exo-3a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione

Base Information

• Chemical Name: exo-3a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione
• CAS No.: 6118-51-0
• Molecular Formula: C8H6 O4
• Molecular Weight: 166.133
• Hs Code.: 2932999099
• European Community (EC) Number: 629-406-1
• Nikkaji Number: J3.665.710C
• Mol file: 6118-51-0.mol

Synonyms:exo-3a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione;6118-51-0;(2R,6S)-4,10-dioxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione;exo-3,6-Epoxy-1,2,3,6-tetrahydrophthalic anhydride;SCHEMBL1105712;AKOS004906116;(2S,6R)-4,10-dioxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Chemical Property of exo-3a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione

Chemical Property:

• Vapor Pressure: 9.91E-06mmHg at 25°C
• Melting Point: 118oC
• Boiling Point: 372°Cat760mmHg
• Flash Point: 172.2°C
• PSA: 52.60000
• Density: 1.54g/cm³
• LogP: -0.36060
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Hydrolyzes in water.
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 166.02660867
• Heavy Atom Count: 12
• Complexity: 278

Purity/Quality:

98.0% ^*data from raw suppliers

4,10-Dioxatricyclo[5.2.1.02.6]dec-8-ene-3,5-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2C3C(C1O2)C(=O)OC3=O
• Isomeric SMILES: C1=CC2[C@@H]3[C@H](C1O2)C(=O)OC3=O
• Uses: Intermediate in a useful synthesis of 4,4-dialkyl-2-butenolides, based on reaction with two moles of Grignard reagent, followed by cycloreversion (elimination of furan) to release the double bond.

Technology Process of exo-3a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione

There total 10 articles about exo-3a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione 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: 100.0%

furan (110-00-9) + maleic anhydride (108-31-6) → exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0)

Guidance literature:

In neat (no solvent, solid phase); for 1h; Milling;

DOI:10.1039/c9sc05823k

Reference yield: 98.0%

furan (110-00-9) + maleic anhydride (108-31-6) → 4,10-dioxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (5426-09-5,6118-51-0,6766-44-5)

Guidance literature:

at 20 ℃; for 24h;

DOI:10.1016/j.ejmech.2017.07.045

Reference yield: 85.75%

furan (110-00-9) + maleic anhydride (108-31-6) + diethyl ether (60-29-7,927820-24-4) → exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0)

Guidance literature:

In diethyl ether; at 38 ℃; for 1h;

upstream raw materials:

furan

maleic anhydride

diethyl ether

water

Downstream raw materials:

4-(4'-bromophenyl)-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

(3aR,4S,7R,7aS)-2-(4-nitrophenyl)-3a,4,7,7a-tetrahydro-4,7-epoxy-1H-isoindole-1,3(2H)-dione

4-(4'-methoxyphenyl)-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

4-(4'-chlorophenyl)-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

Refernces

• 1、 Chola, Joshua,Masesane, Ishmael B.. "Stereoselective synthesis of 3,4,5,6-tetrahydroxycyclohexyl β-amino acid derivatives". . p. 5680 - 5682. Retrieved 2008.
• 2、 Zhulin, V. M.,Bogdanov, V. S.,Kel'tseva, M. V.,Kabotyanskaya, E. B.,Koreshkov, Yu. D.. "EFFECT OF HIGH PRESSURE ON THE COMPOSITION OF STEREOISOMERS OF THE DIELS-ALDER REACTION BETWEEN FURAN AND MALEIC ANHYDRIDE". . p. 2303 - 2308. Retrieved 1989.
• 3、 K?se, Aytekin. "A simple route for the synthesis of novel norcantharimide derivatives via acidolysis with hydrochloric acid(gas)". . p. 1171 - 1178. Retrieved 2021/03/08.
• 4、 Asbjarnarson, Arni,Gudjonsson, Thorarinn,Hartmann, Rafael W.,Helgudottir, Hildur Run,Lehmann, Fredrik,Nilvebrant, Johan,Nygren, Per-?ke,Odell, Luke R.,Pijnappel, Matthijs,Traustadottir, Gunnhildur Asta. "The Wittig bioconjugation of maleimide derived, water soluble phosphonium ylides to aldehyde-tagged proteins". supporting information. p. 10417 - 10423. Retrieved 2021/12/17.