Category: tetrahydropyran

In 2018,Yan, Xiao-Biao; Li, Chun-Ling; Jin, Wen-Jie; Guo, Peng; Shu, Xing-Zhong published 《Reductive coupling of benzyl oxalates with highly functionalized alkyl bromides by nickel catalysis》.Chemical Science published the findings.Reference of 4-Bromotetrahydropyran The information in the text is summarized as follows:

Coupling reactions involving non-sulfonated C-O electrophiles provide a promising method for forming C-C bonds, but the incorporation of functionalized or secondary alkyl groups remains a challenge due to the requirement for well-defined alkylmetal species. In this study, a reductive nickel-catalyzed cross-coupling of benzyl oxalates with alkyl bromides, using oxalate as a new leaving group is reported. A broad range of highly functionalized alkyl units (such as functional groups: alkyl chloride, alc., aldehyde, amine, amide, boronate ester, ether, ester, heterocycle, phosphonate, strained ring) were efficiently incorporated at the benzylic position. The utility of this synthetic method was further demonstrated by late-stage modification of complex bioactive compounds Preliminary mechanistic experiments revealed that a radical process might be involved in the reaction. The results came from multiple reactions, including the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Reference of 4-Bromotetrahydropyran)

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.Reference of 4-Bromotetrahydropyran

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

In 2022,Liu, Hong-Chao; Gong, Xiao-Ping; Wang, Yu-Zhao; Niu, Zhi-Jie; Yue, Heng; Liu, Xue-Yuan; Liang, Yong-Min published an article in Organic Letters. The title of the article was 《Three-Component Ru-Catalyzed Regioselective Alkylarylation of Vinylarenes via Meta-Selective C(sp2)-H Bond Functionalization》.Recommanded Product: 4-Bromotetrahydropyran The author mentioned the following in the article:

A novel Ru-catalyzed regioselective alkylarylation of vinylarenes with alkyl halides and arenes was reported via meta-C(sp2)-H bond functionalization to construct 1,1-diarylalkanes I [R = n-Bu, cyclohexyl, Bn, etc.; R1 = Ph, 4-MeC6H4, 2-naphthyl, etc.; R2 = H, 2-Me, 3-F, etc.; R3 = H, 5-Me, 4-MeO, etc.] that generally show bioactivity. In this transformation, a wide spectrum of primary, secondary, and tertiary alkyl halides and electronically varied arenes was well-tolerated. This reaction was characterized by its exquisite regioselectivity of vinylarenes, unique meta-C(sp2)-H selectivity, and redox-neutral conditions. The mechanism presented was supported by radical probes and kinetic isotope effect studies. In the part of experimental materials, we found many familiar compounds, such as 4-Bromotetrahydropyran(cas: 25637-16-5Recommanded Product: 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.Recommanded Product: 4-Bromotetrahydropyran

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

In 2022,Zhou, Chunlin; Wang, Xinchao; Yang, Lei; Fu, Lei; Li, Gang published an article in Green Chemistry. The title of the article was 《Visible-light-driven regioselective carbocarboxylation of 1,3-dienes with organic halides and CO2》.Application In Synthesis of 4-Bromotetrahydropyran The author mentioned the following in the article:

An unprecedented visible-light-driven regioselective carbocarboxylation of 1,3-dienes with CO2 using aryl and alkyl halides under mild conditions with low-cost potassium formate (HCOOK) to produce carbon dioxide radical anions as the potent reducing agent for the challenging organic halide reduction was reported. Highly 3,4-regioselective carbocarboxylation was achieved with 1,1-diaryl-substituted 1,3-dienes, while major 1,4-carbocarboxylation products were obtained with less hindered mono-aryl substituted 1,3-dienes. This protocol rendered a rapid method for producing complex β,γ-unsaturated carboxylic acids from easily available 1,3-dienes and organic halides with CO2. In the part of experimental materials, we found many familiar compounds, such as 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

