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CAS No. : | 495-02-3 | MDL No. : | MFCD00075948 |
Formula : | C19H22O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RSDDHGSKLOSQFK-RVDMUPIBSA-N |
M.W : | 298.38 | Pubchem ID : | 1550607 |
Synonyms : |
7-Geranyloxycoumarin
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.32 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 91.29 |
TPSA : | 39.44 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.5 cm/s |
Log Po/w (iLOGP) : | 3.96 |
Log Po/w (XLOGP3) : | 5.1 |
Log Po/w (WLOGP) : | 4.86 |
Log Po/w (MLOGP) : | 3.51 |
Log Po/w (SILICOS-IT) : | 5.13 |
Consensus Log Po/w : | 4.51 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.84 |
Solubility : | 0.00428 mg/ml ; 0.0000143 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.67 |
Solubility : | 0.000635 mg/ml ; 0.00000213 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.9 |
Solubility : | 0.000378 mg/ml ; 0.00000127 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.43 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With potassium carbonate In N,N-dimethyl-formamide for 3 h; Inert atmosphere; Reflux | Aurapten (5). Geranyl bromide (159 l, 0.80 mmol) was added to a stirred mixture of umbelliferone (2) (100 mg, 0.62 mmol) and K2CO3 (171 mg, 1.24 mmol) in dry DMF (5 ml) under argon. The reaction mixture was stirred under reflux for 3 h. The reaction mixture was neutralised by addition of aq. HCl (1M). The resulting brown residue was added in DCM (20 ml), washed with water (2 .x. 20 ml), brine (30 ml) and dried Na2SO4). Removal of solvent yielded a brown oil, which was purified by flash column chromatography, eluting with diethylether-hexane (1:1) to give a white powder 5 (181 mg, 76percent): 1H NMR (CDCl3, 700 MHz) 7.64 (1H, d, J = 9.5 Hz, H-4), 7.36 (1H, d, J = 8.6 Hz, H-5), 6.86 (1H, dd, J = 8.4, 2.4 Hz, H-6), 6.82 (1H, d, J = 2.4 Hz, H-8), 6.25 (1H, d, J = 9.5 Hz, H-3), 5.47 (1H, tq, J = 6.6, 1.4 Hz, H-2'), 5.08 (2H, m, H-1'), 4.61 (2H, d, J = 6.6 Hz, H-1'), 2.13 (2H, m, H-5'), 2.09 (2H, m, H-4'), 1.76 (3H, brs, H-9'), 1.67 (3H, brs, H-8'), 1.60 (3H, brs, H-10'); 13C NMR (CDCl3, 175 MHz) 162.2 (C, C-7), 161.3 (C, C-2), 155.9 (C, C-8a), 143.4 (CH, C-4), 142.4 (C-3'), 131.9 (C, C-7'), 128.7 (CH, C-5), 123.6 (CH, C-6'), 118.4 (CH, C-2'), 113.2 (CH, C-6), 112.9 (CH, C-3), 112.4 (C, C-4a), 101.6 (CH, C-8), 65.5 (CH2, C-1'), 39.5 (CH2, C-4'), 26.2 (CH2, C-5'), 25.6 (CH3, C-8'), 17.7 (CH3, C-10'), 16.7 (CH3, C-9'); HR-FABMS (pos) m/z 299.3877 [M + H]+ (calcd. for C19H23O3, 299.3860). |