Category: 13417-49-7

Synthesis of hydroxy-γ-lactones from α,β-unsaturated aldehydes was written by Marschall, Helga;Penninger, Josef;Weyerstahl, Peter. And the article was included in Liebigs Annalen der Chemie in 1982.Reference of 13417-49-7 This article mentions the following:

RCH:CR¹CHO [I; R = Me, R¹ = H; RR¹ = (CH₂)_3-5, CH₂CH₂OCH₂, CH₂CH₂CH₂CMe₂], Me₂C:CHCHO (II), and III (R³ = CHO, R⁴R⁵ = bond) reacted in three steps (epoxidation, PO olefination, and selective hydrogenation to give the corresponding esters IV (R² = CH₂CH₂CO₂Et), IV (R = CH₂CH₂CO₂Et, R¹ = R² = Me) and III (R³ = CH₂CH₂CO₂Et, R⁴R⁵ = O). These steps were interchangeable, especially the epoxidation and olefination. These esters were hydrolyzed to give V [R⁶ = H, R⁷ = R⁸ = Me; R⁶R⁷ = (CH₂)_n, CH₂OCH₂CH₂, R⁸ = H; R⁶R⁷ = CMe₂CH₂CH₂CH₂, R⁸ = Me; n = 4-5]. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Reference of 13417-49-7).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) 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.Reference of 13417-49-7

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

Formation of dihydroxybenzenes in cigarette smoke. part 2. contribution from quinic acid and myo-inositol was written by Moldoveanu, Serban C.;Davis, Michael F.. And the article was included in Beitraege zur Tabakforschung International in 2013.Quality Control of 5,6-Dihydro-2H-pyran-3-carbaldehyde This article mentions the following:

Formation of dihydroxybenzenes in cigarette smoke is a subject of considerable interest because some dihydroxybenzenes are co-carcinogens, (e.g., catechol and certain alkylcatechols), and others such as hydroquinone can form metabolites that have toxic or carcinogenic properties. This present study describes the contribution of tobacco quinic acid (or (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid) and myo-inositol (or (1R,2R,3S,4S,5R,6S)-cyclohexane-1,2,3,4,5,6-hexol) to the formation of dihydroxybenzenes in cigarette smoke. The study is a continuation of a previous one showing the contribution of chlorogenic acid and rutin as precursors for these compounds (6). The yields of dihydroxybenzenes formed by pyrolysis of quinic acid and myo-inositol are relatively high and both quinic acid and myo-inositol can be present in some tobacco types at levels as high as 1% by weight The level of these compounds makes them potentially important contributors to the formation of dihydroxybenzenes in cigarette smoke. Similar to the previous study on other dihydroxybenzene precursors from tobacco, this present study was done in three parts: (1) pyrolytic evaluation of the amount of dihydroxybenzenes in smoke generated from isolated quinic acid and myo-inositol; (2) anal. of smoke from cigarettes made from a variety of tobaccos (14 single grades) and two blended cigarettes, followed by correlations of dihydroxybenzene yields from these cigarettes with the level of quinic acid and myo-inositol in the tobaccos; (3) addition of quinic acid or myo-inositol to several tobaccos followed by the smoking of the spiked cigarettes and measurement of the dihydroxybenzenes yield increase. The study performed on a variety of single-grade tobacco cigarettes and for two blended-tobacco cigarettes (one being the 2R4F Kentucky reference) shows that the contribution of quinic acid and of inositol to the formation of catechol and hydroquinone in smoke depends on the blend, as previously shown for chlorogenic acid and rutin. The study results suggest that quinic acid and myo-inositol may be major contributors to the formation of dihydroxybenzenes in cigarette smoke. Although the calculations do not provide precise numbers for the contribution of quinic acid and inositol to the formation of dihydroxybenzenes, these results suggest that the contribution could be as high as 50 to 60% of the level of dihydroxybenzenes. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Quality Control of 5,6-Dihydro-2H-pyran-3-carbaldehyde).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) 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.Quality Control of 5,6-Dihydro-2H-pyran-3-carbaldehyde

