Category: tetrahydropyran

Barton, Derek H. R. published the artcileSynthesis of the insect molting hormone, ecdysone, and related compounds, Product Details of C10H16O2, the publication is Journal of the Chemical Society [Section] C: Organic (1970), 1584-91, database is CAplus and MEDLINE.

A relatively short synthesis of the insect molting hormone, ecdysone, and of its C-22 isomer is described, starting from ergosterol. A key step is the direct transformation of the 3α,5α-cycloergosta-7,22-dien-6-one into the 14α- and 14β-ergosta-2,7,22-trien-6-ones. Selective cis-hydroxylation of the 2-enes, followed by enol acetylation and oxidation with perphthalic acid afforded the 5α-ecdysone nucleus. Ozonolysis of the C-22 double bond gave (20S)-2β,3β-diacetoxy-20-formyl-14α-hydroxy-5α-pregn-7-en-6-one, to which the ecdysone side chain was attached in a known manner.

Journal of the Chemical Society [Section] C: Organic published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Product Details of C10H16O2.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Alexander, Cameron published the artcileSynthesis of a series of ethynyl-substituted triphenylmethanes, Formula: C10H16O2, the publication is Synthesis (1992), 735-7, database is CAplus.

Triphenylmethyl-substituted alkynyl monomers I (R = H, Me) and II, required as part of a study concerning conjugated polyradicals, were prepared in multistep processes. Thus, II was prepared from Ph₃CH in 3 steps involving Friedel-Crafts monoacetylation with AcCl, followed by Vilsmeier formylation to give β-chloro aldehyde III, and elimination by KOH in aqueous MeOH/THF.

Synthesis published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Formula: C10H16O2.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Visalli, Giuseppa published the artcileBergamot Juice Extract Inhibits Proliferation by Inducing Apoptosis in Human Colon Cancer Cells, Synthetic Route of 69097-99-0, the publication is Anti-Cancer Agents in Medicinal Chemistry (2014), 14(10), 1402-1413, database is CAplus and MEDLINE.

Colorectal cancer (CRC) is a leading cause of cancer mortality in the industrialized world, second to lung cancer. A lot of evidences highlight that a diet rich in fruits and vegetables may reduce the risk of some types of cancer including CRC. In this study we demonstrate that Citrus bergamia juice extracts (BJe) reduces CRC cell growth by multiple mechanisms. Low BJe concentrations inhibit MAPKs pathway and alter apoptosis-related proteins, that in turn induce cell cycle arrest and apoptosis in HT-29 cells. Instead, high concentrations of BJe induce oxidative stress causing DNA damage. Our study highlights the role of BJe as modulator of cell apoptosis in CRC cells and strengthens our previous hypothesis that the flavonoid fraction of bergamot juice may play a role as anti-cancer drug.

Anti-Cancer Agents in Medicinal Chemistry published new progress about 69097-99-0. 69097-99-0 belongs to tetrahydropyran, auxiliary class Other Aliphatic Heterocyclic,Benzene,Phenol,Ether,Inhibitor, name is 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, and the molecular formula is C12H15ClO3, Synthetic Route of 69097-99-0.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Nguyen, Sean S. published the artcileButenolide Synthesis from Functionalized Cyclopropenones, Synthetic Route of 27943-46-0, the publication is Organic Letters (2019), 21(21), 8695-8699, database is CAplus and MEDLINE.

A general method to synthesize substituted butenolides I (R¹ = Me, C₆H₅, 2-thiophenyl, etc.; R²,R³ = H,Me) from hydroxymethylcyclopropenones is reported. Functionalized cyclopropenones undergo ring-opening reactions with catalytic amounts of phosphine, forming reactive ketene ylides. These intermediates can be trapped by pendant hydroxy groups to afford target butenolide scaffolds. The reaction proceeds efficiently in diverse solvents and with low catalyst loadings. Importantly, the cyclization is tolerant of a broad range of functional groups, yielding a variety of α- and γ-substituted butenolides.

Organic Letters published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Synthetic Route of 27943-46-0.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Ficarra, Paola published the artcileDirect enantiomeric separation of flavanones by high performance liquid chromatography using various chiral stationary phases, Synthetic Route of 69097-99-0, the publication is Planta Medica (1995), 61(2), 171-6, database is CAplus and MEDLINE.

The performance of four chiral liquid chromatog. columns (Chiralcel OA, OJ, OC, OD) was studied with respect to the enantioseparation of flavanones and some derivatives The effect of mobile phase composition on the retention time and stereoselectivity was studied. A good enantioseparation (α up to 1.45) was achieved for most of the racemates. Further, the elution order of the enantiomers from the chiral stationary phases has been determined by using a CD based detection system.

Planta Medica published new progress about 69097-99-0. 69097-99-0 belongs to tetrahydropyran, auxiliary class Other Aliphatic Heterocyclic,Benzene,Phenol,Ether,Inhibitor, name is 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, and the molecular formula is C16H14O6, Synthetic Route of 69097-99-0.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Nachman, Rebecca M. published the artcileSerial Free Bisphenol A and Bisphenol A Glucuronide Concentrations in Neonates, Computed Properties of 267244-08-6, the publication is Journal of Pediatrics (New York, NY, United States) (2015), 167(1), 64-69, database is CAplus and MEDLINE.

To determine the balance of metabolism of free bisphenol A (BPA) to the inactive conjugate, BPA glucuronide (BPAG), in neonates. Free BPA and BPAG concentrations were measured in 78 urine samples collected between Dec. 2012 and August 2013 from a cohort of 44 healthy full term (≥37 wk’ gestation) neonates at 2 intervals (3-6 days and 7-27 days of age). A questionnaire was administered at the time of sample collection. Neonates recruited into the study were born in an urban, tertiary care hospital. Only BPAG was detected in the urine samples; concentrations ranged from <0.1 μg/L to 11.21 μg/L (median: 0.27 μg/L). Free BPA concentrations were below the limit of quantification of 0.1 μg/L. Age, but not sex or type of diet, was significantly associated with urinary BPAG concentration (P = .002). Our results illustrate widespread BPA exposure in healthy full-term neonates and efficient conjugation of BPA to its readily excretable and biol. inactive form (BPAG) as early as 3 days of age. Factors other than type of diet may be important contributors to BPA exposure in neonates.

Journal of Pediatrics (New York, NY, United States) published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Computed Properties of 267244-08-6.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Karlsen, Steinar published the artcileNew syntheses of the bark beetle pheromones 2-methyl-6-methylene-7-octen-4-ol (ipsenol) and 2-methyl-6-methylene-2,7-octadien-4-ol (ipsdienol), Computed Properties of 27943-46-0, the publication is Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry (1976), B30(7), 664-8, database is CAplus.

H2C:CHC(:CH2)CH2CHO, obtained by thermal [3,3] sigmatropic rearrangement of CH2:C:CHCH2OCH:CH2, was treated with Me2CHCH2MgBr or Me2C:CHMgBr to give the Ips pheromone CH2:CHC(:CH2)CH2CH(OH)CHCHMe2 (ipsenol) or CH2:CHC(:CH2)CH2CH(OH):CMe2 (ipsdienol), resp.

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Computed Properties of 27943-46-0.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Deceuninck, Y. published the artcileQuantitative method for conjugated metabolites of bisphenol A and bisphenol S determination in food of animal origin by Ultra High Performance Liquid Chromatography-Tandem Mass Spectrometry, SDS of cas: 267244-08-6, the publication is Journal of Chromatography A (2019), 232-242, database is CAplus and MEDLINE.

With the objectives of both generating bisphenols (BPs) conjugates occurrence data in food from animal origin but also investigating the origin of associated contamination, the present study deals with the development of an efficient anal. method aiming at monitoring both BPA and BPS conjugated metabolites in food from animal origin. The objective of such monitoring is to determine the origin of BPs contamination (FCM or animal contamination). The targeted compounds were BPA-monoglucuronide (BPA-1G), BPA-diglucuronide (BPA-2G), BPA-monosulfate (BPA-1S), BPA-disulfate (BPA-2S) and BPS-monoglucuronide (BPS-1G). The developed standard operating procedure includes a preliminary solid-liquid extraction step followed by two successive solid phase extraction (SPE) stages, using successively a non-polar phase and a strong cation exchange polymer. Quantification was achieved according to both the isotopic dilution and surrogated quantification methods, using ¹³C-BPA-1G and BPA-d₆-1S as internal standards Linearity was validated (R² > 0.99) for each mol. within the concentration range [0-10] μg kg^-1. Detection limits ranged from 0.02 μg kg^-1 (BPA-1G in muscle, BPA-1S and BPA-2G in liver) to 0.50 μg kg^-1 (BPA-2S in muscle). The strategy was then proven on liver samples collected from pregnant ewes s.c. exposed to BPA during 105 days, at 50 μg kg^-1 per day. BPA-1G, BPA-2G and BPA-1S were detected and quantified at a concentration of 3.81 μg kg^-1, 0.80 μg kg^-1 and 0.09 μg kg^-1, resp. The anal. method was finally implemented on fifty unpacked food samples from animal origin in which significant free BPA concentrations were previously measured. Since no metabolites of BPA could be measured (<LOD), it means that such free BPA present in the samples originates from direct contact of the food item with a material containing BPA.

