Category: 725251-81-0

Molander, Gary A. published the artcileAccessing Molecularly Complex Azaborines: Palladium-Catalyzed Suzuki-Miyaura Cross-Couplings of Brominated 2,1-Borazaronaphthalenes and Potassium Organotrifluoroborates, Product Details of C8H11BO3, the publication is Journal of Organic Chemistry (2014), 79(14), 6663-6678, database is CAplus and MEDLINE.

Despite their potential applications in both medicinal chem. and materials science, there have been limited reports on the functionalization of 2,1-borazaronaphthalenes since their discovery in 1959. To access new chem. space and build mol. complexity, the Suzuki-Miyaura cross-coupling of brominated 2,1-borazaronaphthalenes has been investigated. The palladium-catalyzed cross-coupling proceeds with an array of potassium (hetero)aryltrifluoroborates in high yield with low catalyst loadings under mild reaction conditions. By the use of a high-yielding bromination of various 2,1-borazaronaphthalenes to generate electrophilic azaborine species, a library of 3-(hetero)aryl and 3,6-diaryl-2,1-borazaronaphthalenes has been synthesized.

Journal of Organic Chemistry published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C8H11BO3, Product Details of C8H11BO3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Gargano, Emanuele M. published the artcileMetabolic stability optimization and metabolite identification of 2,5-thiophene amide 17β-hydroxysteroid dehydrogenase type 2 inhibitors, Name: (3-Methoxy-5-methylphenyl)boronic acid, the publication is European Journal of Medicinal Chemistry (2014), 203-219, database is CAplus and MEDLINE.

17β-HSD2 is a promising new target for the treatment of osteoporosis. In this paper, a rational strategy to overcome the metabolic liability in the 2,5-thiophene amide class of 17β-HSD2 inhibitors is described, and the biol. activity of the new inhibitors. Applying different strategies, as lowering the cLogP or modifying the structures of the mols., three compounds with strongly improved metabolic stability were obtained. For understanding biotransformation in the 2,5-thiophene amide class the main metabolic pathways of three properly selected compounds were elucidated.

European Journal of Medicinal Chemistry published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C8H11BO3, Name: (3-Methoxy-5-methylphenyl)boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Trost, Barry M. published the artcileA short and concise asymmetric synthesis of hamigeran B, Synthetic Route of 725251-81-0, the publication is Chemistry – A European Journal (2005), 11(3), 951-959, database is CAplus and MEDLINE.

The interesting biol. properties of the hamigerans wherein hamigeran B (I) is a potent antiviral agent with low cytotoxicity to host cells make these deceptively simple looking structures challenging synthetic targets. A strategy to hamigeran B evolved wherein the three contiguous stereocenters are established ultimately from a Pd catalyzed asym. allylic alkylation (AAA). The latter involves an asym. allylation of a non-stabilized ketone enolate in 77% yield and 93% ee. By using this process, (S)-5-allyl-2-isopropyl-5-methyl-1-trifluoromethanesulfonyloxycyclopentene becomes available in four steps from 2-methylcyclopentanone. Introduction of the aryl unit by cross-coupling proceeded intermolecularly but failed intramolecularly. On the other hand, reductive removal of the triflate permitted a Heck reaction to effect intramol. introduction of the aryl ring. The unusual conformational properties of this mol. architecture are revealed by the regioselectivity of the β-hydrogen elimination in the Heck reaction and the diastereoselectivity of the reduction establishing the stereochem. of the carbon bearing the iso-Pr group. The successful route consists of 15 steps from 2-methylcyclopentanone and dimethylorcinol illustrating the efficiency of the route based upon the Pd AAA.

Chemistry – A European Journal published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C9H12O, Synthetic Route of 725251-81-0.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Neel, Andrew J. published the artcileEnantiodivergent Fluorination of Allylic Alcohols: Data Set Design Reveals Structural Interplay between Achiral Directing Group and Chiral Anion, Name: (3-Methoxy-5-methylphenyl)boronic acid, the publication is Journal of the American Chemical Society (2016), 138(11), 3863-3875, database is CAplus and MEDLINE.

Enantioselectivity values represent relative rate measurements that are sensitive to the structural features of the substrates and catalysts interacting to produce them. Therefore, well-designed enantioselectivity data sets are information rich and can provide key insights regarding specific mol. interactions. However, if the mechanism for enantioselection varies throughout a data set, these values cannot be easily compared. This premise, which is the crux of free energy relationships, exposes a challenging issue of identifying mechanistic breaks within multivariate correlations. Herein, we describe an approach to addressing this problem in the context of a chiral phosphoric acid catalyzed fluorination of allylic alcs. using aryl boronic acids as transient directing groups. By designing a data set in which both the phosphoric and boronic acid structures were systematically varied, key enantioselectivity outliers were identified and analyzed. A mechanistic study was executed to reveal the structural origins of these outliers, which was consistent with the presence of several mechanistic regimes within the data set. While 2- and 4-substituted aryl boronic acids favored the (R)-enantiomer with most of the studied catalysts, meta-alkoxy substituted aryl boronic acids resulted in the (S)-enantiomer when used in combination with certain (R)-phosphoric acids. We propose that this selectivity reversal is the result of a lone pair-π interaction between the substrate ligated boronic acid and the phosphate. On the basis of this proposal, a catalyst system was identified, capable of producing either enantiomer in high enantioselectivity (77% (R)-2 to 92% (S)-2) using the same chiral catalyst by subtly changing the structure of the achiral boronic acid.

Journal of the American Chemical Society published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C8H11BO3, Name: (3-Methoxy-5-methylphenyl)boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Wada, Yuuki published the artcileEnantioselective bromination of axially chiral cyanoarenes in the presence of bifunctional organocatalysts, Name: (3-Methoxy-5-methylphenyl)boronic acid, the publication is RSC Advances (2019), 9(54), 31654-31658, database is CAplus and MEDLINE.

Enantioselective bromination of axially chiral cyanoarenes bearing high intrinsic rotational barriers via dynamic kinetic resolution using bifunctional organocatalysts was afforded brominated axially chiral cyanoarenes I [R = H, Me, CF₃, etc.; R¹ = F, Br, OMe, etc.]. Sequential addition of a brominating reagent in several portions at an optimized temperature was effective in accomplishing high enantioselectivities.

RSC Advances published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C11H22N2O4, Name: (3-Methoxy-5-methylphenyl)boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Shao, Ailong published the artcileElectrochemical Intramolecular C-H/O-H Cross-Coupling of 2-Arylbenzoic Acids, COA of Formula: C8H11BO3, the publication is Chinese Journal of Chemistry (2018), 36(7), 619-624, database is CAplus.

A synthetic protocol to lactones, e.g. I, by electro-oxidative induced C-H activation of 2-arylbenzoic acids was developed using aqueous Na₂SO₄ as a cheap and green supporting electrolyte in 30%-90% yields. This reaction could be conducted on a gram scale with a good efficiency as well as showed high utility for natural product synthesis like Sabilactone.

Chinese Journal of Chemistry published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C7H5ClN2S, COA of Formula: C8H11BO3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Nguyen, Thi Le Nhon published the artcileEnantioselective nickel-catalyzed arylative intramolecular 1,4-allylations, HPLC of Formula: 725251-81-0, the publication is Chemical Communications (Cambridge, United Kingdom) (2018), 54(44), 5622-5625, database is CAplus and MEDLINE.

The enantioselective nickel-catalyzed desymmetrization of allenyl cyclohexa-2,5-dienones I (R¹ = CH₃, C₂H₅, CH(CH₃)₂, C₆H₅; X = O, NTs) by reaction with arylboronic acids ArB(OH)₂ (R² = C₆H₅, 3-NCC₆H₄, 2-naphthyl, etc.) is described. Nickel-catalyzed arylation of the allene gives allyl nickel species, which undergo cyclization by 1,4-allylation to produce hexahydroindol-5-ones/hexahydrobenzofuran-5-ones II with three contiguous stereocenters in high diastereo- and enantioselectivities.

Chemical Communications (Cambridge, United Kingdom) published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C8H11BO3, HPLC of Formula: 725251-81-0.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Yoshida, Tatsuki published the artcileN-Methylphenothiazine S-Oxide Enabled Oxidative C(sp²)-C(sp²) Coupling of Boronic Acids with Organolithiums via Phenothiaziniums, Category: ethers-buliding-blocks, the publication is Organic Letters (2021), 23(24), 9664-9668, database is CAplus and MEDLINE.

The development of a transition-metal-free oxidative C(sp²)-C(sp²) coupling of readily available boronic acids RB(OH)₂ (R = Ph, 2-naphthyl, 1-hexenyl, 2-(4-bromophenyl)vinyl, etc.) and organolithiums R¹Li (R¹ = 4-bromophenyl, vinyl, 2-naphthyl, etc.) via phenothiazinium ions I was reported. Various biaryl, styrene, and diene derivatives RR¹ were obtained using this reaction system. The key to this process is N-methylphenothiazine S-oxide (PTZSO), which allows efficient conversion of boronic acids to phenothiazinium ions I. The mechanism of phenothiazinium formation using PTZSO was investigated using theor. calculations and experiments, which provided insight into the unique reactivity of PTZSO.

Organic Letters published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C8H5F3O3, Category: ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Binder, Randall J. published the artcileFacile synthesis of 1,2-dione-containing abietane analogs for the generation of human carboxylesterase inhibitors, Application of (3-Methoxy-5-methylphenyl)boronic acid, the publication is European Journal of Medicinal Chemistry (2018), 79-89, database is CAplus and MEDLINE.

Recently, a series of selective human carboxylesterase inhibitors have been identified based upon the tanshinones, with biol. active mols. containing a 1,2-dione group as part of a naphthoquinone core. Unfortunately, the synthesis of such compounds is complex. Here we describe a novel method for the generation of 1,2-dione containing diterpenoids using a unified approach, by which boronic acids are joined to vinyl bromo-cyclohexene derivatives via Suzuki coupling, followed by electrocyclization and oxidation to the o-phenanthroquinones. This has allowed the construction of a panel of miltirone analogs containing an array of substituents (Me, iso-Pr, fluorine, methoxy) which have been used to develop preliminary SAR with the two human carboxylesterase isoforms. As a consequence, we have synthesized highly potent inhibitors of these enzymes (K_i < 15 nM), that maintain the core tanshinone scaffold. Hence, we have developed a facile and reproducible method for the synthesis of abietane analogs that have resulted in a panel of miltirone derivatives that will be useful tool compounds to assess carboxylesterase biol.

European Journal of Medicinal Chemistry published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C8H11BO3, Application of (3-Methoxy-5-methylphenyl)boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Ding, Yun published the artcileDesign and Synthesis of Biaryl DNA-Encoded Libraries, Name: (3-Methoxy-5-methylphenyl)boronic acid, the publication is ACS Combinatorial Science (2016), 18(10), 625-629, database is CAplus and MEDLINE.

DNA-encoded library technol. (ELT) is a powerful tool for the discovery of new small-mol. ligands to various protein targets. Here we report the design and synthesis of biaryl DNA-encoded libraries based on the scaffold of 5-formyl 3-iodobenzoic acid. Three reactions on DNA template, acylation, Suzuki-Miyaura coupling and reductive amination, were applied in the library synthesis. The three cycle library of 3.5 million diversity has delivered potent hits for phosphoinositide 3-kinase α (PI3Kα).

ACS Combinatorial Science published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C8H11BO3, Name: (3-Methoxy-5-methylphenyl)boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem