Month: January 2023

Ruthenium Hydride/Bronsted Acid-Catalyzed Tandem Isomerization/N-Acyliminium Cyclization Sequence for the Synthesis of Tetrahydro-β-carbolines was written by Hansen, Casper L.;Clausen, Janie W.;Ohm, Ragnhild G.;Ascic, Erhad;Le Quement, Sebastian T.;Tanner, David;Nielsen, Thomas E.. And the article was included in Journal of Organic Chemistry in 2013.HPLC of Formula: 14425-64-0 This article mentions the following:

This paper describes an efficient tandem sequence for the synthesis of 1,2,3,4-tetrahydro-β-carbolines (THBCs) relying on a ruthenium hydride/Bronsted acid-catalyzed isomerization of allylic amides to N-acyliminium ion intermediates which are trapped by a tethered indole nucleophile. The methodol. provides not only a convenient “aldehyde-free” alternative to the classical Pictet-Spengler reaction but also attractive possibilities for total synthesis, including rapid generation of mol. complexity and formation of quaternary stereogenic centers. THBCs can also be accessed by harnessing the Suzuki cross-coupling reaction to the isomerization/N-acyliminium cyclization sequence. Finally, diastereo- and enantioselective versions of the title reaction have been examined using substrate control (with dr >15:1) and asym. catalysis (ee up to 57%), resp. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0HPLC of Formula: 14425-64-0).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.HPLC of Formula: 14425-64-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Total Synthesis and Biological Evaluation of Tiancimycins A and B, Yangpumicin A, and Related Anthraquinone-Fused Enediyne Antitumor Antibiotics was written by Nicolaou, K. C.;Das, Dipendu;Lu, Yong;Rout, Subhrajit;Pitsinos, Emmanuel N.;Lyssikatos, Joseph;Schammel, Alexander;Sandoval, Joseph;Hammond, Mikhail;Aujay, Monette;Gavrilyuk, Julia. And the article was included in Journal of the American Chemical Society in 2020.Product Details of 143945-65-7 This article mentions the following:

The family of anthraquinone-fused enediyne antitumor antibiotics was established by the discovery of dynemicin A and deoxy-dynemicin A. It was then expanded, first by the isolation of uncialamycin, and then by the addition to the family of tiancimycins A-F and yangpumicin A. This family of natural products provides opportunities in total synthesis, biol., and medicine due to their novel and challenging mol. structures, intriguing biol. properties and mechanism of action, and potential in targeted cancer therapies. Herein, the total syntheses of tiancimycins A and B, yangpumicin A, and a number of related anthraquinone-fused enediynes are described. Biol. evaluation of the synthesized compounds revealed extremely potent cytotoxicities against a number of cell lines, thus enriching the structure-activity relationships within this class of compounds The findings of these studies may facilitate future investigations directed toward antibody-drug conjugates for targeted cancer therapies and provide inspiration for further advances in total synthesis and chem. biol. In the experiment, the researchers used many compounds, for example, 2-Amino-5-bromo-4-fluorobenzoic acid (cas: 143945-65-7Product Details of 143945-65-7).

2-Amino-5-bromo-4-fluorobenzoic acid (cas: 143945-65-7) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Product Details of 143945-65-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Building fluorescent sensors for carbohydrates using template-directed polymerizations was written by Gao, Shouhai;Wang, Wei;Wang, Binghe. And the article was included in Bioorganic Chemistry in 2001.Application of 166821-88-1 This article mentions the following:

The ability to custom-make fluorescent sensors for different analytes could have a tremendous impact in a variety of areas. Template-directed polymerization or mol. imprinting seems to be a promising approach for the preparation of high-affinity and specific binding sites for different template mols. However, the application of mol. imprinting in the preparation of fluorescent sensors has been hampered by the lack of suitable fluorescent tags, which would respond to the binding event with significant fluorescence intensity changes. We have designed and synthesized a fluorescent monomer (1) that allows for the preparation of fluorescent sensors of cis diols using mol. imprinting methods. This monomer has been used for the preparation of imprinted polymers as sensitive fluorescent sensors for d-fructose. The imprinted polymers prepared showed significant fluorescence intensity enhancement upon binding with the template carbohydrate. (c) 2001 Academic Press. In the experiment, the researchers used many compounds, for example, 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1Application of 166821-88-1).