Journal of Chromatography A published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, SDS of cas: 267244-08-6.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Gosav, Steluta published the artcileMultivariate study of flavonoids active against Caco-2 colon carcinoma, Product Details of C16H14O6, the publication is Romanian Reports in Physics (2014), 66(2), 411-426, database is CAplus.

A multivariate study involving flavonoids with activity against human colon carcinoma Caco-2 is reported. The data set is composed of 26 flavonoids which can be separated, depending on their EC50 value i.e. the half maximal effective concentration, into active and less active compounds Our purpose was to transform the chem. structure of each compound into a set of numbers, and to correlate them with the biol. activity establishing a qual./quant. relationship between calculated mol. descriptors and antiproliferative activity. The geometries of the studied flavonoids were fully optimized employing the D. Functional Theory (DFT) with the hybrid functional B3LYP in conjunction with the 6-31G(d) basis set. For each optimized structure we computed a set of parameters (1,356 descriptors) which characterizes the mol. from structural, topol., steric, electronic, hydrophobic, etc. points of view. Using the Fisher’s weight and the correlation matrix, we reduced the number of descriptors from 1,356 to 15. Aiming to investigate which mol. descriptors would be more efficient in classifying flavonoid compounds according to their degree of anticancer activity, we applied two unsupervised learning methods, Principal Component Anal. (PCA) and Cluster Anal. (CA), and a supervised learning method, Stepwise Discriminant Anal. (SDA). Using the 15 selected descriptors as input, the PCA and SDA techniques supplied us with the following parameters as common relevant descriptors: C-16, EN, Mor08e, HATS8m. The reliability of the structure-activity relationship model is verified using the cross-validation technique, the percentage of correct classifications being of 92.31 %.

Romanian Reports in Physics published new progress about 69097-99-0. 69097-99-0 belongs to tetrahydropyran, auxiliary class Other Aliphatic Heterocyclic,Benzene,Phenol,Ether,Inhibitor, name is 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, and the molecular formula is C16H14O6, Product Details of C16H14O6.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Peil, Sebastian published the artcileHydrogenative Metathesis of Enynes via Piano-Stool Ruthenium Carbene Complexes Formed by Alkyne gem-Hydrogenation, Computed Properties of 27943-46-0, the publication is Journal of the American Chemical Society (2020), 142(43), 18541-18553, database is CAplus and MEDLINE.

The only recently discovered gem-hydrogenation of internal alkynes is a fundamentally new transformation, in which both H atoms of dihydrogen are transferred to the same C atom of a triple bond while the other position transforms into a discrete metal carbene complex. [Cp*RuCl]₄ is presently the catalyst of choice: the resulting piano-stool ruthenium carbenes can engage a tethered alkene into either cyclopropanation or metathesis, and a prototypical example of such a reactive intermediate with an olefin ligated to the ruthenium center has been isolated and characterized by X-ray diffraction. It is the substitution pattern of the olefin that determines whether metathesis or cyclopropanation takes place: a systematic survey using alkenes of largely different character in combination with a computational study of the mechanism at the local coupled cluster level of theory allowed the preparative results to be sorted and an intuitive model with predictive power to be proposed. This model links the course of the reaction to the polarization of the double bond as well as to the stability of the secondary carbene complex formed, if metathesis were to take place. The first application of “hydrogenative metathesis” to the total synthesis of sinularones E and F concurred with this interpretation and allowed the proposed structure of these marine natural products to be confirmed. During this synthesis, it was found that gem-hydrogenation also provides opportunities for C-H functionalization. Moreover, silylated alkynes are shown to participate well in hydrogenative metathesis, which opens a new entry into valuable allylsilane building blocks. Crystallog. evidence suggests that the polarized [Ru-Cl] bond of the catalyst interacts with the neighboring R₃Si group. Since attractive interligand Cl/R₃Si contacts had already previously been invoked to explain the outcome of various ruthenium-catalyzed reactions, including trans-hydrosilylation, the exptl. confirmation provided herein has implications beyond the present case.

Journal of the American Chemical Society published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Computed Properties of 27943-46-0.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics