Month: October 2022

In 2020,New Journal of Chemistry included an article by Boufroua, Naouel; Dunach, Elisabet; Fontaine-Vive, Fabien; Achouche-Bouzroura, Samia; Poulain-Martini, Sophie. SDS of cas: 85825-79-2. The article was titled 《In(OTf)3-catalysed easy access to dihydropyranocoumarin and dihydropyranochromone derivatives》. The information in the text is summarized as follows:

In(OTf)3-catalyzed, regioselective and generalizable method, for allylation/cyclization of β-ketolactone-type heterocyclic compounds was developed. This reaction is proposed to proceed one-pot, through a Friedel-Crafts C-allylation followed by cyclization. This process represents a green synthetic method, as AcOH is the only isolated byproduct. A protocol applicable for the construction of biol. active dihydropyranocoumarin and dihydropyranochromone derivatives was reported. In the experimental materials used by the author, we found 6-Methyldihydro-2H-pyran-2,4(3H)-dione(cas: 85825-79-2SDS of cas: 85825-79-2)

6-Methyldihydro-2H-pyran-2,4(3H)-dione(cas: 85825-79-2) belongs to tetrahydropyran. 2-Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and 3,4-dihydropyran are commonly used as protecting groups in organic synthesis. Furthermore, a tetrahydropyran ring system, i.e., five carbon atoms and an oxygen, is the core of pyranose sugars, such as glucose.SDS of cas: 85825-79-2

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

In 2018,Zhang, Rui; Li, Guoqing; Wismer, Michael; Vachal, Petr; Colletti, Steven L.; Shi, Zhi-Cai published 《Profiling and Application of Photoredox C(sp3)-C(sp2) Cross-Coupling in Medicinal Chemistry》.ACS Medicinal Chemistry Letters published the findings.Related Products of 25637-16-5 The information in the text is summarized as follows:

Recent visible-light photoredox catalyzed C(sp3)-C(sp2) cross-coupling provides a novel transformation to potentially enable the synthesis of medicinal chem. targets. Here, we report a profiling study of photocatalytic C(sp3)-C(sp2) cross-coupling, both decarboxylative coupling and cross-electrophile coupling, with 18 pharmaceutically relevant aryl halides by using either Kessil lamp or our newly developed integrated photoreactor. Integrated photoreactor accelerates reaction rate and improves reaction success rate. Cross-electrophile coupling gives higher success rate with broad substrate scope on alkyl halides than that of the decarboxylative coupling. In addition, a successful application example on a discovery program demonstrates the efficient synthesis of medicinal chem. targets via photocatalytic C(sp3)-C(sp2) cross-coupling by using our integrated photoreactor. In the experiment, the researchers used many compounds, for example, 4-Bromotetrahydropyran(cas: 25637-16-5Related Products of 25637-16-5)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Related Products of 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Delgado, Pete; Glass, Raoul J.; Geraci, Gina; Duvadie, Rohit; Majumdar, Dyuti; Robinson, Richard I.; Elmaarouf, Imran; Mikus, Malte; Tan, Kian L. published an article in 2021. The article was titled 《Use of Green Solvents in Metallaphotoredox Cross-Electrophile Coupling Reactions Utilizing Lipophilic Modified Dual Ir/Ni Catalyst System》, and you may find the article in Journal of Organic Chemistry.Formula: C5H9BrO The information in the text is summarized as follows:

Facilitating photoredox coupling reactions in process friendly green solvents was achieved by the successful application of the dual Ir/Ni catalyst system with enhanced solubility properties. These photochem. reactions (specifically Br-Br sp2-sp3 cross electrophile coupling) are reported in a head to head comparison to the reactions using standard di-t-Bu bipyridine ligand Ir/Ni catalyst system. This presentation highlights the benefits of altering the solubility properties of the ligands used in the Ir/Ni dual catalyst. The experimental part of the paper was very detailed, including the reaction process of 4-Bromotetrahydropyran(cas: 25637-16-5Formula: C5H9BrO)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Formula: C5H9BrO

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

In 2018,Rohe, Samantha; McCallum, Terry; Morris, Avery O.; Barriault, Louis published 《Transformations of Isonitriles with Bromoalkanes Using Photoredox Gold Catalysis》.Journal of Organic Chemistry published the findings.Application In Synthesis of 4-Bromotetrahydropyran The information in the text is summarized as follows:

Isonitriles have excellent electronic compatibility to react with free radicals. Recently, photoredox catalysis has emerged as a powerful tool for the construction of C-C bonds with few protocols for alkylative heterocycle synthesis through isonitrile addition Herein, it is describe the photocatalytic generation of alkyl radicals from unactivated bromoalkanes as part of an efficient cross-coupling strategy for the diversification of isonitriles using a dimeric gold(I) photoredox catalyst, [Au2(dppm)2]Cl2. In addition to this study using 4-Bromotetrahydropyran, there are many other studies that have used 4-Bromotetrahydropyran(cas: 25637-16-5Application In Synthesis of 4-Bromotetrahydropyran) was used in this study.

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Application In Synthesis of 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

In 2018,Perry, Ian B.; Brewer, Thomas F.; Sarver, Patrick J.; Schultz, Danielle M.; DiRocco, Daniel A.; MacMillan, David W. C. published 《Direct arylation of strong aliphatic C-H bonds》.Nature (London, United Kingdom) published the findings.Related Products of 25637-16-5 The information in the text is summarized as follows:

In the presence of tetrabutylammonium decatungstate (TBADT) as a photocatalyst for hydrogen atom transfer and (4,4′-di-tert-butyl-2,2′-bipyridine)NiBr2 as a coupling catalyst, unfunctionalized hydrocarbons, carbocycles, and heterocycles were arylated with aryl bromides; in most cases, the method was selective for a single product or a mixture of two products. A variety of aryl bromides were effective arylating agents under the reaction conditions; cycloalkanes, cycloalkanones, heterocycles, methylarenes, and alkanes reacted under the conditions. Terpene natural products such as eucalyptol, fenchone, and sclareolide were arylated selectively, and the method was used to prepare racemic N-Boc epibatidine and two analogs in two steps from com. available materials. The experimental part of the paper was very detailed, including the reaction process of 4-Bromotetrahydropyran(cas: 25637-16-5Related Products of 25637-16-5)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Related Products of 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Aguirre, Ana L.; Loud, Nathan L.; Johnson, Keywan A.; Weix, Daniel J.; Wang, Ying published their research in Chemistry – A European Journal in 2021. The article was titled 《ChemBead Enabled High-Throughput Cross-Electrophile Coupling Reveals a New Complementary Ligand》.COA of Formula: C5H9BrO The article contains the following contents:

Herein, the adaptation of nickel-catalyzed cross-electrophile coupling of aryl bromides with alkyl halides to HTE was enabled by AbbVie ChemBeads technol. By using this approach, the reactivity space at a global level with a challenging array of 3×222 micromolar reactions was mapped. The observed hit rate (56%) was competitive with other often-used HTE reactions and the results were scalable. A key to this level of success was the finding that bipyridine 6-carboxamidine (BpyCam), a ligand that had not previously been shown to be optimal in any reaction, was as general as the best-known ligands with complementary reactivity. Such “”cryptic”” catalysts may be common and modern HTE methods should facilitate the process of finding these catalysts. In addition to this study using 4-Bromotetrahydropyran, there are many other studies that have used 4-Bromotetrahydropyran(cas: 25637-16-5COA of Formula: C5H9BrO) was used in this study.

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.COA of Formula: C5H9BrO

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Barlaam, Bernard; De Savi, Chris; Dishington, Allan; Drew, Lisa; Ferguson, Andrew D.; Ferguson, Douglas; Gu, Chungang; Hande, Sudhir; Hassall, Lorraine; Hawkins, Janet; Hird, Alexander W.; Holmes, Jane; Lamb, Michelle L.; Lister, Andrew S.; McGuire, Thomas M.; Moore, Jane E.; O’Connell, Nichole; Patel, Anil; Pike, Kurt G.; Sarkar, Ujjal; Shao, Wenlin; Stead, Darren; Varnes, Jeffrey G.; Vasbinder, Melissa M.; Wang, Lei; Wu, Liangwei; Xue, Lin; Yang, Bin; Yao, Tieguang published their research in Journal of Medicinal Chemistry in 2021. The article was titled 《Discovery of a Series of 7-Azaindoles as Potent and Highly Selective CDK9 Inhibitors for Transient Target Engagement》.Application In Synthesis of 4-Bromotetrahydropyran The article contains the following contents:

Optimization of a series of azabenzimidazole54387894As identified from screening hit 2 and the information gained from a co-crystal structure of the azabenzimidazole-based lead 6 bound to CDK9 led to the discovery of azaindoles as highly potent and selective CDK9 inhibitors. With the goal of discovering a highly selective and potent CDK9 inhibitor administered i.v. that would enable transient target engagement of CDK9 for the treatment of hematol. malignancies, further optimization focusing on physicochem. and pharmacokinetic properties led to azaindoles 38 (I) and 39 (II). These compounds are highly potent and selective CDK9 inhibitors having short half-lives in rodents, suitable phys. properties for i.v. administration, and the potential to achieve profound but transient inhibition of CDK9 in vivo. The results came from multiple reactions, including the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Application In Synthesis of 4-Bromotetrahydropyran)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Application In Synthesis of 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Liu, Yi; Zhou, Cuihan; Jiang, Meijing; Arndtsen, Bruce A. published an article in 2022. The article was titled 《Versatile Palladium-Catalyzed Approach to Acyl Fluorides and Carbonylations by Combining Visible Light- and Ligand-Driven Operations》, and you may find the article in Journal of the American Chemical Society.Reference of 4-Bromotetrahydropyran The information in the text is summarized as follows:

The development of a general palladium-catalyzed carbonylative method to synthesize acyl fluorides RC(O)F (R = n-Bu, cyclohexyl, 4-methylphenyl, pyridin-3-yl, etc.) from aryl, heteroaryl, alkyl, and functionalized organic halides RX was described. Mechanistic anal. suggests that the reaction proceeds via the unique, synergistic combination of visible light photoexcitation of Pd(0) to induce oxidative addition with a ligand-favored reductive elimination. These together create a unidirectional catalytic cycle that is uninhibited by the classical effect of carbon monoxide coordination. Coupling the catalytic formation of acyl fluorides with their subsequent nucleophilic reactions has opened a method to perform carbonylation reactions with unprecedented breadth, including the assembly of highly functionalized carbonyl-containing products.4-Bromotetrahydropyran(cas: 25637-16-5Reference of 4-Bromotetrahydropyran) was used in this study.

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Reference of 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Computed Properties of C5H9BrOIn 2021 ,《Design, synthesis and biological evaluations of a series of Pyrido[1,2-a]pyrimidinone derivatives as novel selective FGFR inhibitors》 appeared in European Journal of Medicinal Chemistry. The author of the article were Ran, Kai; Zeng, Jun; Wan, Guoquan; He, Xiaojie; Feng, Zhanzhan; Xiang, Wang; Wei, Wei; Hu, Xiang; Wang, Ningyu; Liu, Zhihao; Yu, Luoting. The article conveys some information:

Herein, the design and synthesis of pyrido[1,2-a]pyrimidinone derivatives I (R1 = methoxyethoxy, tert-butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl, 1H-pyrazol-4-yl, etc.) and II (R2 = Me, azetidin-3-yl, etc.; R3 = 3-[(propan-2-yl)amino]propyl, prop-2-yn-1-yl, cyclopropylmethyl, etc.) as potent FGFR inhibitors were described. Examination of structure-activity relationships and preliminary assessment identified I (R1 = 1-methyl-1H-pyrazol-4-yl) as a novel FGFR inhibitor that displayed excellent potency in vitro. Candidate I [R1 = 1-methyl-1H-pyrazol-4-yl (III)] suppressed the phosphorylation of FGFR signaling pathways and induced cell cycle arrest and apoptosis at low nanomolar concentration In the kinase inhibition profile, III showed excellent kinase selectivity for the FGFR family. Furthermore, III showed higher aqueous solubility than Erdafitinib. Moreover, III exhibited potent antitumor activity (tumor growth inhibition = 106.4%) in FGFR2-amplified SNU-16 gastric cancer xenograft model using a daily oral dose of 30 mg/kg. These results suggest that III is a promising candidate for further drug development. In the experimental materials used by the author, we found 4-Bromotetrahydropyran(cas: 25637-16-5Computed Properties of C5H9BrO)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Computed Properties of C5H9BrO

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

SDS of cas: 25637-16-5In 2020 ,《A general carbonyl alkylative amination for tertiary amine synthesis》 was published in Nature (London, United Kingdom). The article was written by Kumar, Roopender; Floden, Nils J.; Whitehurst, William G.; Gaunt, Matthew J.. The article contains the following contents:

The ubiquity of tertiary alkylamines in pharmaceutical and agrochem. agents, natural products and small-mol. biol. probes has stimulated efforts towards their streamlined synthesis. Arguably the most robust method for the synthesis of tertiary alkylamines is carbonyl reductive amination, which comprises two elementary steps: the condensation of a secondary alkylamine with an aliphatic aldehyde to form an all-alkyl-iminium ion, which is subsequently reduced by a hydride reagent. Direct strategies were sought for a ‘higher order’ variant of this reaction via the coupling of an alkyl fragment with an alkyl-iminium ion that was generated in situ. However, despite extensive efforts, the successful realization of a ‘carbonyl alkylative amination’ has not yet been achieved. Here the authors present a practical and general synthesis of tertiary alkylamines through the addition of alkyl radicals to all-alkyl-iminium ions. The process is facilitated by visible light and a silane reducing agent, which trigger a distinct radical initiation step to establish a chain process. This operationally straightforward, metal-free and modular transformation forms tertiary amines, without structural constraint, via the coupling of aldehydes and secondary amines with alkyl halides. The structural and functional diversity of these readily available precursors provides a versatile and flexible strategy for the streamlined synthesis of complex tertiary amines. In addition to this study using 4-Bromotetrahydropyran, there are many other studies that have used 4-Bromotetrahydropyran(cas: 25637-16-5SDS of cas: 25637-16-5) was used in this study.

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.SDS of cas: 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics