| Identification | Back Directory | [Name]
2-(4-(adaMantan-1-yl)phenoxy)acetic acid | [CAS]
52804-26-9 | [Synonyms]
ST071038
BAS 00285042
CBDivE_002637
Oprea1_157400
Oprea1_723072
[4-(Adamantyl-1)phenoxy]acetic acid
2-[4-(1-adamantyl)phenoxy]acetic acid
(4-AdaMantan-1-yl-phenoxy)-aceticacid
2-[4-(1-adamantyl)phenoxy]ethanoic acid
2-(4-(adaMantan-1-yl)phenoxy)acetic acid
2-(4-((3R,5R,7R)-ADAMANTAN-1-YL)PHENOXY)ACETIC ACID
(4-Tricyclo[3.3.1.1(3,7)]dec-1-ylphenoxy)acetic acid
Acetic acid, 2-(4-tricyclo[3.3.1.13,7]dec-1-ylphenoxy)- | [Molecular Formula]
C18H22O3 | [MDL Number]
MFCD00168197 | [MOL File]
52804-26-9.mol | [Molecular Weight]
286.37 |
| Chemical Properties | Back Directory | [Melting point ]
168-170℃ (acetic acid water ) | [Boiling point ]
441.1±28.0 °C(Predicted) | [density ]
1.226±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
3.21±0.10(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Synthesis]
LiOH-H2O (0.29 g, 7.00 mmol) was added to a solution of 2-(4-(1-adamantyl)phenoxy)ethyl acetate (1.10 g, 3.50 mmol) in THF/H2O (1:1, 20.0 mL). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, it was acidified with 10% HCl solution to pH 2. The organic layer was separated by adding EtOAc for extraction. After concentration of the organic phase, the residue was purified by silica gel column chromatography (eluent: CH2Cl2/MeOH = 30:1) to afford 2-(4-(1-adamantyl)phenoxy)acetic acid as a white solid (0.61 g, 61.3% yield).1H NMR (CDCl3, 500 MHz) δ 7.29 (d, 2H, J = 6.75 Hz, Ar-H), 6.87 (d, 2H, Ar-H), 6.87 (d, 2H, J = 6.75 Hz, Ar-H), 7.29 (d, 2H, J = 6.75 Hz, Ar-H). 6.87 (d, 2H, J = 6.74 Hz, Ar-H), 4.61 (s, 2H, -OCH2COO-), 2.04 (s, 4H, adamantyl), 1.86 (m, 6H, adamantyl), 1.76 (m, 6H, adamantyl); 13C NMR (CDCl3, 125 MHz) δ 156.16, 142.71, 127.35, 114.31, 64.21, 42.51, 36.84, 36.17, 28.16; LCMS m/z calculated value (MH+) 287.16, measured value 287.26. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6305 - 6310
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 7, p. 1675 - 1684
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7456 - 7460
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1453 - 1456
[5] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 12, p. 3826 - 3829 |
|
|