Month: December 2022

Fumagalli, Fernando published the artcileArene-Ligand-Free Ruthenium(II/III) Manifold for meta-C-H Alkylation: Remote Purine Diversification, Computed Properties of 401-55-8, the publication is Chemistry – A European Journal (2018), 24(16), 3984-3988, database is CAplus and MEDLINE.

Meta-Selective C-H alkylations of bioactive purine derivatives were accomplished by versatile ruthenium catalysis. Thus, the arene-ligand-free complex [Ru(OAc)₂(PPh₃)₂] enabled remote C-H functionalizations with ample scope and excellent levels of chemo- and positional selectivities. Detailed exptl. and computational mechanistic studies provided strong support for a facile C-H activation within a ruthenium(II/III) manifold.

Chemistry – A European Journal published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C4H6BrFO2, Computed Properties of 401-55-8.

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

Hardy, A. published the artcile7-Nitro-1-naphthylamine. I. Its preparation, halogenation, and diazo coupling; and 1,2,4,7-tetrahalonaphthalenes, Product Details of C10H6Br2, the publication is Journal of the Chemical Society (1956), 1979-84, database is CAplus.

7-Nitro-1-naphthylamine (I), m. 132-3° (from EtOH), was prepared in 38-45% yield by rearrangement of 1,2,3,4-tetrahydro-7-nitro-1-oxonaphthalene oxime acetate (cf. Schroeter, et al., C.A. 24, 4291), in 22% yield by passage of HCl for 2 hrs. through a suspension of 3.6 g. of the oxime phenylcarbamate in 30 cc. EtOH at 90°, in 10% yield by rearrangement of the oxime in tetraphosphoric acid, and in 42 % yield by reduction of 1,7-dinitronaphthalene (cf. Hodgson and Turner, C.A. 37, 6258¹). The first method was considered to be the best. Derivatives of I had the following m.ps.: N-formyl, 218°; N-acetyl (II), 213°; N-(p-toluenesulfonyl), 202°; N-(p-nitrobenzylidene), 210°. I.HCl was unstable in air. Slow passage of Cl into a solution of 1 g. II in 25 cc. HOAc at 50° until l’mole was absorbed gave 50% 1-acetamido-4-chloro-7-nitronaphthalene (III), m. 256° (from HOAc). Refluxing 0.8 g. III 6 hrs. with 10 cc. EtOH and 10 cc. 50% weight/volume aqueous H₂SO₄ gave after basification with aqueous NH₃ 90% 4-chloro-7-nitro-1-naphthylamine (IV), m. 206° (from EtOH). Deamination of IV gave 37% 1-chloro-6-nitronaphthalene, m. 126° (from EtOH). Passage of Cl through 1 g. II in 25 cc. HOAc at 50° until 2 moles were absorbed gave 64% 1-acetamido-2,4-dichloro-7-nitronaphthalene (V), m. 237° (from HOAc). Hydrolysis of V in EtOH-H₂SO₄ 8 hrs. gave 97% 2,4-dichloro-7-nitro-1-naphthylamine (VI), m. 228° (from EtOH). Diazotization of VI and addition of the solution to aqueous NaOAc gave 4-chloro-1-diazo-7-nitro-2-naphthol, m. 175° (decomposition), in quant. yield. VI was converted to 2,4-dichloro-1,7-naphthylenediamine (VII), m. 135-6° (from EtOH), by refluxing 1.0 g. 10 hrs. with 20 cc. H₂O containing 2.5 g. Fe dust and 0.2 g. FeNH₄(SO₄)₂ under CO₂. VII (0.75 g.) in 12 cc. HOAc and 2 cc. H₂SO₄ was diazotized with 0.6 g. NaNO₂ in 4 cc. H₂SO₄, and the mixture added rapidly to 15 cc. MeOH containing 1.75 g. Cu₂O and then to 100 cc. H₂O to give 1,3-dichloronaphthalene. VII was diazotized as above, the solution poured into 6 cc. aqueous HCl containing 0.6 g. CuCl at 60°, and then into 25 cc. H₂O to give 1,2,4,7-tetrachloronaphthalene, m. 143-4° (from EtOH), identical with the 1,2,4,x-tetrachloronaphthalene of Turner and Wynne (C.A. 35 5885⁷). Dropwise addition of 10 g. I in 200 cc. CHCl₃ to 18.5 g. Br in 6 cc. CHCl₃ gave after basification 90% 2,4-dibromo-7-nitro-1-naphthylamine (VIII), m. 237° (from EtOH). Use of 1 mole Br gave the same product. Addition of 0.6 g. VIII in 12 cc. HOAc to 0.2 g. NaNO₂ in 1 cc. H₂SO₄ and after 30 min. to 5 g. NaOAc in 50 cc. H₂O gave 4-bromo-1-diazo-7-nitro-2-naphthol, m. 156.5° (from aqueous dioxane). Reduction of VIII by a method similar to that used for VI gave 51% 2,4-dibromo-1,7-naphthylenediamine (IX), m. 122° (decomposition) (from aqueous EtOH). IX was diazotized and converted to 7% 1,3-dibromonaphthalene, m. 63°. Addition of Br in 10 cc. HOAc to 2 g. II in 10 cc. HOAc containing 0.75 g. NaOAc during 45 min. under reflux and heating 30 min. gave 84% 1-acetamido-4-bromo-7-nitronaphthalene (X), m. 265° (from HOAc). X (2 g.) was refluxed with 10 cc. aqueous H₂SO₄ and 10 cc. EtOH for 3 hrs., and the residue was separated and refluxed again with the hydrolyzing solution 5 hrs. The amine sulfates from the 2 solutions were basified with aqueous NH₃ at 0° to give 92% 4-bromo-7-nitro-1-naphthylamine (XI), m. 197° (from ligroine b. 100-20°). Deamination of XI gave 18% 1-bromo-6-nitronaphthalene, m. 129°. Diazotization of 0.8 g. IX and reaction of the solution with 0.9 g. CuBr in 6 cc. aqueous HBr (50% weight/volume) gave 20% 1,2,4,7-tetrabromonaphthalene, m. 165° (from EtOH). This differed from the tetrabromonaphthalene of Guareschi [Gazz. chim. ital. 16, 146 (1886)], indicating that the latter was the 1,2,4,6-derivative Slow addition of 0.65 g. p-O₂NC₆H₄N₂HSO₄ in 15 cc. H₂O to 0.5 g. I in 15 cc. EtOH containing 0.36 g. NaOAc at 0° gave after 30 min. 88% 7-nitro-4-(p-nitrophenylazo)-1-naphthylamine (XII), purple-black needles, m. 297° (from PhNO₂). XII (0.15 g.) was acetylated by refluxing in 10 cc. AcOH, 2 cc. Ac₂O, and 1 g. NaOAc to give 75% 1-acetamido-7-nitro-4-(p-nitrophenylazo)naphthalene, m. 329-30°. Diazotization of XII and coupling with β-naphthol in aqueous NaOH gave 7-nitro-4-(p-nitrophenylazo)-1-naphthylazo-2-naphthol, violet-black needles, m. 292° (decomposition).

Journal of the Chemical Society published new progress about 52358-73-3. 52358-73-3 belongs to bromides-buliding-blocks, auxiliary class Bromide,Naphthalene, name is 1,3-Dibromonaphthalene, and the molecular formula is C10H6Br2, Product Details of C10H6Br2.

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

Hellenbrand, Tim published the artcileConjugate addition of organomagnesium cuprates to guvacine derivatives, Recommanded Product: (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is European Journal of Organic Chemistry (2014), 2014(20), 4398-4409, database is CAplus.

The synthesis of 4-substituted piperidine-3-carboxylates was achieved by conjugate addition of organomagnesium cuprates to N-Me and N-tert-butoxycarbonyl guvacine derivatives Good to excellent yields were obtained with primary Grignard reagents containing alkyl, alkenyl, alkynyl, or masked aldehyde groups in a copper(I)-trimethylsilylacetylide-catalyzed and Me₃SiCl-mediated procedure.

European Journal of Organic Chemistry published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C7H13BrSi, Recommanded Product: (4-Bromobut-1-yn-1-yl)trimethylsilane.

