Heterocyclic Building Blocks-Tetrahydropyran

Kaiser, Roman published the artcileThe (5R*,9S*)- and (5R*,9R*)-2,2,9-trimethyl-1,6-dioxaspiro[4.4]non-3-ene and their dihydro derivatives as new constituents of geranium oil, Formula: C10H16O2, the publication is Helvetica Chimica Acta (1984), 67(5), 1198-203, database is CAplus.

(5R ,9S )- (I) [92356-08-6] and (5R ,9R )-2,2,9-trimethyl-1,6-dioxaspiro[4.4]non-3-ene (II) [92356-04-2] and their dihydro derivatives, III  [92356-09-7] and IV  [92356-10-0], were isolated from geranium oil and their structures determined by spectra and synthesis. Other trace monoterpenes such as nerol oxide  [1786-08-9] were also isolated.

Helvetica Chimica Acta 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

Jouve, Pierre published the artcileNuclear magnetic resonance of the acetylenic proton in 1-alkynes, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Compt. Rend. (1963), 1497-9, database is CAplus.

The frequency of the N.M.R. signal of the acetylenic proton (CC-H) is determined for dilute CCl₄ solutions of 1-alkynes at 60 Mc. (A Varian A-60 instrument was used). An external reference, 5% Me₄Si in CCl₄, χ_r = 0.684 × 10^-6, is used Me₄Si is taken as zero. The value of the chem. shift when dilution no longer influences its position, σ_∞CCl4, is determined for 6 linear acetylenes, 1.73-1.87 (branching caused displacement toward weak fields, contrary to the inductive effect); for 4α- and ω-diynes, 1.78-1.84 (considerable interaction between bonds at ends of chain, but with longer chains similar to linear acetylenes); for 5 ene-ynes, 2.60-2.89 (strong displacement toward weak fields, resonance stabilization); for 3 acetylenes with conjugated benzene rings in the a position, 2.92-3.06 (same as ene-ynes, but more so); for 5 α-acetylenic alcs., 2.20-2.33 (characteristic for these compounds); for 3 acetals and propargyl ethers, 2.26-2.33 (like α-alcs., conjugation is not possible, only the electroneg. character of the O being affected the displacement); for 3 alcs. with benzene rings in the β position to the ethynyl group, 2.46-2.77 (homoallyl activation with orbital electrons of the triple bonds partially conjugated with those of the ring); and for 4 γ-oxygenated acetylenes, 1.89-1.93 (more like the corresponding hydrocarbons).

Compt. Rend. 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, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

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

Dick, William E. Jr. published the artcileStructure-taste correlations for flavans and flavanones conformationally equivalent to phyllodulcin, Product Details of C16H14O6, the publication is Journal of Agricultural and Food Chemistry (1981), 29(2), 305-12, database is CAplus.

Preparation of a conformationally defined series of compounds related to phyllodulcin (I) [21499-23-0] allows more accurate correlations of structural features with taste. Four flavans (3,4-dihydro-2H-1-benzopyrans) and their parent flavones (2,3-dihydro-4H-1-benzopyran-4-ones) were prepared from chalcones derived from 2-hydroxyacetophenone [582-24-1], 2,4-dihydroxyacetophenone [89-84-9], 2,6-dihydroxyacetophenone [699-83-2], or 2,4,6-trihydroxyacetophenone [480-66-0], and isovanillin (3-hydroxy-4-methoxybenzaldehyde) [621-59-0]. These compounds can exist both as semiplanar and bent conformers, equivalent to those of phyllodulcin, permitting a close comparison of structural features with taste. Semiplanar conformations were established for phyllodulcin and the analogous compounds by ¹H NMR. Evidence for bent conformations was lacking. Flavans derived from 2-hydroxy and 2,4-dihydroxyacetophenone were sweet, the latter intensely so, whereas the 2,3 analog was intensely bitter. Comparisons with phyllodulcin and derivatives demonstrated the effects of nonaromatic ring heteroatom location A-ring hydroxylation, and a carbonyl group.

Journal of Agricultural and Food 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 C16H14O6, Product Details of C16H14O6.

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

Claesson, Alf published the artcileAllenes and acetylenes. X. Convenient method for conversion of acetylenic derivatives into conjugated dienes via α-allenic alcohols, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry (1975), 29(5), 609-16, database is CAplus.