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

Process simulation and technol-economic analysis on hydration and hydrogenation technology of acrolein for 1,3-propanediol production was written by Zeng, Hong;Fang, Bai-shan;Qu, Yin-di. And the article was included in Guocheng Gongcheng Xuebao in 2013.SDS of cas: 13417-49-7 This article mentions the following:

Based on laboratory and pilot experiments of hydration and hydrogenation of acrolein for production of 1,3-propanediol (PDO), the Superpro Designer simulation was applied to simulate the scale-up process for 10000 t/a PDO production, coupling with costing and economic evaluation on the flowsheet. Simulation results show that the process design is reasonable with main process data complying with exptl. results. The economic anal. indicates that raw material cost shares 49% of operating cost, equipment purchase cost is about 22.42 million yuan and the total investment is of approx. 150.88 million yuan. The expected returns on investment reach 28.21% as the after-tax profit is about 42.56 million yuan annually. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7SDS of cas: 13417-49-7).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Tetrahydropyrans are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. 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.SDS of cas: 13417-49-7

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

Oximes as artificial sweeteners. Part 23. Unsaturated oximes was written by Unterhalt, Bernard;Ghori, Mahmood. And the article was included in Zeitschrift fuer Lebensmittel-Untersuchung und -Forschung in 1980.Formula: C6H8O2 This article mentions the following:

Cyclization of acrolein with H₂S in CH₂Cl₂ containing Cu turnings and NEt₃ at -10° gave 86% aldehyde I, which was oximated with H₂NOH to give 53% oxime II (R = R¹ = H, X = S). Similarly, II (R = R¹ = Me, X = S) and II (R = R¹ = H, X = O) were prepared from the aldehydes. On comparison with the sweet-tasting II (R = R¹ = H, X = CH₂), only II (R = R¹ = H, X = S) had a slightly sweet taste. 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. Tetrahydropyran is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuff. 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.Formula: C6H8O2

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

Chiral Hetero- and Carbocyclic Compounds from the Asymmetric Hydrogenation of Cyclic Alkenes was written by Verendel, J. Johan;Li, Jia-Qi;Quan, Xu;Peters, Byron;Zhou, Taigang;Gautun, Odd R.;Govender, Thavendran;Andersson, Pher G.. And the article was included in Chemistry – A European Journal in 2012.COA of Formula: C6H8O2 This article mentions the following:

Several types of chiral hetero- and carbocyclic compounds have been synthesized by using the asym. hydrogenation of cyclic alkenes. N,P-Ligated iridium catalysts reduced six-membered cyclic alkenes, e.g., I, with various substituents and heterofunctionality in good to excellent enantioselectivity, whereas the reduction of five-membered cyclic alkenes, e.g., II, was generally less selective, giving modest enantiomeric excesses. The stereoselectivity of the hydrogenation depended more strongly on the substrate structure for the five- rather than the six-membered cyclic alkenes. The major enantiomer formed in the reduction of six-membered alkenes could be predicted from a selectivity model and isomeric alkenes had complementary enantioselectivity, giving opposite optical isomers upon hydrogenation. The utility of the reaction was demonstrated by using it as a key step in the preparation of chiral 1,3-cis-cyclohexane carboxylates. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7COA of Formula: C6H8O2).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Tetrahydropyran is a useful synthetic intermediate. Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and dihydropyran are common intermediates in organic synthesis. 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.COA of Formula: C6H8O2

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

Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and Arylnitroso Compounds was written by Francois, Benjamin;Eberlin, Ludovic;Berree, Fabienne;Whiting, Andrew;Carboni, Bertrand. And the article was included in Journal of Organic Chemistry in 2020.Application of 13417-49-7 This article mentions the following:

