(3aR,4R,7R,7aS)-3a,4,7,7a-Tetrahydro-4,7-ethanoisobenzofuran-1,3-dione

Base Information

• Chemical Name: (3aR,4R,7R,7aS)-3a,4,7,7a-Tetrahydro-4,7-ethanoisobenzofuran-1,3-dione
• CAS No.: 24327-08-0
• Molecular Formula: C10H10O3
• Molecular Weight: 178.188
• Hs Code.: 29172090
• European Community (EC) Number: 246-171-7
• Mol file: 24327-08-0.mol

Synonyms:(3aR,4R,7R,7aS)-3a,4,7,7a-Tetrahydro-4,7-ethanoisobenzofuran-1,3-dione;24327-08-0;1620738-28-4;AKOS016009478;AS-70051;A877965;(1R,2R,6S,7R)-4-oxatricyclo[5.2.2.0?,?]undec-8-ene-3,5-dione;(1R,2R,6S,7R)-4-oxatricyclo[5.2.2.02,6]undec-8-ene-3,5-dione;(1R,2R,6S,7R)-4-OXATRICYCLO[5.2.2.0(2),?]UNDEC-8-ENE-3,5-DIONE

Chemical Property of (3aR,4R,7R,7aS)-3a,4,7,7a-Tetrahydro-4,7-ethanoisobenzofuran-1,3-dione

Chemical Property:

• Appearance/Colour: White to beige needle-like crystals or powder
• Vapor Pressure: 8.35E-05mmHg at 25°C
• Melting Point: 144-147 °C(lit.)
• Refractive Index: 1.563
• Boiling Point: 340.9 °C at 760 mmHg
• Flash Point: 166.5 °C
• PSA: 43.37000
• Density: 1.324 g/cm³
• LogP: 0.89820
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 178.062994177
• Heavy Atom Count: 13
• Complexity: 288

Purity/Quality:

98%,99%, ^*data from raw suppliers

endo-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride powder ^*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

Useful:

• Canonical SMILES: C1CC2C=CC1C3C2C(=O)OC3=O
• Isomeric SMILES: C1C[C@@H]2C=C[C@@H]1[C@@H]3[C@H]2C(=O)OC3=O

Technology Process of (3aR,4R,7R,7aS)-3a,4,7,7a-Tetrahydro-4,7-ethanoisobenzofuran-1,3-dione

There total 18 articles about (3aR,4R,7R,7aS)-3a,4,7,7a-Tetrahydro-4,7-ethanoisobenzofuran-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: 98.0%

maleic anhydride (108-31-6) + cyclohexa-1,3-diene (1165952-91-9) → meso-endo-tetrahydro-4,7-ethanoisobenzofuran-1,3-dione (24327-08-0)

Guidance literature:

With methyltrioxorhenium(VII); In chloroform; for 0.75h; Ambient temperature;

DOI:10.1021/ja963172y

Reference yield: 92.0%

maleic anhydride (108-31-6) + 2-cyclohexen-1-yl trichloroacetate (66928-68-5) → cis-endo-bicyclo<2.2.2>oct-5-ene-2,3-dicarboxylic acid anhydride (6708-37-8,24327-08-0,85081-13-6,85081-14-7,3769-13-9)

Guidance literature:

Grubbs catalyst first generation; In chloroform-d1; Heating;

DOI:10.1016/j.tetlet.2005.12.018

Reference yield: 90.0%

meso-endo-tetrahydro-4,7-ethanoisobenzofuran-1,3-dione (24327-08-0) → cis-endo-bicyclo<2.2.2>oct-5-ene-2,3-dicarboxylic acid anhydride (6708-37-8,24327-08-0,85081-13-6,85081-14-7,3769-13-9)

Guidance literature:

With triethylamine; In ethanol; Irradiation; 2-6 h;

upstream raw materials:

(+/-)-5endo,6exo-dibromo-bicyclo[2.2.2]octane-2exo,3exo-dicarboxylic acid-anhydride

maleic anhydride

cyclohexa-1,3-diene

bicyclo<2.2.2>oct-5-ene 2,3-endo,exo-dicarboxylic acid

Downstream raw materials:

dimethyl endo,endo-bicyclo<2.2.2>oct-5-ene-2,3-dicarboxylate

(1'RS,2SR,3RS,4'SR)-2,3-(cyclohex-2'-en-1',4'-ylene)-N-(4''-methylphenyl)succinimide

3,5-dioxo-4,9-dioxatetracyclo<5.3.2.0^2,6.0^8,10>dodecane

cis-endo-bicyclo<2.2.2>oct-5-ene-2,3-dicarboxylic acid anhydride

Refernces

• 1、 Weinstein,Leffler,Currie. "PHASE TRANSITIONS IN BICYCLIC COMPOUNDS.". . p. 95 - 109. Retrieved 1984.
• 2、 -. "Heterocyclic compounds and, their compositions and their use as anti-influenza virus drugs (by machine translation)". Paragraph 0082-0085. . Retrieved 2020/01/03.
• 3、 Kotha, Sambasivarao,Pulletikurti, Sunil. "Synthesis of propellanes containing a bicyclo[2.2.2]octene unit: Via the Diels-Alder reaction and ring-closing metathesis as key steps". . p. 14906 - 14915. Retrieved 2018/04/30.