1703-61-3

Basic information

• Product Name: 4-oxocyclopentane-1,2-dicarboxylic acid
• Synonyms: 4-oxocyclopentane-1,2-dicarboxylic acid;1,2-Cyclopentanedicarboxylic acid, 4-oxo-;4-Oxo-1,2-cyclopentanedicarboxylic acid;Cyclopentanone-3,4-dicarboxylic acid
• CAS NO: 1703-61-3
• Molecular Formula: C₇H₈O₅
• Molecular Weight: 172.13542
• Mol File: 1703-61-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 189℃
• Boiling Point: 466.732 °C at 760 mmHg
• Flash Point: 250.188 °C
• Appearance: /
• Density: 1.569
• Vapor Pressure: 5.29E-10mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.92±0.40(Predicted)
• CAS DataBase Reference: 4-oxocyclopentane-1,2-dicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-oxocyclopentane-1,2-dicarboxylic acid(1703-61-3)
• EPA Substance Registry System: 4-oxocyclopentane-1,2-dicarboxylic acid(1703-61-3)

Safety Data

• Hazardous Substances Data: 1703-61-3(Hazardous Substances Data)

Usage

General Description

4-oxocyclopentane-1,2-dicarboxylic acid is a chemical compound with the molecular formula C7H8O5. It belongs to the class of organic compounds known as dicarboxylic acids and derivatives. 4-oxocyclopentane-1,2-dicarboxylic acid is a white crystalline solid with a melting point of 160-163 degrees Celsius. It is used as a precursor in the synthesis of pharmaceuticals and agricultural chemicals, and as a building block in the production of polymers and plastics. Additionally, 4-oxocyclopentane-1,2-dicarboxylic acid has been researched for its potential application in drug delivery and as a chelating agent in metal coordination chemistry.

InChI:InChI=1/C7H8O5/c8-3-1-4(6(9)10)5(2-3)7(11)12/h4-5H,1-2H2,(H,9,10)(H,11,12)

Upstream product

• 105-53-3 diethyl malonate 
• 92334-74-2 trans(3,4)-3-Hydroxymethyl-4-(1',2'-dihydroxy-ethyl)-cyclopentanol-⁽¹⁾ 
• 4373-15-3 1,2,3,4-butanetetracarboxylic acid tetraethyl ester 
• 4534-68-3 1,2,3,4-butanetetracarboxylic acid 
• 1641-42-5 meso-butane-1,2,3,4-tetracarboxylic acid tetramethyl ester 
• 4534-68-3 (2S,3R)-1,2,3,4-butanetetracarboxylic acid 
• 6261-04-7 2,3,4-tris(ethoxycarbonyl)cyclopentanone 
• 18852-51-2 sodium cyanoacetic acid ethyl ester 
• 64-17-5 ethanol 
• 77-93-0 citric acid triethyl ester 
• 67885-96-5 2.3.4-Trimethoxycarbonylcyclopentanon 
• 115794-30-4 (+)-(1S,2S)-dimethyl-4-oxocyclopentane 1,2-dicarboxylate 

Downstream Products

• 6453-07-2 dimethyl 4-oxocyclopentane-1,2-dicarboxylate 
• 6453-07-2 (+/-)-trans-4-oxo-1,2-cyclopentanedicarboxylic acid bis(methyl ester) 
• 187528-23-0 (3aR,6aR)-Tetrahydro-cyclopenta[c]furan-5-one 
• 923604-56-2 ethyl (1R,2S)-2-ethenyl-1-({[(1R,2R,4R)-2-[hex-5-en-1-yl-(methyl)carbamoyl]-4-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)cyclopentyl]carbonyl}-amino)cyclopropanecarboxylate 
• 1042695-87-3 methyl (1R,2R,4S)-2-[5-hexen-1-yl(methyl)carbamoyl]-4-[[2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxy-8-methyl-4-quinolinyl]oxy]cyclopentanecarboxylate 
• 35079-19-7 trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane 
• 1333964-81-0 benzyl methyl (1R,2R,4R)-4-hydroxy-1,2-cyclopentanedicarboxylate 
• 1333964-84-3 benzyl methyl (1R,2R,4S)-4-([2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxy-8-methyl-4-quinolinyl]oxy)-1,2-cyclopentanedicarboxylate 
• 1333964-95-6 benzyl methyl (1R,2R,4S)-4-[(4-nitro-benzoyl)oxy]-1,2-cyclopentanedicarboxylate 
• 1333964-98-9 (1R,2R,4R)-2-(methoxycarbonyl)-4-[(4-nitrobenzoyl)oxy]cyclopentanecarboxylic acid 
• 1333965-01-7 (1R,3R,4R)-3-[5-hexen-1-yl(methyl)-carbamoyl]-4-(methoxycarbonyl)cyclopentyl 4-nitrobenzoate 
• 862174-60-5 (1R,4R,5R)-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid 
• 1042695-89-5 (1R,2R,4S)-1-benzyl 2-methyl 4-hydroxycyclopentane-1,2-dicarboxylate 
• 115694-82-1 (1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid 

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A process for preparing [(1R,2R)-4-oxo-1,2-cyclopentanedicarboxylic acid II, by the resolution of racemic 4-oxo-1,2-cyclopentanedicarboxylic acid (V), said process comprising: (a) reacting 4-oxo-1,2-cyclopentanedicarboxylic acid (V) with brucine or (1R,2S)-(-)- ephedrine, thus preparing the bis-brucine or bis-(1R,2S)-(-)-ephedrine salt of (V), and (b) precipitating selectively the bis-brucine or bis-(1R,2S)-(-)-ephedrine salt of (1R,2R)-4-oxo-1,2-cyclopentanedicarboxylic acid II, while the bis-brucine or bis- (1R,2S)-(-)-ephedrine salt of [(1S,2S)-4-oxo-1,2-cyclopentanedicarboxylic acid stays in solution; (c) liberating the acid II by removal of brucine or (1R,2S)-(-)-ephedrine from the precipitated salt obtained in step (b).

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The β-amino acid BAY 10-8888/PLD-118 is currently being investigated in phase II clinical studies as a novel antifungal for the treatment of yeast infections. An efficient asymmetric synthesis of this compound is described. The key step employed a highly enantioselective, quinine-mediated alcoholysis of a mesoanhydride intermediate.