Tag: 100-200

Linchpin Construction of Unsymmetrical 1,4-Alkynediols was written by Taber, Douglass F.;Storck, Pierre H.. And the article was included in Journal of Organic Chemistry in 2002.Recommanded Product: 13417-49-7 This article mentions the following:

Unsym. 1,4-alkynediols such as I are prepared by the coupling of trimethylsilylacetylene with two different aldehydes or ketones. Lithiation of trimethylsilylacetylene followed by addition of one aldehyde or ketone generates a lithium alkoxide; treatment with methyllithium removes the trimethylsilyl protecting group to generate a alkynyllithium which can add to a second aldehyde or ketone to give 1,4-alkynediols after workup. The desilylation reaction occurs only in THF. Aldehydes are preferable to ketones as the substrates for the first addition reaction; substrates with groups sensitive to base, such as easily lithiated arenes, should be added last. I, prepared in 65% yield from trimethylsilyllithium, cyclopropanecarboxaldehyde, and a dihydrobenzofurancarboxaldehyde, is converted to the diketone II, a metabolite of a potent nonsteroidal antiinflammatory agent, in two steps by oxidation of I to a 1,4-alkynyldione followed by reduction of the triple bond with palladium and barium sulfate. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Recommanded Product: 13417-49-7).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Dihydropyrans and tetrahydropyrans are examples of cyclic ethers widespread in nature. One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation of the 3,4-isomer of dihydropyran with Raney nickel.Recommanded Product: 13417-49-7

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

Lyoluminescent dosimetry of ionizing radiation was written by Matyushkov, V. V.;Mikhal’chenko, G. A.;Sigaev, V. Ya.;Yudin, I. V.;Lymarev, A. V.. And the article was included in Izvestiya Akademii Nauk SSSR, Seriya Fizicheskaya in 1977.COA of Formula: C6H14O7 This article mentions the following:

The possibility is discussed of a method of dosimetry of ionizing radiation based on the dissolution of irradiated solid substances. The anticipated limiting sensitivity of the method is 10-3 rad. The carbohydrates studied were glucose monohydrate [14431-43-7] and trehalose dihydrate [6138-23-4], as well as standard muscle tissue. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7COA of Formula: C6H14O7).

(2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7) belongs to tetrahydropyran derivatives. Numerous natural products have tetrahydropyran skeleton as the building block for designing new natural products and their derivatives e.g. aplysiatoxins, avermectins, oscillatoxins, talaromycins, latrunculins and acutiphycins. 2-(Arylmethylene)cyclopropylcarbinols could be converted to the corresponding tetrahydropyrans stereoselectively in the presence of Brønsted acids under mild conditions. A plausible Prins-type reaction mechanism has been proposed.COA of Formula: C6H14O7

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

The compressional properties of dextrose monohydrate and anhydrous dextrose of varying water contents was written by Armstrong, N. Anthony;Patel, Anil;Jones, Trevor M.. And the article was included in Drug Development and Industrial Pharmacy in 1986.Product Details of 14431-43-7 This article mentions the following:

The effect of moisture on the compressional properties of anhydrous dextrose  [50-99-7] and dextrose monohydrate (I) [14431-43-7] was examined Relations between moisture content and both tablet tensile strength and tablet toughness were evaluated. An increase in the moisture content of anhydrous dextrose produced a corresponding increase in both strength parameters up to the 8.9% moisture level, possibly due to a recrystallizing effect. However any further increase in moisture content beyond this point produced a marked reduction in both tablet tensile strength and tablet toughness. For I, any increase in moisture content obtained by exposure to elevated humidities led to a reduction in both tensile strength and toughness. The consolidation of both anhydrous dextrose and I was improved with increasing moisture content, presumably due to a lubrication effect. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7Product Details of 14431-43-7).

(2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7) belongs to tetrahydropyran derivatives. Tetrahydropyrans are useful synthons for biologically important compounds. The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Various fragrant compounds have been synthesized using this method.Product Details of 14431-43-7

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

Tricarbocyanines with dihydropyran, dihydrothiapyran, and N-methyltetrahydropyridine rings in chromophore was written by Tolmachev, A. I.;Slominskii, Yu. L.;Belaya, Zh. N.;Rodova, E. Z.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1976.Synthetic Route of C6H8O2 This article mentions the following:

Tricarbocyanines with γ,γ’-oxydimethylene, -thiodimethylene, or -(methylimino)dimethylene bridges [I; R = H or (RR) = benzo; R1 = H, Cl; X = Br, iodine, p-MeC6H4SO3; X1 = O, S, NMe] were prepared from benzothiazolium salts and the resp. diformyl heterocyclic compound dianils, and their spectra determined The hetero atom in the bridge causes a slight hypsochromic shift in the spectra of both I and the dianil intermediates, presumably due to a neg. inductive effect. Protonation of the imino group magnifies the effect. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Synthetic Route of C6H8O2).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Tetrahydropyrans and furans principally constitute as a central motif in diverse medicinally privileged molecules. One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation of the 3,4-isomer of dihydropyran with Raney nickel.Synthetic Route of C6H8O2

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

Alkaline epoxidation of α,β-unsaturated aldehydes was written by Payne, George B.. And the article was included in Journal of Organic Chemistry in 1961.Category: tetrahydropyran This article mentions the following:

Using the previously described procedure, MeCH:CHCHO (I) was epoxidized to yield 77% flashed aqueous epoxy aldehyde, RCH.CR'(CHO).O (II, R = Me, R’ = H), which gave 56% anhydrous product. For epoxidation of relatively H₂O-insoluble unsaturated aldehydes, MeOH was used as solvent. MeOH (300 ml.) containing 0.55 mole 30% H₂O₂ stirred at 35-40°, with cooling in a 5-necked flask provided with stirrer, dropping funnels, and standard electrodes attached to a Beckman pH meter, with dropwise addition in 10 min. of 56 g. 3-formyl-5,6-dihydro-2H-pyran (III) and addition of N NaOH to maintain meter pH 9 (corresponding to indicator paper pH 8), the mixture stirred 1.5 hrs. (consumption of 0.52 mole peroxide and 19 ml. N NaOH) and concentrated in vacuo, the concentrate saturated with (NH₄)₂SO₄ and extracted 3 times with 150 ml. CHCl₃, the washed (saturated (NH₄)₂SO₄) and dried (MgSO₄) extract concentrated, and the residue distilled through a glass helices-packed column yielded 70% epoxy aldehyde. In a similar flask 1 l. MeOH and 0.10 mole 30% H₂O₂ stirred with cooling at 35-40° 1 hr. with alternate portionwise addition of 132 g. PhCH:CHCHO (IV) in 100 ml. MeOH, 1.0 mole 30% H₂O₂, and N aqueous NaOH at constant meter pH 10.5-11.0 (pH 8-8.5 by indicator paper), the mixture kept 1 hr. at meter pH 10.0-10.5 and 35°, concentrated to 300 ml. and diluted with 1 l. H₂O, extracted 3 times with 300 ml. Et₂O and concentrated at 20° to constant weight (136 g. containing 0.08 mole organic peroxide), the residue taken up in 50 ml. C₆H₆ and hydrogenated 30 min. at 20°/50 lb./sq. in. with 3 g. 5% Pd-C, the filtered solution distilled and the product (79 g., b_0.5 65-90°) redistilled through a 10-tray Oldershaw column yielded 24% β-phenylglycidaldehyde. Results obtained similarly with I, MeCH:CMeCHO, III, IV, and citral are summarized (R, R’ of II, or starting compound, % yield, b.p./mm., n²⁰_D, and m.p. of 2,4-dinitrophenylhydrazone given): Me, H, 56, 60-1°/80, 1.4179, 136-8°; Me, Me, 46, 58-9°/60, 1.4198, -; III, 70, 56-7°/2.0, 1.4739, 136-6.5°; Ph, H, 24, 70-2°/0.3, 1.5448, 138-9°; citral, 75, 63-7°/1.0, 1.4609, -. II from I, MeCH:CMeCHO, and citral are new compounds In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Category: tetrahydropyran).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Tetrahydropyrans and furans principally constitute as a central motif in diverse medicinally privileged molecules. The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Various fragrant compounds have been synthesized using this method.Category: tetrahydropyran

