Category: tetrahydropyran

Electric Literature of C6H13NO2. 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: (S)-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-methylamine, is researched, Molecular C6H13NO2, CAS is 82954-65-2, about Design and preparation of a novel prolinamide-based organocatalyst for the solvent-free asymmetric aldol reaction. Author is Martins, Rafaela de S.; Pereira, Mathias P.; de Castro, Pedro P.; Bombonato, Fernanda I..

The preparation of novel organocatalysts I (R = i-Pr, i-Bu, Bn) and II as highly diastereo and enantioselective catalysts for the solvent-free asym. aldol reaction was described. These organocatalysts I and II were synthesized in eight steps applying simple and com. available starting materials. The best results were obtained for the proline-derived catalyst II, providing access to the desired adducts III (R1 = H, Me, Et; Ar = 4-nitrophenyl, naphthalen-2-yl, furan-2-yl, etc.) in up to 95% yield, 1:19 syn/anti and 98% e.e. Moreover, even sterically bulky aldehydes ArCHO and substituted cyclohexanones IV were well tolerated. DFT calculations and control experiments indicated that several hydrogen bonding interactions between the aldehyde and the enamine intermediate are responsible for the stereoselective chiral induction process and that the trifluoroacetate counter-anion is crucial for the attainment of higher stereoselectivities.

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

Orejarena Pacheco, Julio Cesar; Pusch, Stefan; Geske, Leander; Opatz, Till published an article about the compound: 1-Bromo-2-pentyne( cas:16400-32-1,SMILESS:CCC#CCBr ).Electric Literature of C5H7Br. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:16400-32-1) through the article.

Herein, the design and development of a new one-pot and metal-free oxidative C-H activation/aza-Prins type cyclization of alkynylamines was reported. The scope of this method was demonstrated by the preparation of ten new pyrido[2,1-a]isoquinolines I [R1 = R2 = H, OMe; R3 = H, Ph, 2-thienyl, etc.; R4 = H, Et; stereo = cis, trans] in moderate to high yields (38-92%). Furthermore, a mechanistic proposal for the alkyne aza-Prins cyclization was described based on DFT calculations

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

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.Kawamoto, Momoyo; Moriyama, Mizuki; Ashida, Yuichiro; Matsuo, Noritada; Tanabe, Yoo researched the compound: 1-Bromo-2-pentyne( cas:16400-32-1 ).Safety of 1-Bromo-2-pentyne.They 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》 about this compound( cas:16400-32-1 ) in Journal of Organic Chemistry. Keywords: pyrethrin synthesis insecticidal; cinerin synthesis insecticidal; jasmolin synthesis insecticidal. We’ll tell you more about this compound (cas:16400-32-1).

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

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Tandem and One-Pot Hydroformylation/Michael Reactions of Acrylates, published in 2017-02-28, which mentions a compound: 97739-46-3, mainly applied to hydroformylation Michael tandem acrylate rhodium catalyst; carbonyl compound preparation tandem hydroformylation Michael aldol rhodium catalyst, HPLC of Formula: 97739-46-3.

The combination of various reactions in one operational step leads to many advantages in synthetic strategies, such as a lower consumption of resources, effort, and time, when intermittent workup and purification steps can be avoided. The hydroformylation reaction of acrylates gives access to 2-formylpropanoates, which, thanks to their structural features, constitute useful intermediates in the synthesis of more complex compounds Herein, we report a simple and convenient one-pot strategy to synthesize functionalized carbonyl compounds starting from these readily available substrates, via tandem or one-pot hydroformylation, Michael addition, and aldol reactions.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Aromatic silicon systems. II. The silacyclopentadienide anion》. Authors are Benkeser, Robert A.; Grossman, Richard F.; Stanton, Garth M..The article about the compound:1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantanecas:97739-46-3,SMILESS:CC1(C2)OC(C3)(C)OC2(C)OC3(C)P1C4=CC=CC=C4).Product Details of 97739-46-3. Through the article, more information about this compound (cas:97739-46-3) is conveyed.

