properties of C6H10O3).

(R)-2,2-Dimethyl-1,3-dioxolane-4-carbaldehyde (cas: 15186-48-8) 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. Although benzodioxole is not particularly important, many related compounds containing the methylenedioxyphenyl group are bioactive, and thus are found in pesticides and pharmaceuticals.Computed Properties of C6H10O3

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

Polyvinyl alcohol-potassium iodide: An efficient binary catalyst for cycloaddition of epoxides with CO₂ was written by Chang, Haibo;Li, Qingshuo;Cui, Xuemin;Wang, Hongxia;Qiao, Congzhen;Bu, Zhanwei;Lin, Tong. And the article was included in Molecular Catalysis in 2018.Application of 13818-44-5 This article mentions the following:

In this study, synthesis of cyclic carbonates from epoxide and CO₂ using polyvinyl alc. (PVA) and potassium iodide (KI) as an efficient catalytic system is reported. The catalytic reaction happens in solvent-free conditions. A synergetic effect occur between PVA and KI which considerably increases the reaction yield. This binary catalytic system is mainly suitable for mono-substituted terminal epoxides. In the optimized reaction condition, over 90% reaction yield can be achieved. The binary catalyst is reusable and can be recycled at least five times without significant loss of the catalytic activity. The PVA hydrolysis degree affect the catalytic activity as well. A possible mechanism of synergetic effect of the binary system was proposed. PVA and KI may form a non-toxic, low cost, recyclable, highly-efficiency catalyst for fixing CO₂ through cycloaddition with epoxides. In the experiment, the researchers used many compounds, for example, (2-Oxo-1,3-dioxolan-4-yl)methyl methacrylate (cas: 13818-44-5Application of 13818-44-5).

(2-Oxo-1,3-dioxolan-4-yl)methyl methacrylate (cas: 13818-44-5) 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.Application of 13818-44-5

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

Relation between chemical constitution and pepper taste. I was written by Staudinger, H.;Schneider, Hermann. And the article was included in Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen in 1923.Safety of Benzo[d][1,3]dioxol-5-yl(piperidin-1-yl)methanone This article mentions the following:

Crystallized piperine (I) has only a very slightly sharp taste while an alc. solution, even when very dilute, is so sharp that the characteristic pleasant taste of pepper does not appear. Again, if I is ground with 20 parts flour only a short time (6 hrs.) the product has only a faint pepper taste, while after 10 days’ grinding it has the same sharpness as pepper. There seems to be no doubt, therefore, that I is the chief active principle of pepper and that the characteristic pepper taste is produced by a reaction with colloidal substances on the tongue and is therefore dependent on a suitable degree of dispersion of the I. A systematic study has shown that the I mol. can be varied considerably without destroying the pepper taste. An essential factor is the amide-like union of piperidine (II) with an aliphatic-aromatic acid and the taste is most pronounced in derivatives of δ-phenylvaleric acid, so that the grouping seems to be of importance for the production of the pepper taste. The II salt of piperic acid (III) is not sharp, showing that the amide union in I is essential for the pepper taste. On the other hand β-cinnamenylacrylic piperidide (IV) has an even sharper taste than I, a 2.5% mixture of IV having about the same sharpness as ground pepper, which contains 5-10% of I. The same is true of the allo-isomer (V) of IV. The methylenedioxy group in I is therefore not essential for its taste. The 3 dihydro and the tetrahydro derivatives of IV have an equally strong pepper taste, which consequently does not depend on the double bonds. Tetrahydropiperine (VI) likewise has a pepper taste. The piperidides of sorbic and many other purely aliphatic or purely aromatic acids either have an unpleasant burning taste or are tasteless. Cinnamylidenemalonic acid (VII) is obtained in 88.6% yield from 189 g. PhCH:CHCHO and 1.5 mols. CH₂(CO₂)₂Ca in 400 g. AcOH heated at 60-70° until the mass solidifies (0.5-1.0 hr.), then 2 days at 80° and 1 day at 100°; with PCl₅ in C₆H₆ it gives the golden yellow chloride, m. 83°; the piperidide, prepared by the Schotten-Baumann method, has no pronounced pepper taste. β-Cinnamenylacrylic acid (VIII), m. 165°, was prepared by Döbner’s method (condensation of PhCH:CHCHO with CH₂(CO₂H)₂ in the presence of C₅H₅N; with quinoline as the condensing agent, the alloisomer (IX) of VIII, m. 138°, is obtained). The acid pyridine salt of VII m. 114-5° with evolution of CO₂ and formation of a mixture of about 60% VIII and a low melting acid, and the acid quinoline salt m. 114-5° and decomposes about 130° with formation chiefly of IX and only very little VIII. Chloride of VIII, from the acid refluxed 4 hrs. in petroleum ether with SOCl₂, m. 47° (that of IX has thus far not been obtained in crystalline form). IV m. 91-2° (Riedel, C. A. 2, 2238, gives 203°, and his product was evidently not IV). V could not be obtained crystalline and could not be distilled even in a high vacuum without decomposition The β,γ-dihydro derivative of VII decomposes in boiling H₂O with formation of 90-5% of phenyl-β,γ-pentenic acid (X), whereas with 4 parts of boiling 5% C₅H₅N it gives 90% of a mixture containing about 30% X and 70% of its α,β-isomer (XI). Chloride of XI, prepared with excess of SOCl₂, b₁₅ 149-50° (yield, 68%); Et(?) ester, b₁₃ 156-9°; piperidide, obtained in 77% yield from the acid heated 24 hrs. with II at 195-200°, also made by the Schotten-Baumann method, b_0.2 164-9°. Chloride of X, b₁₂, 139-40°, b_0.2 98-100°; Et ester, b₁₁ 154-6°; piperidide (17-8 g. from 17 6 g. of the acid heated 7 hrs. at 80-90° with 8.5 g. II), b_0.2 163-5°. Chloride of the γ,δ-isomer of X, b_0.15 100-5°; piperidide, faintly yellow, b_0.2 165-7°. α-Phenylcinnamenylacrylic chloride, from the acid heated a long time with SOCl₂ in C₆H₆, m. 87-9°; piperidide, m. 135°, has no sharp taste when ground with flour. Sorbic chloride, obtained in 50% yield from the acid and SOCl₂ in boiling C₆H₆, b₁₂ 69-71°; piperidide, m. 83-4°. The following piperidides have an unpleasant, generally not very sharp taste or are tasteless: valeric, b₁₂ 122-5°; caproic, b₁₂ 140°; heptylic, b₁₂ 158-62°; acetic, b₃₀ 125°; crotonic, b₃₀ 160°; palmilic, m. 35-6°; mono-Me malonic, b_0.5 130-5°; benzoic, m. 48°, b₁₅ 180°; p-methoxybenzoic, m. 35°, b₁₆ 210°; methyleneprotocatechuic, m. 45°; α-naphthoic, m. 85-7°; ε-naphthoic, m. 88-90°; toluene-p-sulfonic, m. 98-9°; cinnamic, m. 122°; p-methoxycinnamic, b₀ 200-10°; methylenecaffeic, m. 80-2°. In the experiment, the researchers used many compounds, for example, Benzo[d][1,3]dioxol-5-yl(piperidin-1-yl)methanone (cas: 34023-62-6Safety of Benzo[d][1,3]dioxol-5-yl(piperidin-1-yl)methanone).

Benzo[d][1,3]dioxol-5-yl(piperidin-1-yl)methanone (cas: 34023-62-6) 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.Safety of Benzo[d][1,3]dioxol-5-yl(piperidin-1-yl)methanone

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

Preparation of H₄SiW₁₂O₄₀ and its application in catalytic synthesis of ketal was written by Luo, Yumei;Lv, Yinhua;Liu, Jiangyan. And the article was included in Huaxue Yanjiu Yu Yingyong in 2005.Name: 2-Ethyl-2-methyl-1,3-dioxolane This article mentions the following:

A method for preparing catalyst H₄SiW₁₂O₄₀ was discussed. The catalytic activity of H₄SiW₁₂O₄₀ was validated in synthesizing cyclohexanone 1,2-propanediol ketal and the reaction conditions in synthesizing the other ketal (acetal) were also discussed. The yields of the other products were 85.5% for cyclohexanone 1,2-propanediol ketal, 89.6% for cyclohexanone ethylene ketal, 79.5% for butanone ethylene ketal, 89.1% for butyraldehyde ethylene acetal, and 81.5% for butyraldehyde 1,2-propanediol acetal. In the experiment, the researchers used many compounds, for example, 2-Ethyl-2-methyl-1,3-dioxolane (cas: 126-39-6Name: 2-Ethyl-2-methyl-1,3-dioxolane).

2-Ethyl-2-methyl-1,3-dioxolane (cas: 126-39-6) 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. Although benzodioxole is not particularly important, many related compounds containing the methylenedioxyphenyl group are bioactive, and thus are found in pesticides and pharmaceuticals.Name: 2-Ethyl-2-methyl-1,3-dioxolane

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