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

New high affinity H₃ receptor agonists without a basic side chain was written by Kitbunnadaj, Ruengwit;Hoffmann, Marcel;Fratantoni, Silvina A.;Bongers, Gerold;Bakker, Remko A.;Wieland, Kerstin;el Jilali, Ahmed;De Esch, Iwan J. P.;Menge, Wiro M. P. B.;Timmerman, Henk;Leurs, Rob. And the article was included in Bioorganic & Medicinal Chemistry in 2005.Synthetic Route of C9H16O3 This article mentions the following:

In this study, we replaced the basic amine function of the known histamine H₃ receptor agonists imbutamine or immepip with non-basic alc. or hydrocarbon moieties. All compounds in this study show a moderate to high affinity for the cloned human H₃ receptor and, unexpectedly, almost all of them act as potent agonists. Moreover, in the alc. series, we consistently observed an increased selectivity for the human H₃ receptor over the human H₄ receptor, but none of the compounds in this series possess increased affinity and functional activity compared to their alkylamine congeners. In this new series of compounds VUF5657, 5-(1H-imidazol-4-yl)-pentan-1-ol, is the most potent histamine H₃ receptor agonist (pK_i = 8.0 and pEC₅₀ = 8.1) with a 320-fold selectivity at the human H₃ receptor over the human H₄ receptor. In the experiment, the researchers used many compounds, for example, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (cas: 103260-44-2Synthetic Route of C9H16O3).

Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (cas: 103260-44-2) belongs to tetrahydropyran derivatives. Tetrahydropyrans are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. There is large number of marine macrolide natural products that contain tetrahydropyran and tetrahydrofuran ring together. For instance, goniodomin A (actin targeting polyether), prorocentrolide (toxin halistatins), and percentotoxineSynthetic Route of C9H16O3

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

Quinuclidine. Bicyclo[2.2.2]-aza-1-octane was written by Kohlbach, D.;Cerkovnikov, E.;Rezek, A.;Piantanida, M.. And the article was included in Justus Liebigs Annalen der Chemie in 1937.Recommanded Product: Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate This article mentions the following:

Tetrahydropyranyl-4-carbinol and PBr₃ in C₅H₅N give, after 2 days, 58.5% of 4-bromomethyltetrahydropyran, b₁₇ 85-6°; refluxing with KCN in EtOH yields 83% of tetrahydropyran-4-acetonitrile, b₂₁ 125-6°; alk. hydrolysis gives 63% of tetrahydropyran-4-acetic acid (I), b₂₀ 178°, m. 54-5°. Tetrahydropyran-4-ol (II) and PhSO₂Cl with 5 N NaOH give 58% of the phenylsulfonate (III), pale brown oil, which was not purified but was caused to react with CHNa(CO₂Et)₂ to give 81% of the di-Et ester (IV), b₁₃ 156-60°, of tetrahydropyran-4-malonic acid, m. 151°; on heating it yields I. II and PBr₃ in C₅H₅N yield 52% of 4-bromotetrahydropyran, b₁₅ 60-1°; the reaction with CHNa(CO₂Et)₂ gives a smaller yield of IV than does III. Tetrahydro-γ-pyrone (V), BrCH₂CO₂Et and Zn in C₆H₆ give 43% of Et 4-hydroxy-tetrahydropyran-4-acetate, b₁₅ 132-40°, Ac derivative, b₂₁ 140-5°; distillation of the Ac derivative at room temperature (the operation is repeated 3 times) gives 77% of Et tetrahydropyranylidene-4-acetate, b₁₅ 113°, d₄^13.1 1.0663, n 1.4766, 1.4798, 1.4886, 1.4961 for α, He, β and γ at 13.1°; catalytic reduction (PtO₂) gives 91% of Et tetrahydropyran-4-acetate (VI), b₁₄ 108-10°, d₄^13.4 1.0268, n 1.4448, 1.4469, 1.4526, 1.4572 for α, He, β and γ at 13.4°. I, NCCH₂CO₂Et and piperidine in C₆H₆, heated 12 hrs., give 84% of Et tetrahydropyranylidene-4-(α-cyanoacetate) (VII), b₁₅ 156-9°, m. 66-7°; the free acid m. 137-8° (hydrolysis with dilute HCl); saponification with EtOH-KOH does not give the desired dicarboxylic acid; distillation of the free acid yields 50% of Δ³-dihydropyranacetonitrile, b₂₃ 135°, transformed by refluxing with 20% EtOH-H₂SO₄ for 62 hrs. into 15% of Et Δ³-dihydropyranacetate, b. 112-20° (in vacuo), d₄^17.8 1.0610, n 1.4614, 1.4639, 1.4711 for α, He and β at 17.6°; catalytic reduction gives VI. VII and p-BrC₆H₄COCH₂Br with EtONa in EtOH give Et α-cyano-α-Δ³-dihydropyranyl-4-β-(p-bromobenzoyl) propionate, m. 153-4°. A by-product of VII is the compound C₁₈H₂₀O₅N₂, m. 260° (decomposition); it contains an EtO group and a H atom titratable with alkali and phenolphthalein. Reduction of VI (Na and EtOH in benzine) gives 40% of 4-(β-hydroxyethyl)tetrahydropyran, b₁₄ 119-20°; phenylurethan, m. 70-1°; fuming HBr (6 hrs. at 100-10°) yields 80% of 3-(2-bromoethyl)-1,5-dibromopentane, b₁₇ 185-6°; heating with 20% MeOH-NH₃ at 130-40° gives 50% of quinuclidine, m. 158-9°; picrate, yellow, m. 275-6°. I and fuming HBr give β-(β’-bromoethyl)-δ-bromovaleric acid, which was esterified and heated with 20% MeOH-NH₃, yielding 20% of the Et ester, b₁₅ 123-7° (chloroplatinate, m. 192° (decomposition)), of piperidine-4-acetic acid, m. 237-8° (decomposition); chloroplatinate, orange, m. 210-13° (decomposition); phenylsulfonate. In the experiment, the researchers used many compounds, for example, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (cas: 103260-44-2Recommanded Product: Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate).

Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (cas: 103260-44-2) belongs to tetrahydropyran derivatives. Tetrahydropyran is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuff. The bismuth chloride-assisted cross-cyclization between homoallylic alcohols and epoxides provided various benzyl tetrahydropyran derivatives. The reaction afforded good yields of desired products and occurred under mild conditions.Recommanded Product: Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate

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

New phase diagram of the D-glucose water system was written by Smelik, A.;Torok, S.;Vukov, K.. And the article was included in Acta Alimentaria in 1990.Application In Synthesis of (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate This article mentions the following:

Saturated D-glucose solutions, depending on temperature, may be in equilibrium with the following solid phases: β-D-glucopyranose, α,β-D-glucopyranose hemihydrate, anhydrous α-D-glucopyranose, β-D-glucopyranose monohydrate, simultaneously present α-D-glucopyranose monohydrate and β-D-glucopyranose monohydrate, α-D-glucopyranose monohydrate. The solubility curves, presented anal. and graphically, are indispensable in the production of high-purity allotroph-identical crystalline glucose by means of crystallization at the appropriate temperature and concentration region. The formation and properties of α,β-D-glucopyranose hemihydrate crystals were also demonstrated. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7Application In Synthesis of (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate).

