(1,3-Dioxo-3,3a,7,7a-tetrahydro-4,7-epoxy-2-benzofuran-4(1h)-yl)methyl acetate

Base Information

• Chemical Name: (1,3-Dioxo-3,3a,7,7a-tetrahydro-4,7-epoxy-2-benzofuran-4(1h)-yl)methyl acetate
• CAS No.: 6331-95-9
• Molecular Formula: C7H6Cl2O
• Molecular Weight: 177.02794
• NSC Number: 37391
• DSSTox Substance ID: DTXSID50284474
• ChEMBL ID: CHEMBL301817
• Mol file: 6331-95-9.mol

Synonyms:6331-95-9;(1,3-dioxo-3,3a,7,7a-tetrahydro-4,7-epoxy-2-benzofuran-4(1h)-yl)methyl acetate;NSC37391;CHEMBL301817;SCHEMBL16248002;DTXSID50284474;NSC-37391

Chemical Property of (1,3-Dioxo-3,3a,7,7a-tetrahydro-4,7-epoxy-2-benzofuran-4(1h)-yl)methyl acetate

Chemical Property:

• Vapor Pressure: 4.61E-07mmHg at 25°C
• Boiling Point: 414°C at 760 mmHg
• Flash Point: 188.6°C
• Density: 1.487g/cm³
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 238.04773803
• Heavy Atom Count: 17
• Complexity: 453

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC12C=CC(O1)C3C2C(=O)OC3=O

Technology Process of (1,3-Dioxo-3,3a,7,7a-tetrahydro-4,7-epoxy-2-benzofuran-4(1h)-yl)methyl acetate

There total 3 articles about (1,3-Dioxo-3,3a,7,7a-tetrahydro-4,7-epoxy-2-benzofuran-4(1h)-yl)methyl acetate 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: 86.0%

maleic anhydride (108-31-6) + furfurylacetate (623-17-6) → (+/-)-(1RS,2SR,6RS,7SR)-(3,5-dioxo-4,10-dioxatricyclo[5.2.1.02,6]dec-8-en-1-yl)methyl acetate (6331-95-9,19308-92-0)

Guidance literature:

In toluene; at 23 ℃;

DOI:10.1016/S0960-894X(97)00316-8

Reference yield:

(2-furyl)methyl alcohol (98-00-0,25212-86-6,93793-62-5) → (+/-)-(1RS,2SR,6RS,7SR)-(3,5-dioxo-4,10-dioxatricyclo[5.2.1.02,6]dec-8-en-1-yl)methyl acetate (6331-95-9,19308-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Et₃N / CH₂Cl₂ / 19 h / 20 °C

2: 74 percent / toluene / 97 h / 23 °C

With triethylamine; In dichloromethane; toluene; 2: Diels-Alder reaction;

DOI:10.1021/ja034694y

Reference yield:

→ Acetic acid (1R,2R,6S,7S)-3,5-dioxo-4,10-dioxa-tricyclo[5.2.1.02,6]dec-8-en-1-ylmethyl ester (6331-95-9,19308-92-0)

Guidance literature:

entspr. Anhydrid 2, Methylchlorformiat, Pyridin;

upstream raw materials:

maleic anhydride

furfurylacetate

(2-furyl)methyl alcohol

Downstream raw materials:

1-acetoxymethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride