Tag: 200-300

《Vinylidene Homologation of Boronic Esters and its Application to the Synthesis of the Proposed Structure of Machillene》 was written by Fordham, James M.; Grayson, Matthew N.; Aggarwal, Varinder K.. Product Details of 78782-17-9This research focused onvinylidene homologation boronic ester lithiated epoxysilane; machillene proposed structure synthesis; homologation; natural product; organoboron; stereospecificity; vinyl boronic ester. The article conveys some information:

Alkenyl boronic esters are important reagents in organic synthesis. Herein, we report that these valuable products can be accessed by the homologation of boronic esters with lithiated epoxysilanes [thus, e.g., treatment of epoxysilane I in pentane at -95° with TMEDA/tBuLi followed by addition of boronic ester II in pentane, stirring for 1 h, warming to -78° for an addnl. hour and finally warming to room temperature and then 40° for 1 h afforded III (77%)]. Aliphatic and electron-rich aromatic boronic esters provided vinylidene boronic esters in moderate to high yields, while electron-deficient aromatic and vinyl boronic esters were found to give the corresponding vinyl silane products. Through DFT calculations, this divergence in mechanistic pathway has been rationalized by considering the stabilization of neg. charge in the C-Si and C-B bond breaking transition states. This vinylidene homologation was used in a short six-step stereoselective synthesis of the proposed structure of machillene, however, synthetic and reported data were found to be inconsistent. In the experiment, the researchers used many compounds, for example, Bis[(pinacolato)boryl]methane(cas: 78782-17-9Product Details of 78782-17-9)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry. This stems from their ease of preparation combined with their ability to undergo a broad range of chemical transformations.Product Details of 78782-17-9

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Choi, Seon-Hee; Lee, Dong-Yeon; Kang, Sohi; Lee, Min-Kyung; Lee, Jae-Heun; Lee, Sang-Heon; Lee, Hye-Lim; Lee, Hyo-Young; Jeong, Young-IL published their research in International Journal of Molecular Sciences in 2021. The article was titled 《Caffeic acid phenethyl ester-incorporated radio-sensitive nanoparticles of phenylboronic acid pinacol ester-conjugated hyaluronic acid for application in radioprotection》.COA of Formula: C12H17BO2 The article contains the following contents:

We synthesized phenylboronic acid pinacol ester (PBPE)-conjugated hyaluronic acid (HA) via thiobis(ethylamine) (TbEA) linkage (abbreviated as HAsPBPE conjugates) to fabricate the radiosensitive delivery of caffeic acid phenetyl ester (CAPE) and for application in radioprotection. PBPE was primarily conjugated with TbEA and then PBPE-TbEA conjugates were conjugated again with hyaluronic acid using carbodiimide chem. CAPE-incorporated nanoparticles of HAsPBPE were fabricated by the nanopptn. method and then the organic solvent was removed by dialysis. CAPE-incorporated HAsPBPE nanoparticles have a small particle size of about 80 or 100 nm and they have a spherical shape. When CAPE-incorporated HAsPBPE nanoparticles were irradiated, nanoparticles became swelled or disintegrated and their morphologies were changed. Furthermore, the CAPE release rate from HAsPBPE nanoparticles were increased according to the radiation dose, indicating that CAPE-incorporated HAsPBPE nanoparticles have radio-sensitivity. CAPE and CAPE-incorporated HAsPBPE nanoparticles appropriately prevented radiation-induced cell death and suppressed intracellular accumulation of reactive oxygen species (ROS). CAPE and CAPE-incorporated HAsPBPE nanoparticles efficiently improved survivability of mice from radiation-induced death and reduced apoptotic cell death. We suggest that HAsPBPE nanoparticles are promising candidates for the radio-sensitive delivery of CAPE.4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane(cas: 24388-23-6COA of Formula: C12H17BO2) was used in this study.

4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane(cas: 24388-23-6) can be used as a substrate in the study of Suzuki–Miyaura coupling of various aryl iodides over SiliaCat Pd(0).COA of Formula: C12H17BO2

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《Catalytic Behavior of Mono-N-Protected Amino-Acid Ligands in Ligand-Accelerated C-H Activation by Palladium(II)》 was written by Salazar, Chase A.; Gair, Joseph J.; Flesch, Kaylin N.; Guzei, Ilia A.; Lewis, Jared C.; Stahl, Shannon S.. Recommanded Product: 24388-23-6 And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:

Mono-N-protected amino acids (MPAAs) are increasingly common ligands in Pd-catalyzed C-H functionalization reactions. Previous studies have shown how these ligands accelerate catalytic turnover by facilitating the C-H activation step. Here, it is shown that MPAA ligands exhibit a second property commonly associated with ligand-accelerated catalysis: the ability to support catalytic turnover at substoichiometric ligand-to-metal ratios. This catalytic role of the MPAA ligand is characterized in stoichiometric C-H activation and catalytic C-H functionalization reactions. Palladacycle formation with substrates bearing carboxylate and pyridine directing groups exhibit a 50-100-fold increase in rate when only 0.05 equiv of MPAA are present relative to PdII. These and other mechanistic data indicate that facile exchange between MPAAs and anionic ligands coordinated to PdII enables a single MPAA to support C-H activation at multiple PdII centers. In addition to this study using 4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane, there are many other studies that have used 4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane(cas: 24388-23-6Recommanded Product: 24388-23-6) was used in this study.

4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane(cas: 24388-23-6) also known as boronate ester, is generally used in metal-catalyzed C-C bond formation reactions like Suzuki–Miyaura reaction.Recommanded Product: 24388-23-6

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In 2018,Iacono, Carmelo E.; Stephens, Thomas C.; Rajan, Teena S.; Pattison, Graham published 《A Coupling Approach for the Generation of α,α-Bis(enolate) Equivalents: Regioselective Synthesis of gem-Difunctionalized Ketones》.Journal of the American Chemical Society published the findings.Application of 78782-17-9 The information in the text is summarized as follows:

Regioselective α,α-difunctionalization adjacent to a ketone is a significant synthetic challenge. Here, we present a solution to this problem through the transition-metal-free coupling of esters with geminal bis(boron) compounds This forms an α,α-bis(enolate) equivalent which can be trapped with electrophiles including alkyl halides and fluorinating agents. This presents an efficient, convergent synthetic strategy for the synthesis of unsym. blocked ketones. After reading the article, we found that the author used Bis[(pinacolato)boryl]methane(cas: 78782-17-9Application of 78782-17-9)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.Application of 78782-17-9

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In 2018,Armstrong, Roly J.; Nandakumar, Meganathan; Dias, Rafael M. P.; Noble, Adam; Myers, Eddie L.; Aggarwal, Varinder K. published 《Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer》.Angewandte Chemie, International Edition published the findings.Product Details of 78782-17-9 The information in the text is summarized as follows:

Nonracemic di-, tri-, and tetrasubstituted allenes were prepared by an enantiodivergent route using the homologation of (phenylselenyl)alkenylboronates such as I with lithiated alkyl diisopropylcarbamates generated with (+)-sparteine and s-BuLi and stereoselective oxidative syn-elimination and alkylative anti-elimination reactions as key steps. Nonracemic boronic esters such as II were prepared by homologation of α-seleno alkenyl boronic esters such as I with lithiated diisopropylcarbamates such as 4-MeOC6H4CH2CH2CH2OCONi-Pr2. Syn-elimination of II using mCPBA yielded the nonracemic (P)-allene III in >99% enantiospecificity, while anti-elimination of II by alkylation with MeOTf in CH2Cl2 followed by NaHCO3 in MeOH yielded (M)-allene IV in 98% enantiospecificity. By employing either oxidative or alkylative conditions, both syn and anti elimination could be achieved with complete stereospecificity. The process enables the synthesis of either M or P allenes from a single isomer of a point-chiral precursor and can be employed for the enantioselective assembly of di-, tri-, and tetrasubstituted allenes. In the experimental materials used by the author, we found Bis[(pinacolato)boryl]methane(cas: 78782-17-9Product Details of 78782-17-9)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.Product Details of 78782-17-9

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In 2017,Edelstein, Emma K.; Namirembe, Sheila; Morken, James P. published 《Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents》.Journal of the American Chemical Society published the findings.Product Details of 78782-17-9 The information in the text is summarized as follows:

Pd-catalyzed conjunctive cross-coupling was used for the synthesis of enantioenriched allylboron reagents. This reaction employs nonsym. bis(alkenyl)borates as substrates and appears to occur by a mechanism that involves selective activation of the less substituted alkene followed by migration of the more substituted alkene during a Pd-induced metalate rearrangement.Bis[(pinacolato)boryl]methane(cas: 78782-17-9Product Details of 78782-17-9) was used in this study.

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Product Details of 78782-17-9 Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.

Referemce:
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Pajouhesh, Hassan; Feng, Zhong-Ping; Ding, Yanbing; Zhang, Lingyun; Pajouhesh, Hossein; Morrison, Jerrie-Lynn; Belardetti, Francesco; Tringham, Elizabeth; Simonson, Eric; Vanderah, Todd W.; Porreca, Frank; Zamponi, Gerald W.; Mitscher, Lester A.; Snutch, Terrance P. published an article on February 15 ,2010. The article was titled 《Structure-activity relationships of diphenylpiperazine N-type calcium channel inhibitors》, and you may find the article in Bioorganic & Medicinal Chemistry Letters.Application In Synthesis of (3-Chlorophenyl)(phenyl)methanol The information in the text is summarized as follows:

A novel series of compounds derived from the previously reported N-type calcium channel blocker NP118809 (1-(4-benzhydrylpiperazin-1-yl)-3,3-diphenylpropan-1-one) is described. Extensive SAR studies resulted in compounds with IC50 values in the range of 10-150 nM and selectivity over the L-type channels up to nearly 1200-fold. Orally administered compounds 5 and 21 (I) exhibited both anti-allodynic and anti-hyperalgesic activity in the spinal nerve ligation model of neuropathic pain. The results came from multiple reactions, including the reaction of (3-Chlorophenyl)(phenyl)methanol(cas: 63012-03-3Application In Synthesis of (3-Chlorophenyl)(phenyl)methanol)

(3-Chlorophenyl)(phenyl)methanol(cas: 63012-03-3) belongs to hydroxy-containing compounds. Hydroxy groups participate in the dehydration reactions that link simple biological molecules into long chains. The joining of a fatty acid to glycerol to form a triacylglycerol removes the −OH from the carboxy end of the fatty acid.Application In Synthesis of (3-Chlorophenyl)(phenyl)methanol

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Kushwaha, Pragati; Tripathi, Ashish Kumar; Gupta, Sampa; Kothari, Priyanka; Upadhyay, Akanksha; Ahmad, Naseer; Sharma, Tanuj; Siddiqi, M. I.; Trivedi, Ritu; Sashidhara, Koneni V. published their research in European Journal of Medicinal Chemistry on August 5 ,2018. The article was titled 《Synthesis and study of benzofuran-pyran analogs as BMP-2 targeted osteogenic agents》.Application of 153759-59-2 The article contains the following contents:

Twenty-four novel benzofuran-pyran derivatives were synthesized and evaluated for their anti-osteoporotic activity in primary cultures of rat calvarial osteoblasts in vitro. Among all the compounds screened for the alk. phosphatase activity, three compounds 9-(2-(4-fluorobenzoyl)-7-methylbenzofuran-5-yl)3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione , 9-(7-Ethyl-2-(4-fluorobenzoyl)benzofuran-5-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione and 9-(7-Ethyl-2-(4-fluorobenzoyl)benzofuran-5-yl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione showed potent activity at picomolar concentrations in osteoblast differentiating stimulation. Addnl., these compounds were found effective in mineralization, assessed by alizarin red-S staining assay. Compounds were again validated through a series of other in vitro experiments Moreover, mol. dynamics simulations demonstrated that both benzofuran and pyran moieties are requisite to fit into the active site of BMP-2 receptor, a key target of the osteogenic agents. The obtained results strongly convey that compound 9-(2-(4-fluorobenzoyl)-7-methylbenzofuran-5-yl)3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione is a potential bone anabolic agent among synthesized series, which can be further explored as a drug lead for treating osteoporosis. After reading the article, we found that the author used 5-(tert-Butyl)-4-hydroxyisophthalaldehyde(cas: 153759-59-2Application of 153759-59-2)

5-(tert-Butyl)-4-hydroxyisophthalaldehyde(cas: 153759-59-2) belongs to phenols.Deprotonation of a phenol forms a corresponding negative phenolate ion or phenoxide ion, and the corresponding salts are called phenolates or phenoxides (aryloxides according to the IUPAC Gold Book).Application of 153759-59-2

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Ishiyama, Tatsuo; Takagi, Jun; Ishida, Kousaku; Miyaura, Norio; Anastasi, Natia R.; Hartwig, John F. published an article on January 23 ,2002. The article was titled 《Mild Iridium-Catalyzed Borylation of Arenes. High Turnover Numbers, Room Temperature Reactions, and Isolation of a Potential Intermediate》, and you may find the article in Journal of the American Chemical Society.Reference of 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane The information in the text is summarized as follows:

The borylation of arenes leads to the formation of synthetically versatile products from unactivated arene reagents. It is reported that Ir(I) precursors in conjunction with bipyridine ligands catalyze in high yields the borylation of arenes under mild conditions. These reactions encompass arenes bearing both electron-withdrawing and electron-donating substituents. The temperatures required for the transformation are much lower than those previously reported for direct arene borylation. The combination of [Ir(COE)2Cl]2 and (4,4-di-t-butyl)bipyridine even allows for reaction at room temperature The same catalyst system at 100° provides remarkably high turnover numbers for a hydrocarbon functionalization process. Mechanistic studies show that the reactions involve uncommon, Ir(II) tris-boryl complexes. An example of this type of complex ligated by di-t-butylbipyridine, [Ir(COE)(Bpin)3(4,4′-di-t-Bu-BPY)], was isolated and structurally characterized. It reacted rapidly at room temperature to produce aryl boronate esters in high yields. In the part of experimental materials, we found many familiar compounds, such as 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 401797-00-0Reference of 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 401797-00-0) belongs to hydroxy-containing compounds. Hydroxy groups participate in the dehydration reactions that link simple biological molecules into long chains. The joining of a fatty acid to glycerol to form a triacylglycerol removes the −OH from the carboxy end of the fatty acid.Reference of 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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In 2015,Organic & Biomolecular Chemistry included an article by Bheeter, Charles Beromeo; Chowdhury, Abhishek Dutta; Adam, Rosa; Jackstell, Ralf; Beller, Matthias. Recommanded Product: 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The article was titled 《Efficient Rh-catalyzed C-H borylation of arene derivatives under photochemical conditions》. The information in the text is summarized as follows:

Photocatalysis allows innovations in organic synthesis. Among the various catalytic reactions, CH-functionalizations offer valuable possibilities for the refinement of easily available building blocks. In this respect, catalytic borylation is of interest, too. So far, most of the catalytic borylation reactions are performed under thermal conditions at comparably high temperatures Here, authors describe a new synthetic route for efficient borylation reactions of arenes using a photocatalytic pathway. This novel approach allows the synthesis of a broad variety of borylated arenes and heteroarenes under mild conditions. Applying trans-[Rh(PMe3)2(CO)Cl] as an active photocatalyst and HBPin as an boron source, authors achieved high TON. A catalytic cycle that relies on a Rh(i)-Rh(iii) interconversion is proposed. In the experiment, the researchers used many compounds, for example, 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 401797-00-0Recommanded Product: 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 401797-00-0) belongs to hydroxy-containing compounds. Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this functional group.Recommanded Product: 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Organic compounds, which are often poorly soluble in water, become water-soluble when they contain two or more hydroxy groups, as illustrated by sugars and amino acid.

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