2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Application of 166821-88-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Iron-catalyzed remote functionalization of inert C(sp³)-H bonds of alkenes via 1,n-hydrogen-atom-transfer by C-centered radical relay was written by Bian, Kang-Jie;Li, Yan;Zhang, Kai-Fan;He, Yan;Wu, Tian-Rui;Wang, Cheng-Yu;Wang, Xi-Sheng. And the article was included in Chemical Science in 2020.Application of 14425-64-0 This article mentions the following:

Enabled by 1,n (n = 5, 6)-hydrogen atom transfer (HAT), a most prevalent moiety, alkene, as the precursor to an sp³ C-centered radical to promote selective cleavage of inert C(sp³)-H bonds for the generation of azidotrifluoromethylated mols. I [R¹ = Me, n-Bu, Ph, etc.; R² = H, Me, Et, n-octyl; R¹R² = (CH₂)₃, (CH₂)₄, (CH₂)₂O(CH₂)₂, etc.; X = C(CO₂Et)₂, C(CH₂OBz)₂, NTs] was used. Mild conditions, broad scope and excellent regioselective control (>20 : 1) were observed in the reactions. Deuterium labeling studies disclosed the kinetic characteristics of the transformations and verify a direct 1,n-HAT pathway. The key to this C-centered radical relay was that iron played a dual role as a radical initiator and terminator to incorporate the azide functionality through radical oxidation via azido-ligand-transfer. The methods and the later derivatization promised expeditious synthesis of CF₃-containing organic azides, γ-lactam and triazoles that were widely used in designing new fluorescent tags and functional materials. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Application of 14425-64-0).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Application of 14425-64-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Rh^II-Catalyzed Intermolecular C-H Arylation of Aromatics with Diazo Quinones was written by Wu, Kai;Cao, Bei;Zhou, Cong-Ying;Che, Chi-Ming. And the article was included in Chemistry – A European Journal in 2018.Computed Properties of C6H6BrNO This article mentions the following:

An efficient synthesis of biaryls R-R¹ [R = 4-H₃COC₆H₄, thiophen-2-yl, 2-methoxynaphthalen-1-yl, 1,3-benzothiazol-2-yl, etc.; R¹ = 2-OH-3,5-Cl₂C₆H₂, 2-Br-4-HOC₆H₃, 3-C(O)OCH₃-4-HOC₆H₃, etc.] by a dirhodium(II)-catalyzed aromatic C-H arylation with diazo quinones such as 4-bromo-6-diazocyclohexa-2,4-dien-1-one, 2,6-dichloro-4-diazocyclohexa-2,5-dien-1-one, 3-bromo-4-diazocyclohexa-2,5-dien-1-one, etc. has been developed. The new biaryl synthesis can be performed under mild and neutral conditions and without directing group chelation assistance. The reaction tolerates various functionalities and is applicable to a broad range of aromatics The regioselectivity of the C-H arylation was often high and predictable. The synthetic utility of the method was demonstrated by the late-stage modifications of a series of pharmaceuticals and functional materials as well as a short synthesis of a transthyretin amyloid inhibitor e.g., Me 2-hydroxy-5-(2-methoxy-6-(3-oxobutyl)naphthalen-1-yl)benzoate. In the experiment, the researchers used many compounds, for example, 4-Amino-3-bromophenol (cas: 74440-80-5Computed Properties of C6H6BrNO).

4-Amino-3-bromophenol (cas: 74440-80-5) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Computed Properties of C6H6BrNO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Structure-activity relationship for a series of 2-substituted 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indoles: potent subtype-selective inhibitors of N-methyl-D-aspartate (NMDA) receptors was written by Tamiz, Amir P.;Whittemore, Edward R.;Woodward, Richard M.;Upasani, Ravindra B.;Keana, John F. W.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 1999.Electric Literature of C10H13BrO This article mentions the following:

A series of 2-substituted 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indoles was synthesized as potential antagonists for the NR1A/2B subtype of N-methyl-D-aspartate (NMDA) receptors. Assayed by elec. recording under steady-state conditions, 7-hydroxy-2-(4-phenylbutyl)-1,2,3,4-tetrahydropyrido-[3,4-b]indole (30) was the most potent compound in the series having an IC₅₀ value of 50 nM at the NR1A/2B receptors. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Electric Literature of C10H13BrO).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Electric Literature of C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Critical role of structural order in bipolar redox-active molecules for organic redox flow batteries was written by Li, Min;Agarwal, Garvit;Shkrob, Ilya A.;VanderLinden, Ryan T.;Case, Julia;Prater, Matthew;Rhodes, Zayn;Assary, Rajeev S.;Minteer, Shelley D.. And the article was included in Journal of Materials Chemistry A: Materials for Energy and Sustainability in 2021.Application of 954-81-4 This article mentions the following:

