ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate

• ChemBase ID: 68606
• Molecular Formular: C14H17NO3
• Molecular Mass: 247.28968
• Monoisotopic Mass: 247.12084341
• SMILES: N1(C(C=Cc2ccccc12)OCC)C(=O)OCC
• Canonical SMILES: CCOC(=O)N1C(OCC)C=Cc2c1cccc2
• InChI: InChI=1S/C14H17NO3/c1-3-17-13-10-9-11-7-5-6-8-12(11)15(13)14(16)18-4-2/h5-10,13H,3-4H2,1-2H3
• InChIKey: GKQLYSROISKDLL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate
• IUPAC Traditional name: ethyl 2-ethoxy-2H-quinoline-1-carboxylate
• Synonyms: N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline; 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline; ethyl 2-ethoxyquinoline-1(2H)-carboxylate; N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; EEDQ; Ethyl 1,2-dihydro-2-ethoxyquinoline-1-carboxylate; 2-乙氧基-1,2-二氢-1-喹啉羧酸乙酯; N-乙氧羰基-2-乙氧基-1,2-二氢喹啉; 2-乙氧基-1-乙氧羰基-1,2-二氢喹啉; 2-乙氧基-1-乙氧基羰基-1,2-二氢喹啉

Database IDs

• CAS Number: 16357-59-8
• EC Number: 240-418-2
• MDL Number: MFCD00006703
• Beilstein Number: 533048
• Merck Index: 143518
• PubChem SID: 162034336; 24848976
• PubChem CID: 27833
• Wikipedia Title: N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.0479748
• LogD (pH = 7.4): 3.0479748
• Log P: 3.0479748
• Molar Refractivity: 69.812 cm^3
• Polarizability: 26.739895 Å^3
• Polar Surface Area: 38.77 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 62-67 °C; 62-67 °C(lit.); 63-66°C
• Boiling Point: 125-128°C/0.1mm

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: IRRITANT; Moisture Sensitive
• RTECS: VB2010000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 38
• Safety Statements: 22-24/25; 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99%; 95+%; 98%; 99%
• Empirical Formula (Hill Notation): C14H17NO3

DETAILS

MP Biomedicals - 02151086

Crystalline
Peptide condensing agent that causes little or no racemization. Useful in studies of central and peripheral adrenergic nervous system, and for selective N4-acylation of cytidine.

Sigma Aldrich - 149837

Application
Irreversible membrane-bound receptor antagonist.1,2
Packaging
25, 100 g in poly bottle
5 g in glass bottle

REFERENCES

• Belleau, B., et al., J. Am. Chem. Soc., 90: 823 (1968).
• Martel, R., et al., Can. J. Physiol. Pharmacol., 47: 909 (1969).
• Biochim. Biophys. Acta, 238: 27 (1971).
• Reagent for peptide coupling. Reaction proceeds via the anhydride of the acid component: J. Am. Chem. Soc., 90, 823, 1651 (1968); Int. J. Pept. Prot. Res., 26, 493 (1985). See Appendix 6.
• For activation of ɑ -hydroxy acids, see: Tetrahedron Lett, 40, 3435 (1999) . Also used for the mild esterification of alcohols, e.g. for introduction of the levulinate protecting group (see Levulinic acid, A10813): Tetrahedron Lett., 23, 2615 (1982). For a useful esterification technique applicable to primary, secondary and tertiary alcohols, see: J. Org. Chem., 60, 7072 (1995).