Tag: M.W=150-200

Zhang, Huihui published the artcileHeterocyclization reagents for rapid assembly of N-fused heteroaromatic compounds from alkenes, Product Details of C4H6BrFO2, the publication is Angewandte Chemie, International Edition (2021), 60(7), 3714-3719, database is CAplus and MEDLINE.

N-Fused heterocycles are of particular use and upmost importance in multiple fields. Herein, we disclose a conceptually new approach for the rapid assembly of N-fused heteroaromatic compounds from alkenes. A portfolio of strategically designed heterocyclization reagents are readily prepared for the cascade reaction. A plethora of N-fused heteroaromatic compounds including seven types of heterocyclic core are furnished. The protocol features a broad functional-group compatibility and high product diversity, and provides a practical tool for late-stage heteroaryl compound elaboration.

Angewandte Chemie, International Edition 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 C6H13BO3, Product Details of C4H6BrFO2.

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

Li, Kejie published the artcileFull-spectrum fluoromethyl sulfonation via modularized multicomponent coupling, Recommanded Product: Ethylbromofluoroacetate, the publication is CCS Chemistry (2022), 4(5), 1526-1534, database is CAplus.

Modular free-assembly construction of mono-, di-, and tri-fluoromethyl sulfones was comprehensively achieved by a combination of halides, a sulfur dioxide surrogate, and halofluorocarbons. The industrial raw material thiourea dioxide served as the sulfur dioxide source, combined with readily available fluorocarbon sources such as 2-bromo-2-fluoroacetate and chlorodifluoromethane employed as fluoromethyl reagents. Notably, four Me sulfone-containing pharmaceuticals were modified into three types of fluoromethyl sulfones, displaying their great potential for drug discovery via the current strategy. Mechanistic studies further demonstrated that C-F···H-N interactions between thiourea dioxide and halofluorocarbons play a key role in stabilizing monofluoromethyl electrophiles and difluorocarbene species.

CCS 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 C4H6BrFO2, Recommanded Product: Ethylbromofluoroacetate.

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

Slegel, P. published the artcileEnantiomeric separation of chiral carboxylic acids, as their diastereomeric carboxamides, by thin-layer chromatography, Product Details of C4H7BrO2, the publication is Journal of Pharmaceutical and Biomedical Analysis (1987), 5(7), 665-73, database is CAplus and MEDLINE.

A thin-layer chromatog. (TLC) method is described for the enantiomeric separation of chiral carboxylic acids using chiral derivatization and nonchiral TLC conditions (ordinary plates and mobile phases) to sep. the diastereomeric carboxamides obtained. New chiral derivatizing agents, “levobase” (1R, 2R)-(-)-1-(4-nitrophenyl)-2-amino-1,3-propanediol, and “dextrobase” (the enantiomer of levobase) are used for carboxamide formation in the presence of dicyclohexylcabodiimide as coupling agent. The procedure is very simple and convenient to carry out. Good resolution is obtained for a wide range of carboxylic acid enantiomeric pairs containing 1 to 2 chiral centers.

Journal of Pharmaceutical and Biomedical Analysis published new progress about 56970-78-6. 56970-78-6 belongs to bromides-buliding-blocks, auxiliary class Bromide,Carboxylic acid,Aliphatic hydrocarbon chain,Inhibitor, name is 3-Bromo-2-methylpropanoic acid, and the molecular formula is Al2H32O28S3, Product Details of C4H7BrO2.

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

Depre, Dominique published the artcileOrigin of the E/Z Selectivity in the Synthesis of Tetrasubstituted Olefins by Wittig Reaction of α-Fluorophosphonium Ylides: An Explanation for the Low Stereoselectivity Observed in Reactions of α-Alkoxy Aldehydes, Application In Synthesis of 401-55-8, the publication is Organic Letters (2017), 19(6), 1414-1417, database is CAplus and MEDLINE.

A series of tetrasubstituted fluoroalkenes were synthesized in good yield and high E/Z selectivity (up to 96/4) by Wittig reaction between α-heterosubstituted ketones and α-fluorophosphonium ylides. A detailed study of factors that control stereoselectivity in these reactions shows that stereoselectivity is the result of stabilizing CH···F and N···C=O interactions in the addition TS leading to the E isomer. This anal. provides a rationale for the observed decrease in selectivity for reactions of stabilized ylides with α-alkoxy aldehydes.

Organic Letters 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, Application In Synthesis of 401-55-8.

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

Lednicer, Daniel published the artcile4-Amino-4-arylcyclohexanones and their derivatives: a novel class of analgesics. 2. Modification of the carbonyl function, Quality Control of 18928-94-4, the publication is Journal of Medicinal Chemistry (1981), 24(4), 404-8, database is CAplus and MEDLINE.

The cyclohexanols I (R = H, alkyl, alkenyl, alkynyl, PhCH₂, PhCH₂CH₂, etc.; R¹ = H, Cl, Br, Me), prepared by the reduction of or addition of nucleophiles to the corresponding cyclohexanones, were separated into cis and trans isomers and tested for analgesic activity. The trans (OH and N) isomers were invariably more potent than the cis. I (R = PhCH₂CH₂) are among the most potent opioids reported to date; possibly the ring system may be providing an addnl. binding site for these compounds, and thus greatly enhance their affinity for the opioid receptor.

Journal of Medicinal Chemistry published new progress about 18928-94-4. 18928-94-4 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic cyclic hydrocarbon, name is (2-Bromoethyl)cyclopentane, and the molecular formula is C7H13Br, Quality Control of 18928-94-4.

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

Cain, Caitlin N. published the artcileTile-Based Pairwise Analysis of GC x GC-TOFMS Data to Facilitate Analyte Discovery and Mass Spectrum Purification, Recommanded Product: 1-Bromooctane, the publication is Analytical Chemistry (Washington, DC, United States) (2022), 94(14), 5658-5666, database is CAplus and MEDLINE.

A new tile-based pairwise anal. workflow, termed 1v1 anal., is presented to discover and identify analytes that differentiate two chromatograms collected using comprehensive two-dimensional (2D) gas chromatog. coupled with time-of-flight mass spectrometry (GC x GC-TOFMS). Tile-based 1v1 anal. easily discovered all 18 non-native analytes spiked in diesel fuel within the top 30 hits, outperforming standard pairwise chromatog. analyses. However, eight spiked analytes could not be identified with multivariate curve resolution-alternating least-squares (MCR-ALS) nor parallel factor anal. (PARAFAC) due to background contamination. Analyte identification was achieved with class comparison enabled-mass spectrum purification (CCE-MSP), which obtains a pure analyte spectrum by normalizing the spectra to an interferent mass channel (m/z) identified from 1v1 anal. and subtracting the two spectra. This report also details the development of CCE-MSP assisted MCR-ALS, which removes the identified interferent m/z from the data prior to decomposition In total, 17 out of 18 spiked analytes had a match value (MV) > 800 with both versions of CCE-MSP. For example, MCR-ALS and PARAFAC were unable to decompose the pure spectrum of Me decanoate (MVs < 200) due to its low 2D chromatog. resolution (~0.34) and high interferent-to-analyte signal ratio (~30:1). By leveraging information gained from 1v1 anal., CCE-MSP and CCE-MSP assisted MCR-ALS obtained a pure spectrum with an average MV of 908 and 964, resp. Furthermore, tile-based 1v1 anal. was applied to track moisture damage in cacao beans, where 86 analytes with at least a 2-fold concentration change were discovered between the unmolded and molded samples. This 1v1 anal. workflow is beneficial for studies where multiple replicates are either unavailable or undesirable to save anal. time.

Analytical Chemistry (Washington, DC, United States) published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C8H17Br, Recommanded Product: 1-Bromooctane.

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

Bugera, Maksym published the artcileDeoxofluorination of Aliphatic Carboxylic Acids: A Route to Trifluoromethyl-Substituted Derivatives, Name: 3-Bromo-2-methylpropanoic acid, the publication is Journal of Organic Chemistry (2019), 84(24), 16105-16115, database is CAplus and MEDLINE.

A practical method for the synthesis of functionalized aliphatic trifluoromethyl-substituted derivatives from aliphatic acids was developed. The transformation proceeds with sulfur tetrafluoride in the presence of water as a key additive. Compared to previous methods, the reaction gives products with full retention of stereo- and absolute configuration of chiral centers.

Journal of Organic Chemistry published new progress about 56970-78-6. 56970-78-6 belongs to bromides-buliding-blocks, auxiliary class Bromide,Carboxylic acid,Aliphatic hydrocarbon chain,Inhibitor, name is 3-Bromo-2-methylpropanoic acid, and the molecular formula is C4H7BrO2, Name: 3-Bromo-2-methylpropanoic acid.

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

Pilat, S. published the artcileFormation of cyclopentylalkanesulfonates, Product Details of C7H13Br, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1939), 1527-31, database is CAplus.

The Na naphthenesulfonates obtained from natural naphthenic acids through the naphthenyl alcs. and chlorides (C. A. 32, 8753.5) are characterized by their excellent foaming and wetting properties in aqueous solution For comparison with these substances, whose structure has not been fully cleared up, P. and T. undertook the preparation of some cyclic sulfonates (chiefly cyclopentane derivatives, since the naphthenic acids in petroleums are for the most part derived from cyclopentane) in which the sulfonic acid is in primary combination, i. e., as CH₂SO₃H. The starting point for the preparation of sulfonates with a straight alkyl chain, C₅H₉(CH₂)_nSO₃Na (n = 2, 4 or 7) was cyclopentanol, which was converted with boiling concentrated HCl and CaCl₂ into the chloride (87% yield); this through the Grignard reagent with HCHO gave the carbinol, C₅H₉CH₂OH, which, in turn, was converted into the chloride. 2-Cyclopentylethanol (I) and 4-cyclopentylbutanol (II), as also 2-menthylethanol (III), were prepared by the Grignard method for introducing CH₂.CH₂ chains: RMgBr + CH₂.CH₂.O → RCH₂CH₂OMgBr. Chains of 3 CH₂ groups were introduced by treating Grignard compounds with p-MeC₆H₄SO₃(CH₂)₃Cl (IV) or with trimethylene oxide; in this way (7-chloroheptyl)cyclopentane (V) was prepared from C₅H₉(CH₂)₄Br and II from C₅H₉CH₂Cl. For the preparation of sulfonates with a branched chain fenchone was used, which was converted by KOH at 240° into fencholic acid (VI). Reduction of the Et ester of VI gave fencholyl alc. (VII), converted with PCl₅ into the chloride, which with Na₂SO₃ gave 50% Na fencholylsulfonate and, through fencholylmalonic acid, yielded fencholylacetic acid (VIII). Reduction of the Et ester of VIII, conversion of the 2-fencholylethanol (IX) into the chloride and subsequent Strecker reaction yielded Na fencholylethanesulfonate (50% yield), very hygroscopic. Investigation of aqueous solutions of the Na salts so obtained, which will be described in detail later, showed, among other things, that sulfonates in which a cyclopentane ring carries small alkyl groups are characterized by an especially high degree of surface activity and in this respect surpass both cyclopentanes with a long side chain and alkylated cyclohexanes. I, b₁₁ 85°, was obtained in 45% yield by a modification of the Yohe and Adams method (C. A. 22, 2148). Chloride (71% from I and 1.1 mols. PCl₅ refluxed 2 h. in petr. ether), b₆₀ 85-6°, d₄²⁰ 0.955, n_D²⁰ 1.4527; 26.5 g. heated 8 h. at 200° with 80 g. crystallized Na₂SO₃ in an autoclave, with stirring, gave 39 g. (97.5%) Na 2-cyclopentylethanesulfonate, silvery non-hygroscopic needles. (2-Bromoethyl)cyclopentane (71.2% from I heated 2.5 h. with HBr-concentrated H₂SO₄), b₁₉ 77°, d₄²⁰ 1.290, n_D²⁰ 1.4865; its Grignard reagent with ethylene oxide gave 68% II, b₂ 87-92°, n_D²⁰ 1.4610, d₄²⁰ 0.903 (from C₅H₉CH₂Cl and trimethylene oxide the yield was only 5%). (4-Bromobutyl)cyclopentane (90% from II with HBr-H₂SO₄), b₁₇ 110-11°, n_D²⁰ 1.4820, d₄²⁰ 1.187, gives with Na₂SO₃ after 8 h. at 160° in a rotating autoclave Na 4-cyclopentylbutanesulfonate. V (10% from C₅H₉(CH₂)₄Br and IV), b. 120-5°; Na 7-cyclopentylheptanesulfonate, strongly hygroscopic. Menthyl bromide (80% from menthol and HBr-H₂SO₄), b₁₃ 105.5°, d₄²⁰ 1.162, n_D²⁰ 1.4852. III (20%), b₁₀ 132-6°; chloride (35%), b₁₀ 120-5°; Na 2-menthylethanesulfonate. VII (84.5%), b₁₀ 96.5°, [α]_D 8.6°; chloride, b₉ 84°, d₄^21.5 0.949, n_D¹⁷ 1.4702. VIII (46%), b₁₀ 165-6°; Et ester, b₁₀ 146-8°. IX (5% from the Grignard compound of fencholyl chloride with ethylene oxide, or 76% by reduction of the Et ester of VIII with Na in absolute alc.), b₁₀ 134-5°, n_D¹⁸ 1.4761; chloride (65%), b₁₀ 120-6°.

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 18928-94-4. 18928-94-4 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic cyclic hydrocarbon, name is (2-Bromoethyl)cyclopentane, and the molecular formula is C7H13Br, Product Details of C7H13Br.

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

Fang, Jason published the artcileBiocatalytic Asymmetric Construction of Secondary and Tertiary Fluorides from β-Fluoro-α-Ketoacids, Recommanded Product: Ethylbromofluoroacetate, the publication is Angewandte Chemie, International Edition (2022), 61(21), e202201602, database is CAplus and MEDLINE.

Fluorine is a critical element for the design of bioactive compounds, driving advances in selective and sustainable fluorination. However, stereogenic tertiary fluorides pose a synthetic challenge and are thus present in only a few approved drugs (fluticasone, solithromycin, and sofosbuvir). The aldol reaction of fluorinated donors provides an atom-economical approach to asym. C-F motifs via C-C bond formation. Authors report that the type II pyruvate aldolase HpcH and engineered variants perform addition of β-fluoro-α-ketoacids (including fluoropyruvate, β-fluoro-α-ketobutyrate, and β-fluoro-α-ketovalerate) to diverse aldehydes. The reactivity of HpcH towards these fluoro-donors grants access to enantiopure secondary or tertiary fluorides. In addition to representing the first synthesis of tertiary fluorides via biocatalytic carboligation, the afforded products could improve the diversity of fluorinated building blocks and enable the synthesis of fluorinated drug analogs.

Angewandte Chemie, International Edition 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, Recommanded Product: Ethylbromofluoroacetate.

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

Tanaka, Hiroki published the artcileHypoiodite-Catalyzed Oxidative Umpolung of Indoles for Enantioselective Dearomatization, Application In Synthesis of 111-83-1, the publication is Journal of the American Chemical Society (2022), 144(13), 5756-5761, database is CAplus and MEDLINE.

Reported the oxidative umpolung of 2,3-disubstituted indoles toward enantioselective dearomative aza-spirocyclization to give the corresponding spiroindolenines using chiral quaternary ammonium hypoiodite catalysis. Mechanistic studies revealed the umpolung reactivity of C3 of indoles by iodination of the indole nitrogen atom. Moreover, the introduction of pyrazole as an electron-withdrawing auxiliary group at C2 suppressed a competitive dissociative racemic pathway and enantioselective spirocyclization proceeded to give not only spiropyrrolidines but also four-membered spiroazetidines that were otherwise difficult to access.

Journal of the American Chemical Society published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C15H16O3, Application In Synthesis of 111-83-1.

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