3-Pentanone, 1-[(4-methoxyphenyl)methoxy]-2-methyl-, (2S)-

Base Information

• Chemical Name: 3-Pentanone, 1-[(4-methoxyphenyl)methoxy]-2-methyl-, (2S)-
• CAS No.: 182193-69-7
• Molecular Formula: C14H20O3
• Molecular Weight: 236.311
• DSSTox Substance ID: DTXSID00471776
• Nikkaji Number: J991.487K
• Wikidata: Q82300432
• Mol file: 182193-69-7.mol

Synonyms:3-Pentanone, 1-[(4-methoxyphenyl)methoxy]-2-methyl-, (2S)-;182193-69-7;SCHEMBL6820652;DTXSID00471776

Chemical Property of 3-Pentanone, 1-[(4-methoxyphenyl)methoxy]-2-methyl-, (2S)-

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 236.14124450
• Heavy Atom Count: 17
• Complexity: 220

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)C(C)COCC1=CC=C(C=C1)OC
• Isomeric SMILES: CCC(=O)[C@@H](C)COCC1=CC=C(C=C1)OC

Technology Process of 3-Pentanone, 1-[(4-methoxyphenyl)methoxy]-2-methyl-, (2S)-

There total 7 articles about 3-Pentanone, 1-[(4-methoxyphenyl)methoxy]-2-methyl-, (2S)- 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: 91.0%

ethylmagnesium bromide (925-90-6) + methyl (S)-N-methyl-N-methoxy-3-(4-methoxybenzyloxy)-2-methylpropanoate (185203-71-8) → (S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one (182193-69-7)

Guidance literature:

DOI:10.1021/ja020091v

Reference yield: 91.0%

(S)-1-(4-Methoxy-benzyloxy)-2-methyl-pentan-3-ol → (S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one (182193-69-7)

Guidance literature:

With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane; at 20 - 25 ℃;

DOI:10.1021/ja108906e

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one (182193-69-7)

Guidance literature:

Multi-step reaction with 3 steps

1: triflic acid / diethyl ether / 1 h / 20 °C

2: i-PrMgCl / tetrahydrofuran / 0.75 h / -20 - -15 °C

3: tetrahydrofuran; diethyl ether / 1 h / -20 °C

With trifluorormethanesulfonic acid; isopropylmagnesium chloride; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ol026046+

upstream raw materials:

ethylmagnesium bromide

methyl (S)-N-methyl-N-methoxy-3-(4-methoxybenzyloxy)-2-methylpropanoate

O-(4-methoxybenzyl)-trichloroacetimidate

methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate

Downstream raw materials:

(2S,3R,4S,5S)-1-(4-methoxybenzyloxy)-7-(benzyloxy)-2,4-dimethylheptane-3,5-diol

(2S,4S,5R)-6-(tert-butyldimethylsilyloxy)-5-hydroxy-1-(4-methoxybenzyloxy)-2,4-dimethylhexan-3-one

(2S,4S)-1-hydroxy-5-(p-methoxybenzyloxy)-2,4-dimethylpentan-3-one

(2S,4S,5S,6S)-5-hydroxy-1-(p-methoxybenzyloxy)-7-triisopropyloxy-2,4,6-trimethylheptan-3-one