(2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7) belongs to tetrahydropyran derivatives. In organic synthesis, the 2-tetrahydropyranyl group is used as a protecting group for alcohols. 2-(Arylmethylene)cyclopropylcarbinols could be converted to the corresponding tetrahydropyrans stereoselectively in the presence of Brønsted acids under mild conditions. A plausible Prins-type reaction mechanism has been proposed.Application In Synthesis of (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate

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

Synthesis, SAR study, and biological evaluation of novel quinoline derivatives as phosphodiesterase 10A inhibitors with reduced CYP3A4 inhibition was written by Hamaguchi, Wataru;Masuda, Naoyuki;Miyamoto, Satoshi;Shiina, Yasuhiro;Kikuchi, Shigetoshi;Mihara, Takuma;Moriguchi, Hiroyuki;Fushiki, Hiroshi;Murakami, Yoshihiro;Amano, Yasushi;Honbou, Kazuya;Hattori, Kouji. And the article was included in Bioorganic & Medicinal Chemistry in 2015.COA of Formula: C9H16O3 This article mentions the following:

A novel class of phosphodiesterase 10A inhibitors with potent PDE10A inhibitory activity and reduced CYP3A4 inhibition was designed and synthesized starting from I. Replacement of pyridine ring of I with N-Me pyridone ring drastically improved CYP3A4 inhibition, and further optimization of these quinoline analogs identified compound II, which showed potent PDE10A inhibitory activity and a good CYP3A4 inhibition profile. A PET study with ¹¹C-labeled II indicated that II exhibited good brain penetration and specifically accumulated in the rodent striatum. Further, oral administration of II dose-dependently attenuated phencyclidine-induced hyperlocomotion in mice with an ED₅₀ value of 2.0 mg/kg and improved visual-recognition memory impairment at 0.1 and 0.3 mg/kg in mice novel object recognition test. In the experiment, the researchers used many compounds, for example, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (cas: 103260-44-2COA of Formula: C9H16O3).

Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (cas: 103260-44-2) belongs to tetrahydropyran derivatives. Tetrahydropyrans are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation of the 3,4-isomer of dihydropyran with Raney nickel.COA of Formula: C9H16O3

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

Derivatives of acraldehyde dimer was written by Hall, R. H.. And the article was included in Chemistry & Industry (London, United Kingdom) in 1955.Formula: C6H8O2 This article mentions the following:

Acid treatment of HOCH₂CH₂CHO (C.A. 44, 10725c) gave a final product formulated as 3-formyl-Δ³-dihydropyran 2,4-dinitrophenylhydrazone (I), m. 228° and the probable parent aldehyde (II) is described (C.A. 44, 8378a) but there is no proof of structure of I or II. Preparation of II [b₁₂ 77-8° n_D²⁰ 1.4979; semicarbazone, m. 216-17° (cf. C.A. 44, 8378a)] and formation of the 2,4-dinitrophenylhydrazone, m. 234.5° (decomposition, pre-heated bath) showed that I was this derivative of II by mixed m.p. and ultraviolet spectra (λ in EtOH 376 mμ, E about 28,000). Reduction of II over Pt gave 45% 3-formyltetrahydropyran (III), b_10.5 69-70°, n_D²⁰ 1.4533; 2,4-dinitrophenylhydrazone, m. 154-5°. Ag₂O-Ba(OH)₂ oxidation of III yielded 90% of the acid, m. 97-8°; anilide, m. 131-2° (this and other derivatives were identical with authentic material). The ultraviolet spectrum showed α,β-unsaturation in II and the double bond was shown by nonidentity of the acid and derivative from II with authentic Δ²-derivative thus showing that I and II have a Δ³-structure. Complete reduction of II gave 3-hydroxymethyltetrahydropyran, b₁₁ 104°, n_D²⁰ 1.4624; phenylurethan, m. 89°. Treatment of Δ³-dihydropyran-3-carboxylic acid with Raney Ni in aqueous alkali at 100° yielded only a trace of Δ²-acid and this on decarboxylation gave only a trace of Δ²-dihydropyran. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Formula: C6H8O2).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Dihydropyrans and tetrahydropyrans are examples of cyclic ethers widespread in nature. The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Various fragrant compounds have been synthesized using this method.Formula: C6H8O2

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