cf. ibid. 4723. Silacyclopentadiene (I) has been found to react directly with K forming H and II. Comparison of the nuclear magnetic resonance spectra of I and II provides graphic evidence that it is the silanic hydrogens which are replaced by the metal in this reaction. Significantly, divinylsilane (the open chain analog of I) does not react with K at any appreciable rate under comparable conditions. This suggests that resonance stabilization of the silacyclopentadienide anion is providing a driving force for this reaction. II reacts with bromobenzene forming a mixture of 1-phenyl- and 1,1-diphenylsilacydopentadiene. The structure of the latter two compounds was established by reducing them catalytically to phenylated silacydopentanes which, in turn, could be prepared by unequivocal routes. II is colored in tetrahydrofuran solutions and possesses a spectrum which is quite similar to K in the visible region. All of the foregoing observations point to some measure of resonance stabilization in the silacyclopentadienide ring system, suggesting that the “”Hueckel rule”” will enjoy some success in predicting aromatic character for certain silicon ring systems

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

Safety of 1-(Bis(4-chlorophenyl)methyl)piperazine. 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-(Bis(4-chlorophenyl)methyl)piperazine, is researched, Molecular C17H18Cl2N2, CAS is 27469-61-0, about Development of small-molecule probes that selectively kill cells induced to express mutant RAS. Author is Weiwer, Michel; Bittker, Joshua A.; Lewis, Timothy A.; Shimada, Kenichi; Yang, Wan Seok; MacPherson, Lawrence; Dandapani, Sivaraman; Palmer, Michelle; Stockwell, Brent R.; Schreiber, Stuart L.; Munoz, Benito.

Synthetic lethal screening is a chem. biol. approach to identify small mols. that selectively kill oncogene-expressing cell lines with the goal of identifying pathways that provide specific targets against cancer cells. We performed a high-throughput screen of 303,282 compounds from the National Institutes of Health-Mol. Libraries Small Mol. Repository (NIH-MLSMR) against immortalized BJ fibroblasts expressing HRASG12V followed by a counterscreen of lethal compounds in a series of isogenic cells lacking the HRASG12V oncogene. This effort led to the identification of two novel mol. probes (PubChem CID 3689413, ML162 and CID 49766530, ML210) with nanomolar potencies and 4-23-fold selectivities, which can potentially be used for identifying oncogene-specific pathways and targets in cancer cells.

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

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《The electric strengths of hexane vapor and liquid in the critical region》. Authors are Watson, P. K.; Sharbaugh, A. H..The article about the compound:1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantanecas:97739-46-3,SMILESS:CC1(C2)OC(C3)(C)OC2(C)OC3(C)P1C4=CC=CC=C4).Electric Literature of C16H21O3P. Through the article, more information about this compound (cas:97739-46-3) is conveyed.

Extrapolated elec. breakdown field strengths of hexane vapor to pressure giving d. corresponding to the liquid state are higher than those actually observed for the liquid. Above the critical temperature, the observed breakdown strengths are less than the extrapolated curve for d. more than 0.01 g./cc., probably due to field emission. The breakdown strengths of the liquid are significantly lower than those of the vapor, but new measurements show that the values converge as one approaches the critical point. The observations suggest that the lower strengths in the liquid result from formation of vapor bubbles (CA 54, 18131b).

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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 Cu(I)- and Au(I)-catalyzed regioselective oxidation of diynes: divergent synthesis of N-heterocycles. Author is Shen, Wen-Bo; Zhang, Ting-Ting; Zhang, Meng; Wu, Jing-Jing; Jiang, Xiao-Lei; Ru, Guang-Xin; Gao, Guang-Qin; Zhu, Xiu-Hong.

