4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-, (3aR,4S,7R,7aS)-rel-

Base Information

• Chemical Name: 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-, (3aR,4S,7R,7aS)-rel-
• CAS No.: 29745-04-8
• Molecular Formula: C8H8O4
• Molecular Weight: 168.149
• Hs Code.: 2932999099
• European Community (EC) Number: 681-692-7
• UNII: 8452E71EO7
• DSSTox Substance ID: DTXSID901017225
• Nikkaji Number: J469.128H
• Metabolomics Workbench ID: 130081
• ChEMBL ID: CHEMBL298246
• Mol file: 29745-04-8.mol

Synonyms:4,7-epoxyisobenzofuran-1,3-dione, hexahydro-, (3a-alpha, 4beta, 7beta, 7a-alpha)-;demethylcantharate;norcantharidin;norcantharidin, (3aalpha,4beta,7beta,7aalpha)-isomer;sodium norcantharidate

Chemical Property of 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-, (3aR,4S,7R,7aS)-rel-

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 114-116 °C
• Refractive Index: 1.55
• Boiling Point: 362.464 °C at 760 mmHg
• Flash Point: 167.017 °C
• PSA: 52.60000
• Density: 1.468 g/cm³
• LogP: -0.13660
• Sensitive.: Moisture Sensitive
• Water Solubility.: Hydrolyzes in water.
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 246

Purity/Quality:

99% ^*data from raw suppliers

Norcantharidin ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C3C(C1O2)C(=O)OC3=O
• Isomeric SMILES: C1C[C@H]2[C@H]3[C@@H]([C@@H]1O2)C(=O)OC3=O
• Uses: Norcantharidin is a potential antitumor agent.

Technology Process of 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-, (3aR,4S,7R,7aS)-rel-

There total 7 articles about 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-, (3aR,4S,7R,7aS)-rel- 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%

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) → norcantharidin (29745-04-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; water; In tetrahydrofuran; Ambient temperature;

DOI:10.1248/cpb.39.2288

Reference yield: 87.0%

furan (110-00-9) + maleic anhydride (108-31-6) → norcantharidin (29745-04-8)

Guidance literature:

In toluene; at 80 ℃; for 6h;

DOI:10.1021/ja0430999

Reference yield:

4,10-dioxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (5426-09-5,6118-51-0,6766-44-5) → norcantharidin (29745-04-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; acetone; for 16h; under 2585.81 Torr;

DOI:10.1016/j.bmcl.2011.04.031

upstream raw materials:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

endothall

furan

maleic anhydride

Downstream raw materials:

norcantharidimide

3-exo-benzyloxycarbonyl-7-oxabicyclo[2.2.1]heptane-2-exo-carboxylic acid

4-{2-[2-(dimethylamino)ethoxy]phenyl}-10-oxa-4-azatricyclo[5.2.1]decane-3,5-dione

Refernces

• 1、 Sharma, Shikha,Panja, Surajit,Bhattacharyya, Arunasis,Dhami, Prem S.,Gandhi, Preetam M.,Ghosh, Sunil K.. "Synthesis and extraction studies with a rationally designed diamide ligand selectIVe to actinide(IV) pertinent to the plutonium uranium redox extraction process". . p. 7737 - 7747. Retrieved 2016.
• 2、 Zhang, Jie,Lawrance, Geoffrey A.,Chau, Ngoc,Robinson, Phillip J.,McCluskey, Adam. "From Spanish fly to room-temperature ionic liquids (RTILs): Synthesis, thermal stability and inhibition of dynamin 1 GTPase by a novel class of RTILs". . p. 28 - 36. Retrieved 2008.
• 3、 Stewart, Scott G.,Hill, Timothy A.,Gilbert, Jayne,Ackland, Stephen P.,Sakoff, Jennette A.,McCluskey, Adam. "Synthesis and biological evaluation of norcantharidin analogues: Towards PP1 selectivity". . p. 7301 - 7310. Retrieved 2007.
• 4、 Wang, Xianheng,Wu, Caoyuan,Zhang, Jidong,Zhao, Changkuo,Zhou, Yiqi. "Synthesis of l-ascorbic acid-amino acid-norcantharidin conjugates and their biological activity evaluation in vitro". . . Retrieved 2022/01/06.
• 5、 -. "Synthesis and anti-tumor application of norcantharidin carboxylic acid difluorobenzyl ester". Paragraph 0038-0039. . Retrieved 2020/07/13.