6-Butyl-3,6-dihydro-2,4-dimethyl-2H-pyran

Base Information

• Chemical Name: 6-Butyl-3,6-dihydro-2,4-dimethyl-2H-pyran
• CAS No.: 24237-00-1
• Molecular Formula: C₁₁H₂₀O
• Molecular Weight: 168.279
• European Community (EC) Number: 246-098-0
• DSSTox Substance ID: DTXSID7051898
• Nikkaji Number: J278.553F
• Mol file: 24237-00-1.mol

Synonyms:6-Butyl-3,6-dihydro-2,4-dimethyl-2H-pyran;Gyrane;6-butyl-2,4-dimethyl-3,6-dihydro-2h-pyran;24237-00-1;6-Butyl-2,4-dimethyldihydropyrane;2H-Pyran, 6-butyl-3,6-dihydro-2,4-dimethyl-;2-Butyl-4,6-dimethyldihydropyran;EINECS 246-098-0;2H-Pyran, 3,6-dihydro-6-butyl-2,4-dimethyl-;SCHEMBL757656;C12H17N2OS.I;DTXSID7051898;C12-H17-N2-O-S.I;AKOS006274426;LS-127302;2H-Pyran,6-butyl-3,6-dihydro-2,4-dimethyl-;W-110588;6 - butyl - 3,6 - dihydro - 2,4 - dimethyl - 2H - pyran

Chemical Property of 6-Butyl-3,6-dihydro-2,4-dimethyl-2H-pyran

Chemical Property:

• Vapor Pressure: 0.186mmHg at 25°C
• Refractive Index: 1.4930 (estimate)
• Boiling Point: 218.4 ºC at 760 mmHg
• Flash Point: 81.1ºC
• PSA: 9.23000
• Density: 0.844 g/cm³
• LogP: 3.30030
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 168.151415257
• Heavy Atom Count: 12
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC1C=C(CC(O1)C)C

Technology Process of 6-Butyl-3,6-dihydro-2,4-dimethyl-2H-pyran

There total 7 articles about 6-Butyl-3,6-dihydro-2,4-dimethyl-2H-pyran 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: 92.0%

2-((E)-hex-1-en-1-yl)-2,4-dimethyloxetane → 6-butyl-2,4-dimethyl-3,6-dihydro-2H-pyran (24237-00-1)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/anie.201201367

Reference yield:

(2RS,4RS,6RS)-2-(hydroxymethyl)-4,6-dimethyl-tetrahydro-2H-pyran-4-yl acetate → (2RS,6SR)-6-butyl-2,4-dimethyl-3,6-dihydro-2H-pyran (24237-00-1)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

2: 1.31 g / Li₂CuCl₄ / tetrahydrofuran / -10 - 0 °C

3: pyridine; phosphorus oxychloride / 0 - 20 °C

With pyridine; dilithium tetrachlorocuprate; trichlorophosphate; In tetrahydrofuran; 2: Schlosser reaction;

DOI:10.1021/jo060581w

Reference yield:

(2RS,4SR,6RS)-2-(hydroxymethyl)-4,6-dimethyl-tetrahydro-2H-pyran-4-yl acetate → (2RS,6SR)-6-butyl-2,4-dimethyl-3,6-dihydro-2H-pyran (24237-00-1)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

2: 1.36 g / tetrahydrofuran / -10 °C

3: pyridine; phosphorus oxychloride / 0 - 20 °C

With pyridine; trichlorophosphate; In tetrahydrofuran; 2: Schlosser reaction;

DOI:10.1021/jo060581w

Refernces

• 1、 Abate, Agnese,Brenna, Elisabetta,Costantini, Alessia,Fuganti, Claudio,Gatti, Francesco G.,Malpezzi, Luciana,Serra, Stefano. "Enzymatic approach to enantiomerically pure 5-alken-2,4-diols and 4-hydroxy-5-alken-2-ones: Application to the synthesis of chiral synthons". . p. 5228 - 5240. Retrieved 2007/10/03.