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

Bao, Yinwei published the artcilePalladium-catalyzed tandem cyclization of fluorinated imidoyl chlorides with 2-bromophenylboronic acid: synthesis of 6-fluoroalkyl-phenanthridines, Synthetic Route of 89694-44-0, the publication is Tetrahedron (2019), 75(10), 1450-1456, database is CAplus.

An efficient method was developed to synthesize 6-fluoroalkyl-phenanthridines I [R = CF₃, C₂F₅, CF₂Cl; R¹ = H, 8-MeO, 8-CF₃; R² = H, 2-F, 4-Cl, etc.] via the palladium-catalyzed tandem cyclization of fluorinated imidoyl chlorides with 2-bromophenylboronic acid. This methodol. facilitated the rapid synthesis of 6-fluoroalkyl-phenanthridines I through dual C-C bond formation in an oxidant-free one-pot manner.

Tetrahedron published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C7H8BBrO3, Synthetic Route of 89694-44-0.

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

Qu, Yongzheng published the artcileAsymmetric Total Synthesis of (+)-Waihoensene, Quality Control of 69361-41-7, the publication is Journal of the American Chemical Society (2020), 142(14), 6511-6515, database is CAplus and MEDLINE.

The asym. total synthesis of (+)-waihoensene (I), which has a cis-fused [6,5,5,5] tetracyclic core bearing an angular triquinane, a cis-fused six-membered ring, and four contiguous quaternary carbon atoms, was achieved through a sequence of chem. reactions in a stereochem. well-defined manner. The total synthesis features the following: (1) Cu-catalyzed asym. conjugated 1,4-addition; (2) diastereoselective Conia-ene type reaction; (3) diastereoselective intramol. Pauson-Khand reaction; (4) Ni-catalyzed diastereoselective conjugated 1,4-addition; and (5) radical-initiated intramol. hydrogen atom transfer (HAT). Control experiments and d. functional theory calculations support the proposed HAT process.

Journal of the American Chemical Society published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C7H13BrSi, Quality Control of 69361-41-7.

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

Zou, Jian-Yu published the artcilePhotoredox-catalyzed redox-neutral difluoroalkylation to construct perfluoroketones with difluoroenoxysilanes, Name: Ethylbromofluoroacetate, the publication is Organic & Biomolecular Chemistry (2021), 19(40), 8696-8700, database is CAplus and MEDLINE.

A mild and facile approach to construct various perfluoroketones via photo-catalyzed difluoroalkylation of difluoroenoxysilanes is developed. The reaction includes a strategy of combination of two fluorine-containing functional groups, which confers the reaction with characteristics like high efficiency, mild conditions, and broad scope. A variety of fluoroalkyl halides including perfluoroalkyl iodides, bromo difluoro esters and amides can be employed as radical precursors. Control experiments indicate that a single-electron transfer pathway may be involved in the reaction.

Organic & Biomolecular Chemistry published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C16H14O6, Name: Ethylbromofluoroacetate.

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

Xu, Jun published the artcileCopper-catalyzed endo-type trifluoromethylarylation of alkynes, Quality Control of 1997-80-4, the publication is Chemical Communications (Cambridge, United Kingdom) (2014), 50(85), 12915-12918, database is CAplus and MEDLINE.

A new copper-catalyzed trifluoromethylarylation reaction of alkynes has been developed. The transformation represents the first example of endo-type carbotrifluoromethylation of unsaturated carbon-carbon bonds and provides efficient access to a variety of CF₃-substituted dihydronaphthalenes and chromenes.

Chemical Communications (Cambridge, United Kingdom) 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 C17H18N3NaO3S, Quality Control of 1997-80-4.

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

Chen, Fengli published the artcileSelective adsorption of C₂H₂ and CO₂ from CH₄ in an isoreticular series of MOF constructed from unsymmetrical diisophthalate linkers and the effect of alkoxy group functionalization on gas adsorption, Application of 1,3-Dibromonaphthalene, the publication is Journal of Materials Chemistry A: Materials for Energy and Sustainability (2018), 6(8), 3471-3478, database is CAplus.

For acetylene production and natural gas purification, development of porous materials exhibiting highly selective C₂H₂/CH₄ and CO₂/CH₄ separations is very important but remains a major challenge. This work used three unsym. diisophthalate ligands to construct an isoreticular series of Cu-based metal-organic frameworks (MOF) exhibiting highly selective adsorption of C₂H₂ and CO₂ from CH₄ under ambient conditions. Gravimetric uptake capacities at 298° K and 1 atm varied from 171.7 to 200.4 cm³ (STP)/g for C₂H₂ and from 104.1 to 115.6 cm³ (STP)/g for CO₂. IAST adsorption selectivity was 27.6-34.5 for an equimolar C₂H₂/CH₄ mixture, and 5.73-7.14 for an equimolar CO₂/CH₄ mixture at 298° K and 1 atm. These values are among the highest reported for MOF constructed from bent diisophthalate ligands under the same conditions. The effect of alkoxy group functionalization on gas adsorption was also examined and showed, that compared to the parent compound, alkoxy group functionalized MOF exhibited a reduced uptake capacity but an improved adsorption selectivity. Results showed the three MOF are promising materials for C₂H₂/CH₄ and CO₂/CH₄ separations, and provided a fundamental understanding of alkoxy group functionalization on gas adsorption properties.

Journal of Materials Chemistry A: Materials for Energy and Sustainability published new progress about 52358-73-3. 52358-73-3 belongs to bromides-buliding-blocks, auxiliary class Bromide,Naphthalene, name is 1,3-Dibromonaphthalene, and the molecular formula is C10H6Br2, Application of 1,3-Dibromonaphthalene.

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

Fan, Tian-Yun published the artcileSynthesis and antibacterial evaluation of 13-substituted cycloberberine derivatives as a novel class of anti-MRSA agents, Safety of (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane, the publication is European Journal of Medicinal Chemistry (2018), 877-886, database is CAplus and MEDLINE.

A series of new 13-substituted cycloberberine (CBBR) derivatives I [R = H, 2-Me, 4-iso-Pr, 3′,5′-(CF₃)₂, etc.], II (R = 3′-pyridyl, 4′-pyridyl), and III (R = Me, CO₂Me) were prepared and evaluated for their antibacterial activities against Gram-pos. bacteria taking CBBR as the lead. Structure-activity relationship revealed that the introduction of a suitable electron-donating group at the 13-position in CBBR might be beneficial for the antibacterial potency. Among them, compounds I (R = 2-Me) (IV) and III (R = Me) exhibited high potency against methicillin-sensitive (MSSA) and resistant strains of S. aureus (MRSA) with MIC values of 1-4 μg/mL. Both of them also displayed high stabilities in blood, and good in vivo safety profiles with LD₅₀ values of 65.6 and 41.2 mg kg^-1 in i.v. route, resp. Mol. docking anal. indicated that compound IV might target FtsZ protein that could inhibit cell division, with the advantage of activity against multidrug resistant S. aureus. Therefore, we consider 13-substituted CBBR derivatives to be a novel class of anti-MRSA agents worthy of further investigation.

European Journal of Medicinal Chemistry published new progress about 21101-63-3. 21101-63-3 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,sulfides,Benzyl bromide,Benzene, name is (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane, and the molecular formula is C8H6BrF3S, Safety of (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane.

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

Sokolsky, Alexander published the artcileSpirastrellolide E: synthesis of an advanced C(1)-C(24) southern hemisphere, Formula: C7H13BrSi, the publication is Tetrahedron Letters (2015), 56(23), 3160-3164, database is CAplus and MEDLINE.

The synthesis of a C(1)-C(24) advanced southern hemisphere fragment (I) towards the total synthesis of spirastrellolide E has been achieved. Highlights of the route include a highly convergent Type I Anion Relay Chem. (ARC) tactic for fragment assembly, in conjunction with a directed, regioselective gold-catalyzed alkyne functionalization to generate the central unsaturated [6,6]-spiroketal.

Tetrahedron Letters published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C5H9IO2, Formula: C7H13BrSi.

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