Tag: M.W=200-250

Molander, Gary A. published the artcileSequential epoxide fragmentation/radical cyclizations mediated by samarium(II) iodide, COA of Formula: C7H13BrSi, the publication is Tetrahedron (1998), 54(22), 5819-5832, database is CAplus.

A sequential reductive coupling process promoted by samarium(II) iodide is described. Cascade epoxide ring opening and two sequential radical cyclizations lead to a variety of bicyclo[m.n.0] systems as mixtures of diastereomers. The cyclization of epoxide I gave II in 62% yield.

Tetrahedron 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, COA of Formula: C7H13BrSi.

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

Kim, Duk-Ki published the artcileSimple bromination of activated arenes by IBX amide resin and tetraethylammonium bromide, Related Products of bromides-buliding-blocks, the publication is Synlett (2005), 279-282, database is CAplus.

A mild and operationally simple method of brominating activated aromatic compounds using a polymer supported IBX reagent (IBX amide resin) and tetraethylammonium bromide (TEAB) was developed. The activated aromatics, when reacted with IBX amide resin in the presence of TEAB, were easily converted into the brominated aromatics in high yields at room temperature

Synlett published new progress about 1998-61-4. 1998-61-4 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzene,Phenol, name is 4-Bromo-2,3,5,6-tetrafluorophenol, and the molecular formula is C6HBrF4O, Related Products of bromides-buliding-blocks.

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

Chen, Hsiu-Hui published the artcileSelf-assembling discotic materials with low symmetry for organic photovoltaics, Category: bromides-buliding-blocks, the publication is Journal of Molecular Liquids (2022), 118868, database is CAplus.

Three new discotic liquid crystalline (DLC) penta(phenylethynyl)benzene derivatives (HSC0X, X = 1-3) in nonchiral, homogeneously chiral, and racemic conformations were used as smart dopants between poly[[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b]dithiophene-2,6-diyl][s-fluoro-2-[2-ethylhexyl]carbonyl]thirno[3,4-b]thiophene- diyl](PTB7) and [6,6]-phenyl-C71-butyric acid Me ester (PC71BM) which can achieve one-dimensional (1D) charge transportation for organic solar cells (OSCs). All HSC0X exhibits columnar rectangular phase stability over a reasonably broad temperature and is characterized by powder X-ray anal. and polarized optical microscopy (POM). The thermal imaging revealed the best homogeneity of heat distribution for devices PTB7:PC71BM:HSC0X ternary active layer with resistance value 26.4-53.5 Ω. The resulting power conversion efficiency (PCE) values were strongly dependent on the mol. conformation and specific amount of the dopants in an active layer. A narrow band gap at 1.01 eV was found for the nonchiral discotic material (HSC01) as well as a low-lying HOMO (HOMO) energy level of ∼ -5.34 eV and the best PCE of 3.02%.

Journal of Molecular Liquids published new progress about 143-15-7. 143-15-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromododecane, and the molecular formula is C12H25Br, Category: bromides-buliding-blocks.

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

King, F. E. published the artcileStructures of some supposed 2,4-azetidinediones. III. The “alloxan-5-o-dimethylaminoanil” of Rudy and Cramer, and its alkali hydrolysis product, Safety of 4-Bromo-N-methyl-2-nitroaniline, the publication is Journal of the Chemical Society (1951), 3080-5, database is CAplus.

o-Me₂NC₆H₄NH₂ (I) and BzH yield N-benzylidene-o-dimethylaminoaniline (II), viscous yellow oil, absorption maximum at 248 mμ, min. at 231 mμ (ε 16,500 and 13,100); cold dilute mineral acid yields BzH. I and alloxan-H₂O (III), by the method of Rudy and Cramer (C.A. 32, 7041.6), yield 15% 1,1′,2,2′,3,3′,4,4′,5,6-decahydro-4′-methyl-[spiropyrimidine-5,2′-quinoxaline]-2′,4′,6′-trione (IV), C₁₂H₁₂N₄O₃, yellow, m. 250° (decomposition), absorption maximum at 217, 250, and 306 μ (ε 36,540, 7520, and 4500) and min. at 242 and 283 mμ (ε 7250 and 2275); IV results in 19% yield from the reactants in aqueous EtOH (3 days at room temperature) in the presence of a few drops of concentrated HCl; CH₂N₂ gives the di-N-Me derivative (V), C₁₄H₁₆N₄O₃, pale yellow, m. 194°, absorption maximum at 218, 250, and 306 mμ (ε 40,000, 7710, and 5030) and min. at 246 and 282 mμ (ε 7400 and 2280); V yields an Ac derivative, C₁₆H₁₈N₄O₄, m. 288°. III is the alloxan-5-o-dimethylaminoanil (VI) of R. and C. [Ann. 333, 37 (1904)]. p-Me₂NC₆H₄NH₂ and III in boiling EtOH give the p-isomer of VI, a nearly black powder, absorption maximum at 256 and 405 mμ (ε 26,400 and 7500) and min. at 225, 355, and 440 mμ (ε 13,240, 3820, and 5220). IV, boiled with 30% aqueous NaOH, gives 1,2,2′,3,4,4′-hexahydro -2′,4′-dioxo-4-methylglyoxalino [1′,5′:1,2]quinoxaline (VII), m. 240°; CH₂N₂ gives the 3′,4-di-Me analog (VIII) of VII, m. 154°, absorption maximum at 218, 260, and 307 mμ (ε 26,500, 8600, and 4700) and min. at 248 and 284 mμ (ε 7590 and 1930); picrate, chocolate-brown, m. 133°, unstable. VII was designated by R. and C. as mesoxalimide. VI and VII have a high degree of acid stability (cf. behavior of II) and the stability of VII to 50% aqueous NaOH or concentrated HCl argues against the proposed formulas of R. and C.; the p-isomer of VI is decomposed by acid. o-O₂ NC₆H₄NMeSO₂C₆H₄Me-p on reduction over Raney Ni at 20°/6 atm., gives 94% N-(o-aminophenyl)-N-methyl-p-toluenesulfonamide (IX), m. 107-8°. IX (62 g.), 37 g. ClCH₂CONHCO₂Et, and 27.7 g. PhNMe₂, heated 6 hrs. at 120-30°, give 45% 1-[o-(N-methyl-p-tolylsulfonamido)phenyl]hydantoin (X), m. 268-70°, largely unchanged after 14 hrs. at room temperature with 90% H₂SO₄. The use of EtOH in the above reaction gives a poor yield of X, together with 8.5% N-[o-(N-methyl-p-tolylsulfonamido)phenyl]glycine Et ester, m. 150°. X, heated 1 hr. on a steam bath with H₂SO₄ in AcOH, gives 85% 1-(o-methylaminophenyl)hydantoin (XI), m. 224-6°; CH₂N₂ gives the 3-Me derivative (XII), m. 153-4°. X and MeI in Me₂CO containing K₂CO₃, refluxed 36 hrs., give the 3-Me derivative, m. 134-5°; hydrolysis yields XII (Ac derivative, m. 187-8°). XI (4 g.), 17.5 g. HCO₂Et, and 0.4 g. Na, heated 2 hrs. on a steam bath, give 85% 1,2′,4,4’tetrahydro-2′,4′-dioxo-3′,4-dimethylglyoxalino[1′,5′:1,2]quinoxaline (XIII), orange-yellow, m. 260°; XIII is not reduced by Na in boiling EtOH or catalytically. XIII (1.4 g.) in 20 cc. AcOH and 100 cc. concentrated HCl, heated 3 hrs. on a steam bath while 25 g. granulated Sn is added, and the filtrate (cooled in ice H₂O) basified with 40% NaOH, gives 47% VIII (picrate, chocolate-brown, m. 133°). XI, HCO₂Et, and Na, heated on the steam bath 1 hr. and kept 14 hrs., give 44% unchanged XI and 28% 1,2′,4,4’tetrahydro-2′,4′-dioxo-4-methylglyoxalino[1′,5′:1,2]quinoloxaline, yellow, m. 270°; reduction with Sn and HCl gives VII. XII (2 g.), 20 cc. AcOEt, and 0.4 g. Na, heated 5 hrs. on the steam bath, give 47% unchanged XII and 1,2′,4,4’tetrahydro-2′,4′-dioxo-3,3′,4-trimethylglyoxalino[1′,5′:1,2]quinoxaline, yellow, m. 190-1°. XII does not react with BzOEt and Na. BrCH₂CO₂Et (62 g.) and 103 g. o-O₂NC₆H₄NH₂ (XIII), heated 4.5 hrs. at 120-35°, give 52 g. XIII.HBr and 60% N-(o-nitrophenyl)glycine Et ester (XIV), yellow, m. 77-8°; XIV does not react with ClCO₂Et (alone or with C₅H₅N); evaporation of XIV with concentrated HCl gives 90% o-O₂NC₆H₄NHCH₂CO₂H, m. 190°. The acid or its ester did not yield (o-nitrophenyl)hydantoin. 3,4-Me₂C₆H₃NH₂ (XV) (43 g.) and 20 g. ClCH₂CO₂Et, heated 1 hr. at 100°, give 67.5% N-(3,4-dimethylphenyl)glycine Et ester (XVI), m. 49-50°. XV (21.2 g.) and 14.5 g. ClCH₂CONHCO₂Et give 70% 1-(3,4-dimethylphenyl)hydantoin (XVII), m. 206-7°; it results also from XVI and CO(NH₂)₂ at 150-60°. XVII with MeI and K₂CO₃ in Me₂CO give 79% of the 3-Me derivative (XVIII), m. 169-70°; CH₂N₂ gives the same product. XVIII and HNO₃-H₂SO₄ (10 min. at 0°) give 34% of a diNO₂ derivative, m. 226°; XVIII and HNO₃ in AcOH (14 hrs. at room temperature) give 10% of a mono-NO₂ derivative, pale yellow, m. 130-2°. o-O₂NC₆H₄NH₂ and BrCH₂COCO₂Et (4 hrs. at 120-30°) give 35% 4,2-Br(O₂N)C₆H₃NH₂ (XIX); 7.5 g. XIII and 13.2 g. HO₂CCOCHBrCO₂Et (4 hrs. at 130-5°) give 5 g. XIX.

