Tetrahydro-2H-pyran-2-carbaldehyde

Base Information

• Chemical Name: Tetrahydro-2H-pyran-2-carbaldehyde
• CAS No.: 19611-45-1
• Molecular Formula: C6H10 O2
• Molecular Weight: 114.144
• Hs Code.: 2932999099
• European Community (EC) Number: 838-779-1
• DSSTox Substance ID: DTXSID50452873
• Nikkaji Number: J403.280B
• Mol file: 19611-45-1.mol

Synonyms:Tetrahydro-2H-pyran-2-carbaldehyde;19611-45-1;Oxane-2-carbaldehyde;2H-PYRAN-2-CARBOXALDEHYDE, TETRAHYDRO-;2H-PYRAN-2-CARBOXALDEHYDE,TETRAHYDRO-;TETRAHYDRO-PYRAN-2-CARBALDEHYDE;tetrahydropyrane carbaldehyde;SCHEMBL96873;DTXSID50452873;XEZQLSOFXLPSJR-UHFFFAOYSA-N;MFCD08235010;AKOS012322187;MB05934;AS-41199;CS-0183379;FT-0728998;EN300-112132;Tetrahydro-2H-pyran-2-carbaldehyde, AldrichCPR;Tetrahydro-2H-pyran-2-carbaldehyde, tech grade;Z1079442734

Chemical Property of Tetrahydro-2H-pyran-2-carbaldehyde

Chemical Property:

• PSA: 26.30000
• LogP: 0.75440
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 0.5
• 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

2H-Pyran-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCOC(C1)C=O

Technology Process of Tetrahydro-2H-pyran-2-carbaldehyde

There total 7 articles about Tetrahydro-2H-pyran-2-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: 98.0%

Tetrahydropyran-2-methanol (100-72-1) → tetrahydro-pyran-2-carbaldehyde (19611-45-1)

Guidance literature:

With silica gel supported bis(trimethylsilyl) chromate; In dichloromethane; at 40 ℃; for 0.666667h;

DOI:10.1080/00397919608003647

Reference yield: 61.0%

2,6-Dibromo-hexanal (110811-44-4) → tetrahydro-pyran-2-carbaldehyde (19611-45-1)

Guidance literature:

With silver nitrate; In water; dimethyl sulfoxide; at 110 ℃; for 3h;

DOI:10.1246/cl.1987.333

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:

acrolein dimer

Tetrahydropyran-2-methanol

2,6-Dibromo-hexanal

oxalyl dichloride

Downstream raw materials:

4-Phenyl-1-(tetrahydropyran-2-yl)-1,4-butandion

1,2-Diphenyl-5-(tetrahydropyran-2-yl)pyrrol

hexahydro-2H-oxepin-2-one

2-amino-6-mercapto-4-(tetrahydro-2H-pyran-2-yl)pyridine-3,5-dicarbonitrile

Refernces

Intramolecular Michael-type additions to vinyl bissulfoxides: Enantioselective synthesis of chiral aldehydes

10.1055/s-2008-1067176

The research investigates the diastereoselective and enantioselective synthesis of chiral aldehydes through intramolecular Michael-type additions to alkylidene bissulfoxides derived from dithiane and dithiolane. Key chemicals involved include various substrates bearing N- and O-nucleophilic functions, which upon reaction, form cyclic substrates with selectivities ranging from 51:49 to 85:15. The bissulfoxide moiety is subsequently cleaved in a two-step sequence to yield chiral carbaldehydes. Notably, compounds such as tetrahydropyran-2-carbaldehyde and homopipecolic aldehyde, which are difficult to access by other routes, are obtained in enantiomerically pure forms. The stereochemical information is introduced via readily available diethyl D- and L-tartrates, allowing for the synthesis of both enantiomers of the target molecules. The study also explores the optimization of conditions for these additions and the synthesis of the underlying bissulfoxides, utilizing methods like asymmetric oxidation and various synthetic protocols for the preparation of ketene S,S-acetals.