Catalyst-dependent oxidative cyclization of diynes 2-NH(C(O)R4)-4-R3C6H3CCCH2N(R2)CC(R1) [R1 = Ph, 2-phenylethenyl, thiophen-3-yl, etc.; R2 = Ts, Bs, Ms, benzenesulfonyl; R3 = H, Me, Cl, Br; R4 =Me, Ac, Bz, 4-fluorophenyl, etc.]/(R2)N(CH2CCR5)CCAr [R5 = Me, Et, pentyl, 3-phenylpropyl; Ar = Ph, 4-(trifluoromethyl)phenyl, 3,5-dichlorophenyl, etc.] with 3,5-dichloropyridine N-oxide is achieved using an amide directing group. Non-polarized and aminated alkyne could be selectively activated by copper and gold, thus leading to divergent synthesis of a range of pyrroles I and dihydroindeno[1,2-c]pyrrol-3(2H)-ones II (R6 = H, Cl, Me; R7 = H, Me, F, CF3, etc.; R8 = H, Cl, Me, etc.). It should be noted that this difference might be attributed to the multicoordinated Cu center and the linearly aligned dicoordinated Au center.

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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 Acrylamide derivatives as antiallergic agents. 2. Synthesis and structure activity relationships of N-[4-[4-(diphenylmethyl)-1-piperazinyl]butyl]-3-(3-pyridyl)acrylamides, Author is Nishikawa, Yoshinori; Shindo, Tokuhiko; Ishii, Katsumi; Nakamura, Hideo; Kon, Tatsuya; Uno, Hitoshi, which mentions a compound: 27469-61-0, SMILESS is ClC1=CC=C(C=C1)C(N2CCNCC2)C3=CC=C(Cl)C=C3, Molecular C17H18Cl2N2, Reference of 1-(Bis(4-chlorophenyl)methyl)piperazine.

A new series of 3-(3-pyridyl)acrylamides, e.g., I (R = H, R1 = 4-F, 4-Cl, 4-OMe, 3-Me, 4-Me, R2 = H, 4-Cl, 4-Me; R = 2-Cl, 2-NHMe, 2-Me, 5-F, 5-Cl, 5-Br, 5-OMe, 5-OH, 6-Cl, 6-OMe, 6-Me, 6-Bu, R1 = R2 = H), and 5-(3-pyridyl)-2,4-pentadienamides, e.g., II (R = H, Me, n = 3,4) were prepared and evaluated for antiallergic activity. Several of these compounds exhibited more potent inhibitory activities than the parent compound I (R = R1 = R2 = H) against the rat passive cutaneous anaphylaxis (PCA) reaction and the enzyme 5-lipoxygenase. Particularly, I (R = 6-Me, R1 = R2 = H) (III) showed an ED50 value of 3.3 mg/kg po in the rat PCA test, which was one-fifth of ketotifen and oxatomide. As compared with ketotifen and oxatomide, III showed a better balance of antiallergic properties due to inhibition of chem. mediator release, inhibition of 5-lipoxygenase, and antagonism of histamine.

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

Angrick, Michael; Rewicki, Dieter published the article 《Reactions of sugars and related polyfunctional compounds with amino acids. 2. N-Acylation of 3-amino-1,2-propanediol with amino acids》. Keywords: acylation aminopropanediol amino acid; propanediol amino acylation.They researched the compound: (S)-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-methylamine( cas:82954-65-2 ).Application In Synthesis of (S)-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-methylamine. 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:82954-65-2) here.

Racemic H2NCH2CH(OH)CH2OH was N-acylated with Z-X-OH (Z = PhCH2O2C; X = Ala, Phe, Val, Leu) by 1,1′-carbonyldiimidazole in THF to give Z-X-NHCH2CH(OH)CH2OH (II). In some cases (e.g., X = Ala), one of the 2 diastereoisomers of II spontaneously formed a precipitate, which can be separated The S,S-configuration of II (X = Ala) was established by N-acylating (S)-(aminomethyl)dioxolane (S)-III (R = H) with Z-Ala-OH and cleaving the resulting (S)-III (R = Z-Ala) to give (S,S)-II (X = Ala).

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