Dienylboronates such as I were prepared by hydroboration of enynes with terminal alkyne moieties, by boron-Wittig reactions of bis(pinacolato)methane with enals, or by newly optimized tandem ring closing and olefin cross-metathesis and ring closing metathesis reactions of enynes or of triene II in the presence of the first- or second-generation Grubbs catalysts. Reaction of dienylboronates with aryl nitroso compounds RNO mediated by DBU in methanol yielded fused arylpyrroles such as III by a nitroso-Diels-Alder reaction followed by ring contraction. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Application of 13417-49-7).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) 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 of 13417-49-7

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

Synthesis, characterization, crystal structure and electrochemical behavior of a nickel(II) complex of 5,6-dihydro-2H-pyran-3-aldehyde thiosemicarbazone was written by Harek, Yahia;Larabi, Lahcene;Boukli, Leila;Kadri, Fatima;Benali-Cherif, Noureddine;Mostafa, Mohsen M.. And the article was included in Transition Metal Chemistry (Dordrecht, Netherlands) in 2005.Synthetic Route of C6H8O2 This article mentions the following:

A new Ni^II complex of 5,6-dihydro-2H-pyran-3-aldehyde thiosemicarbazone (HDPTSC) was synthesized and characterized by microanalyses, magnetic susceptibility, molar conductance measurements and by spectral methods (IR, UV-visible, ¹H-NMR). The structure of [Ni(DPTSC)₂]· DMF was solved using x-ray diffraction and is highly sym. with a trans arrangement of the two bidentate ligands. The thiosemicarbazone coordinates as an anionic ligand via the thiosemicarbazone moiety’s azomethine N and thiolate S [on loss of the N2 H]. The electrochem. behavior of the ligand and its Ni^II complex, determined by cyclic voltammetry, shows that the redox process of the ligand was highly irreversible, whereas the redox process of the Ni^II complex was observed as a one electron transfer process in a quasi-reversible and diffusion-controlled reaction. 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 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.Synthetic Route of C6H8O2

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

Polymethine dyes based on pyrylium salts with unsaturated cyclic groups in the 4-position was written by Kurdyukov, V. V.;Tolmachev, A. I.. And the article was included in Dopovidi Natsional’noi Akademii Nauk Ukraini in 2017.Application of 13417-49-7 This article mentions the following:

2,6-Diphenyl-substituted pyrylium salts containing unsaturated cyclic groups are synthesized. They are shown to be feasible precursors for the synthesis of sym. and unsym. dyes. The spectral properties of synthesized dyes are studied in solvents of different polarities. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Application of 13417-49-7).

5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Tetrahydropyran is a useful synthetic intermediate. Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and dihydropyran are common intermediates in organic synthesis. The Prins reaction of homoallylic alcohols with aldehydes afforded an alternative method for the preparation of tetrahydropyrans.Application of 13417-49-7

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

Synthesis, characterization, crystal structure and electrochemical behavior of a nickel(II) complex of 5,6-dihydro-2H-pyran-3-aldehyde thiosemicarbazone was written by Harek, Yahia;Larabi, Lahcene;Boukli, Leila;Kadri, Fatima;Benali-Cherif, Noureddine;Mostafa, Mohsen M.. And the article was included in Transition Metal Chemistry (Dordrecht, Netherlands) in 2005.Synthetic Route of C6H8O2 This article mentions the following:

A new Ni^II complex of 5,6-dihydro-2H-pyran-3-aldehyde thiosemicarbazone (HDPTSC) was synthesized and characterized by microanalyses, magnetic susceptibility, molar conductance measurements and by spectral methods (IR, UV-visible, ¹H-NMR). The structure of [Ni(DPTSC)₂]· DMF was solved using x-ray diffraction and is highly sym. with a trans arrangement of the two bidentate ligands. The thiosemicarbazone coordinates as an anionic ligand via the thiosemicarbazone moiety’s azomethine N and thiolate S [on loss of the N2 H]. The electrochem. behavior of the ligand and its Ni^II complex, determined by cyclic voltammetry, shows that the redox process of the ligand was highly irreversible, whereas the redox process of the Ni^II complex was observed as a one electron transfer process in a quasi-reversible and diffusion-controlled reaction. 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 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.Synthetic Route of C6H8O2

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