3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one

Base Information

• Chemical Name: 3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one
• CAS No.: 64550-47-6
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.177
• NSC Number: 97125
• DSSTox Substance ID: DTXSID90983171
• Nikkaji Number: J2.191.319G
• Mol file: 64550-47-6.mol

Synonyms:85718-44-1;3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one;4,7-Methanoisobenzofuran-1(3H)-one, 3a,4,7,7a-tetrahydro-;64550-47-6;NSC97125;endo-4-Oxatricyclo[5.2.1.0(2,6)]dec-8-en-3-one;NCIOpen2_001693;SCHEMBL1218407;DTXSID90983171;NSC-97125;SB47058;4-oxatricyclo[5.2.1.02, 6]dec-8-en-3-one;3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1(3H)-one;4,7-Methanoisobenzofuran-1(3H)-one,3a,4,7,7a-tetrahydro-, (3aR,4R,7S,7aS)-rel-

Chemical Property of 3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one

Chemical Property:

• Vapor Pressure: 0.00106mmHg at 25°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 150.068079557
• Heavy Atom Count: 11
• Complexity: 244

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C2C=CC1C3C2COC3=O

Technology Process of 3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one

There total 15 articles about 3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-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: 86.9%

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride (129-64-6) → (3aS*,4R*,7S*,7aR*)-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one (64550-47-6,85718-44-1,95340-88-8,95340-89-9,95340-92-4,95340-93-5,115269-21-1)

Guidance literature:

With sodium tetrahydroborate; In N,N-dimethyl-formamide; Ambient temperature;

Reference yield: 83.0%

(2S,3R)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (25165-18-8,86161-91-3,129172-67-4,135357-70-9,135357-71-0) → (2S,6R)-4-Oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one (64550-47-6,85718-44-1,95340-88-8,95340-89-9,95340-92-4,95340-93-5,115269-21-1)

Guidance literature:

With toluene-4-sulfonic acid; In benzene;

DOI:10.1016/S0040-4039(01)93947-4

Reference yield: 80.0%

(1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol (941567-71-1,448922-61-0) → (3aS*,4R*,7S*,7aR*)-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one (64550-47-6,85718-44-1,95340-88-8,95340-89-9,95340-92-4,95340-93-5,115269-21-1)

Guidance literature:

With Celite; pyridinium chlorochromate; In dichloromethane; for 8h; Ambient temperature;

DOI:10.1002/jccs.199700094

upstream raw materials:

(2S,3R)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(2S,5R,6R)-5-Hydroxy-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

(2S,5R,6R)-5-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

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

Downstream raw materials:

6-<(2-endo,3-exo)-3-<<2-(3-Chlorphenyl)ethyl>carbamoyl>bicyclo<2.2.1>hept-2-yl>hexansaeure

Methyl-6-<(2-endo,3-exo)-3-<<2-(3-chlorphenyl)ethyl>carbamoyl>bicyclo<2.2.1>hept-2-yl>hexanoat

6-<(2-endo,3-exo)-3-<<2-(3-Methoxyphenyl)ethyl>carbamoyl>bicyclo<2.2.1>hept-2-yl>hexansaeure

6-<(2-endo,3-exo)-3-<<2-(2-Chlorphenyl)ethyl>carbamoyl>bicyclo<2.2.1>hept-2-yl>hexansaeure