1-[2-Hydroxy-4,6-diMethoxy-3-(MethoxyMethoxy)phenyl]-1-propanone

Base Information

• Chemical Name: 1-[2-Hydroxy-4,6-diMethoxy-3-(MethoxyMethoxy)phenyl]-1-propanone
• CAS No.: 276690-11-0
• Molecular Formula: C₁₃H₁₈O₆
• Molecular Weight: 270.282
• Mol file: 276690-11-0.mol

Synonyms:1-[2-hydroxy-4,6-dimethoxy-3-(methoxymethoxy)phenyl]propan-1-one

Chemical Property of 1-[2-Hydroxy-4,6-diMethoxy-3-(MethoxyMethoxy)phenyl]-1-propanone

Chemical Property:

• Boiling Point: 412.9±45.0 °C(Predicted)
• PKA: 6.65±0.50(Predicted)
• Density: 1.171±0.06 g/cm3(Predicted)
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

1-[2-Hydroxy-4,6-dimethoxy-3-(methoxymethoxy)phenyl]-1-propanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1-[2-Hydroxy-4,6-dimethoxy-3-(methoxymethoxy)phenyl]-1-propanone is a reactant used in the preparation of Stigmatellin A (S686780).

Technology Process of 1-[2-Hydroxy-4,6-diMethoxy-3-(MethoxyMethoxy)phenyl]-1-propanone

There total 7 articles about 1-[2-Hydroxy-4,6-diMethoxy-3-(MethoxyMethoxy)phenyl]-1-propanone 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%

1-(2,3-Dihydroxy-4,6-dimethoxyphenyl)propan-1-one (94190-89-3) + chloromethyl methyl ether (107-30-2) → 1-[2-hydroxy-4,6-dimethoxy-3-(methoxymethoxy)phenyl]propan-1-one (276690-11-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

Reference yield: 63.7%

(4S,5S,6S,7R)-3,5-dimethoxy-2-(methoxymethoxy)-6-propionylphenyl-5,7-dimethoxy-4,6-dimethyl-8-[(triisopropylsilyl)oxy]octanoate → (4S,5S,6S,7R)-5,7-dimethoxy-4,6-dimethyl-8-[(triisopropylsilyl)oxy]octanoic acid + 2-[(3S,4S,5S,6R)-4,6-dimethoxy-3,5-dimethyl-7-{(triisopropylsilyl)oxy}heptyl]-5,7-dimethoxy-8-(methoxymethoxy)-3-methyl-4H-chromen-4-one + 1-[2-hydroxy-4,6-dimethoxy-3-(methoxymethoxy)phenyl]propan-1-one (276690-11-0)

Guidance literature:

With sodium; In methanol; for 2h; Inert atmosphere; Cooling with ice; Reflux;

DOI:10.1246/bcsj.20140271

Reference yield:

3,5-dimethoxyphenol (500-99-2) → 1-[2-hydroxy-4,6-dimethoxy-3-(methoxymethoxy)phenyl]propan-1-one (276690-11-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / P₄O₁₀; H₃PO₄ / 1 h / 70 °C

2: 87 percent / TFA; MCPBA / CH₂Cl₂ / 16 h / 0 - 5 °C

3: 99 percent / aq. HCl / methanol / 2 h / Heating

4: 98 percent / DIPEA / CH₂Cl₂ / 20 °C

With hydrogenchloride; phosphorus pentoxide; phosphoric acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In methanol; dichloromethane; 1: Acylation / 2: Baeyer-Villiger oxidation / 3: Hydrolysis / 4: Etherification;

upstream raw materials:

1-(2,3-Dihydroxy-4,6-dimethoxyphenyl)propan-1-one

chloromethyl methyl ether

3,5-dimethoxyphenol

1-(2-Hydroxy-4,6-dimethoxy-3-propionylphenyl)-1-propanone

Downstream raw materials:

2-[(3S,4S,5S,6R)-7-Benzyloxy-4,6-dimethylheptyl]-5,7-dimethoxy-8-methoxymethoxy-3-methyl-4H-1-benzopyran-4-one

stigmatellin A

(2R,3S,4S,5S)-7-[5,7-dimethoxy-8-methoxymethoxy-3-methyl-4-oxo-4H-2-chromenyl]-2,4-dimethoxy-3,5-dimethylheptanol

(4S,5S,6S,7R)-8-Benzyloxy-5,7-dimethoxy-4,6-dimethyloctanoic acid 3,5-dimethoxy-2-methoxymethoxy-6-propionylphenyl ester

Refernces

• 1、 Infante-Rodriguez, Carolina,Domon, Lisianne,Breuilles, Pascal,Uguen, Daniel. "Asymmetric synthesis of stigmatellin and crocacin C". . p. 308 - 326. Retrieved 2015/03/04.