ethyl 2-{[(1S,2S,3Z,5S)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylidene]amino}acetate

• ChemBase ID: 168607
• Molecular Formular: C14H23NO3
• Molecular Mass: 253.33732
• Monoisotopic Mass: 253.1677936
• SMILES: C1([C@H]2C/C(=N/CC(=O)OCC)/[C@]([C@@H]1C2)(O)C)(C)C
• Canonical SMILES: CCOC(=O)C/N=C\1/C[C@H]2C[C@@H]([C@]1(C)O)C2(C)C
• InChI: InChI=1S/C14H23NO3/c1-5-18-12(16)8-15-11-7-9-6-10(13(9,2)3)14(11,4)17/h9-10,17H,5-8H2,1-4H3/b15-11-/t9-,10-,14-/m0/s1
• InChIKey: XVHYGWSRXODAMH-ALQHDMARSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-{[(1S,2S,3Z,5S)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylidene]amino}acetate
• IUPAC Traditional name: ethyl 2-{[(1S,2S,3Z,5S)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylidene]amino}acetate
• Synonyms: N-[(1S,2S,5S)-2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylidene]glycine Ethyl Ester; (1S,2S,5S)-Ethyl [(2-Hydroxypinan-3-ylene)amino]acetate

Database IDs

• CAS Number: 90473-00-0
• PubChem SID: 162262739
• PubChem CID: 11054174

CALCULATED PROPERTIES

• Acid pKa: 13.672286
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.5954366
• LogD (pH = 7.4): 1.5976522
• Log P: 1.5976807
• Molar Refractivity: 68.6497 cm^3
• Polarizability: 27.18346 Å^3
• Polar Surface Area: 58.89 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO; Ethyl Acetate; Methanol
• Apperance: Light Yellow Oil

Safety Information

• Storage Condition: Hygroscopic, -86°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E919160

A 3-carboxy homolog of AMPA.

REFERENCES

• Stensbol, T., et al.: Eur. J. Pharmacol., 380, 153 (1999)
• Kunishima, N., et al.: Nature, 407, 971 (1999)
• Hogner, A., et al.: J. Mol. Biol., 322, 93 (1999)
• Brehm, L., et al.: J. Med. Chem., 46, 1350 (1999)