Day: April 8, 2022

Application of 20028-53-9. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Amino-5-chlorobenzaldehyde, is researched, Molecular C7H6ClNO, CAS is 20028-53-9, about A novel and efficient methodology for the construction of quinazolines based on supported copper oxide nanoparticles. Author is Zhang, Jintang; Yu, Chenmin; Wang, Sujing; Wan, Changfeng; Wang, Zhiyong.

A series of quinazolines were synthesized from 2-aminobenzophenones and benzylic amines in good to excellent yields by employing a new heterogeneous catalyst based on the copper oxide nanoparticles supported on kaolin.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Related Products of 51856-79-2. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Methyl 2-(1-methyl-1H-pyrrol-2-yl)acetate, is researched, Molecular C8H11NO2, CAS is 51856-79-2, about Selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles via tandem reactions of alkynones with pyrrole derivatives. Author is Zhao, Yulei; Yuan, Yang; Xu, Murong; Zheng, Zhong; Zhang, Runhua; Li, Yanzhong.

Methodologies for the selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles starting from pyrrole derivatives and alkynones were described. When reactions were carried out with 1,2,4-trisubstituted N-propargyl pyrroles using a ZnI2 catalyst, pyrrolo[1,2-a]azepines were obtained. Whereas 4,6-dicarbonyl indoles were produced selectively with 1,2-disubstituted pyrroles in the presence of silica gel. The reaction outcomes were dependent on the substituent pattern of the substrates and the nature of the catalysts chosen. Control reactions suggested that the formation of a conjugated enamine intermediate was crucial for both the processes. With easily accessible starting materials, inexpensive catalysts and an easy-to-handle procedure, this reaction had the potential to become a general protocol for the synthesis of pyrrolo[1,2-a]azepines or indoles.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: (S)-Butan-2-ol, is researched, Molecular C4H10O, CAS is 4221-99-2, about Mechanistic insight into the stereoselective cationic polymerization of vinyl ethers.Name: (S)-Butan-2-ol.

The control of the tacticity of synthetic polymers enables the realization of emergent phys. properties from readily available starting materials. While stereodefined polymers derived from nonpolar vinyl monomers can be efficiently prepared using early transition metal catalysts, general methods for the stereoselective polymerization of polar vinyl monomers remain underdeveloped. We recently demonstrated asym. ion pairing catalysis as an effective approach to achieve stereoselective cationic polymerization of vinyl ethers. Herein, we provide a deeper understanding of stereoselective ion-pairing polymerization through comprehensive exptl. and computational studies. These findings demonstrate the importance of ligand deceleration effects for the identification of reaction conditions that enhance stereoselectivity, which was supported by computational studies that identified the solution-state catalyst structure. An evaluation of monomer substrates with systematic variations in steric parameters and functional group identities established key structure-reactivity relationships for stereoselective homo- and copolymerization Expansion of the monomer scope to include enantioenriched vinyl ethers enabled the preparation of an isotactic poly(vinyl ether) with the highest stereoselectivity (95.1% ± 0.1 meso diads) reported to date, which occurred when monomer and catalyst stereochem. were fully matched under a triple diastereocontrol model. The more complete understanding of stereoselective cationic polymerization reported herein offers a foundation for the design of improved catalytic systems and for the translation of isotactic poly(vinyl ether)s to applied areas.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Xu, Chao; Muir, Calum W.; Leach, Andrew G.; Kennedy, Alan R.; Watson, Allan J. B. published the article 《Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation》. Keywords: azaheterocycle vinyl aniline phosphoric acid chiral conjugate addition catalyst; ethylamine azaheteroaryl stereoselective preparation; Brønsted acids; asymmetric catalysis; heterocycles; organocatalysis; stereochemistry.They researched the compound: Methyl 6-bromonicotinate( cas:26218-78-0 ).Safety of Methyl 6-bromonicotinate. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:26218-78-0) here.

The direct enantioselective synthesis of chiral azaheteroaryl ethylamines from vinyl-substituted N-heterocycles and anilines is reported. A chiral phosphoric acid (CPA) catalyst promotes dearomatizing aza-Michael addition to give a prochiral exocyclic aryl enamine, which undergoes asym. protonation upon rearomatization. The reaction accommodates a broad range of N-heterocycles, nucleophiles, and substituents on the prochiral center, generating the products in high enantioselectivity. DFT studies support a facile nucleophilic addition based on catalyst-induced LUMO lowering, with site-selective, rate-limiting, intramol. asym. proton transfer from the ion-paired prochiral intermediate.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Liu, Changhui; Zhou, Li; Jiang, Dan; Gu, Yanlong published the article 《Multicomponent Reactions of Aldo-X Bifunctional Reagent α-Oxoketene Dithioacetals and Indoles or Amines: Divergent Synthesis of Dihydrocoumarins, Quinolines, Furans, and Pyrroles》. Keywords: dihydrocoumarin quinoline furan pyrrole preparation; indole oxoketene dithioacetal aldehyde multicomponent reaction.They researched the compound: 2-Amino-5-chlorobenzaldehyde( cas:20028-53-9 ).Application of 20028-53-9. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:20028-53-9) here.

Six multicomponent reactions were developed by using aldo-X reagents such as 2-hydroxybenzaldehyde, Et 2-oxoacetate, Me 2-(dimethoxymethyl)benzoate, etc. and α-oxoketene dithioacetals, e.g., I with indoles or amines as substrates, which can be used to prepare many heterocycles, such as dihydrocoumarins II (R1 = H, 6-Br; R2 = OMe, F, t-Bu, etc.; R3 = H, Et; R4 = Me, Ph; R5 = H, F, OMe), quinolines III (R6 = 6-Cl, 6,8-Br2; R7 = H, 4-OMe, 4-F; R8 = H, 4-F, 4-NO2, etc.), furans and pyrroles IV [R9 = H, 5-F; R10 = Ph, 4-fluorophenyl, 4-methoxyphenyl; X = O, N-Ph, N-4-fluorophenyl, N-(4-trifluoromethoxyphenyl)] in a straightforward way. A combination of two bifunctional aldo-X reagents and α-oxoketene dithioacetals was the key to make the discovery of these multicomponent reactions possible because these reagents have a min. of two reactive sites, which enable different substrates to be assembled together in various manners.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 20028-53-9, is researched, SMILESS is NC1=CC=C(Cl)C=C1C=O, Molecular C7H6ClNOJournal, Article, Research Support, U.S. Gov’t, Non-P.H.S., Bioorganic & Medicinal Chemistry called Synthesis, biological evaluation and virtual screening of some acridone derivatives as potential anticancer agents, Author is Oyedele, Abiodun S.; Bogan, Deanna N.; Okoro, Cosmas O., the main research direction is acridone dihydro preparation antitumor activity topoisomerase inhibitor; 1,3-cyclohexanedione, 2-aminobenzaldehyde; Acridones; Amsacrine; Anticancer activity; Imidazoacridinone.Product Details of 20028-53-9.

Eleven novel acridone derivatives I (R1 = Ph, CF3; R2 = 7-Cl, 7-Br, 7-F, 5,7-Br2, 7-OMe, 5-OMe) were synthesized and evaluated for their anticancer activity against 60 human cancer cell lines. Five compounds I (R1 = Ph, R2 = 7-Cl, R2 = 7-Br, 7-MeO, 5,7-Br2; R1 = CF3, R2 = 7-OMe) displayed very good in vitro antiproliferative activities well over 95% of the panels. The most active compound is I (R1 = Ph; R2 = 3,5-Br2). In addition, this compound was the most effective in all 9 panels including prostate (0.075μm), leukemia (0.116μm), non-small cell lung cancer (0.164μm), colon cancer (0.193μm), CNS cancer (0.264μm), melanoma (0.317μm), renal cancer (0.403μm), ovarian cancer (0.410μm), and breast cancer (0.608μm). Virtual screening studies also revealed that nine of the eleven compounds I formed good binding interaction with the active site ATPase domain of human topoisomerase II α (PDB: 1zxm). Some of synthesized derivatives exhibited binding affinities that ranged in values from -8.5 to -7.9 kcal/mol, indicating that they could be catalytic inhibitors of the nuclear enzyme, topoisomerase.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Synthesis and enantioselective pharmacokinetic/pharmacodynamic analysis of new CNS-active sulfamoylphenyl carbamate derivatives, published in 2021, which mentions a compound: 4221-99-2, Name is (S)-Butan-2-ol, Molecular C4H10O, Category: tetrahydrofurans.

