Thieno[3,4-c]furan-1,3(4H,6H)-dione

Base Information

• Chemical Name: Thieno[3,4-c]furan-1,3(4H,6H)-dione
• CAS No.: 75532-25-1
• Molecular Formula: C6H4O3S
• Molecular Weight: 156.162
• European Community (EC) Number: 889-019-0
• Mol file: 75532-25-1.mol

Synonyms:75532-25-1;Thieno[3,4-c]furan-1,3(4H,6H)-dione;4,6-Dihydro-1H,3H-thieno[3,4-c]furan-1,3-dione;1H,3H-Thieno[3,4-c]furan-1,3-dione, 4,6-dihydro-;4,6-dihydrothieno[3,4-c]furan-1,3-dione;2,5-dihydrothiophene-3,4-dicarboxylic anhydride;SCHEMBL1568451;OEPDMUMGYXMSJZ-UHFFFAOYSA-N;GEO-04022;AKOS027324017;FT-0768237;A935096

Chemical Property of Thieno[3,4-c]furan-1,3(4H,6H)-dione

Chemical Property:

• PSA: 68.67000
• LogP: 0.11320
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 155.98811516
• Heavy Atom Count: 10
• Complexity: 230

Purity/Quality:

99% ^*data from raw suppliers

4,6-Dihydro-1H,3H-thieno[3,4-c]furan-1,3-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(CS1)C(=O)OC2=O
• Uses: 4,6-Dihydro-1H,3H-thieno[3,4-c]furan-1,3-dione is used in the synthetic preparation of (-)- and (+)-palasonin via Diels-Alder reaction of citraconic anhydride.

Technology Process of Thieno[3,4-c]furan-1,3(4H,6H)-dione

There total 12 articles about Thieno[3,4-c]furan-1,3(4H,6H)-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: 84.0%

2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid (20688-07-7) → 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride (75532-25-1)

Guidance literature:

With acetyl chloride; for 1h; Reflux;

Reference yield: 70.0%

2,5-dihydrothiophene-3,4-dicarboxylic acid (89533-87-9) → 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride (75532-25-1)

Guidance literature:

With thionyl chloride; Heating;

DOI:10.1021/jo00214a034

Reference yield:

methyl 4-oxotetrahydrothiophene-3-carboxylate (2689-68-1,99328-39-9) → 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride (75532-25-1)

Guidance literature:

Multi-step reaction with 3 steps

1: AcOH / methanol; H₂O / 8 h / 0 °C

2: aq. HCl; AcOH / 20 h / Heating

3: Ac₂O / 4 h / Heating

With hydrogenchloride; acetic anhydride; acetic acid; In methanol; water;

DOI:10.1016/j.bmcl.2005.07.053

upstream raw materials:

methyl 4-oxotetrahydrothiophene-3-carboxylate

hydrogen cyanide

2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid

2,5-dihydrothiophene-3,4-dicarboxylic acid

Downstream raw materials:

C₁₀H₈O₄S

5-phenyl-1,3-dihydro-thieno[3,4-c]pyrrole-4,6-dione

2,2-dioxo-5-phenyl-2,3-dihydro-1H-2λ⁶-thieno[3,4-c]pyrrole-4,6-dione

2,6-diphenyl-3a,4,8,8a-tetrahydro-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone

Refernces

• 1、 -. "SYNTHESIS OF CANTHARIDIN". Paragraph 00259; 00271. . Retrieved 2019/04/27.
• 2、 -. "COMMERCIALLY VIABLE SYNTHESIS OF CANTHARIDIN AND BIOACTIVE CANTHARIDIN DERIVATIVES". Paragraph 0109. . Retrieved 2016/07/05.