1,3,3a,4,7,7-alpha-Hexahydro-1,3-dimethoxy-4,7-methanoisobenzofuran

Base Information

• Chemical Name: 1,3,3a,4,7,7-alpha-Hexahydro-1,3-dimethoxy-4,7-methanoisobenzofuran
• CAS No.: 14882-64-5
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.246
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID60376293
• Mol file: 14882-64-5.mol

Synonyms:1,3,3a,4,7,7-alpha-Hexahydro-1,3-dimethoxy-4,7-methanoisobenzofuran;14882-64-5;3,5-dimethoxy-4-oxatricyclo[5.2.1.02,6]dec-8-ene;1,3-Dimethoxy-1,3,3a,4,7,7a-hexahydro-4,7-methano-2-benzofuran;DTXSID60376293;FT-0606487

Chemical Property of 1,3,3a,4,7,7-alpha-Hexahydro-1,3-dimethoxy-4,7-methanoisobenzofuran

Chemical Property:

• Vapor Pressure: 0.0152mmHg at 25°C
• Refractive Index: 1.522
• Boiling Point: 265.2°Cat760mmHg
• Flash Point: 87.3°C
• PSA: 27.69000
• Density: 1.15g/cm³
• LogP: 1.39990
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 196.109944368
• Heavy Atom Count: 14
• Complexity: 239

Purity/Quality:

98%Min ^*data from raw suppliers

1,3,3A,4,7,7-ALPHA-HEXAHYDRO-1,3-DIMETHOXY-4,7-METHANOISOBENZOFURAN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C2C3CC(C2C(O1)OC)C=C3

Technology Process of 1,3,3a,4,7,7-alpha-Hexahydro-1,3-dimethoxy-4,7-methanoisobenzofuran

There total 6 articles about 1,3,3a,4,7,7-alpha-Hexahydro-1,3-dimethoxy-4,7-methanoisobenzofuran 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: 64.0%

2,5-dihydro-2,5-dimethoxyfuran (332-77-4) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1S,2R,6S,7R)-3,5-Dimethoxy-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene (14882-64-5,678142-13-7)

Guidance literature:

With hydrogenchloride; In water; 1.) ice bath, 12h, 2.) tap water cooling, 24h;

DOI:10.1021/jo00175a001

Reference yield:

(1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol (941567-71-1,448922-61-0) → cis-endo-3,5-dimethoxy-4-oxatricyclo[5.2.1.02,6]dec-8-ene (14882-64-5,678142-13-7)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 7.0 g / p-toluenesulfonic acid / 3 h / 20 °C

With oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In dichloromethane; 1: Swern oxidation;

DOI:10.1016/j.tet.2003.12.014

Reference yield:

methanol (67-56-1) + (1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarbaldehyde (63904-57-4) → cis-endo-3,5-dimethoxy-4-oxatricyclo[5.2.1.02,6]dec-8-ene (14882-64-5,678142-13-7)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2003.12.014

upstream raw materials:

methanol

(1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarbaldehyde

(1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol

2,5-dihydro-2,5-dimethoxyfuran

Downstream raw materials:

2-(p-Sulfonamidophenyl)-4,7-dihydro-4,7-methanoisoindole

4-phenyl-4-azatricyclo[5.2.1.0(2,6)]deca-2,5,8-triene

Bicyclo[2.2.1]hept-5-ene-2,3-dicarbaldehyde

2-(1-Hydroxyethyl)-4,7-dihydro-4,7-methanoisoindole