We recently reported a new class of carbamate derivatives as anticonvulsants. Among these, 3-methylpentyl(4-sulfamoylphenyl)carbamate (MSPC) stood out as the most potent compound with ED50 values of 13 mg/kg (i.p.) and 28 mg/kg (p.o.) in the rat maximal electroshock test (MES). 3-Methylpropyl(4-sulfamoylphenyl)carbamate (MBPC), reported and characterized here, is an MSPC analogus compound with two less aliphatic carbon atoms in its structure. As both MSPC and MBPC are chiral compounds, here, we studied the carbonic anhydrase inhibitory and anticonvulsant action of both MBPC enantiomers in comparison to those of MSPC as well as their pharmacokinetic properties. Racemic-MBPC and its enantiomers showed anticonvulsant activity in the rat maximal electroshock (MES) test with ED50 values in the range of 19-39 mg/kg. (R)-MBPC had a 65% higher clearance than its enantiomer and, consequently, a lower plasma exposure (AUC) than (S)-MSBC and racemic-MSBC. Nevertheless, (S)-MBPC had a slightly better brain permeability than (R)-MBPC with a brain-to-plasma (AUC) ratio of 1.32 (S-enantiomer), 1.49 (racemate), and 1.27 (R-enantiomer). This may contribute to its better anticonvulsant-ED50 value. The clearance of MBPC enantiomers was more enantioselective than the brain permeability and MES-ED50 values, suggesting that their anticonvulsant activity might be due to multiple mechanisms of action.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Jiang, Zhenzhen; Fan, Lihui; Zhou, Ping; Xu, Tingting; Chen, Jingxian; Hu, Simin; Chen, De-Li; He, Yabing researched the compound: Methyl 6-bromonicotinate( cas:26218-78-0 ).Reference of Methyl 6-bromonicotinate.They published the article 《An N-oxide-functionalized nanocage-based copper-tricarboxylate framework for the selective capture of C2H2》 about this compound( cas:26218-78-0 ) in Dalton Transactions. Keywords: oxide functionalized nanocage copper tricarboxylate framework selective capture acetylene. We’ll tell you more about this compound (cas:26218-78-0).

The selective capture of C2H2 from C2H2-C2H4 and C2H2-CO2-CH4 mixtures is a very essential but highly challenging process during C2H4 and C2H2 purification in the chem. industry. In this work, by virtue of using oxygen-atom-rich C2H2 recognition sites, we, for the first time, designed and synthesized an N-oxide-functionalized tricarboxylate ligand and utilized it to successfully construct a copper-based MOF. N-Oxide functionalization exerted a significant effect on the ligand conformation, thus resulting in a new topol. network that is different from that of the unoxidized parent compound With a moderate surface area and the immobilization of N-oxide functionality and carboxylate oxygen atoms in two nanocages, the title MOF exhibited promising potential for the multifunctional separation of C2H2/C2H4 and C2H2/CO2/CH4 mixtures under ambient conditions, as shown by pure-composition isotherm measurements, IAST predictions, and mol. modeling studies.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Chen, Jie; Kong, Fanhui; Ma, Nana; Zhao, Panxia; Liu, Chuanfei; Wang, Xiling; Cong, Zhiqi published the article 《Peroxide-Driven Hydroxylation of Small Alkanes Catalyzed by an Artificial P450BM3 Peroxygenase System》. Keywords: alkane hydroxylation P450BM3 peroxygenase hydrogen peroxide protein engineering.They researched the compound: (S)-Butan-2-ol( cas:4221-99-2 ).Product Details of 4221-99-2. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:4221-99-2) here.

We report the selective hydroxylation of small alkanes with H2O2 catalyzed by an artificial P 450 peroxygenase system generated from engineered cytochrome P450BM3 variants in assistance with dual-functional small mol. (DFSM), in which DFSM acts as a general acid-base co-catalyst for activating H2O2. This peroxygenase system exhibited comparable catalytic turnover number (TON) to the fungal peroxygenase AaeUPO, the only known H2O2-dependent natural alkane hydroxylase. Moreover, when compared with evolved/engineered NADPH-dependent P 450 variants, the current system yielded similar or even better product formation rates (PFRs) but lower total TONs. The substitution of the highly conserved T268 with amino acids having hydrophobic side chains was identified to play critical roles in improving the hydroxylation activity of the DFSM-facilitated P450BM3 peroxygenase system, which is distinct from NADPH-dependent P 450 enzymes. These results offer useful insights into how to tune the catalytic functions and chem. of P 450 peroxygenases.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Methyl 6-bromonicotinate, is researched, Molecular C7H6BrNO2, CAS is 26218-78-0, about [4+2] cycloaddition of trifluoromethyl ketimines with 2-alkenyl azaarenes through selective C-F bond cleavage of CF3.Reference of Methyl 6-bromonicotinate.

A new [4+2] cycloaddition of trifluoromethyl ketimines R1C6H4C(CF3)=NCH2C6H4R2 (R1 = H, 3-Me, 4-Br, 3-Cl, etc.; R2 = H, 3-F-4-Cl, 2-Me, 4-OMe, etc.) with 2-alkenyl azaarenes R3CH=CH2 (R3 = 5-cyano-3-methylpyridin-2-yl, 4-methylpyridin-2-yl, 6-chloroquinolin-2-yl, etc.) through selective C-F bond cleavage of CF3 has been developed. The reactions are promoted by 2,2,6,6-tetramethylpiperidine (TMP) under mild conditions to give cis-tetrahydropyridine I products in moderate yields. D. functional theory (DFT) calculations reveal that the in situ formed (E)-N-(2,2-difluoro-1-phenylvinyl)-1-phenylmethanimine is the key intermediate for the formation of cis-tetrahydropyridine products I which have the lowest energy among the four possible products.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem