methyl 6-{4-methoxy-3-[(3R,5S,7s)-adamantan-1-yl]phenyl}naphthalene-2-carboxylate

• ChemBase ID: 159540
• Molecular Formular: C29H30O3
• Molecular Mass: 426.5467
• Monoisotopic Mass: 426.21949482
• SMILES: C12(C[C@H]3C[C@@H](C1)C[C@H](C2)C3)c1cc(ccc1OC)c1ccc2c(c1)ccc(c2)C(=O)OC
• Canonical SMILES: COc1ccc(cc1C12C[C@@H]3C[C@@H](C2)C[C@H](C1)C3)c1ccc2c(c1)ccc(c2)C(=O)OC
• InChI: InChI=1S/C29H30O3/c1-31-27-8-7-24(14-26(27)29-15-18-9-19(16-29)11-20(10-18)17-29)22-3-4-23-13-25(28(30)32-2)6-5-21(23)12-22/h3-8,12-14,18-20H,9-11,15-17H2,1-2H3/t18-,19+,20-,29?
• InChIKey: PGXNMQBGOVUZNC-VIBOSYLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 6-{4-methoxy-3-[(3R,5S,7s)-adamantan-1-yl]phenyl}naphthalene-2-carboxylate
• IUPAC Traditional name: methyl 6-{4-methoxy-3-[(3R,5S,7s)-adamantan-1-yl]phenyl}naphthalene-2-carboxylate
• Synonyms: Methyl 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthalenecarboxylate; 6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic Acid Methyl Ester; Adapalene Methyl Ester

Database IDs

• CAS Number: 106685-41-0
• PubChem SID: 162253675
• PubChem CID: 10526466

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 6.8043957
• LogD (pH = 7.4): 6.8043957
• Log P: 6.8043957
• Molar Refractivity: 126.841 cm^3
• Polarizability: 51.974884 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White to Off-White Solid
• Melting Point: 223-225°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A225010

Adapalene intermediate, an ester of Adapalene.

REFERENCES

• Charpentier, B., et al.: J. Med. Chem., 38, 4993 (1995)