Tag: M.W=150-200

Heckershoff, Robin published the artcileEfficient Synthesis of Dipyrrolobenzenes and Dipyrrolopyrazines via Bidirectional Gold Catalysis: a Combined Synthetic and Photophysical Study, Category: bromides-buliding-blocks, the publication is Journal of the American Chemical Society (2022), 144(18), 8306-8316, database is CAplus and MEDLINE.

A straightforward synthesis to access meta/para-dipyrrolobenzenes I [R = R¹ = Ph, 2-naphthyl, 4-MeOC₆H₄, etc.; R³ = R⁴ = H, n-octyl], II [R⁵ = R⁶ = H, Ph, 2-H₂NC₆H₄, 2-BrC₆H₄] and para-dipyrrolopyrazines III [R⁷ = R⁸ = TIPS, Ph] in high yields using a bidirectional gold-catalyzed cyclization strategy. The versatility of reaction protocol was showcased by preparing dipyrroloarenes with different substituents, various functional groups, and in a multitude of substitution patterns. Furthermore, the dipyrroloarenes could be post-modified by N-alkylation to improve the solubility or bromination to yield precursors for further derivatization via cross-coupling. Investigation of the photophys. properties of the-mostly unprecedented-dipyrroloarenes I, II, III and dialkyne precursors were identified strong blue emitters such as the di-Ph meta-dipyrrolobenzene with a quantum yield of 98%. Moreover, changes in the solvent polarity or interactions with Lewis acids such as borane could be used to fine-tune the photophys. properties of the fluorophores.

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 C8H17Br, Category: bromides-buliding-blocks.

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

Burschkies, Karl published the artcileThe importance of cyclic acids and alcohols for the chemotherapy of leprosy, Application In Synthesis of 18928-94-4, the publication is Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft (1943), 328-36, database is CAplus.

New cyclopentyl derivatives are prepared and their effect on rat leprosy is examined Refluxing 23 g. Na, 130 g. AcCH₂CO₂Et in 500 cc. xylene, and 149 g. freshly distilled cyclopentyl bromide for 20 hrs. at 140° gives Et cyclopentaneacetoacetate (I), b₁₂ 120-2°, n²⁰_D 1.4646. Refluxing 198 g. of I with 23 g. Na in 600 cc. absolute alc. for several hrs. gives Et cyclopentaneacetate (II), b₁₂ 74-5°, n²⁰_D 1.4357. II (156 g.) in 1200 cc. absolute alc. treated with 100 g. Na gives cyclopentaneëthanol (III), b₁₃ 80-1°, n¹⁹_D 1.4572. Saponification of II during the previous reaction transforms part of it into cyclopentaneacetic acid (IV) which is isolated by acidifying, shaking with Et₂O, washing and drying over Na₂SO₄, b₁₃ 119-20°, n¹⁹_D 1.4527. Treating IV with SOCl₂ at 0°, heating to 70° for 1/2 hr., and distilling off the SOCl₂ gives cyclopentaneacetyl chloride, b₁₂ 60°, which is reacted with hydnocarpic alc. to form hydnocarpyl cyclopentaneacetate (V), b_0.02 205-10°, n²⁰_D 1.4720. Adding PBr₃ to III in toluene gives 2-cyclopentylethyl bromide (VI), b. 78-9°, n²⁰_D 1.4866. After combining finely powd. Na with CH₂(CO₂Et)₂ in xylene solution VI is added. By refluxing for 24 hrs. at 130° di-Et (2-cyclopentylethyl)malonate (VII) is formed, b₁₃ 158-60°, n²²_D 1.4470. By saponification of VII (2-cyclopentylethyl)malonic acid, m. 120°, and by subsequent decarboxylation at 15 mm. and 200° cyclopentanebutyric acid (VIII), b_0.0-80.1 115-17°, n²⁰_D 1.4579, are formed. By heating VIII with benzyl alc. in a N atm. for 6 hrs. at 160-80°, taking up with Et₂O, and shaking with 4% KOH benzyl cyclopentanebutyrate, b_0.05, 138-40°, n²¹_D 1.5248, is formed. Esterification of VIII with EtOH gives the Et ester (IX), b_0.08 75°, n²⁰_D 1.4433. By reduction of IX with Na and absolute alc. cyclopentanebutanol (X), b₁₂ 109-10°, n²²_D 1.4610, is formed. Reacting X in toluene with freshly distilled PBr₃ gives 4-cyclopentylbutyl bromide (XI), b₁₅ 107°, n²²_D 1.4815, which gives with CH₂(CO₂Et)₂ and Na di-Et(4-cyclopentylbutyl)malonate (XII), b_0.1 140-2°, n²²_D 1.4494. By saponification of XII (4-cyctopentylbutyl)malonic acid, m. 125-6°, and by further decarboxylation cyclopentanecaproic acid (XIII), b_0.1 133°, m. 36-7°, are formed. By heating XIII in N for 4 hrs. with benzyl alc. to 190-200° the benzyl ester, b_0.1 163°, n²¹_D 1.5010, is obtained. Esterification of XIII with EtOH gives the Et ester, b₁₂ 136-7°, n²²_D 1.4462, which is reduced by Na to cyclopentanehexanol (XIV), b₁₂ 130-2°, n²⁰_D 1.4630. Esterification of III, X, XIV with PhCH:CHCOCl gives 2-cyclopentylethyl cinnamate, b_0.1 188°, n²⁰_D 1.5521, 4-cyclopentylbutyl cinnamate, b_0.1 190°, n_21D 1.5428, 6-cyclopentylhexyl cinnamate, b_0.0 190°, n_20D 1.5372. The study of the therapeutic effect of cyclopentyl compounds shows that compounds with over 3 CH₂-groups are effective on rat leprosy. The cyclopentyl compounds are better tolerated than the corresponding cyclopentenyl compounds The cinnamic esters of III, X, XIV show a very good therapeutic effect on rat leprosy.

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 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, Application In Synthesis of 18928-94-4.

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

Sharma, Vinay S. published the artcileUpper/lower rim functionalized calixarene based AIE-active liquid crystals with self-assembly behavior: Photophysical and electrochemical studies, Formula: C8H17Br, the publication is Journal of Molecular Liquids (2022), 118047, database is CAplus.

Four novel bowl-shaped aggregation-induced emission (AIE)-active liquid crystalline compounds based on calix[4]arene having upper/lower unit functionalized by amide group and carrying six peripheral alkoxy chains, I (R = n-Bu, n-hexyl, n-octyl, n-decyl), were prepared Their mesogenic, electrochem., and photoactive properties were extensively examined X-ray diffraction (XRD) studies showed columnar type self-assembly behavior of I possessing alkyl chains of varying lengths with D-A-π-D systems. The thermal study of all the materials was examined by DSC and TGA anal. Their electrochem. studies were identified by cyclic voltammetry. The synthesized materials showed light blue emission in solution as well as thin-film under long UV light. The supramol. amide-thiadiazole linked compounds displayed enantiotropic columnar mesophase with good thermal stability. This new class of upper functionalized three-dimensional supramol. materials exhibited AIE and stabilized the columnar hexagonal phase with a higher temperature range.

Journal of Molecular Liquids 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 C13H9FO2, Formula: C8H17Br.

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

Wan, Yimei published the artcilePhotocatalytic 1,1-Hydrofluoroalkylation of Alkynes with a Concurrent Vicinal Acylation: An Access to Fluoroalkylated Cyclic Ketones, Category: bromides-buliding-blocks, the publication is Organic Letters (2019), 21(11), 4187-4191, database is CAplus and MEDLINE.

A visible-light-induced 1,1-hydrofluoroalkylation of alkynes with a concomitant vicinal acylation is developed using THF (THF) as the hydrogen atom source. Various fluoroalkylated cyclic ketones, such as indanones, chroman-4-ones, 2,3-dihydroquinolin-4(1H)-ones, and 3,4-dihydronaphthalen-1(2H)-ones, can be efficiently synthesized with excellent trans-diastereoselectivity. The reaction represents the first example of 1,1-hydrofluoroalkylation of alkynes, thus providing a novel method for the construction of fluoroalkanes.

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 C19H21N3O3S, Category: bromides-buliding-blocks.

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

Goryaev, M. I. published the artcileSynthesis of cyclopentane carbocylic acids, HPLC of Formula: 18928-94-4, the publication is Trudy Instituta Khimicheskikh Nauk, Akademiya Nauk Kazakhskoi SSR (1967), 77-87, database is CAplus.

C5H9 = cyclopentyl throughout this abstract A homologous series of cyclopentanecarboxylic acids of the general type I was synthesized and their ir spectra studied. Grignard reaction between C5H9Br and CO2 yielded 45% I (n = 0), b2 83°, n20D 1.4535. Treatment of di-Et Na malonate with C5H9Br gave 60% di-Et cyclopentanemalonate, b3 130-2°, n20D 1.4430, converted into the free acid and decarboxylated to yield I (n = 1), b3 93°, n20D 1.4522. Grignard reagent prepared from 140 g. C5H9Br and 9 g. Mg was treated at -10° with 20 g. ethylene oxide in 35 ml. ether to yield a distillation fraction containing crude C5H9(CH2)2OH, brominated to give 71% C5H9(CH2)2Br, b19 75-7°, n20D 1.4860; treatment with KCN yielded 53% corresponding nitrile, b2-3 62-8°, n20D 1.4500; hydrolysis of this gave 65.4% I (n = 2), b2 96-7°, n20D 1.4563. Condensation of C5H9(CH2)2Br with di-Et Na malonate yielded 30% di-Et (2-cyclopentylethyl)malonate, b2 136-8°, n20D 1.4442, decarboxylation of which gave 90% I (n = 3), b7 145-50°, n20D 1.4518. Cyclopentanebutanol, b2 85-6°, n20D 1.4610, d2020 0.9033; C5H9(CH2)4Br, b17 110-12°, n20D 1.4820, d2020 1.1872; C5H9(CH2)4CN, b17 124-6°, n20D 1.4575; and I (n = 4), b2 124-8°, n20D 1.4595, d2020 0.9752, were obtained from C5H9(CH2)2Br and ethylene oxide as starting materials in 55, 64, 88, and 81% yields, resp. Reaction between C5H9(CH2)4Br and di-Et Na malonate yielded 49.3% di-Et (4-cyclopentylbutyl)malonate, which on decarboxylation gave 69.7% I (n = 5), b2 127-30°, n20D 1.4542, d2020 0.9520. A mixture of air and ozone was passed through a solution of 60 g. Me oleate in AcOEt until neutral to reaction with Br; to the cooled solution 4 g. Zn dust in 2 ml. H2O was added, followed by 36 g. Zn in small portions and 4 ml. H2O on completion of the reaction; the mixture was stirred until neutral to the KI-starch test and worked up to yield 70% Me 8-formyloctanoate (II), b2 113°, n20D 1.4380. Grignard reaction between C5H9(CH2)2Br and II yielded 20% Me 11-cyclopentyl-9-hydroxyundecanoate; C5H9(CH2)4Br and II gave 15% Me 13-cyclopentyl-9-hydroxytridecanoate. Extensive ir data were given.

Trudy Instituta Khimicheskikh Nauk, Akademiya Nauk Kazakhskoi SSR 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, HPLC of Formula: 18928-94-4.

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

Venkateswararao, Eeda published the artcileAnti-proliferative effect of chalcone derivatives through inactivation of NF-κB in human cancer cells, SDS of cas: 18928-94-4, the publication is Bioorganic & Medicinal Chemistry (2014), 22(13), 3386-3392, database is CAplus and MEDLINE.

To investigate the anti-proliferative effect of NF-κB inhibitor, a series of analogs of (E)-1-(2-hydroxy-6-(isopentyloxy)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one were prepared and evaluated for their NF-κB inhibition and anti-proliferative activity against various human cancer cell lines. Compounds (E)-1-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one and (E)-4-(3-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3-oxoprop-1-enyl)benzenesulfonamide showed good NF-κB inhibition as well as potent anti-proliferative activity. SAR studies showed that all the compounds with potent or moderate NF-κB inhibition displayed good anti-proliferative activity. All the analogs maintained a good correlation between their NF-κB inhibition and anti-proliferative activity though the extent is not directly proportional to each other.

Bioorganic & 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 C13H19Br2ClN2O, SDS of cas: 18928-94-4.

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

Kong, Shuai published the artcileFluorescently visualizing the penetration of anionic surfactants across cytoplasmic membrane and the subsequent damage on human cells, Product Details of C8H17Br, the publication is Environmental Science and Pollution Research (2022), 29(14), 20593-20602, database is CAplus and MEDLINE.

The extensive application of chem. synthesized anionic surfactants would cause serious pollution of water and increase health risk to humans. However, the adverse impact of anionic surfactant on human cells has never been systematically demonstrated. In this paper, a series of fluorescent anionic surfactants containing a varying length of alkyl chain from C8 to C18 and a fixed hydrophilic head of 8-hydroxypyrene-1,3,6-trisulfonic acid trisodium salt (HPTS) were synthesized and utilized for visualizing the interaction between surfactants and cells. The obtained mols. exhibited blue fluorescence presenting a decreasing fluorescent intensity with the increasing length of alkyl chain from C8 to C18 while showed the same sequence of HPTS-C16>HPTS-C18>HPTS-C12>HPTS-C8 on either surface activity, cellular adsorption, or cytotoxicity. In opposite, HPTS which contained no hydrophobic chain and thus exhibited no surface activity showed no cellular adsorption and cytotoxicity. It seems that the ligand of the appropriate chain length (C16) onto the hydrophilic HPTS mols. could cause the largest surface activity, the most distinguished cellular adsorption as well as the most adverse cytotoxicity. As reflected by the dynamic fluorescent visualization, the surfactant mols. of HPTS-C16 initially bound with cell membrane and entered into the intracellular lumen before finally localized at the (ER) and damaged it into a swollen structure. It is most likely that the structure of hydrophobic chain could determine the surface activities of surfactants and hence affect their cellular uptake and cytotoxicity. This study could help us to understand the adverse impact of anionic surfactant on human cells and its correlation with the surface activities or, in another word, the hydrophobic chain length.

Environmental Science and Pollution Research 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, Product Details of C8H17Br.

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

Nagrimanov, Ruslan N. published the artcileAdditive scheme of solvation enthalpy for halogenated aliphatic hydrocarbons at 298.15 K., Product Details of C8H17Br, the publication is Thermochimica Acta (2022), 179155, database is CAplus.

In this work, an additive scheme for the estimation of solvation enthalpy of halogenated aliphatic hydrocarbons in n-heptane was developed. The proposed structural fragments for halogen group contributions are dependent on the nature of neighboring atoms. A linear relationship between solvation and vaporization enthalpy at 298.15 K for mono- and di-α,ω-halogen aliphatic compounds was found. These relationships can be used for the quick estimation of standard vaporization and solution enthalpies at 298.15 K. Proposed approaches for estimation of solvation, solution and vaporization enthalpies at 298.15 K were verified by conventional methods. In most cases, absolute deviations between exptl. and estimated values for halogenated aliphatic hydrocarbons do not exceed 1-2 kJ mol^-1.

Thermochimica Acta 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, Product Details of C8H17Br.

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

Thangarasu, Arun K. published the artcileDesign, synthesis, and preliminary immunopotentiating activity of new analogues of nojirimycin, Computed Properties of 111-83-1, the publication is Carbohydrate Research (2022), 108479, database is CAplus and MEDLINE.

Three new classes of nojirimycin analogs viz. N-alkyl with C₁-substituent (4-phenylbutyl), N-substituted 1-deoxynojirimycin and its congener Δ-lactam, and a 4-phenylbutyl-β-C-glycoside were designed and synthesized for immunol. studies. The resulting diverse compound library exhibited proliferation of B Cells and T cells induced by LPS and Con A, resp. The majority of the analogs augmented the secretion of IL-12 in dendritic cells and TNF-α secretion in murine peritoneal macrophages compared to LPS (10μg/mL). A deoxynojirimycin-triazole conjugate of phytosphingosine analog was superior in the responses mentioned above and exhibited nitric oxide response equal to LPS. In comparison to findings on its congeners with immunosuppressive action, early immunol. tests show that the novel nojirimycin analogs have immunopotentiating effect. Nojirimycin analogs offer tremendous potential in tuning the immunomodulatory activity of iminosugars by subtle to substantial structural variations.

Carbohydrate Research 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 C20H12N2O2, Computed Properties of 111-83-1.

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

Silvi, Mattia published the artcileMerging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes, COA of Formula: C4H6BrFO2, the publication is Journal of the American Chemical Society (2017), 139(16), 5736-5739, database is CAplus and MEDLINE.

Vinyl boronates react with electron-deficient alkyl iodides in the presence of visible light to give boronic esters in which two new C-C bonds were created. The reaction occurs by radical addition of an electron-deficient alkyl radical to the vinyl boronate followed by electron transfer with another mol. of alkyl iodide, continuing the chain, and triggering a 1,2-metalate rearrangement. In a number of cases, the use of a photoredox catalyst enhances yields significantly. The scope of the radical precursor includes α-iodo ketones, esters, nitriles, primary amides, α-fluorinated halo-acetates and perfluoroalkyl iodides.

Journal of the American Chemical Society 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 C10H16Br3N, COA of Formula: C4H6BrFO2.

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