Month: April 2022

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine( cas:1265884-98-7 ) is researched.Related Products of 1265884-98-7.Han, Min; Yang, Min; Wu, Rui; Li, Yang; Jia, Tao; Gao, Yuanji; Ni, Hai-Liang; Hu, Ping; Wang, Bi-Qin; Cao, Peng published the article 《Highly Enantioselective Iridium-Catalyzed Coupling Reaction of Vinyl Azides and Racemic Allylic Carbonates》 about this compound( cas:1265884-98-7 ) in Journal of the American Chemical Society. Keywords: enantioselective iridium catalyst coupling reaction vinyl azide allylic carbonate; amide nitrile stereoselective preparation. Let’s learn more about this compound (cas:1265884-98-7).

The iridium-catalyzed enantioselective coupling reaction of vinyl azides and allylic electrophiles is presented and provides access to β-chiral carbonyl derivatives Vinyl azides are used as acetamide enolate or acetonitrile carbanion surrogates, leading to γ,δ-unsaturated β-substituted amides as well as nitriles with excellent enantiomeric excess. These products are readily transformed into chiral N-containing building blocks and pharmaceuticals. A mechanism is proposed to rationalize the chemoselectivity of this coupling reaction.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – 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: 2-Bromomethyl-1,3-dioxolane, is researched, Molecular C4H7BrO2, CAS is 4360-63-8, about Synthesis and Unexpected Transformation of 5-[(1,3-Dioxolan-2-ylmethyl)sulfanyl]-1H-pyrrol-2-amine into 5-{[2-(2-Hydroxyethoxy)ethenyl]sulfanyl}-1H-pyrrol-2-amine in the Presence of a Superbase.HPLC of Formula: 4360-63-8.

Successive one-pot reactions of monolithiated N,N-diethylprop-2-yn-1-amine with 2-(ethenyloxy)ethyl isothiocyanate and 2-(bromomethyl)-1,3-dioxolane afforded I in 91% yield. In the system t-BuOK-DMSO at room temperature (1 h), the product was converted to E/Z-II (yield 68%) instead of expected 1-vinyl derivative

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – 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: 4360-63-8, is researched, SMILESS is BrCC1OCCO1, Molecular C4H7BrO2Journal, Russian Journal of Organic Chemistry called Mass Spectra of New Heterocycles: XXIII. Electron Impact and Chemical Ionization Study of 5-[(Cyanomethyl)sulfanyl]- and 5-[(1,3-Dioxolan-2-ylmethyl)sulfanyl]-1H-pyrrol-2-amines, Author is Klyba, L. V.; Nedolya, N. A.; Sanzheeva, E. R.; Tarasova, O. A., the main research direction is cyanomethyl sulfanyl dioxolanylmethyl pyrrolamine preparation.Category: dioxole.

The fragmentation of pyrroles I [R1 = R2 = Me, Et, n-Pr; R3 = Me, s-Bu, c-hexyl, etc.; -R1R2- = -(CH2)4-, -(CH2)5-, -(CH2)2O(CH2)2; R4 = CN, 1,3-dioxolan-2-yl] under electron impact (70 eV) and chem. ionization with methane as reactant gas has been studied for the first time. Electron impact ionization of 5-[(cyanomethyl)sulfanyl]-substituted pyrroles generates low-stability mol. ions {M+., Irel 4-22%; compared to Irel 16-69% for 5-[(1,3-dioxolan-2-ylmethyl)sulfanyl] analogs} whose primary fragmentation involves cleavage of the C-S bond with expulsion of NCCH2 radical. Other fragmentation pathways of the mol. ions include formation of [M – CHR4]+. ions (R4 = CN) and substituent decomposition products. The mass spectra of 5-[(1,3-dioxolan-2-ylmethyl)sulfanyl]pyrroles characteristically show [M – SCH2R4]+ ion peak. The most intense ion peaks in the chem. ionization mass spectra of 5-[(cyanomethyl)sulfanyl] derivatives are those of M+. (Irel 18-69%) and [M + H]+ (Irel 34-100%). Both 5-[(cyanomethyl)sulfanyl]- and 5-[(1,3-dioxolan-2-ylmethyl)sulfanyl]pyrroles decompose mainly through cleavage of the CH2-S and C5-S bonds with the formation of stable [M – CH2R4]+ (Irel 92-100%), [M + H – CH2R4]+. (Irel 22-75%), and [M + H – SCH2R4]+. ions (Irel 6-25%).

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – 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 Phospho sugars; novel preparation and their glycosyl compounds, published in 1989-08-31, which mentions a compound: 707-61-9, Name is 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, Molecular C11H13OP, Application of 707-61-9.

Treatment of 1-phenyl-2-, and -3-phospholene 1-oxides with NBS affords 4-bromo-1-phenyl-2-phospholene 1-oxide (I). Substitution of the bromide with acetate, followed by stereoselective oxidation with osmium tetroxide and peracetylation with acetic anhydride/pyridine affords phospho sugar derivatives II of tetrafuranose. Furthermore, glycosyl compounds III (R = iodo, OAc, SCN, N3) of phospho sugars were prepared from 3-methyl-1-phenyl-2-phospholene 1-oxide by bromination and nucleophilic substitution reactions.

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

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, International Immunopharmacology called The indole-hydantoin derivative exhibits anti-inflammatory activity by preventing the transactivation of NF-κB through the inhibition of NF-κB p65 phosphorylation at Ser276, Author is Lin, Xin; Tago, Kenji; Okazaki, Nozomi; So, Takanori; Takahashi, Kyoko; Mashino, Tadahiko; Tamura, Hiroomi; Funakoshi-Tago, Megumi, which mentions a compound: 7524-52-9, SMILESS is N[C@@H](CC1=CNC2=CC=CC=C12)C(OC)=O.[H]Cl, Molecular C12H15ClN2O2, Synthetic Route of C12H15ClN2O2.

Indole- and hydantoin-based derivatives both exhibit anti-inflammatory activity, suggesting that the structures of indole and hydantoin are functional for this activity. In the present study, we synthesized two types of indole-hydantoin derivatives, IH-1 (5-(1H-indole-3-ylmethylene) imidazolidine-2,4-dione) and IH-2 (5-(1H-indole-3-ylmethyl) imidazolidine-2,4-dione) and examined their effects on LPS-induced inflammatory responses in murine macrophage-like RAW264.7 cells. LPS-induced inflammatory responses were not affected by indole, hydantoin, or IH-2. In contrast, IH-1 significantly inhibited the LPS-induced production of nitric oxide (NO) and secretion of CCL2 and CXCL1 by suppressing the mRNA expression of inducible NO synthase (iNOS), CCL2, and CXCL1. IH-1 markedly inhibited the LPS-induced activation of NF-κB without affecting the degradation of IκBα or nuclear translocation of NF-κB. IH-1 markedly attenuated the transcriptional activity of NF-κB by suppressing the LPS-induced phosphorylation of the NF-κB p65 subunit at Ser276. Furthermore, IH-1 prevented the LPS-induced interaction of NF-κB p65 subunit with a transcriptional coactivator, cAMP response element-binding protein (CBP). Collectively, these results revealed the potential of the novel indole-hydantoin derivative, IH-1 as an anti-inflammatory drug.

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

Carlson, Lars A.; Hedbom, Christina; Helgstrand, Erik; Sjoberg, Berndt; Stjernstrom, Nils E. published the article 《Potential hypolipidemic agents. III. Heterocyclic compounds affecting free fatty acid mobilization in vivo》. Keywords: fatty acid mobilization fluoronicotinate blood; fluoropyridylacetate fatty acid mobilization blood; methylpyrazole fatty acid mobilization blood.They researched the compound: Methyl 5-fluoro-3-pyridinecarboxylate( cas:455-70-9 ).Recommanded Product: Methyl 5-fluoro-3-pyridinecarboxylate. 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:455-70-9) here.

Compounds such as 3-methyl-5-isoxazolecarboxylic acid [4857-42-5], 5-fluoronicotinic acid [402-66-4], 5-fluoro-3-pyridylacetic acid [38129-24-7], and 3-methylpyrazole [1453-58-3] exhibited the highest inhibition of free fatty acid mobilization in blood among 188 heterocyclic compounds tested in dogs, while compounds such as 5-methyl-3-isoxazolecarboxylic acid [3405-77-4], 2-fluoronicotinic acid [393-55-5], and 3-aminobenzoic acid [99-05-8] had no effect on free fatty acid mobilization.

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

HPLC of Formula: 707-61-9. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Intermolecular Reductive C-N Cross Coupling of Nitroarenes and Boronic Acids by PIII/PV=O Catalysis. Author is Nykaza, Trevor V.; Cooper, Julian C.; Li, Gen; Mahieu, Nolwenn; Ramirez, Antonio; Luzung, Michael R.; Radosevich, Alexander T..

A main group-catalyzed method for the synthesis of aryl- and heteroarylamines by intermol. C-N coupling is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane) and a terminal hydrosilane reductant (phenylsilane) to drive reductive intermol. coupling of nitro(hetero)arenes with boronic acids. Applications to the construction of both Csp2-N (from arylboronic acids) and Csp3-N bonds (from alkylboronic acids) are demonstrated; the reaction is stereospecific with respect to Csp3-N bond formation. The method constitutes a new route from readily available building blocks to valuable nitrogen-containing products with complementarity in both scope and chemoselectivity to existing catalytic C-N coupling methods.

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

SDS of cas: 7524-52-9. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: H-Trp-OMe.HCl, is researched, Molecular C12H15ClN2O2, CAS is 7524-52-9, about A facile synthesis of meta- and para-terphenylglyoxamide-based peptidomimetics. Author is Yu, Tsz Tin; Bhadbhade, Mohan; Kuppusamy, Rajesh; Black, David St. C.; Kumar, Naresh.

A series of meta- and para-terphenylglyoxamide peptidomimetics have been synthesized by the ring-opening of 5-(biphenylyl)-N-acylisatins with alcs., amines and amino acid Me esters. The starting 5-(biphenylyl)isatins were synthesized via the Suzuki-Miyaura coupling reaction in a convenient and efficient manner.

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

Product Details of 22353-34-0. 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. Compound: 5-Chloropyridin-3-amine, is researched, Molecular C5H5ClN2, CAS is 22353-34-0, about Pyridyl-urea catalysts for the solvent-free ring-opening polymerization of lactones and trimethylene carbonate.

The ring-opening polymerization (ROP) of lactones is an effective method for the preparation of biocompatible and biodegradable aliphatic polyesters, for which the development of efficient organocatalysts with high activity and good controllability is highly desirable. A series of novel pyridyl-urea catalysts was synthesized and applied in the solvent-free ROP of lactones and trimethylene carbonate. Combined with 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), the pyridyl-urea/MTBD systems showed a fast and living/controlled behavior in the ROP, generating polymers with narrow mol. weight distributions. The influences of catalyst structure, type of base, pyridyl-urea/base ratio, feed ratio of monomer/initiator and reaction temperature on the catalytic properties were investigated. A possible mechanism was proposed on the basis of NMR titration and dilution experiments

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – 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.Panda, Santanu; Ready, Joseph M. researched the compound: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine( cas:1265884-98-7 ).Application of 1265884-98-7.They published the article 《Tandem Allylation/1,2-Boronate Rearrangement for the Asymmetric Synthesis of Indolines with Adjacent Quaternary Stereocenters》 about this compound( cas:1265884-98-7 ) in Journal of the American Chemical Society. Keywords: indole boronate ester allylic acetate palladium allylation boronate rearrangement; indoline stereoselective preparation. We’ll tell you more about this compound (cas:1265884-98-7).

A three-component coupling using lithiated indoles, boronate esters and allylic acetates generates chiral indolines with adjacent quaternary stereocenters. Successful stereocontrol required the use of phosphoramidite ligands not previously described for organopalladium chem. Mechanistic studies indicate a monodentate PdL intermediate, and a stepwise allylation-aryl/alkyl migration. A protodeborylation strategy was used to install a C-H bond in place of the C-B bond. A photoredox coupling was used to replace C-B bond with a C-C bond in a highly diastereoselective manner. In the specific case of methyl-vinyl ketone, a novel radical-mediated annulation provides polycyclic products with high enantio- and diastereoselectivity.

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