| Identification | More | [Name]
Methyl 3-cyclopentenecarboxylate | [CAS]
58101-60-3 | [Synonyms]
METHYL 3-CYCLOPENTENECARBOXYLATE
Methyl-3-cyclopentene-1-carboxylate
3-Cyclopentene CarboxylicAcid Methyl Ester
3-Cyclopentene-1-Carboxylic AcidMethyl Ester
Methyl3-Cyclopentene-1-CarBonate | [Molecular Formula]
C7H10O2 | [MDL Number]
MFCD04038661 | [Molecular Weight]
126.15 | [MOL File]
58101-60-3.mol |
| Chemical Properties | Back Directory | [Boiling point ]
74 °C(Press: 24 Torr) | [density ]
1.031 g/mL at 25 °C | [Fp ]
48°(118°F) | [refractive index ]
1.4500 | [storage temp. ]
2-8°C | [form ]
Liquid | [color ]
Colorless to pale brown | [InChI]
InChI=1S/C7H10O2/c1-9-7(8)6-4-2-3-5-6/h2-3,6H,4-5H2,1H3 | [InChIKey]
CEOILRYKIJRPBZ-UHFFFAOYSA-N | [SMILES]
C1(C(OC)=O)CC=CC1 | [CAS DataBase Reference]
58101-60-3(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
Methyl 3-Cyclopentene-1-carboxylate has been used as a reactant in the preparation of (silyloxy)methylcyclopentanone as a key intermediate of sphingosine phosphate receptor agonists. | [Synthesis]
At 0 °C and under nitrogen protection, 3-cyclopentenecarboxylic acid (10 g, 89 mmol) was dissolved in dichloromethane (100 mL), followed by the addition of 1,1'-carbonyl diimidazole (43 g, 267 mmol). The reaction mixture was stirred at room temperature for 4 hours, after which methanol (100 mL) was added. Stirring of the reaction mixture was continued overnight. The solvent was removed by low temperature evaporation to afford methyl 3-cyclopentene-1-carboxylate (11.2 g, 99% yield). | [References]
[1] Patent: US2007/254952, 2007, A1. Location in patent: Page/Page column 35
[2] Nucleosides, Nucleotides and Nucleic Acids, 2001, vol. 20, # 4-7, p. 661 - 664
[3] ChemMedChem, 2011, vol. 6, # 9, p. 1559 - 1565
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 19, p. 5336 - 5339 |
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