Day: February 27, 2023

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

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

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

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

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

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

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

Sulfite-Induced N-Alkylation and Thioketonization of Azoles Enable Access to Diverse Azole Thiones was written by Deng, Jian-Chao;Chen, Jia-Hao;Zhang, Jun-Rong;Lu, Ting-Ting;Tang, Ri-Yuan. And the article was included in Advanced Synthesis & Catalysis in 2018.Application of 4360-63-8 This article mentions the following:

The direct modification of azole skeletons enables access to drug-like mols. The development of a highly compatible reaction platform for this pursuit still remains challenging. Herein, we report the use of sulfite as the single electron transfer (SET) reducing agent for the activation of functionalized bromoalkanes, elemental sulfur, and imidazoliniums for the transition metal-free and base-free N-alkylation and thioketonization of azoles. Excellent functional group tolerance and high synthetic efficiency proved particularly advantageous for the rapid assembly of a large array of pharmaceutically-oriented azole thiones , e.g., I, many of which contain synthetically and biol. useful functional groups. The direct transformation of drug mols. (such as Ketoconazole, Econazole, and Fluconazole) into their corresponding azole thiones has also been successfully achieved. Reactions with selenium also proceeded smoothly under the optimized conditions. Successful gram-scale reactions demonstrate the good applicability of this methodol. In the experiment, the researchers used many compounds, for example, 2-Bromomethyl-1,3-dioxolane (cas: 4360-63-8Application of 4360-63-8).

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. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Application of 4360-63-8

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

Stereoselective synthesis of amino acid-derived β-lactams. Experimental evidence for TADDOL as a memory of chirality enhancer was written by Bonache, M. Angeles;Lopez, Pilar;Martin-Martinez, Mercedes;Garcia-Lopez, M. Teresa;Cativiela, Carlos;Gonzalez-Muniz, Rosario. And the article was included in Tetrahedron in 2006.Quality Control of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) This article mentions the following:

In model experiments, concerning the modulation of memory of chirality during the intramol. alkylation of N-(4-methoxybenzyl)-N-chloroacetyl-Phe-O-tert-Bu derivative to the corresponding β-lactam I, TADDOL was selected from a panel of different phase-transfer catalysts as the best chiral additive (ee up to 82%). We have demonstrated here that the degree and sign of the cyclization selectivity was virtually independent on TADDOL configuration, providing exptl. proof that in this reaction this additive works as a memory of chirality enhancer and not as a real catalyst. The effect of TADDOL is strongly dependent on the starting amino acid derivative, the increase of selectivity being only observed for those with aromatic side chains. In the experiment, the researchers used many compounds, for example, ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8Quality Control of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)).

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8) 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. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Quality Control of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)

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

Cyclic amidine hydroiodide for the synthesis of cyclic carbonates and cyclic dithiocarbonates from carbon dioxide or carbon disulfide under mild conditions was written by Aoyagi, Naoto;Furusho, Yoshio;Endo, Takeshi. And the article was included in Tetrahedron in 2019.Synthetic Route of C8H10O5 This article mentions the following:

Hydroiodides of amidines can catalyze the reaction of carbon dioxide and epoxides under mild conditions such as ordinary pressure and ambient temperature, and the corresponding five-membered cyclic carbonates were obtained in high yields. The reaction of epoxide with carbon disulfide was also examined under the same conditions. Detailed investigation showed that the catalytic activity was highly affected by the counter anions of the amidine salts; the iodides were effective catalysts for both of the reaction of epoxide with carbon dioxide and carbon disulfide, whereas the bromide, chloride and fluoride counterparts exhibited almost no catalysis. In the experiment, the researchers used many compounds, for example, (2-Oxo-1,3-dioxolan-4-yl)methyl methacrylate (cas: 13818-44-5Synthetic Route of C8H10O5).

(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.Synthetic Route of C8H10O5

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