Journal of the Chemical Society published new progress about 53484-26-7. 53484-26-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Nitro Compound,Amine,Benzene, name is 4-Bromo-N-methyl-2-nitroaniline, and the molecular formula is C7H7BrN2O2, Safety of 4-Bromo-N-methyl-2-nitroaniline.

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

Clive, Derrick L. J. published the artcileRadical cyclizations of geminal radical precursors, Recommanded Product: (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1991), 3263-70, database is CAplus.

Polycyclic structures, e.g., I (R = SiMe₃, SiPh₂Me), can be generated by double radical cyclization, using compounds, e.g., (RCCCH₂CH₂)₂C(OH)CHCl₂, having two groups, capable of being homolyzed, attached to a single carbon that is suitably located with respect to two unsaturated pendants.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) 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

Gotchev, Dimitar B. published the artcileSynthetic Studies Toward (-)-FR901483 Using a Conjugate Allylation To Install the C-1 Quaternary Carbon, Safety of (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is Journal of Organic Chemistry (2006), 71(25), 9393-9402, database is CAplus and MEDLINE.

Two approaches to the aza-tricyclo dodecane skeleton of (-)-FR901483 are reported. Both routes utilized a Grignard addition to an N-acylpyridinium salt, e.g. from 4-methoxypyridine and PhOCOCl, to establish the absolute stereochem. at C-6 and a highly diastereoselective conjugate allylation reaction to form the quaternary center at C-1 of the natural product in an excellent yield. Although the desired polysubstituted piperidine intermediates, e.g. I, were prepared regio- and stereoselectively, the construction of the C-8/C-9 bond connectivity could not be achieved. All attempts at a pinacol cyclization or an intramol. 6-exo-tet epoxide opening were unsuccessful because of an unfavorable A^(1,3) strain inherent in the mol.

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, Safety of (4-Bromobut-1-yn-1-yl)trimethylsilane.

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

Fujii, Akira published the artcileProbiotics. Antistaphylococcal and antifibrinolytic activities of ω-amino- and ω-guanidinoalkanesulfonic acids, HPLC of Formula: 55788-44-8, the publication is Journal of Medicinal Chemistry (1975), 18(5), 502-5, database is CAplus and MEDLINE.

A series of 5 H2N(CH2)nSO3H (I, n = 1-5) was prepared by reacting the dibromoalkane with Na2SO3 followed by NH4OH, while the guanidino analogs (II, n = 2-5) were prepared from the corresponding I by reaction with S-ethylisothiourea sulfate [22722-03-8]. All 9 compounds significantly protected mice against Staphylococcus aureus, but did not inhibit growth of S. aureus in vitro, while most of I had antifibrinolytic activity. δ-Aminobutanesulfonic acid (I, n = 4) [14064-34-7] had significantly greater antistaphylococcal activity than γ-aminobutyryl-L-histidine [3650-73-5], and had antifibrinolytic activity equal to ε-aminohexanoic acid [60-32-2]. None of II had antifibrinolytic activity. Structure-activity relations are discussed.

Journal of Medicinal Chemistry published new progress about 55788-44-8. 55788-44-8 belongs to bromides-buliding-blocks, auxiliary class Bromide,Salt,Aliphatic hydrocarbon chain,Aliphatic hydrocarbon chain, name is Sodium 3-bromopropane-1-sulfonate, and the molecular formula is C3H6BrNaO3S, HPLC of Formula: 55788-44-8.

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

Steward, Kimberly M. published the artcileAsymmetric Synthesis of Diverse Glycolic Acid Scaffolds via Dynamic Kinetic Resolution of α-Keto Esters, Synthetic Route of 69361-41-7, the publication is Journal of the American Chemical Society (2012), 134(49), 20197-20206, database is CAplus and MEDLINE.

The dynamic kinetic resolution of α-keto esters via asym. transfer hydrogenation has been developed as a technique for the highly stereoselective construction of structurally diverse β-substituted-α-hydroxy carboxylic acid derivatives Through the development of a privileged m-terphenylsulfonamide for (arene)RuCl(monosulfonamide) complexes with a high affinity for selective α-keto ester reduction, excellent levels of chemo-, diastereo-, and enantiocontrol can be realized in the reduction of β-aryl- and β-chloro-α-keto esters.

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 C6H8O6, Synthetic Route of 69361-41-7.

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

Steward, Kimberly M. published the artcileAsymmetric Synthesis of Diverse Glycolic Acid Scaffolds via Dynamic Kinetic Resolution of α-Keto Esters [Erratum to document cited in CA158:36961], Recommanded Product: (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is Journal of the American Chemical Society (2015), 137(11), 3991, database is CAplus and MEDLINE.

In follow up experiments the authors discovered errors in analyzing the unpurified ¹H NMR spectra, which led to incorrect reporting of the crude diastereomer ratios for the lactone products; the correct ratios are given and an alternative exptl. procedure is presented that generally results in improved stereoselectivity.

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 C16H20N2, Recommanded Product: (4-Bromobut-1-yn-1-yl)trimethylsilane.

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

Chretien, Jacques R. published the artcileSolvation and steric effects on electrophilic reactivity of ethylenic compounds. 3. Stereo-, regio-, and chemoselectivity of alkene bromination in methanol, Formula: C6H12Br2, the publication is Journal of Organic Chemistry (1993), 58(7), 1917-21, database is CAplus.

The stereo-, regio- and chemoselectivities of the bromination of 30 alkenes bearing 1-3 alkyl groups (Me, Et, Pr, iso-Pr, tert-Bu, neopentyl) were investigated in methanol containing 0.2 M NaBr at 25° under kinetic conditions. The reaction of cis– and trans-alkenes, RC_αH:C_βHR’, with R more electron-donating than R’, is stereospecific, in agreement with the occurrence of a bromonium ion intermediate. Methanol and bromide ion trap the bridged ion anti with respect to the bridging bromine atom, independently of the crowding of the double bond. In contrast to the usual belief, the anti-Markovnikov regioselectivity of attack by methanol is always favored, even in the absence of bulky substituents; the better a donor R is, the more the nucleophile attacks C_β. The chemoselectivity dependence on the double-bond substituents is also unexpected; dibromide formation increases with respect to that of methoxy bromide as electron-donation by R and R’ increases, although the increasing carbocationic character of the carbon atoms of the bridged ion should favor trapping of the intermediate by methanol. Analogous trends for the regio- and chemoselectivity dependence on the substituents are observed in the bromination of monosubstituted alkenes, RCH:CH₂, via bromonium ions. These results are attributed to a decrease in the pos. charge densities on the carbon atoms of the bridged ions when the ability of the donor substituents to delocalize charge increases. gem-Disubstituted alkenes, RR’C:CH₂, and trimethylethylene behave differently as regards the regio- and chemoselectivity. They react 100% Markovnikov and chemoselectively (about 80%) in favor of attack by methanol. It is shown that these selectivities agree fairly well with highly dissym. bromonium ions as intermediates in the bromination of these alkenes.

Journal of Organic Chemistry published new progress about 594-81-0. 594-81-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 2,3-Dibromo-2,3-dimethylbutane, and the molecular formula is C6H12Br2, Formula: C6H12Br2.

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