4-Alkoxy- and 4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ols are in most cases quantitatively converted into conjugated dienes when treated with LiAlH4 in refluxing THF or similar solvents. The reactions proceed via α- allenic alcohols. The dienes are free from positional isomers and the formation of alkenynes, which occurs in some cases, can be completely suppressed by a combination of LiAlH4 and AlCl3. Most of the conjugated dienes seem to be formed with low stereoselectivity. The E,E form is the predominant isomer of 2,4-hexadiene while of 4,6-decadiene the E,Z isomer predominates. These latter results may indicate that the attack by hydride on the central carbon atom of the propadienyl group is sterically hindered when the double bond remaining in the same position is formed with E configuration.

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, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

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

Borujeni, Kaveh Parvanak published the artcileSilica-gel-supported aluminum chloride. A stable, efficient, selective, and reusable catalyst for tetrahydropyranylation of alcohols and phenols, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Synthetic Communications (2006), 36(18), 2705-2710, database is CAplus.

A simple, effective, and highly chemoselective method to form 2-tetrahydropyranyl ethers of alcs. and phenols in the presence of silica-gel-supported aluminum chloride as a heterogeneous Lewis acid catalyst is described. The catalyst can be easily recovered and reused without appreciable change in its efficiency.

Synthetic Communications 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, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

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

Pang, Limin published the artcileEvaluation of perphenylcarbamated cyclodextrin clicked chiral stationary phase for enantioseparations in reversed phase high performance liquid chromatography, Synthetic Route of 69097-99-0, the publication is Journal of Chromatography A (2014), 119-127, database is CAplus and MEDLINE.

Perphenylcarbamated cyclodextrin clicked chiral stationary phase (CSP) was developed with high column efficiency. The characteristics of the column were evaluated in terms of linearity, limit of detection and limit of quantification. The enantioselectivity of the as-prepared clicked CSP was explored with 26 recemates including aryl alcs., flavanoids and adrenergic drugs in reversed phase HPLC. The effect of separation parameters including flow rate, column temperature, organic modifier and buffer on the enantioselectivity of the clicked CSP was studied. The correlation study of the analytes structure and their chiral resolution revealed the great influence of analytes’ structure on the enantioseparations with cyclodextrin CSP. Methanol with 1% of triethylammonium acetate buffer (pH 4) is the best choice for the chiral separation of basic enantiomers.

Journal of Chromatography A 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

Lin, Yuzhou published the artcileCyclodextrin clicked chiral stationary phases with functionalities-tuned enantioseparations in high performance liquid chromatography, COA of Formula: C16H14O6, the publication is Journal of Chromatography A (2015), 342-346, database is CAplus and MEDLINE.

Two cyclodextrin (CD) chiral stationary phases (CSPs) were developed by clicking per-4-chloro-3-methylphenylcarbamoylated mono-6^A-azido-β-CD (CSP1) and per-5-chloro-2-methylphenylcarbamoylated mono-6^A-azido-β-CD (CSP2) onto alkynylated silica support. The enantioslectivies of the as-obtained new CSPs were evaluated using 29 model racemates including aromatic alcs., flavonoids, β-blocker and FMOC-amino acids in both reversed-phase (RP) and normal-phase (NP) HPLC. The CD functionalities tuned enantioselectivities were elucidated in different HPLC elution modes. Higher chiral resolutions were achieved in RP-elution mode with the aid of the inclusion complexation in comparison to NP-elution mode. The π-π stacking interaction and dipole-dipole interaction provided by phenylcarbamate moieties can also contribute to the enantioseparation

Journal of Chromatography A 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, COA of Formula: C16H14O6.

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

Chen, You-Lan published the artcileSystems pharmacology approach reveals protective mechanisms of Jian-Pi Qing-Chang decoction on ulcerative colitis, Safety of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is World Journal of Gastroenterology (2019), 25(21), 2603-2622, database is CAplus and MEDLINE.

To investigate the protective mechanisms of Jian-Pi Qing-Chang (JPQC) decoction on ulcerative colitis (UC) based on systems pharmacol. approach. We performed systems pharmacol. to predict the active ingredients, the matched targets, and the potential pharmacol. mechanism of JPQC on UC. In vivo, we explored the effects of JPQC in a colitis model induced by dextran sulfate sodium. In vitro, we adopted the bone marrow-derived macrophages as well as BMDMs co-cultured with Caco2 cells to verify the underlying mechanisms and effects of JPQC on UC under TNF-α stimulation. Protein-protein interaction networks were established to identify the underlying therapeutic targets of JPQC on UC. Based on enrichment analyses, we proposed our hypothesis that JPQC might have a protective effect on UC via the NF-κB/HIF-1a signaling pathway. Subsequent exptl. validation revealed that treatment with TNFa activated the NF- κB/HIF-1a signaling pathway in BMDMs, thereby damaging the epithelial barrier permeability in co-cultured Caco2 cells, while JPQC rescued this situation. The findings were also confirmed in a dextran sulfate sodium-induced colitis model. JPQC could improve the mucosal inflammatory response and intestinal epithelial barrier function via the NF-κB/HIF-1α signaling pathway, which provides new perspectives on the pharmaceutical development and clin. practice of TCM.

