Category: 1997-80-4

Li, Yuqiang published the artcileReaction scope and mechanistic insights of nickel-catalyzed migratory Suzuki-Miyaura cross-coupling, Formula: C9H8BrF3, the publication is Nature Communications (2020), 11(1), 417, database is CAplus and MEDLINE.

In this work, a Ni-catalyzed migratory Suzuki-Miyaura cross-coupling featuring high benzylic or allylic selectivity has been developed. With this method, unactivated alkyl electrophiles and aryl or vinyl boronic acids can be efficiently transferred to diarylalkane or allylbenzene derivatives under mild conditions. Importantly, unactivated alkyl chlorides can also be successfully used as the coupling partners. To demonstrate the applicability of this method, showcase that this strategy can serve as a platform for the synthesis of terminal, partially deuterium-labeled mols. from readily accessible starting materials. Exptl. studies suggest that migratory cross-coupling products are generated from Ni(0/II) catalytic cycle. Theor. calculations indicate that the chain-walking occurs at a neutral nickel complex rather than a cationic one. In addition, the original-site cross-coupling products can be obtained by alternating the ligand, wherein the formation of the products has been rationalized by a radical chain process.

Nature Communications published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H8BrF3, Formula: C9H8BrF3.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Li, Yuqiang published the artcileReaction scope and mechanistic insights of nickel-catalyzed migratory Suzuki-Miyaura cross-coupling, Formula: C9H8BrF3, the publication is Nature Communications (2020), 11(1), 417, database is CAplus and MEDLINE.

In this work, a Ni-catalyzed migratory Suzuki-Miyaura cross-coupling featuring high benzylic or allylic selectivity has been developed. With this method, unactivated alkyl electrophiles and aryl or vinyl boronic acids can be efficiently transferred to diarylalkane or allylbenzene derivatives under mild conditions. Importantly, unactivated alkyl chlorides can also be successfully used as the coupling partners. To demonstrate the applicability of this method, showcase that this strategy can serve as a platform for the synthesis of terminal, partially deuterium-labeled mols. from readily accessible starting materials. Exptl. studies suggest that migratory cross-coupling products are generated from Ni(0/II) catalytic cycle. Theor. calculations indicate that the chain-walking occurs at a neutral nickel complex rather than a cationic one. In addition, the original-site cross-coupling products can be obtained by alternating the ligand, wherein the formation of the products has been rationalized by a radical chain process.

Nature Communications published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H8BrF3, Formula: C9H8BrF3.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Shapiro, Robert H. published the artcileEvidence for anchimeric assistance in the expulsion of bromine from ring-substituted β-phenylethyl bromides: when is a simple cleavage a rearrangement, HPLC of Formula: 1997-80-4, the publication is Organic Mass Spectrometry (1969), 2(8), 771-80, database is CAplus.

Using the principles of the quasi-equilibrium theory, substituent effects, deuterium labeling, and comparison of compound behavior, evidence is given for aryl participation in the expulsion of Br from the mol. ion of β-phenylethyl bromide and eleven of its ring-substituted derivatives This reaction shows a kinetic behavior which is typical of rearrangements, its activation energy is lower than that of similar reactions where participation is partially or completely precluded and substituent effects are not only consistent with a participation process, but are also consistent with those predicted from solution chemistry.

Organic Mass Spectrometry published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C14H20BBrO2, HPLC of Formula: 1997-80-4.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Tu, Noah P. published the artcileUltrasound-assisted click chemistry in continuous flow, Application of 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, the publication is Molecular Diversity (2012), 16(1), 53-58, database is CAplus and MEDLINE.

We present a study on ultrasound-promoted click chem. reactions in a meso-flow reactor synthesis system with a copper reactor and a custom sonication piezoelec. transducer. Copper catalyzed Huisgen 1,3-dipolar cycloadditions were studied in flow with this system. Our results demonstrate that 1,4-disubstituted 1,2,3-triazole products can be generated at low temperatures and with short reaction time in good yield, due to the rate enhancement effect of sonication.

Molecular Diversity published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H13NO2, Application of 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Wollweber, H. published the artcile1-Phenethyl-2-iminoimidazolidines, a new class of compounds with ganglion-regulating activity, SDS of cas: 1997-80-4, the publication is Med. Chem., Abhandl. Med. Chem. Forschungsstaetten Farbwerke Hoechst A.G. (1963), 248-61, database is CAplus.

To a solution of the Grignard reagent from 225 g. 3-Br-C₆H₄CF₃, 26 g. Mg, and 500 ml. Et₂O was added dropwise a solution of 44 g. ethylene oxide in 200 ml. Et₂O to give after hydrolysis with aqueous NH₄Cl 74.9 g. 3-F₃CC₆H₄CH₂CH₂OH (I), b₁₂ 102-6°. I (38 g.) was saturated at 100° with dry HBr to give 45 g. 3-F₃CC₆H₄CH₂CH₂Br (II), b₁₂ 92-4°. A mixture of 45 g. II and 50 g. (CH₂NH₂)₂ was refluxed overnight, distilled in vacuo, the residue basified, and the oil separated to give 19.4 g. 3-F₃CC₆H₄CH₂CH₂-NHC₂H₄NH₂, b_0.15 96-8°. A mixture of 80 g. PhCH₂CH₂Cl and 160 g. H₂NCH₂CH₂NHCO₂Et was refluxed 8 hrs. to give 62 g. PhCH₂CH₂NHCH₂CH₂NHCO₂Et (III), b_0.05 140°. III (53 g.) in 500 ml. Et₂O was reduced with LiAlH₄ to give 16.1 g. PhCH₂CH₂NHCH₂CH₂NHMe, b₁₂ 84-6°. A mixture of 55 g. PhCH₂CH₂NHCH₂CH₂NH₂ (IV), 47 g. S-methylisothiuronium sulfate, 200 ml. EtOH. and 40 ml. water was refluxed 2 hrs. to give 80 g. 2PhCH₂CH₂NHCH₂CH₂NHC(:NH)NH₂.H₂SO₄ (V), m. 188° (decomposition) (EtOH-AcOEt). V (60 g.) was heated 1.5 hrs. at 150-60, 200 ml. amyl alc. added, and the mixture refluxed 6 hrs. to give 28 g. VI (R¹ = R² = R³ = R⁴ = R⁵ = R⁶ = R⁷ = H, m = n = 1, X = NH) (VII).0.5 H₂SO₄, m. 206.5-7.5°. A solution of 10.6 g. BrCN in 50 ml. benzene was added dropwise at 20-30° to a solution of 18 g. IV in 100 ml. benzene and the mixture stirred 1 hr. to give VII HBr salt, m. 144-6° (AcOEt). PhCH₂CH₂NHCH₂CH₂OH with concentrated HBr at 170° gave PhCH₂CH₂NHCH₂CH₂Br HBr salt, m. 173-5°; this (15.5 g.) in 45 ml. water treated with a solution of 4.05 g. KOCN in 10 ml. water gave an oil which slowly dissolved upon vigorous shaking. After 0.5 hr. the solution was treated with K₂CO₃ and the oil extracted with CH₂Cl₂ to give 8.5 g. X = O analog of VII, b_0.25 122-5°; HCl salt m. 178-9°. Similarly prepared were VI (R¹, R¹, R¹, R¹, R¹, R², R², n, m, m, m.p. HBr salt, and b.p./mm. of diamine corresponding to IV given): H, H, OMe, H, H, H, H, 1, 1, NH, 166-7°, 140°/0.1; H, OMe, H, H, H, H, H, 1, 1, NH, 139°, 124°/0.1; H, (R²R³ =) CH₂O₂, H, H, H, H, 1, 1, NH, 217°, 130°/0.2; H, H, Me, H, H, H, H, 1, 1, NH, 193-5°, 100°/0.2; H, Me, H, H, H, H, H, 1, 1, NH, 148-9°, 116°/0.5; Me, H, H, H, H, H, H, 1, 1, NH, 173-5°, 118°/0.2; H, H, Cl, H, H, H, H, 1, 1, NH, 187°, 112°/0.1; H, Cl, H, H, H, H, H, 1, 1, NH, 138°, 110°/0.05; H, H, H, H, H, H, H, 1, 1, NMe, 180°, 85°/12; H, H, H, H, H, H, Me, 1, 1, NH, 186-7°, 90°/0.1; H, H, H, H, H, Me, H, 1, 1, NH, 111-13°, 80°/0.1; H, OMe, H, H, Me, Me, H, 1, 1, NH, 156°, 125°/0.05; H, H, H, OH, H, H, H, 1, 1, NH, 173°, 164°/0.05; H, H, H, H, H, H, H, 1, 0, NH, 202-3°, 84°/0.2; Cl, H, H, H, H, H, H, 1, 0, NH, 270-3° (decomposition) (1/2H₂SO₄ salt), 102°/0.1. Also prepared were VIII (R¹, R², m.p. HBr salt, and b.p./mm. diamine given): H, H, 153°, 100°/0.1; H, Me, 140°, 125°/12; Me, H, 115-17°, 126°/12. Similarly prepared from α-phenyl-ethylenediamine, b_0.3 84°, was 4-phenyl-2-iminoimidazolidine HBr salt, m. 177°. Toxicity and pharmacol. data are given for all compounds

Med. Chem., Abhandl. Med. Chem. Forschungsstaetten Farbwerke Hoechst A.G. published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C12H9N3O4, SDS of cas: 1997-80-4.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Behnke, Nicole Erin published the artcileTitanium-Mediated Synthesis of Spirocyclic NH-Azetidines from Oxime Ethers, Related Products of bromides-buliding-blocks, the publication is Angewandte Chemie, International Edition (2019), 58(40), 14219-14223, database is CAplus and MEDLINE.

The Ti^IV-mediated synthesis of spirocyclic NH-azetidines from oxime ethers using either an alkyl Grignard reagent or terminal olefin ligand exchange coupling partner is described. Through a proposed Kulinkovich-type mechanism, a titanacyclopropane intermediate forms and serves as a 1,2-aliphatic dianion equivalent, inserting into the 1,2-dielectrophilic oxime ether to ultimately give rise to the desired N-heterocyclic four-membered ring. This transformation proceeds in moderate yield to furnish previously unreported and structurally diverse NH-azetidines in a single step. Thus, e.g., cyclohexanone O-methyloxime + phenethylmagnesium bromide → I (51%) in presence of Ti(Oi-Pr)₄ in Et₂O.

