75532-25-1

Basic information

• Product Name: Thieno[3,4-c]furan-1,3(4H,6H)-dione
• Synonyms: Thieno[3,4-c]furan-1,3(4H,6H)-dione;1H,3H-Thieno[3,4-c]furan-1,3-dione, 4,6-dihydro-;4,6-dihydro-1H,3H-Thieno[3,4-c]furan-1,3-dione
• CAS NO: 75532-25-1
• Molecular Formula: C₆H₄O₃S
• Molecular Weight: 156.15916
• Mol File: 75532-25-1.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Thieno[3,4-c]furan-1,3(4H,6H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: Thieno[3,4-c]furan-1,3(4H,6H)-dione(75532-25-1)
• EPA Substance Registry System: Thieno[3,4-c]furan-1,3(4H,6H)-dione(75532-25-1)

Safety Data

• Hazardous Substances Data: 75532-25-1(Hazardous Substances Data)

Usage

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.

Upstream product

• 170945-21-8 methyl 4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydrothiophene-3-carboxylate 
• 7400-45-5 dimethyl-3-thiaadipate 
• 96307-21-0 3-cyano-2,5-dihydrothiophene-4-carboxylic acid methyl ester 
• 155251-30-2 3-cyano-3-hydroxy-tetrahydrothiophene-4-carboxylic acid methyl ester 
• 20946-32-1 3,4-dimethyl 2,5-dihydrothiophene-3,4-dicarboxylate 
• 155251-31-3 3-hydroxy-tetrahydro-thiophene-3,4-dicarboxylic acid 
• 75532-26-2 C₁₀H₈O₄S 
• 89533-87-9 2,5-dihydrothiophene-3,4-dicarboxylic acid 
• 20688-07-7 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid 
• 2689-68-1 methyl 4-oxotetrahydrothiophene-3-carboxylate 
• 74-90-8 hydrogen cyanide 

Downstream Products

• 75532-26-2 C₁₀H₈O₄S 
• 75558-06-4 C₁₀H₈O₄S 
• 75532-26-2 C₁₀H₈O₄S 
• 80558-50-5 epi-catharidin 
• 56-25-7 cantharidin 
• 10385-74-7 2,3-dimethyl-7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid anhydride 
• 6626-68-2 2,6-diphenyl-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 
• 945561-49-9 2,6-diphenyl-3a,4,8,8a-tetrahydro-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 
• 945561-48-8 2,2-dioxo-5-phenyl-2,3-dihydro-1H-2λ⁶-thieno[3,4-c]pyrrole-4,6-dione 
• 945561-47-7 5-phenyl-1,3-dihydro-thieno[3,4-c]pyrrole-4,6-dione 
• 867287-84-1 4-(Biphenyl-4-ylcarbamoyl)-2,5-dihydro-thiophene-3-carboxylic acid 

Relevant articles and documents

SYNTHESIS OF CANTHARIDIN

The invention provides synthetic methods for the preparation of cantharidin and analogs thereof. In one aspect, the invention provides an improved Diels-Alder cycloaddition to generate a key intermediate en route to cantharidin and analogs thereof. In certain embodiments, the new Diels-Alder reaction involves reacting Compound (2) in the presence of furan, and in the absence of acid or increased pressure, in an aprotic polar solvent with slight warming, to yield Compound (1) in favorable yield and exo-endo ratio. In another aspect, the invention also provides a new Diels-Alder reaction between compounds of Formula (III) and furan to yield compounds of Formula (IV), which can then be transformed into cantharidin or analogs thereof. In yet another aspect, the invention describes a new palladium-mediated carbonylation providing another key intermediate en route to cantharidin and analogs thereof. In addition to synthetic methods, present invention also provides compounds {i.e., intermediates) useful in the synthesis of cantharidin and analogs thereof. Compounds provided herein may have biological activity, and therefore may be used in the treatment of diseases or conditions {e.g., infectious diseases and skin conditions).

Novel green and environment-friendly synthetic process for cantharidin

The invention relates to a novel green and environment-friendly synthetic process for preparing cantharidin under the condition of normal pressure and belongs to the field of synthesis and preparation of medicines. The process comprises the following steps: preparing 3-cyano-3-hydroxy-4-methyl formate-2,5-tetrahydrothiophene from a NaCN aqueous solution; adding benzene, pyridine and POCl3 into thiophene to prepare 3-cyano-4-methyl formate-2,5-dihydrothiophene; then adding acetic acid and concentrated hydrochloric acid, and carrying out reflux reaction to obtain 2,5-dihydrothiophene-3,4-dicarboxylic acid powder; carrying out stirring and refluxing on the prepared dicarboxylic acid and thionyl chloride to prepare 2,5-dihydrothiophene-3,4-dicarboxylic anhydride; carrying out heating reaction according to the solid-liquid ratio of dicarboxylic anhydride to furfuran to ionic liquid being 1mg:(3.5 to 6[mu]l):(2 to 4[mu]l), extracting and carrying out Raney-Ni reflux to obtain the cantharidin. According to the process, superhigh pressure condition and equipment are not needed, and overnight reaction at the temperature of 20 to 50DEG C is carried out; the process has the advantages of mild conditions, high conversion rate, and high yield of the cantharidin, and provides favorable conditions for industrial production of the cantharidin.

Cycloaddition approach to the curing of polyimides via precursor containing thiophene-S,S-dioxide

A new method for linear polymerization of maleimides via the Diels-Alder reaction has been developed. This method involves use of a new cross-linking agent, benzene-3,4-dimethylenesuccinimide, which can be generated in situ from its thiophene precursor, benzene-2,5-dihydrothiophene-3,4dicarboximide-S,S- dioxide. This new cross-linking agent is reasonably reactive, readily prepared, and stable at room temperature. A controlled molecular weight oligomer has been synthesized and applied to the polymerization to yield a highly thermal stable polyimide.