World Journal of Gastroenterology 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, Safety of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one.

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

Yao, Xiaobin published the artcileEngineering Thiol-Ene Click Chemistry for the Fabrication of Novel Structurally Well-Defined Multifunctional Cyclodextrin Separation Materials for Enhanced Enantioseparation, Name: 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is Analytical Chemistry (Washington, DC, United States) (2016), 88(9), 4955-4964, database is CAplus and MEDLINE.

The preparation of two novel multifunctional cyclodextrin (CD) separation materials and their ultimate enantioseparation performances in HPLC are reported. A mild thiol-ene click reaction was used to anchor 1-allylimidazolium-per(p-methyl)phenylcarbamoylated-β-CD and 1-allylimidazolium-per(p-chloride)phenylcarbamoylated-β-CD onto thiol-modified porous silica giving structurally well-defined stable cationic multifunctional CD chiral stationary phases (CSP1 and CSP2, resp.). These covalently bonded CD phases have typical interaction modes such as H-bonding, π-π effect, electrostatic and dipole-dipole interactions as well as steric effects which result in superior chiral resolution for a variety of chiral compounds in different separation modes. In a reverse-phase mode, both CSPs exhibited excellent separation abilities for isoxazolines, flavonoids, β-blockers, and some other neutral and basic racemates. In a polar-organic mode, isoxazolines and flavonoids were well resolved. CSP1 with an electron-rich Ph substitution on the CD rims gave a better resolution for isoxazolines whereas CSP2 with an electron-deficient Ph substitution on the CD rims gave better resolution for flavonoids. Among isoxazolines, 4ClPh-OPr gained a high selectivity and resolution up to 18.6 and 38.7, resp., which is an amazing result for CD enantioseparation materials.

Analytical Chemistry (Washington, DC, United States) 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 C8H11NO, Name: 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one.

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

Lai, Yanni published the artcileGanghuo Kanggan decoction in influenza: integrating network pharmacology and in vivo pharmacological evaluation, SDS of cas: 69097-99-0, the publication is Frontiers in Pharmacology (2020), 607027, database is CAplus and MEDLINE.

Ganghuo Kanggan decoction (GHKGD) is a clin. experience prescription used for the treatment of viral pneumonia in the Lingnan area of China, and its clin. effect is remarkable. However, the mechanism of GHKGD in influenza is still unclear. To predict the active components and signaling pathway of GHKGD and to explore its therapeutic mechanism in influenza and to verified it in vivo using network pharmacol. The potential active components and therapeutic targets of GHKGD in the treatment of influenza were hypothesized through a series of network pharmacol. strategies, including compound screening, target prediction and pathway enrichment anal. Based on the target network and enrichment results, a mouse model of influenza A virus (IAV) infection was established to evaluate the therapeutic effect of GHKGD on influenza and to verify the possible mol. mechanism predicted by network pharmacol. A total of 116 candidate active compounds and 17 potential targets were identified. The results of the potential target enrichment anal. suggested GHKGD may involve the RLR signaling pathway to reduce inflammation in the lungs. In vivo experiments showed that GHKGD had a protective effect on pneumonia caused by IAV-infected mice. Compared with the untreated group, the weight loss in the GHKGD group in the BALB/c mice decreased, and the inflammatory pathol. changes in lung tissue were reduced (p < 0.05). The expression of NP protein and the virus titers in lung were significantly decreased (p < 0.05). The protein expression of RIG-I, NF-kB, and STAT1 and the level of MAVS and IRF3/7 mRNA were remarkably inhibited in GHKGD group (p < 0.05). After the treatment with GHKGD, the level of Th1 cytokines (IFN-γ, TNF-α, IL-2) was increased, while the expression of Th2 (IL-5, IL4) cytokines was reduced (p < 0.05). Through a network pharmacol. strategy and in vivo experiments, the multi-target and multi-component pharmacol. characteristics of GHKGD in the treatment of influenza were revealed, and regulation of the RLR signaling pathway during the anti-influenza process was confirmed. This study provides a theor. basis for the research and development of new drugs from GHKGD.

Frontiers in Pharmacology 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, SDS of cas: 69097-99-0.

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