Tag: M.W:100-200

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, ChemCatChem called A Reusable Cobalt Catalyst for Reversible Acceptorless Dehydrogenation and Hydrogenation of N-Heterocycles, Author is Jaiswal, Garima; Subaramanian, Murugan; Sahoo, Manoj K.; Balaraman, Ekambaram, which mentions a compound: 50501-07-0, SMILESS is O=C(C1NC2=C(C=CC=C2)C1)OCC, Molecular C11H13NO2, Quality Control of Ethyl indoline-2-carboxylate.

A highly efficient reusable cobalt-based heterogeneous catalyst for reversible dehydrogenation and hydrogenation of N-heterocycles was repoted. Both the acceptorless dehydrogenation (ADH) and the hydrogenation processes operated under mild and benign conditions.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 16400-32-1, is researched, Molecular C5H7Br, about Microwave induced synthesis of a new class of pyrano isoxazoline and isoxazole annulated chromones – an intramolecular nitrile oxide cycloaddition with tethered olefins and alkynes, the main research direction is tetracyclic pyrano isoxazolyl annulated chromone green preparation.Related Products of 16400-32-1.

A variety of new highly substituted-tetracyclic pyrano isoxazoline/isoxazole annulated chromone derivatives I [R1 = H, Cl; R2 = H, Me, Ph; R3 = H, Me] and II [R4 = H, Me, Et] were synthesized via eco-friendly microwave assisted/ceric ammonium nitrate (CAN) as an oxidant, intramol. 1,3-dipolar cycloaddition with in situ generated nitrile oxides from aldoximes of alkene/alkyne tethered chromones. This protocol was practically simple and efficient to construct diverse range of substituted pyrano isoxazoline/isoxazole annulated chromone derivatives and gave higher yields of products in microwave irradiation compared to conventional heating. The structures of all the synthesized compounds were established by IR, NMR and mass spectral anal.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Recommanded Product: 1-Bromo-2-pentyne. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 1-Bromo-2-pentyne, is researched, Molecular C5H7Br, CAS is 16400-32-1, about Rhodium-catalysed tetradehydro-Diels-Alder reactions of enediynes via a rhodium-stabilized cyclic allene. Author is Thadkapally, Srinivas; Farshadfar, Kaveh; Drew, Melanie A.; Richardson, Christopher; Ariafard, Alireza; Pyne, Stephen G.; Hyland, Christopher J. T..

Herein, tethered unconjugated enediynes R1CCCH=CHCH(R3)XCH2CCR2 [R1 = Ph, n-pentyl, 4-fluorophenyl, etc.; R2 = H, Et, Ph; R3 = H, Me, n-Pr; X = O, NTs, NNs, C(C(O)OMe)2] have been shown to undergo a facile room-temperature RhI-catalyzed intramol. tetradehydro-Diels-Alder reaction to produce highly substituted isobenzofurans, isoindolines and indane I. Furthermore, exptl. and computational studies suggest a novel mechanism involving an unprecedented and complex RhI/RhIII/RhI/RhIII redox cycle involving the formation of an unusual strained 7-membered rhodacyclic allene intermediate and a RhIII-stabilized 6-membered ring allene complex.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Journal of Medicinal Chemistry called α2-Adrenergic agonists/antagonists: the synthesis and structure-activity relationships of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines, Author is Hlasta, Dennis J.; Luttinger, Daniel; Perrone, Mark H.; Silbernagel, Marla J.; Ward, Susan J.; Haubrich, Dean R., which mentions a compound: 50501-07-0, SMILESS is O=C(C1NC2=C(C=CC=C2)C1)OCC, Molecular C11H13NO2, Related Products of 50501-07-0.

The synthesis and α2-adrenergic activity of a series of indolin-2-yl- and tetrahydroquinolin-2-ylimidazolines, e.g. I (R = Me, Et, allyl, Ph, CH2Ph, etc.; R1 = 5-F, 5-Cl, etc.) and II (R = H, Me) are described. The indolin-2-ylimidazoline I (R = Me, R1 = H) has potent α2-adrenergic agonist and antagonist activity. The modification of the substituents on the indoline ring of I led to the separation of these activities. Substitution on the aromatic ring of I with halogen or increasing the size of the N-alkyl substituent of I gave α2-adrenergic antagonists without agonist activity. The N-allylindoline I (R = allyl, R1 = H) is more potent than idazoxan in vitro and is equipotent in vivo, but is less receptor-selective (α2 vs. α1) than idazoxan. cis-1,3-Dimethylindolin-2-ylimidazoline is an α2-adrenergic agonist equal in potency to clonidine in vitro, whereas trans-1,3-dimethylindolin-2-ylimidazoline is a moderately potent α2-adrenergic antagonist.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Related Products of 16400-32-1. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 1-Bromo-2-pentyne, is researched, Molecular C5H7Br, CAS is 16400-32-1, about Oxygen-Tethered 1,6-Enynes and [4.1.0]-Bicyclic Ether Skeletons as Hedonic Materials for the Fragrance Industry. Author is Laher, Romain; Gentilini, Emilie; Marin, Christophe; Michelet, Veronique.

The synthesis of original structures for the fragrance industry bearing bicyclic scaffolds is described. To the best of authors’ knowledge, these structures are not found in the fragrance industry, neither from natural nor synthetic pathways. NHC-gold-type catalysts showed excellent activities leading to light bicyclic enol ethers. Several bicyclic adducts I (X = O, S; R1 = H, Me, Bn, etc.; R2 = H, Me, Ph; R3 = H, Me; -R2R3- = -(CH2)5-; R4 = n-Pr, Ph, 4-F3CC6H4, etc.; R5 = H, n-Pr) were prepared in good to excellent yields (18-99%). Evaluation of NHC-Au complexes allowed to reach a TOF of 300 h-1. The evaluation for the organoleptic properties of [4.1.0]-bicyclic ethers were compared with the unprecedented properties of the 1,6-enyne precursors. Evaluations of starting materials showed a great interest in these structures with various olfactory facets. In this study, the similarity and differences between starting ethers and their cycloisomerized bicyclic counterparts are depicted.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 1-Bromo-2-pentyne(SMILESS: CCC#CCBr,cas:16400-32-1) is researched.Application In Synthesis of 4-Aminopyrimidine. The article 《Palladium-Catalyzed Carbo-Oxygenation of Propargylic Amines using in Situ Tether Formation》 in relation to this compound, is published in Chemistry – A European Journal. Let’s take a look at the latest research on this compound (cas:16400-32-1).

This work reported a new method for the palladium-catalyzed oxyalkynylation and oxyarylation of propargylic amines. The reaction is perfectly regioselective based on the in-situ introduction of a hemiacetal tether derived from trifluoroacetaldehyde. Cis-selective carbo-oxygenation was achieved for terminal alkynes, whereas internal alkynes gave trans-carbo-oxygenation products. The obtained enol ethers could be easily transformed into 1,2-amino alcs. or α-amino ketones using hydrogenation or hydrolysis, resp.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Product Details of 50501-07-0. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: Ethyl indoline-2-carboxylate, is researched, Molecular C11H13NO2, CAS is 50501-07-0, about Purification, identification and characterization of an esterase with high enantioselectivity to (S)-ethyl indoline-2-carboxylate. Author is Zhang, Yin-Jun; Chen, Chang-Sheng; Liu, Hao-Tian; Chen, Jia-Lin; Xia, Ying; Wu, Shi-Jin.

Objective: To purify an esterase which can selectively hydrolyze (R,S)-Et indoline-2-carboxylate to produce (S)-indoline-2-carboxylic acid and characterize its enzymic properties. Results: An intracellular esterase from Bacillus aryabhattai B8W22 was isolated and the purified protein was identified as a carboxylesterase by MALDI-TOF mass spectrometry. The enzyme (named BaCE) was 59.03-fold purification determined to be of approx. 35 kDa. Its specific activity was 0.574 U/mL with 20% yield. The enzyme showed maximum activity at pH 8.5 and 30°C and was stable at 20-30°C using pNPB as the substrate. The esterase demonstrated high enantioselectivity toward (S)-Et indoline-2-carboxylate with 96.55% e.e.p at 44.39% conversion, corresponding to an E value of 133.45. Conclusions: In this study, a new esterase BaCE with an apparent mol. mass of 35 kDa was purified to homogeneity for the first time. The esterase from Bacillus aryabhattai B8W22 was isolated with a purification more than 59-fold and a yield of 20% by anion exchange chromatog. and hydrophobic interaction chromatog. And its biochem. characterization were described in detail with pNPB as substrate. It displayed high enantioselectivity toward (S)-Et indoline-2-carboxylate. We next plan to highly express esterase BaCE in Escherichia coli, and apply it to industrial production of (S)-indoline-2-carboxylic acid.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Kawamoto, Momoyo; Moriyama, Mizuki; Ashida, Yuichiro; Matsuo, Noritada; Tanabe, Yoo published the article 《Total Syntheses of All Six Chiral Natural Pyrethrins: Accurate Determination of the Physical Properties, Their Insecticidal Activities, and Evaluation of Synthetic Methods》. Keywords: pyrethrin synthesis insecticidal; cinerin synthesis insecticidal; jasmolin synthesis insecticidal.They researched the compound: 1-Bromo-2-pentyne( cas:16400-32-1 ).Recommanded Product: 16400-32-1. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:16400-32-1) here.

Chiral total syntheses of all six insecticidal natural pyrethrins (three pyrethrin-I and three pyrethrin-II compounds) contained in the chrysanthemum (pyrethrum) flower were performed. Three common alc. components [(S)-cinerolone, (S)-jasmololone, (S)-pyrethrolone] were synthesized: (i) Straightforward Sonogashira-type cross-couplings using available (S)-4-hydroxy-3-methyl-2-(2-propynyl)cyclopent-2-en-1-ones (the prallethrin alc.) for (S)-cinerolone (overall 52% yield, 98% ee) and (S)-pyrethrolone (overall 54% yield, 98% ee) and (ii) traditional decarboxylation-aldol condensation and lipase-catalyzed optical resolution for (S)-jasmololone (overall 16% yield, 96% ee). Two counter acid segments of [(1R,3R)-chrysanthemic acid (A) and (1R,3R)-second chrysanthemic acid precursor (B)] were prepared: (i) C(1)-epimerization of Et (±)-chrysanthemates and optical resolution using (S)-naphthylethylamine to afford A (96% ee) and (ii) concise derivatization of A to B (96% ee). All six pyrethrin esters (cinerin I/II, jasmolin I/II, pyrethrin I/II) were successfully synthesized utilizing an accessible esterification reagent (TsCl/N-methylimidazole). To investigate the stereostructure-activity relationship, all four chiral stereoisomers of cinerin I were synthesized. Three alternative syntheses of (±)-jasmololone were investigated (methods utilizing Piancattelli-rearrangement, furan-transformation, and 1-nitropropene-transformation). Insecticidal activity assay (KD50 and IC50) against the common mosquito (Culex pipiens pallens) revealed that (i) pyrethrin-I > pyrethrin-II, (ii) pyrethrin I(II) > cinerin I(II) >> jasmolin I(II), (iii) “”natural”” cinerin I >> three “”unnatural”” cinerin I compounds (apparent chiral discrimination).

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Recommanded Product: 16400-32-1. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 1-Bromo-2-pentyne, is researched, Molecular C5H7Br, CAS is 16400-32-1, about Visible-Light-Induced Radical Carbo-Cyclization/gem-Diborylation through Triplet Energy Transfer between a Gold Catalyst and Aryl Iodides. Author is Zhang, Lumin; Si, Xiaojia; Rominger, Frank; Hashmi, A. Stephen K..

Gem-Diboronates I (X = O, S, NBoc; R1 = H, halo, MeCO, MeO2C, tBu, CF3, MeSO2NH; R2 = H, Me, Et; R3 = H, Me, iPr, Bu) were prepared by photochem. diboration of propargylic substrates 2-I-R1C6H3XCHR3CCR2 with B2pin2 catalyzed by gold complex [Au2(μ-dppm)2(OTf)2] with up to 90% yields. Geminal diboronates have attracted significant attention because of their unique structures and reactivity. However, benzofuran-, indole- and benzothiophene-based benzylic gem-diboronates, building blocks for biol. relevant compounds, are unknown. A promising protocol using visible light and aryl iodides for constructing valuable building blocks, including benzofuran-, indole- and benzothiophene-based benzylic gem-diboronates, via radical carbo-cyclization/gem-diborylation of alkynes with a high functional group tolerance is presented. The utility of these gem-diboronates has been demonstrated by a ten gram scale conversion, by versatile transformations, by including the synthesis of approved drug scaffolds and two approved drugs, and even by polymer synthesis. The mechanistic investigation indicates that the merging of the dinuclear gold catalyst (photoexcitation by 315-400 nm UVA light) with Na2CO3 is directly responsible for photosensitization of aryl iodides (photoexcitation by 254 nm UV light) with blue LEDs light (410-490 nm, λmax = 465 nm) through an energy transfer (EnT) process, followed by homolytic cleavage of the C-I bond in the aryl iodide substrates.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2-Bromo-5-methylpyrazine, is researched, Molecular C5H5BrN2, CAS is 98006-90-7, about Phenethyl nicotinamides, a novel class of NaV1.7 channel blockers: Structure and activity relationship.Formula: C5H5BrN2.

The NaV1.7 ion channel is an attractive target for development of potential analgesic drugs based on strong genetic links between mutations in the gene coding for the channel protein and inheritable pain conditions. The (S)-N-chroman-3-ylcarboxamide series was used as a starting point for development of new channel blockers resulting in the phenethyl nicotinamide series I (X = CH, CF, N; R1 = 3-pyridyl, 2-methoxy-5-pyrimidinyl, 5-methoxy-2-pyrazinyl, etc.; R2 = H, Cl, F, Me, etc.; R3 = R4 = H, F; R3 = Me, R4 = H; R5 = F3CCH2CH2O, F3CCH2OCH2, etc.). The structure and activity relationship for this series was established and the metabolic issues of early analogs were addressed by appropriate substitutions. Compound I (X = CH; R1 = 5-methoxy-2-pyrazinyl; R2 = H; R3 = R4 = F; R5 = F3CCH2OCH2) displayed acceptable overall in vitro properties and in vivo rat PK profile.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics