tetrahydro-2H-pyran-3-carbaldehyde

Base Information

• Chemical Name: tetrahydro-2H-pyran-3-carbaldehyde
• CAS No.: 77342-93-9
• Molecular Formula: C6H10O2
• Molecular Weight: 114.144
• Hs Code.: 2932999099
• European Community (EC) Number: 804-689-6
• DSSTox Substance ID: DTXSID00435914
• Mol file: 77342-93-9.mol

Synonyms:tetrahydro-2H-pyran-3-carbaldehyde;77342-93-9;oxane-3-carbaldehyde;TETRAHYDRO-PYRAN-3-CARBALDEHYDE;Tetrahydropyran-3-carbaldehyde;TETRAHYDROPYRAN-3-CARBOXALDEHYDE;2H-pyran-3-carboxaldehyde, tetrahydro-;(3R)-tetrahydropyran-3-carbaldehyde;(3S)-tetrahydropyran-3-carbaldehyde;3-formyl-tetrahydropyran;TETRAHYDRO-2H-PYRAN-3-CARBOXALDEHYDE;3-Formyltetrahydro-2H-pyran;SCHEMBL98249;DTXSID00435914;KYHPVAHPKYNKOR-UHFFFAOYSA-N;MFCD03789633;AKOS005264591;AB16155;CS-W008553;SB74243;SB74247;AS-41198;Tetrahydro-pyran-3-carbaldehyde, AldrichCPR;AM20100767;BB 0260499;FT-0660723;EN300-72110;A26008;J-524859;F8880-6085;Z1065877672;2H-Pyran-3-carboxaldehyde, tetrahydro- (9CI);Tetrahydro-2H-pyran-3-carbaldehyde

Chemical Property of tetrahydro-2H-pyran-3-carbaldehyde

Chemical Property:

• Vapor Pressure: 0.984mmHg at 25°C
• Refractive Index: 1.513
• Boiling Point: 178.539 °C at 760 mmHg
• Flash Point: 66.389 °C
• PSA: 26.30000
• Density: 1.097 g/cm³
• LogP: 0.61190
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 114.068079557
• Heavy Atom Count: 8
• Complexity: 80.6

Purity/Quality:

97% ^*data from raw suppliers

Tetrahydro-?pyran-?3-?carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(COC1)C=O
• General Description: **TETRAHYDRO-PYRAN-3-CARBALDEHYDE** is a cyclic aldehyde derivative of tetrahydropyran, featuring a formyl group at the 3-position. It serves as a key intermediate in the synthesis of 2,3-substituted tetrahydropyrans, which are structural motifs in polyether antibiotics. The compound can be synthesized via acid-catalyzed rearrangement of 5,6-dihydro-4H-1,3-dioxocins, leveraging Lewis acids like BF3·Et2O. This method highlights its utility in stereoselective transformations, though further studies on its stereochemistry are warranted.

Technology Process of tetrahydro-2H-pyran-3-carbaldehyde

There total 5 articles about tetrahydro-2H-pyran-3-carbaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.6%

5,6-dihydro-2H-pyran-3-carbaldehyde (13417-49-7) → tetrahydro-pyran-3-carbaldehyde (77342-93-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; under 2068.65 Torr;

DOI:10.1124/mol.114.096560

Reference yield: 51.86%

N-methoxy-N-methyltetrahydro-2H-pyran-3-carboxamide → tetrahydro-pyran-3-carbaldehyde (77342-93-9)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 3h;

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → TETRAHYDROPYRANE (142-68-7) + Tetrahydropyran-2-methanol (100-72-1) + rac-(tetrahydro-2H-pyran-3-yl)methanol (14774-36-8) + tetrahydro-pyran-2-carbaldehyde (19611-45-1) + tetrahydro-pyran-3-carbaldehyde (77342-93-9) + bis(2-tetrahydropyranyl)methanol + 2-tetrahydropyranyl tetrahydropyran-2-carboxylate

Guidance literature:

With dicobalt octacarbonyl; hydrogen; In tetrahydrofuran; at 150 ℃; for 10h; under 41346.8 Torr; Time; Concentration; Pressure; Autoclave;

DOI:10.1007/s11243-013-9750-4

upstream raw materials:

5,6-dihydro-2H-pyran-3-carbaldehyde

3,4-dihydro-2H-pyran

formaldehyd

racemic tetrahydropyran-3-carboxylic acid

Downstream raw materials:

N-methyl 2R-(3'R-tetrahydropyranyl)-4R-methyl-5S-phenyloxazolidine

N-methyl 2R-(3'S-tetrahydropyranyl)-4R-methyl-5S-phenyloxazolidine

4-Phenyl-1-(tetrahydropyran-3-yl)-1,4-butandion

1-Methyl-2-phenyl-5-(tetrahydropyran-3-yl)pyrrol

Refernces

Synthesis of 2,3-substituted tetrahydropyrans by rearrangement of 5,6-dihydro-4H-1,3-dioxocins

10.1016/S0040-4039(00)94591-X

The research focuses on the synthesis of 2,3-substituted tetrahydrofurans and tetrahydrofurans, which are structural subunits commonly found in naturally occurring polyether antibiotics. The purpose of the study is to develop a stereoselective synthesis strategy for these compounds through the rearrangement of 5,6-dihydro-4H-1,3-dioxocins. The researchers successfully synthesized 5,6-dihydro-4H-1,3-dioxocins and obtained 2-substituted tetrahydrofuran-3-carbaldehydes through a process involving acetalization, double-bond isomerization, and acid-catalyzed rearrangement. Key chemicals used in the process include aldehydes or ketones, which are acetalated to form the dioxocins, and Lewis acids such as BF3·Et2O, which facilitate the rearrangement to form tetrahydropyran-3-carbaldehydes. The study concluded with the successful synthesis of 2-propyl-tetrahydrofuran-3-carbaldehyde, demonstrating the effectiveness of the developed method, and noted that further stereochemical investigations were underway.