5-Allyl-2,2-dimethyl-benzo[1,3]dioxin-4-one

Base Information

• Chemical Name: 5-Allyl-2,2-dimethyl-benzo[1,3]dioxin-4-one
• CAS No.: 204846-40-2
• Molecular Formula: C13H14O3
• Molecular Weight: 218.252
• DSSTox Substance ID: DTXSID90456931
• Nikkaji Number: J920.072J
• Wikidata: Q82279560
• Mol file: 204846-40-2.mol

Synonyms:5-allyl-2,2-dimethyl-benzo[1,3]dioxin-4-one;204846-40-2;SCHEMBL4605184;DTXSID90456931;PYMNQQRFFNMKMO-UHFFFAOYSA-N;2,2-Dimethyl-5-allyl-4H-1,3-benzodioxin-4-one

Chemical Property of 5-Allyl-2,2-dimethyl-benzo[1,3]dioxin-4-one

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 218.094294304
• Heavy Atom Count: 16
• Complexity: 296

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2=CC=CC(=C2C(=O)O1)CC=C)C

Technology Process of 5-Allyl-2,2-dimethyl-benzo[1,3]dioxin-4-one

There total 1 articles about 5-Allyl-2,2-dimethyl-benzo[1,3]dioxin-4-one 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:

5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9) → 2,2-dimethyl-5-(2-propenyl)-4H-1,3-benzodioxin-4-one (204846-40-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridine

2: 83 percent / KOMe / [PdCl₂(dppf)] / tetrahydrofuran

With pyridine; potassium methanolate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran;

DOI:10.1002/1521-3765(20011217)7:24<5286::AID-CHEM5286>3.0.CO;2-G

Reference yield: 96.0%

2,2-dimethyl-5-(2-propenyl)-4H-1,3-benzodioxin-4-one (204846-40-2) → 2-allyl-6-hydroxy-benzoic acid (312962-10-0)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; at 65 ℃; for 12h;

DOI:10.1021/ol015822v

Reference yield: 90.0%

allyl alcohol (107-18-6) + 2,2-dimethyl-5-(2-propenyl)-4H-1,3-benzodioxin-4-one (204846-40-2) → 2-hydroxy-6-(prop-2-enyl)benzoic acid allyl ester (325172-47-2)

Guidance literature:

allyl alcohol; With ethylmagnesium bromide; In tetrahydrofuran; at 20 ℃; for 0.25h;

2,2-dimethyl-5-(2-propenyl)-4H-1,3-benzodioxin-4-one; In tetrahydrofuran; at 20 - 60 ℃; for 7.5h; Further stages.;

DOI:10.1021/ja0177713

upstream raw materials:

5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

Downstream raw materials:

2-allyl-6-hydroxy-benzoic acid

2-hydroxy-6-(prop-2-enyl)benzoic acid allyl ester

2-[(2R,6S)-6-((2R,4R,5S)-2-Benzyloxy-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

2-{(2R,6S)-6-[(E)-(2R,4R,5S,8R)-2-Benzyloxy-15-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-4,8-dihydroxy-5-methyl-12-oxo-pentadec-10-enyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid benzyl ester