Identification | Back Directory | [Name]
CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID | [CAS]
1461-96-7 | [Synonyms]
cis-Cyclopentanedicarboxylic acid cis-Cyclopentane-1,2-dicarboxylic CIS-1,2-CYCLOPENTANEDICARBOXYLIC ACID CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID 1,2-Cyclopentanedicarboxylic acid, cis- (±)-cis-Cyclopentane-1,2-dicarboxylicaci (1R)-Cyclopentane-1β,2β-dicarboxylic acid (1R,2S)-1,2-Cyclopentanedicarboxylic acid (1R,2S)-cyclopentane-1,2-dicarboxylic acid (+/-)-cis-Cyclopentane-1,2-dicarboxylic acid rel-(1R,2S)-1,2-Cyclopentanedicarboxylic acid (1R,2S)-rel-1,2-Cyclopentanedicarboxylic Acid rel-(1R,2S)-cyclopentane-1,2-dicarboxylic acid 1,2-Cyclopentanedicarboxylic acid, (1R,2S)-rel- TIANFU-CHEM - CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID (+/-)-cis-Cyclopentane-1,2-dicarboxylic acid >=97.0% (GC) | [Molecular Formula]
C7H10O4 | [MDL Number]
MFCD01311172 | [MOL File]
1461-96-7.mol | [Molecular Weight]
158.15 |
Chemical Properties | Back Directory | [Melting point ]
132-136℃ | [Boiling point ]
378.6±35.0 °C(Predicted) | [density ]
1.396±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Store at room temperature | [solubility ]
Chloroform, Methanol, Moderately Solubility in Water | [form ]
crystals | [pka]
pK1:4.43;pK2:6.67 (25°C) | [Appearance]
White to off-white Solid | [BRN ]
2049007 | [InChI]
InChI=1/C7H10O4/c8-6(9)4-2-1-3-5(4)7(10)11/h4-5H,1-3H2,(H,8,9)(H,10,11)/t4-,5+ | [InChIKey]
ASJCSAKCMTWGAH-SYDPRGILSA-N | [SMILES]
[C@@H]1(C(O)=O)CCC[C@@H]1C(O)=O |&1:0,7,r| |
Hazard Information | Back Directory | [Uses]
(1R,2S)-rel-1,2-Cyclopentanedicarboxylic Acid is a Possible inhibitor of prolidase. | [Uses]
Possible inhibitor of prolidase. | [Synthesis]
The general procedure for the synthesis of cis-1,2-cyclopentanedicarboxylic acid from ethyl 2-oxocyclohexanecarboxylate was as follows: bromine (112.8 g, 705.6 mmol) was slowly added dropwise to a solution of ethyl 2-oxocyclohexanecarboxylate (120 g, 705.6 mmol) dissolved in chloroform (360 ml) at 0 °C. The reaction mixture was stirred at room temperature overnight and then washed sequentially with sodium bicarbonate solution (2 x 200 ml) and brine (2 x 100 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated and the resulting residue was added slowly and dropwise to a pre-cooled aqueous solution of potassium hydroxide (168 g, 3 mol) (960 ml). The reaction mixture was continued to be stirred at 0 °C for 6 h and subsequently extracted with ether. The aqueous phase was adjusted to pH 5 with 4.0 M hydrochloric acid and extracted again with ether. All organic layers were combined, washed with brine (200 ml), dried, filtered and concentrated to give a yellow oil. The oil was crystallized by mixed solvent ethyl acetate/ether to give cis-1,2-cyclopentanedicarboxylic acid as colorless crystals (70 g, 63% yield). Mass spectrum (electrospray ionization): 159 [M + H]+. | [References]
[1] Tetrahedron Letters, 2007, vol. 48, # 4, p. 635 - 638 [2] Patent: WO2013/95275, 2013, A1. Location in patent: Page/Page column 35 [3] Journal of the American Chemical Society, 2000, vol. 122, # 50, p. 12610 - 12611 [4] Journal of Organic Chemistry, 1989, vol. 54, # 4, p. 817 - 824 [5] Journal of Organic Chemistry, 1961, vol. 26, p. 22 - 27 |
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