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CAS No. : | 53440-12-3 | MDL No. : | MFCD00001741 |
Formula : | C11H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NTAGXJQHJQUOOA-UHFFFAOYSA-N |
M.W : | 176.21 | Pubchem ID : | 101370 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 50.45 |
TPSA : | 37.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.88 cm/s |
Log Po/w (iLOGP) : | 1.69 |
Log Po/w (XLOGP3) : | 2.11 |
Log Po/w (WLOGP) : | 1.88 |
Log Po/w (MLOGP) : | 2.18 |
Log Po/w (SILICOS-IT) : | 2.28 |
Consensus Log Po/w : | 2.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.54 |
Solubility : | 0.511 mg/ml ; 0.0029 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.52 |
Solubility : | 0.527 mg/ml ; 0.00299 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.65 |
Solubility : | 0.398 mg/ml ; 0.00226 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.11 |
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 |
---|---|---|
< 100% | With thionyl chloride; In toluene; at 60℃; for 2h; | STEP A: Preparation of l,2,3,4-tetrahydro-naphthalene-2-carbonyl chloride (23A).6.5 mmol (1.15 g) l,2,3,4-Tetrahydro-naphthalene-2-carboxylic acid is dissolved in 20 mL toluene, 20 mL of thionylchloride are added, the mixture is heated to 60 C in an oil bath for 2 hours. Then the mixture is concentrated in vacuum. Toluene is added to the residue and evaporated again. The crude product is obtained in almost quantitative yield.ESI-MS: 131 (100), 159 (82), 196 (M+H+, 82). |
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 3h; | Example 42; Synthesis of methyl 3-oxo-3-(1 ,2,3,4-tetrahvdronaphthalen-2- vQpropanoate (Intermediate 78); Anhydrous DMF (5 drops) is added to an ice-cold solution of 1 ,2,3,4- tetrahydronaphthalene-2-carboxylic acid (CAS No 53440-12-3) (3.89g) in anhydrous DCM (50ml) under N2, followed by the dropwise addition of oxalyl chloride (5.78ml). The reaction mixture is stirred under N2, warming to room temperature. After 3 hrs the reaction mixture is evaporated in vacuo, and the residue azeotroped in vacuo with 1:1 DCM/heptane (3 x 10ml). The resultant amber oil is redissolved in anhydrous DCM (20ml), and this solution is added dropwise to a stirred, ice-cold solution of 2,2-dimethyl-1 ,3- dioxane-4,6-dione (CAS No 131376-78-8) (3.18g) and pyridine (5.36ml) in anhydrous DCM (30ml), under N2. The reaction mixture is stirred under N2, warming to room temperature. After 18hrs the now dark reaction mixture is washed with water (30ml), 1 M hydrochloric acid (2 x 50ml), water (30ml), dried (Na2SU4) and evaporated in vacuo. The <n="166"/>resulting dark red oil is dissolved in anhydrous methanol (50ml) and heated to reflux under N2- After 3hrs, the reaction is cooled and evaporated under reduced pressure. The residue is redissolved in EtOAc (80ml) and washed with saturated NaHCtheta3 solution (2 x 4OmI)1 water (3OmI)1 saturated brine (30ml), dried (Na2SO4) and evaporated in vacuo to give the title compound as a red oil (4.41 g, 86%). 1 H NMR 300 MHz (CDCI3) (delta ppm):7.05-7.16 (4H1 m), 3.75 (3H1 s), 3.61 (1 H1 s), 2.69-3.04 (5H1 m), 2.15-2.26 (1 H1 m), 1.70-1.91 (1 H1 m). | |
With oxalyl dichloride; In chloroform; N,N-dimethyl-formamide; at 20℃; for 1h; | 1) Production of N,N-dimethyl-1,2,3,4-tetrahydronaphthalene-2-carboxamide: [Show Image] 1.94 mL of oxalyl chloride and 0.026 mL of N,N-dimethylformamide were added to a chloroform (20 mL) solution of 3 g of 1,2,3,4-tetrahydronaphthalene-2-carboxylic acid, and stirred at room temperature for 1 hour. The reaction liquid was concentrated, and the residue was dissolved in 20 mL of tetrahydrofuran, and 22.13 mL of 2 M dimethylamine/tetrahydrofuran solution was added thereto. Water was added to the reaction liquid, extracted with ethyl acetate, washed with saturated saline water, dried with anhydrous magnesium sulfate, and the solvent was evaporated away to obtain 3.53 g of the entitled compound as a crude product. 1H-NMR (CDCl3) d: 7.13-7.08 (4H, m), 3.12-3.05 (1H, m), 3.10 (3H, s), 3.00 (3H, s), 2.97-2.79 (4H, m), 2.06-1.86 (2H, m) |
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 1h;Inert atmosphere; | General procedure: To the solution of carboxylic acid 10-13 (2.43 mM) in dry CH2Cl2 (5.5 mL) that had been pre-cooledto 0 C, were gradually added the catalytic amount of DMF (1-2 drop) and oxalyl chloride (7.29 mM).The resulting mixture was stirred for 5 min at 0 C and then at room temperature for a further 55 min.Subsequently the solvent was evaporated under vacuum and the crude product was used further. |
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