Tetrahydropyranyl ether

Base Information

• Chemical Name: Tetrahydropyranyl ether
• CAS No.: 709-84-2
• Molecular Formula: C10H18 O3
• Molecular Weight: 186.251
• NSC Number: 97549
• DSSTox Substance ID: DTXSID60294645
• Nikkaji Number: J3.353.293H
• Mol file: 709-84-2.mol

Synonyms:tetrahydropyranyl ether;709-84-2;NSC97549;ditetrahydropyranyl ether;bis(tetrahyropyranyl)ether;di-tetrahydropyranyl ether;monotetrahydropyranyl ether;bis(tetrahydropyranyl)ether;bis-tetrahydropyranyl ether;tetrahydropyran-2-yl ether;mono-tetrahydropyranyl ether;SCHEMBL30805;bistetrahydropyran-2-yl ether;SCHEMBL10926551;DTXSID60294645;(tetrahydro-2H-pyran-2-yl)ether;HUHXLHLWASNVDB-UHFFFAOYSA-N;NSC-97549;FT-0719110

Chemical Property of Tetrahydropyranyl ether

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 186.125594432
• Heavy Atom Count: 13
• Complexity: 133

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCOC(C1)OC2CCCCO2

Technology Process of Tetrahydropyranyl ether

There total 5 articles about Tetrahydropyranyl ether 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:

2-(tert-butylperoxy)tetrahydro-2H-pyran (28627-46-5) → 2-methoxytetrahydropyran (6581-66-4) + 3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + bis-tetrahydropyran-2-yl ether (709-84-2) + acetone (67-64-1)

Guidance literature:

at 250 ℃;

DOI:10.1021/ja01638a012

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → tetrahydro-2H-2-pyranol (694-54-2) + bis-tetrahydropyran-2-yl ether (709-84-2) + 5-hydroxypentanal (4221-03-8)

Guidance literature:

With hydrogenchloride; Yield given. Yields of byproduct given; 1.) 25 deg C, 1 h, 2.) reflux, 24 h;

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → tetrahydro-2H-2-pyranol (694-54-2) + bis-tetrahydropyran-2-yl ether (709-84-2) + 5-(2-tetrahydropyranyloxy)pentanal (14194-86-6) + 5-hydroxypentanal (4221-03-8)

Guidance literature:

With hydrogenchloride; for 0.25h; Product distribution; Ambient temperature; other times and temperatures, other hydration reagent;

upstream raw materials:

3,4-dihydro-2H-pyran

2-(tert-butylperoxy)tetrahydro-2H-pyran

Downstream raw materials:

1 ,5-pentanediol

lithium cyclohexylisopropylamide

tetrahydro-2H-2-pyranol

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Refernces

TOTAL SYNTHESIS OF (+/-)-BISABOLANGELONE

10.1016/S0040-4039(00)85112-6

The research focuses on the total synthesis of the sesquiterpenoid (+)-bisabolangelone, a compound isolated from the seeds of Angelica bisecta, known for its potent insect antifeeding properties. The purpose of the study was to overcome the limitations posed by the unstable nature of the natural product and to create a synthetic approach to form the heterocyclic ring by cyclization of a γ-acetylenic alcohol, a procedure already known in the field. The synthesis process involved a series of chemical reactions using various reagents such as lithium acetylide of Z-methylpent-2-ene-4-yne, MeI/KOH/DMSO for methylation, PPTS for deprotection, t-BuOK for cyclization, and protective groups like tetrahydropyranyl ether (THP), methylthiomethyl ether (MTM), and [2(trimethylsilyl)ethoxy]methyl ether (SEM). The successful synthesis of (+)-bisabolangelone was confirmed by comparing its spectral data (NMR, IR, MS, UV) and TLC behavior with that of the natural product, yielding a final product identical to the naturally occurring bisabolangelone.