Angewandte Chemie, International Edition published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H8BrF3, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Song, Zhidan published the artcileSynthesis and aromatase inhibitory evaluation of 4-N-nitrophenyl substituted amino-4H-1,2,4-triazole derivatives, Related Products of bromides-buliding-blocks, the publication is Bioorganic & Medicinal Chemistry (2016), 24(19), 4723-4730, database is CAplus and MEDLINE.

In this paper, 13 4-N-nitrophenyl substituted amino-4H-1,2,4-triazole derivatives were synthesized and their aromatase inhibitory activities were measured. The results show that the substitution of the groups on benzyl group can further improve their bioactivity and the compound (I) with Cl on the para position of benzyl has the highest bioactivity (IC₅₀ = 9.02 nM). A QSAR model was constructed from the 13 compounds with genetic function approximation using DS 2.1 package. This model can explain 90.09% of the variance (R²_Adj), while it can predict 84.95% of the variance (R²_cv) with the confidence interval of 95%.

Bioorganic & Medicinal Chemistry published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C15H18BF3O4, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Yang, Ting published the artcileDiscovery of Tertiary Amine and Indole Derivatives as Potent RORγt Inverse Agonists, Name: 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, the publication is ACS Medicinal Chemistry Letters (2014), 5(1), 65-68, database is CAplus and MEDLINE.

A novel series of tertiary amines as retinoid-related orphan receptor gamma-t (RORγt) inverse agonists was discovered through agonist/inverse agonist conversion. The level of RORγt inhibition can be enhanced by modulating the conformational disruption of H12 in RORγt LBD. Linker exploration and rational design led to the discovery of more potent indole-based RORγt inverse agonists, e.g., I.

ACS Medicinal Chemistry Letters published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C25H23NO4, Name: 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Li, Yangyang published the artcileNickel-catalyzed migratory alkyl-alkyl cross-coupling reaction, Recommanded Product: 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, the publication is Chemical Science (2020), 11(38), 10461-10464, database is CAplus and MEDLINE.

A migratory cross-coupling strategy, which can overcome this obstacle to access the desired cross-coupling products ArCH(R)(CH₂)_nCR¹R²R³ (Ar = Ph, 4-fluorophenyl, indol-3-yl, etc.; R = cyclopentyl, cyclohexyl, cycloheptyl, N-benzyl-piperidin-4-yl, 2-methyl-propan-1-yl; R¹ = H, D; R² = H, D; R³ = H; n = 0-3, 5), 1-cyclopentyl-indan, 1-cycloheptyl-indan, (1-cyclopentyl-3-methyl-pentyl)benzene was described. Accordingly, a selective migratory cross-coupling of two alkyl electrophiles (RBr, ArCH(R)(CH₂)_nCR¹R²R³ (R³ = Br or Cl), 2-bromoindan, (5-bromo-1-cyclopentyl-3-methyl-pentyl)benzene) has been accomplished by nickel catalysis. Remarkably, this alkyl-alkyl cross-coupling reaction provides a platform to prepare 2°-2° carbon-carbon bonds from 1° and 2° carbon coupling partners. Preliminary mechanistic studies suggest that chain-walking occurs at both alkyl halides in this reaction, thus a catalytic cycle with the key step involving two alkylnickel(II) species is proposed for this transformation.

Chemical Science published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H8BrF3, Recommanded Product: 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Elgendy, Bahaa published the artcileSynthesis and structure activity relationship of the first class of LXR inverse agonists, HPLC of Formula: 1997-80-4, the publication is Bioorganic Chemistry (2022), 105540, database is CAplus and MEDLINE.

Liver X Receptors (LXRs) are members of the nuclear receptor family, and they play significant role in lipid and cholesterol metabolism Moreover, they are key regulators of several inflammatory pathways. Pharmacol. modulation of LXRs holds great potential in treatment of metabolic diseases, neurodegenerative diseases, and cancer. We were the first group to identify LXR inverse agonists SR9238 and SR9243 and demonstrate their potential utility in treating liver diseases and cancer. Here, we present the results of structure-activity relationship (SAR) studies, based around SR9238 and SR9243. This study led to identification of I, II, III and IV which were more potent inverse agonists than SR9238 and SR9243 and inhibited expression of the fatty acid synthase gene in DU145 cells. We previously demonstrated that inhibition of FASN is correlated to the anticancer activity of SR9243 and this suggests that new inverse agonists have great potential as anticancer agents. We identified compounds with distinct selectivity toward both LXR isoforms, which can be excellent tools to study the pharmacol. of both isoforms. We employed mol. dynamic (MD) simulations to better understand the mol. mechanism underlying inverse agonist activity and to guide our future design.

Bioorganic Chemistry published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H8BrF3, HPLC of Formula: 1997-80-4.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary