Month: April 2022

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Chen, Sijia; Zhang, Zhongchao; Jiang, Chongguo; Zhao, Chunbo; Luo, Haojie; Huang, Jun; Yang, Zhen researched the compound: 1-Bromo-2-pentyne( cas:16400-32-1 ).Related Products of 16400-32-1.They published the article 《Stereoselective Synthesis of trans-Decalin-Based Spirocarbocycles via Photocyclization of 1,2-Diketones》 about this compound( cas:16400-32-1 ) in ACS Omega. Keywords: hydroxyl butanone spirocarbocycle preparation diastereoselective DFT crystal structure mol; diketone Norrish Yang photocyclization. We’ll tell you more about this compound (cas:16400-32-1).

Diastereoselective synthesis of the trans-decalin-based α-hydroxyl butanone spirocarbocycles, e.g., I bearing all-carbon quaternary stereogenic centers was achieved via Norrish-Yang photocyclization of trans-decalin-substituted-2,3-butanediones using daylight. D. functional theory (DFT) calculations suggested that this diastereoselective reaction was affected by both substrate conformation and intramol. hydrogen bonds. The developed chem. could be applied to synthesizing the derivatives of the trans-decalin-based biol. important natural products.

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

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1-Bromo-2-pentyne( cas:16400-32-1 ) is researched.SDS of cas: 16400-32-1.Aguilar Troyano, Francisco Jose; Ballaschk, Frederic; Jaschinski, Marcel; Oezkaya, Yasemin; Gomez-Suarez, Adrian published the article 《Light-Mediated Formal Radical Deoxyfluorination of Tertiary Alcohols through Selective Single-Electron Oxidation with TEDA2+.》 about this compound( cas:16400-32-1 ) in Chemistry – A European Journal. Keywords: alc tertiary Selectfluor photochem radical deoxyfluorination; tertiary alkyl fluoride preparation; fluorination; mechanistic studies; organic synthesis; photochemistry; radicals. Let’s learn more about this compound (cas:16400-32-1).

The synthesis of tertiary alkyl fluorides through a formal radical deoxyfluorination process was described. This light-mediated, catalyst-free methodol. was fast and broadly applicable allowing for the preparation of C-F bonds from (hetero)benzylic, propargylic and non-activated tertiary alc. derivatives Preliminary mechanistic studies supported that the key step of the reaction is the single-electron oxidation of cesium oxalates-which are readily available from the corresponding tertiary alcs.-with in situ generated TEDA2+ (TEDA: N-(chloromethyl)triethylenediamine), a radical cation derived from Selectfluor.

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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.Reference of 1-Bromo-2-pentyne. The article 《Asymmetric Synthesis of Alkylzincs by Rhodium-Catalyzed Enantioselective Arylative Cyclization of 1,6-Enynes with Arylzincs》 in relation to this compound, is published in Angewandte Chemie, International Edition. Let’s take a look at the latest research on this compound (cas:16400-32-1).

A chiral diene-rhodium complex was found to catalyze the reaction of 1,6-enynes with ArZnCl to give high yields of 2-(alkylidene)cyclopentylmethylzincs with high enantioselectivity (95-99% ee). The enantioenriched alkylzincs were readily converted in a one-pot approach into a wide variety of functionalized products by taking advantage of their unique reactivity. The catalytic cycle involves arylrhodation of alkyne, intramol. alkenylrhodation of alkene, and transmetalation of the alkyl-rhodium intermediate into alkylzinc. Thus, e.g., treatment of enyne I with 4-MeOC6H4ZnCl and ZnCl2 in presence of chiral Rh complex afforded regioisomers II/III (88%, 20/1) after DOAc quenching, consistent with alkylzinc and arylzinc intermediates.

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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, Research Support, Non-U.S. Gov’t, Journal of Organic Chemistry called Iodine-Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights, Author is Pace, Domenic P.; Robidas, Raphael; Tran, Uyen P. N.; Legault, Claude Y.; Nguyen, Thanh Vinh, which mentions a compound: 16400-32-1, SMILESS is CCC#CCBr, Molecular C5H7Br, Reference of 1-Bromo-2-pentyne.

Substituted pyrans and furans are core structures found in a wide variety of natural products and biol. active compounds Herein, we report a practical and mild catalytic method for the synthesis of substituted pyrans and furans using mol. iodine, a simple and inexpensive catalyst. The method described is performed under solvent-free conditions at an ambient temperature and atm., thus offering a facile and practical alternative to currently available reaction protocols. A combination of exptl. studies and d. functional theory calculations revealed interesting mechanistic insights into this seemingly simple reaction.

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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: 1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane(SMILESS: CC1(C2)OC(C3)(C)OC2(C)OC3(C)P1C4=CC=CC=C4,cas:97739-46-3) is researched.Electric Literature of C5H5BrN2. The article 《Phenylphosphatrioxa-adamantanes: bulky, robust, electron-poor ligands that give very efficient rhodium(I) hydroformylation catalysts》 in relation to this compound, is published in Dalton Transactions. Let’s take a look at the latest research on this compound (cas:97739-46-3).

The cage phosphines 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (1a) and 1,3,5,7-tetraethyl-6-phenyl-2,4,8,trioxa-6-phosphaadamantane (1b) were made by the acid catalyzed addition of PhPH2 to the appropriate β-diketones; the acid used (HCl, H3PO4 or H2SO4) and its concentration affect the rate and selectivity of these condensation reactions. Phosphines 1a and 1b react with [PdCl2(NCPh)2] to form trans-[PdCl2(1a)2] (2a) and trans-[PdCl2(1b)2] (2b) as mixtures of rac and meso diastereoisomers. The Pt(II) chem. is more complicated and when 1a or 1b is added to [PtCl2(cod)], equilibrium mixtures of trans-[PtCl2L2] and [Pt2Cl4L2] (L = 1a or 1b) are formed in CH2Cl2 solution Meso/rac mixtures of trans-[MCl(CO)(1a)2] M = Ir (6a) or Rh (7a) are formed upon treatment of MCl3·nH2O with an excess of 1a and the anionic Co complex [NHEt3][CoCl3(1a)] (9) was isolated from the product formed by CoCl2·6H2O and 1a. The νCO values from the IR spectra of 6a and 7a suggest that 1a resembles a phosphonite in its bonding to Rh and Ir. Crystal structures of meso-2a, meso-2b, rac-6a and 9 are reported and in each case a small intracage C-P-C angle of ∼94° is observed and this may partly explain the bonding characteristics of ligands 1a and 1b. The cone angles for 1a and 1b are similar and large (∼200°). Rh complexes of ligands 1a and 1b are hydroformylation catalysts with similarly high activity to catalysts derived from phosphites. The catalysts derived from 1a and 1b gave unusually low linear selectivity in the hydroformylation of hexenes. This feature was further exploited in quaternary-selective hydroformylations of unsaturated esters; catalysts derived from 1a give better yields and regioselectivities than any previously reported catalyst.

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

Electric Literature of C5H5BrN2. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-Bromo-5-methylpyrazine, is researched, Molecular C5H5BrN2, CAS is 98006-90-7, about Determination of the Alkylpyrazine Composition of Coffee Using Stable Isotope Dilution-Gas Chromatography-Mass Spectrometry (SIDA-GC-MS). Author is Pickard, Stephanie; Becker, Irina; Merz, Karl-Heinz; Richling, Elke.

A stable isotope dilution anal. based on gas chromatog.-mass spectrometry anal. (SIDA-GC-MS) was developed for the quant. anal. of 12 alkylpyrazines found in com. available coffee samples. These compounds contribute to coffee flavor. The accuracy of this method was tested by analyzing model mixtures of alkylpyrazines. Comparisons of alkylpyrazine-concentrations suggested that water as extraction solvent was superior to dichloromethane. The distribution patterns of alkylpyrazines in different roasted coffees were quite similar. The most abundant alkylpyrazine in each coffee sample was 2-methylpyrazine, followed by 2,6-dimethylpyrazine, 2,5-dimethylpyrazine, 2-ethylpyrazine, 2-ethyl-6-methylpyrazine, 2-ethyl-5-methylpyrazine, and 2,3,5-trimethylpyrazine, resp. Among the alkylpyrazines tested, 2,3-dimethylpyrazine, 2-ethyl-3-methylpyrazine, 2-ethyl-3,6-dimethylpyrazine, and 2-ethyl-3,5-dimethylpyrazine revealed the lowest concentrations in roasted coffee. By the use of isotope dilution anal., the total concentrations of alkylpyrazines in com. available ground coffee ranged between 82.1 and 211.6 mg/kg, resp. Decaffeinated coffee samples were found to contain lower amounts of alkylpyrazines than regular coffee samples by a factor of 0.3-0.7, which might be a result of the decaffeination procedure.

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

SDS of cas: 98006-90-7. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. 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. Author is Kers, Inger; Macsari, Istvan; Csjernyik, Gabor; Nyloef, Martin; Skogholm, Karin; Sandberg, Lars; Minidis, Alexander; Bueters, Tjerk; Malmborg, Jonas; Eriksson, Anders B.; Lund, Per-Eric; Venyike, Elisabet; Luo, Lei; Nystroem, Jan-Erik; Besidski, Yevgeni.

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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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Recommanded Product: (S)-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-methylamine. 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: (S)-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-methylamine, is researched, Molecular C6H13NO2, CAS is 82954-65-2, about Direct conversion of (R)-epichlorohydrin to (S)-3-aminopropane-1,2-diol: an important chiral C-3 building block. Author is Bhavani, Ch; Babu, K. Chandra; Naresh, E.; Sridhar, P.; Madhusudhan, G..

A new and effective method for the preparation of (S)-3-amino-1,2-propanediol was established starting from (R)-epichlorohydrin. The synthetic approach involves the reaction of (R)-epichlorohydrin with acetone catalyzed by BF3·OEt2 to give (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane. Subsequent replacement of the Cl with NH2 group by azidation followed by reduction gave ((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methanamine, which was converted into (S)-3-aminopropane-1,2-diol·HCl by acetal deprotection with MeOH·HCl.

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

Category: tetrahydropyran. 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: 1-Bromo-2-pentyne, is researched, Molecular C5H7Br, CAS is 16400-32-1, about Syntheses of methyl jasmonate and analogues. Author is Chapuis, Christian; Skuy, David; Richard, Claude-Alain.

This account corresponds to the presentation given by the main author on the occasion of the 2nd Swiss Industrial Symposium in Basel (Oct. 19th, 2018). After a short historical introduction to methyl-jasmonate and methyl-epijasmonate, it essentially focuses on the reported more promising industrial approaches devoted to the synthesis of these naturally occurring odorants isolated from jasmine flowers. Some attempts to simplify these approaches, as well as independent unreported strategies were also presented. Several asym. methodologies were also discussed such as Xie hydrogenation, Corey-CBS reduction, enzymic resolution, and 1,4-addition

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Gilliard, Robert J.; Suter, Riccardo; Schrader, Erik; Benko, Zoltan; Rheingold, Arnold L.; Grutzmacher, Hansjorg; Protasiewicz, John D. published the article 《Synthesis of P2C2O2 and P2CO via NHC-mediated coupling of the phosphaethynolate anion》. Keywords: heterocyclic carbene mediated coupling phosphaethynolate anion; crystal structure mol phosphorus heterocycle diphosphorus compound optimized.They researched the compound: 2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride( cas:1228185-09-8 ).Synthetic Route of C27H36Cl2N2. 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:1228185-09-8) here.

The reaction of the chloroimidazolium chloride salt, [NHC-Cl][Cl], NHC = C{N(2,6-iPr2C6H3)CH}2 (1) with two equivalent of sodium phosphaethynolate, Na[OCP]·(dioxane)2.5, results in the formation of NHC-{cyclo-(CO)-P2-C(O)} (2) and NHC-P2-C(O)-NHC (3). Notably, in the presence of free NHC ligand, compound 2 converts to compound 3 via extrusion of CO at elevated temperatures The nature of the bonding in these complexes was probed computationally and spectroscopically.

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