25090-33-9

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 35, p. 3200, 1970 DOI: 10.1021/jo00834a091

InChI:InChI=1/C6H8O2/c7-4-6-2-1-3-8-5-6/h4-5H,1-3H2

Upstream product

• 107-02-8 acrolein 
• 117837-38-4 3-(dimethoxymethyl)-2-methoxytetrahydro-2H-pyran 
• 110-87-2 3,4-dihydro-2H-pyran 
• 122-51-0 orthoformic acid triethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 69549-51-5 2-Ethoxytetrahydropyran-3-carboxaldehyde-diethylacetal 

Downstream Products

• 1061704-68-4 C₁₁H₁₅N₃O 
• 1061704-88-8 C₁₆H₁₇N₃O 
• 1061704-91-3 C₂₂H₂₁N₃O₂ 
• 1061704-94-6 C₁₆H₁₇N₃O 
• 1335223-59-0 4-(3,4-dihyro-2H-pyran-5-ylmethyl)-2,6-dimethylphenol 
• 1335223-57-8 2-benzyloxy-3-methylenetetrahydropyran 
• 1261072-67-6 1-(3,4-dihydro-2H-pyran-5-yl)-3-phenylprop-2-yn-1-ol 
• 1261072-68-7 5-(1-ethoxy-3-phenylprop-2-ynyl)-3,4-dihydro-2H-pyran 
• 123476-64-2 1-Benzyl-4-(3-hydroxy-propyl)-1H-pyrrole-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Knoevenagel-Cyclization Cascade Reactions of Substituted 5,6-Dihydro-2H-Pyran Derivatives

The diastereoselective domino-Knoevenagel-IMHDA reactions of 5,6-dihydro-2H-pyran derivatives containing an o-formylaryl amine or ether moiety were performed with active methylene reagents. In the spiro heterocyclic products representing a novel skeleton, a tetrahydroquinoline or chroman unit is fused with two pyran rings and the bridgehead carbon atoms are chirality centers formed diastereoselectively. Depending on the substitution pattern, a domino Knoevenagel-[1,5]-hydride shift-cyclization sequence was identified as a competing pathway, which resulted in the formation of tetrahydroquinoline derivatives with a 5,6-dihydro-2H-pyran-3-yl substituent. The relative configurations of the products were determined by means of the characteristic NOE correlations and single crystal X-ray diffraction analysis. Antiproliferative activity assays of two products against A2780 and WM35 human cancer cell lines showed low micromolar IC50 values down to 2.99 μM.

METHOD FOR PRODUCING CONDENSED HETEROCYCLIC COMPOUND

PROBLEM TO BE SOLVED: To provide a novel and industrially advantageous method for producing a condensed heterocyclic compound useful as an agrochemical. SOLUTION: A high-yield and inexpensive method for producing a compound represented by formula (1) comprises synthesis of a pyridine derivative having a cyclopropyl group at the 5-position, and a subsequent reaction. (In the formula, n and m are integers from 0 to 2.) SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Carbon Dioxide Copolymerization Study with a Sterically Encumbering Naphthalene-Derived Oxide

Poly(1,4-dihydronaphthalene carbonate) has been prepared via the catalytic coupling of carbon dioxide and 1,4-dihydronaphthalene oxide using chromium(III) catalysts. The copolymer formation is found to be greatly dependent on the steric environment around the metal center. Traditional (salen)CrIIIX/cocatalyst systems bearing bulky t-butyl groups hinder the approach of the large monomer, significantly diminishing polymer chain growth and providing the entropically favored cyclic byproduct in excess. In contrast, employing the sterically unencumbered azaannulene-derived catalyst, (tmtaa)CrIIIX/cocatalyst system (tmtaa = tetramethyltetraazaannulene) shows polymer selectivity close to 90% with three times the activity (TOF = 20-30 h-1). With the use of a bifunctional (salen)CrIII catalyst, even higher polymer selectivity (>90%) can be observed. The complete synthesis of a new bifunctional tetraazaannulene ligand for a more effective catalyst is also described herein.

Synthesis and evaluation of pyrazolo[3,4-b]pyridines and its structural analogues as TNF-α and IL-6 inhibitors

In the present article, we have synthesized three different series of pyrazolo[3,4-b]pyridines and their structural analogues using novel synthetic strategy involving one-pot condensation of 5,6-dihydro-4H-pyran-3-carbaldehyde/2-formyl-3,4,6-tri-O-methyl-d-glucal /chromone-3-carbaldehyde with heteroaromatic amines. All synthesized compounds were evaluated for their anti-inflammatory activity against TNF-α and IL-6. Out of 28 compounds screened, 40, 51, 52 and 56 exhibited promising activity against IL-6 with 60-65% inhibition at 10 μM concentration. Amongst these, 51, 52 and 56 showed potent IL-6 inhibitory activity with IC50's of 0.2, 0.3 and 0.16 μM, respectively. Compound 56 was not cytotoxic in CCK-8 cells up to the concentration of >100 μM.

Direct formylation of enol ethers using cyanuric chloride and N,N-dimethylformamide

A new method to prepare α,β-unsaturated enol aldehydes is described. 3-Ethoxymethacrolein (1) and 5-formyl-3,4-dihydro-2H-pyran (5) were effectively prepared from enol ethers and the Vilsmeier-Haack type complex, derived from cyanuric chloride and DMF. One byproduct, amidine 4, was also characterized.

1,8-Dihydro-6,13-bis(3-hydroxypropyl)-1,4,8,11-tetraazaannulenes from 3,4-Dihydro-2H-pyran-5-carbaldehyde

1,8-Dihydro-6,13-bis(3-hydroxypropyl)-1,4,8,11-tetraazaannulenes 6 are synthesized from 1,2-benzenediamines 5 and 3,4-dihydro-2H-pyran-5-carbaldehyde (3a) as a cyclic 3-alkoxyacrolein.These macrocyclic N4 ligands chelate nickel(II) ions.The nickel(II) chelates 7 are also directly obtained by metal template condensation of the 1,2-diamines 5, the aldehyde 3a and nickel(II) acetate.