Bipolar redox-active mols. (BRMs) have been suggested as a means to address crossover related issues in all-organic redox flow batteries (RFBs). In such species, electron donors (anolytes) and electron acceptors (catholytes) are linked by a chain, and the same chem. composition is used in both anode and cathode compartments to reduce chem. gradients and unbalanced ion transport. The resultant RFBs resemble the aqueous vanadium RFBs, but offer greater design flexibility and potentially more favorable electrochem. and physicochem. properties. Yet the complex trade-offs in these properties have been a complication. Here we developed a fundamental rubric to uncover the likely origins in the performance metrics of these BRMs that are salient for their use in RFBs. Methylene linked phenothiazine and phthalimide moieties were employed as model BRMs and variations in their properties and mol. conformations were evaluated by systematically varying the methylene linker. Our results revealed that even minimalistic changes in the linker length resulted in dramatic oscillations in the solubility and stability. Using crystallog., quantum chem., and mol. dynamics, we clarify that the seemingly fluctuating behavior is due to (1) the inter- and intra-mol. charge transfer between the donor and acceptor through bond or/and through space; (2) the formation of distinctive packing/clustering motifs. Both interactions are strongly dependent on the mol. conformation. As these structural factors modify the electronic structure of both electroactive functional groups and do not change monotonically, the structure-property response in BRMs is often complex. Accordingly, these behaviors need to be taken into account in developing BRMs and knowledge of these structural factors will allow the more rational design of BRMs for grid-scale energy storage. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Application of 954-81-4).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Application of 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Polymers of methylchavicol was written by v. d. Zanden, J. M.. And the article was included in Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen in 1937.Related Products of 57293-19-3 This article mentions the following:

Methylchavicol (I) was heated for 48 hrs. at 250° in a sealed tube. After distillation a residue was left from which a solid separated The oil (II) was removed from the crystalline mass (III) by suction. III was recrystallized to give 3 fractions; (a) (IV) m. 98°, (b) (V) m. 166° and (c) m. above 200°. IV and V are probably dimers of I. IV is unsaturated and forms a dibromide, m. 87°. The yield of III is increased by longer heating. II was fractionated. The fraction b₁₅ 283-313° deposited a solid (VI). At 350° the residual mass was cracked. The distillate contained p-methylanisole. Oxidation of IV with KMnO₄ in acetone gave anisic acid (VIII) and an acid, C₁₂H₁₆O₄ (IX), m. 113°. Further oxidation of VIII gave an acid, C₁₂H₁₆O₄ (IX), m. 138°. The Mg compound of p-bromoanisole reacts with allyl bromide to give I; yield 75-80%. When I was polymerized by heating 200 hrs. at 250° and distilled, 60% was recovered unchanged. The distillation temperature was increased to 200° (3 mm.). The fractions up to 300° solidify partially. The residue is a hard asphaltic mass. Extraction and recrystallization from petr. ether of the largest fraction (210-20°) gave a substance (X), m. 93°. Fractions m. 46-7°, 95-8°, 135° (XI) and 167° were also obtained. X is probably a dimer of I and XI is a trimer. Oxidation of X with KMnO₄ in acetone gave VII and an acid, C₁₂H₁₆O₃ (XII), m. 114-14.5°. Further oxidation of XII gave an acid, C₁₂H₁₄O₂ (XIII), m. 140-0.5°. XIII and NH₂OH gave an oxime (XIV), m. 97-7.5°. Treatment of XIV with H₂SO₄, followed by hydrolysis, gave an acid which was shown to be glutaric acid (XV). The suggestion was made that IX is δ-(p-methoxyphenyl)-δ-ketovaleric acid which was confirmed by synthesis from XV and anisole with AlCl₃ as a catalyst; yield 70%, m. 140°. The p-nitrophenylhydrazone of IX m. 198-200°; the 2,4-dinitrophenylhydrazone m. 142.5°. A Beckmann rearrangement of XIV carried out with PCl₅ in Et₂O gave a product, C₁₂H₁₃O₃N (XVI), m. 172-2.5°, which is probably a cyclic imide. KOH (1 mol.) converts XVI to a substance, C₁₂H₁₅O₄N (XVII), m. 147-8°, with an open N ring. Concentrated HCl splits XVII into XV and p-MeOC₆H₄NH₂ (XVIII). XV and XVIII react to produce XVI. Oxidation of XIII by KMnO₄ gave VII and an acid, m. 92-2.5°, which was identical with p-methoxyphenylglyoxylic acid prepared by oxidation of p-MeOC₆H₄COMe (cf. Bougault, Ann. chim. [7], 25,541(1902)). Oxidation of XII gave anisoylbutyric acid, m. 114-14.5°. Therefore XII must be δ-p-methoxyphenylvaleric acid. For confirmation XII was prepared by the following reactions (cf. Claisen, Ber. 23, 977(1890)): Et p-methoxycinnamate was reduced by Na in EtOH to p-methoxyphenylpropanol, b₁₀ 149°, m. 25-6°, which was converted to the bromide (XIX) by PBr₃. Interaction of XIX and CHNa(CO₂Et)₂ gave MeOC₆H₄(CH₂)₃CH(CO₂Et)₂ which was saponified and decarboxylated at 130° to give XII. Oxidation of X gave VII and XII which showed that X is 1,6-bis(p-methoxyphenyl)-1-hexene. X was hydrogenated (Pd) to give 1,6-bis(p-methoxyphenyl)hexane, m. 71.5-2°, which was identical with the compound prepared (Würtz reaction) from p-MeOC₅H₄(CH₂)₂CH₂Br. VI and other fractions are being further investigated. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Related Products of 57293-19-3).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Related Products of 57293-19-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Modulating the catalytic activity of gold nanoparticles using amine-terminated ligands was written by Zhang, Jiangjiang;Huang, Zhentao;Xie, Yangzhouyun;Jiang, Xingyu. And the article was included in Chemical Science in 2022.Name: N-(5-Bromopentyl)phthalimide This article mentions the following:

Nanozymes have broad applications in theranostics and point-of-care tests. To enhance the catalytic activity of nanozymes, the conventional strategy is doping metals to form highly active nanoalloys. However, high-quality and stable nanoalloys are hard to synthesize. Ligand modification is a powerful strategy to achieve chemoselectivity or bioactivity by changing the surface chem. Here, we explore different ligands to enhance the catalytic activity of nanozymes, e.g., gold nanoparticles (AuNPs). We systematically studied the impacts on the enzymic activity of AuNPs by ligand engineering of surface chem. (charge, group, and surface distance). Our work established critical guidelines for surface modification of nanozymes. The amine group favors higher activity of AuNPs than other groups. The flexible amine-rich ligand enhances the catalytic activity of AuNPs in contrast to other ligands and unmodified AuNPs. Using a proof-of-concept model, we screened many candidate ligands to obtain polyamine-AuNPs, which have strongly enhanced peroxidase-like activity and 100 times enhanced sensitivity compared to unmodified AuNPs. The strategy of enhancing the catalytic activity of AuNPs using ligands will facilitate the catalysis-related applications of nanozymes in biol. and diagnostics. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Name: N-(5-Bromopentyl)phthalimide).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Name: N-(5-Bromopentyl)phthalimide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The effect of bromide ions on the reaction of alkylaromatic compounds with cerium(IV) ammonium nitrate in acetic acid. An efficient method for the side-chain bromination of toluenes with electron-withdrawing substituents was written by Baciocchi, Enrico;Rol, Cesare;Sebastiani, Giovanni V.;Serena, Bernardino. And the article was included in Journal of Chemical Research, Synopses in 1984.Application of 6515-58-8 This article mentions the following:

Treatment of RR¹C₆H₃Me [R = 3-CO₂H, 4-NO₂, 4-(2-HO₂C)C₆H₄CO, 4-Br, H, R¹ = H; R = 2-Cl, R¹ = 4-Cl, 6-Cl] with (NH₄)₂Ce(NO₃)₆ in AcOH-KBr at 80° for 1-2.5 h gave RR¹C₆H₃CH₂Br (I) in 50-80% yield. As I can be converted into RR¹C₆H₃CH₂OAc in the same reaction medium, this provides a method for side-chain acetoxylation of toluenes. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Application of 6515-58-8).

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Application of 6515-58-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary