Category: tetrahydropyran

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

Safety of (2-Hydroxypropyl)-β-cyclodextrinIn 2020 ,《Advantages of the combined use of cyclodextrins and nanocarriers in drug delivery: A review》 appeared in International Journal of Pharmaceutics (Amsterdam, Netherlands). The author of the article were Mura, Paola. The article conveys some information:

A review. Complexation with cyclodextrins (CDs) has been widely and successfully used in pharmaceutical field, mainly for enhancing solubility, stability and bioavailability of a variety of drugs. However, some important drawbacks, including rapid removal from the bloodstream after in vivo administration, or possible replacement, in biol. media, of the entrapped drug moieties by other mols. with higher affinity for the CD cavity, can limit the CDs effectiveness as drug carriers. This review is focused on combined strategies simultaneously exploiting CD complexation, and loading of the complexed drug into various colloidal carriers (liposomes, niosomes, polymeric nanoparticles, lipid nanoparticles, nanoemulsions, micelles) which have been investigated as a possible means for circumventing the problems associated with both such carriers, when used sep., and join their relative benefits in a unique delivery system. Several examples of applications have been reported, to illustrate the possible advantages achievable by such a dual strategy, depending on the CD-nanocarrier combination, and mainly resulting in enhanced performance of the delivery system and improved biopharmaceutical properties and therapeutic efficacy of drugs. The major problems and/or drawbacks found in the development of such systems, as well as the (rare) case of failures in achieving the expected improvements have also been highlighted. In the experiment, the researchers used (2-Hydroxypropyl)-β-cyclodextrin(cas: 128446-35-5Safety of (2-Hydroxypropyl)-β-cyclodextrin)

(2-Hydroxypropyl)-β-cyclodextrin(cas: 128446-35-5) belongs to tetrahydropyrans. Tetrahydropyrans and furans principally constitute as a central motif in diverse medicinally privileged molecules.Safety of (2-Hydroxypropyl)-β-cyclodextrin The most notable anticancer agent, bryostatin, and eribulin are marine macrolides having intriguing tetrahydropyran and furan motif.

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

Formula: C5H9BrOIn 2017 ,《Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers》 was published in Chemical Communications (Cambridge, United Kingdom). The article was written by Tota, Arianna; Zenzola, Marina; Chawner, Stephen J.; John-Campbell, Sahra St; Carlucci, Claudia; Romanazzi, Giuseppe; Degennaro, Leonardo; Bull, James A.; Luisi, Renzo. The article contains the following contents:

Direct synthesis of NH-sulfoximines from sulfides were achieved through O and NH transfer in the same reaction, occurring with complete selectivity. The reaction was mediated by bisacetoxyiodobenzene under simple conditions and employs inexpensive N-sources. Preliminary studies indicated that NH-transfer was likely to be first, followed by oxidation, but the reaction proceedes successfully in either order. A wide range of functional groups and biol. relevant compounds were tolerated. The use of AcO15NH4 affords 15N-labeled compounds The experimental process involved the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Formula: C5H9BrO)

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.Formula: C5H9BrO

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

《Terminal-oxidant-free photocatalytic C-H alkylations of heteroarenes with alkylsilicates as alkyl radical precursors》 was written by Ikarashi, Gun; Morofuji, Tatsuya; Kano, Naokazu. SDS of cas: 25637-16-5 And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020. The article conveys some information:

The authors report the photocatalytic C-H alkylations of heteroarenes with alkylsilicates bearing C,O-bidentate ligands under acidic conditions. Irradiation of heteroaromatics in the presence of the silicates and HO2CCF3 produced the corresponding alkylated compounds The present reaction system does not require any terminal oxidant although the reaction seems to be a formal oxidation reaction. Alkylsilicates can be used in photocatalytic radical chem. under acidic conditions. 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

In 2019,Journal of the American Chemical Society included an article by Kornfilt, David J. P.; MacMillan, David W. C.. SDS of cas: 25637-16-5. The article was titled 《Copper-Catalyzed Trifluoromethylation of Alkyl Bromides》. The information in the text is summarized as follows:

Copper oxidative addition into organohalides is a challenging two-electron process. In contrast, formal oxidative addition of copper to Csp2 carbon-bromine bonds can be accomplished by employing latent silyl radicals under photoredox conditions. This novel paradigm for copper oxidative addition has now been applied to a Cu-catalyzed cross-coupling of Csp3-bromides. Specifically, a copper/photoredox dual catalytic system for the coupling of alkyl bromides with trifluoromethyl groups is presented. This operationally simple and robust protocol successfully converts a variety of alkyl, allyl, benzyl, and heterobenzyl bromides into the corresponding alkyl trifluoromethanes. In the experiment, the researchers used many compounds, for example, 4-Bromotetrahydropyran(cas: 25637-16-5SDS of cas: 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.SDS of cas: 25637-16-5

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

In 2019,Journal of the American Chemical Society included an article by Lovett, Gabrielle H.; Chen, Shuming; Xue, Xiao-Song; Houk, K. N.; MacMillan, David W. C.. Synthetic Route of C5H9BrO. The article was titled 《Open-Shell Fluorination of Alkyl Bromides: Unexpected Selectivity in a Silyl Radical-Mediated Chain Process》. The information in the text is summarized as follows:

Herein, author disclose a novel radical strategy for the fluorination of alkyl bromides via the merger of silyl radical-mediated halogen-atom abstraction and benzophenone photosensitization. Selectivity for halogen atom abstraction from alkyl bromides is observed in the presence of an electrophilic fluorinating reagent containing a weak N-F bond despite the predicted favorability for Si-F bond formation. To account for this surprising selectivity, preliminary mechanistic and computational studies were conducted, revealing that a radical chain mechanism is operative in which kinetic selectivity for Si-Br abstraction dominates due to a combination of polar effects and halogen atom polarizability in the transition state. This transition metal-free fluorination protocol tolerates a broad range of functional groups, including alcs., ketones, and aldehydes, which demonstrates the complementary nature of this strategy to existing fluorination technologies. This system has been extended to the generation of gem-difluorinated motifs, which are commonly found in medicinal agents and agrochems. The results came from multiple reactions, including the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Synthetic Route of C5H9BrO)

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.Synthetic Route of C5H9BrO

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

《Nickel-Catalyzed Inter- and Intramolecular Aryl Thioether Metathesis by Reversible Arylation》 was written by Delcaillau, Tristan; Bismuto, Alessandro; Lian, Zhong; Morandi, Bill. Application In Synthesis of 4-Bromotetrahydropyran And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:

A nickel-catalyzed aryl thioether metathesis was developed to access high-value thioethers. 1,2-Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional-group-tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis that does not involve alkene bonds. In-depth organometallic studies support a reversible Ni0/NiII pathway to product formation. Overall, this work not only provides a more sustainable alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information that are highly relevant to the further development and application of unusual single-bond metathesis reactions.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: 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.Application In Synthesis of 4-Bromotetrahydropyran

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

In 2017,Li, Gang; Ma, Xingxing; Jia, Chunqi; Han, Qingqing; Wang, Ya; Wang, Junjie; Yu, Liuyang; Yang, Suling published 《Ruthenium-catalyzed meta/ortho-selective C-H alkylation of azoarenes using alkyl bromides》.Chemical Communications (Cambridge, United Kingdom) published the findings.Category: tetrahydropyran The information in the text is summarized as follows:

Meta/ortho-selective CAr-H (di)alkylation reactions of azoarenes I (R = C6H5, 4-CH3C6H4, 4-ClC6H4, etc.; R1 = H, 4-CH3, 4-Br, etc.) have been achieved via [Ru(p-cymene)Cl2]2 catalyzed ortho-metalation using various types of alkyl bromides such as 3-bromopentane, bromocyclohexane, 2-bromo-2-methylpropane, etc. Particularly, dual meta-alkylation of azoarenes I and reduction offer an attractive strategy for the synthesis of meta-alkylanilines such as 3-(pentan-3-yl)aniline, 4-methyl-3-(pentan-3-yl)aniline, 4-bromo-3-(pentan-3-yl)aniline, etc. which are difficult to access via traditional aniline functionalization methods. After reading the article, we found that the author used 4-Bromotetrahydropyran(cas: 25637-16-5Category: tetrahydropyran)

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.Category: tetrahydropyran

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

In 2019,Organic Process Research & Development included an article by Pomberger, Alexander; Mo, Yiming; Nandiwale, Kakasaheb Y.; Schultz, Victor L.; Duvadie, Rohit; Robinson, Richard I.; Altinoglu, Erhan I.; Jensen, Klavs F.. SDS of cas: 25637-16-5. The article was titled 《A Continuous Stirred-Tank Reactor (CSTR) Cascade for Handling Solid-Containing Photochemical Reactions》. The information in the text is summarized as follows:

Visible-light photoredox reactions have been demonstrated to be powerful synthetic tools to access pharmaceutically relevant compounds However, many photoredox reactions involve insoluble starting materials or products that complicate the use of continuous flow methods. By integrating a new solid-feeding strategy and a continuous stirred-tank reactor (CSTR) cascade, we realize a new solid-handling platform for conducting heterogeneous photoredox reactions in flow. Residence time distributions for single phase and solid particles characterize the hydrodynamics of the heterogeneous flow in the CSTR cascade. Silyl radical-mediated metallaphotoredox cross-electrophile coupling reactions with an inorganic base as the insoluble starting material demonstrate the use of the platform. Gram-scale synthesis is achieved in 13 h of stable operation. In the experiment, the researchers used many compounds, for example, 4-Bromotetrahydropyran(cas: 25637-16-5SDS of cas: 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.SDS of cas: 25637-16-5

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

In 2022,Turro, Raymond F.; Brandstatter, Marco; Reisman, Sarah E. published an article in Angewandte Chemie, International Edition. The title of the article was 《Nickel-Catalyzed Reductive Alkylation of Heteroaryl Imines》.Application of 25637-16-5 The author mentioned the following in the article:

The preparation of heterobenzylic amines, e.g., I [R1 = H, 4-Cl, 5-F, 6-Me, etc.; R2 = i-Pr, n-Bu, t-Bu, cyclopropyl, cyclobutyl, (R)-PhCHMe; R3 = H, Me, R4 = PhCH2; R3 = H, R4 = 4-ClC6H4CH2, 2,6-Me2C6H3CH2, etc.; R3R4 = (CH2)2X(CH2)2; X = CH2, O, CO, NBoc], by a Ni-catalyzed reductive cross-coupling between heteroaryl imines, e.g., II, and C(sp3) electrophiles R3R4CHX1 (X1 = Cl, Br, I, phthalimidyloxycarbonyl) is reported. This umpolung-type alkylation proceeds under mild conditions, avoids the pre-generation of organometallic reagents, and exhibits good functional group tolerance. Mechanistic studies are consistent with the imine substrate acting as a redox-active ligand upon coordination to a low-valent Ni center. The resulting bis(2-imino)heterocycle·Ni complexes can engage in alkylation reactions with a variety of C(sp3) electrophiles, giving heterobenzylic amine products in good yields. After reading the article, we found that the author used 4-Bromotetrahydropyran(cas: 25637-16-5Application 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.Application of 25637-16-5

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