Synthetic Route of C5H9BrOIn 2021 ,《Sulfonamide as Photoinduced Hydrogen-Atom Transfer Catalyst for Regioselective Alkylation of C(sp3)-H Bonds Adjacent to Heteroatoms》 was published in Organic Letters. The article was written by Ma, Zhi-Yong; Li, Mengyang; Guo, Li-Na; Liu, Le; Wang, Dongdong; Duan, Xin-Hua. The article contains the following contents:

Based on the DFT calculations, the sulfonamide was explored as an efficient hydrogen-atom transfer catalyst for the C(sp3)-H alkylation. The combination of a metal-free photoredox catalyst and a sulfonamide catalyst enables highly regioselective alkylation of the C-H bonds adjacent to heteroatoms, which features broad substrate scope and excellent functional group compatibility. Remarkably, the sulfonamide catalyst was also applicable to the C(sp3)-C(sp3) couplings through the merger of photoredox, nickel, and HAT catalysis. In the experimental materials used by the author, we found 4-Bromotetrahydropyran(cas: 25637-16-5Synthetic Route 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.Synthetic Route of C5H9BrO

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

In 2019,Organic Letters included an article by Lin, Zhiyang; Lan, Yun; Wang, Chuan. HPLC of Formula: 25637-16-5. The article was titled 《Reductive Allylic Defluorinative Cross-Coupling Enabled by Ni/Ti Cooperative Catalysis》. The information in the text is summarized as follows:

Tertiary alkyl chlorides, secondary alkyl chlorides and bromides, and primary alkyl bromides underwent chemoselective defluorinative cross-coupling reactions with α-trifluoromethyl aryl alkenes in the presence of (indenyl)TiCl3, NiBr2, and 3,4,7,8-tetramethyl-1,10-phenanthroline to yield α-substituted aryl difluoroalkenes such as 4-MeOC6H4C(:CF2)CH2R (R = t-Bu, cyclohexyl, n-octyl). Unfunctionalized and ester-functionalized alkyl halides underwent cross-coupling under the reaction conditions, while a variety of functionalized aryl alkenes underwent cross-coupling. Using this method, gem-difluoroalkene analogs of azaperone, haloperidol, and benperidol were prepared In the experiment, the researchers used 4-Bromotetrahydropyran(cas: 25637-16-5HPLC of Formula: 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.HPLC of Formula: 25637-16-5

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

Product Details of 25637-16-5In 2021 ,《Pyrazoloadenine Inhibitors of the RET Lung Cancer Oncoprotein Discovered by a Fragment Optimization Approach》 appeared in ChemMedChem. The author of the article were Saha, Debasmita; Ryan, Katie Rose; Lakkaniga, Naga Rajiv; Smith, Erica Lane; Frett, Brendan. The article conveys some information:

A fragment-based drug-discovery approach was used on a pyrazoloadenine fragment library to uncover new mols. that target the RET (REarranged during Transfection) oncoprotein, which is a driver oncoprotein in ∼2 % of non-small-cell lung cancers. The fragment library was screened against the RET kinase and LC-2/ad (RET-driven), KM-12 (TRKA-driven matched control) and A549 (cytotoxic control) cells to identify selective scaffolds that could inhibit RET-driven growth. An unsubstituted pyrazoloadenine fragment was found to be active on RET in a biochem. assay, but reduced cell viability in non-RET-driven cell lines (EC50=1 and 3 μM, resp.). To increase selectivity for RET, the pyrazoloadenine was modeled in the RET active site, and two domains were identified that were probed with pyrazoloadenine fragment derivatives to improve RET affinity. Scaffolds at each domain were merged to generate a novel lead compound, 8 p (I), which exhibited improved activity and selectivity for the RET oncoprotein (A549 EC50=5.92 μM, LC-2/ad EC50=0.016 μM, RET IC50=0.000326 μM). The experimental process involved the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Product Details 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.Product Details of 25637-16-5

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

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,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

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