Structure of 14676-52-9
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CAS No. : | 14676-52-9 |
Formula : | C14H12O2 |
M.W : | 212.24 |
SMILES Code : | O=C(O)CC1=CC=CC=C1C2=CC=CC=C2 |
MDL No. : | MFCD06208460 |
Boiling Point : | No data available |
InChI Key : | YWPABLWXCWUIIT-UHFFFAOYSA-N |
Pubchem ID : | 263373 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.07 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 63.42 |
TPSA ? Topological Polar Surface Area: Calculated from | 37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 1.9 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 3.19 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 2.98 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 3.15 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 3.27 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 2.9 |
Log S (ESOL):? ESOL: Topological method implemented from | -3.52 |
Solubility | 0.0637 mg/ml ; 0.0003 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -3.64 |
Solubility | 0.0481 mg/ml ; 0.000227 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -4.7 |
Solubility | 0.00424 mg/ml ; 0.00002 mol/l |
Class? Solubility class: Log S scale | Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -5.33 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.56 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 1.9 |
* 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 |
---|---|---|
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere; | General procedure: To an over-dried 100 mL three-necked flask, the carboxylic acid (10 mmol), DMF (5 drops) and DCM (30 mL) were added under a N2 atmosphere. Oxalyl chloride (1.0 mL, 12 mmol) was added dropwise at 0 C resulting in vigorous bubbling. The mixture was stirred for 3 h at room temperature, and the solvent was then removed in vacuo. The resulting acid chloride was used immediately without further purification. To a solution of the acid chloride in DCM (30 mL) ,a solution of 1,1,1,3,3,3-hexamethyldisilazane (30 mmol) in DCM (10 mL) was added dropwise at 0 C, and the solution was then allowed to warm to room temperature. After stirring overnight, the reaction system was quenched with 1 M HCl aq. and saturated aqueous NH4Cl (excess amount) and the organic layer was separated. The aqueous layer was extracted with DCM (2x15 mL). The combined organic layers were washed with saturated aqueous NH4Cl (30 mL) and brine (30 mL), dried over MgSO4, filtered and evaporated in vacuo. The resulting crude material was purified by recrystallization from EtOAc and hexane. The resulting product (5 mmol), 8-bromomethylquinoline (6 mmol), Al2O3 (50 mmol), KOH (25 mmol) and dioxane (30 mL) were added to an over-dried 100 mL three-necked flask. The mixture was stirred for 8 h at 60 C and then was filtered through a celite pad. The filtrate was washed with H2O (30 mL) and the organic layer was separated. The aqueous layer was extracted with EtOAc (2x15 mL). The combined organic layers were washed with brine (15 mL), dried over anhydrous Na2SO4, filtrated and evaporated in vacuo. The resulting crude amide was purified by column chromatography on silica gel (eluent: hexane/EtOAc = 1/1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
b 2-[1,1'-Biphenyl]-2-ylacetic acid The compound obtained in Example 62a (1.06 g, 5.48 mmol) was dissolved in ethyleneglycol (30 ml). The solution was added with potassium hydroxide (5.98 g, 90.6 mmol) and heated at 190 C. for 2 hours. The reaction mixture was allowed to cool to room temperature, and then pored into 1N hydrochloric acid (200 ml). The precipitated solids were collected by filtration and washed with water, and then dried under reduced pressure to obtain the title compound as colorless solid (1.05 g, yield: 91%). 1H-NMR(CDCl3): 7.25-7.42(9H,m), 3.63(2H,s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With palladium diacetate; sodium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 1h; | Add 2-bromophenylacetic acid (430 mg, 2 mmol) to a 25 mL round bottom flask.Phenylboronic acid (366 mg, 3 mmol), palladium acetate (1 mol%, 4.5 mg, 0.02 mmol),Sodium carbonate (636 mg, 6 mmol), DMF (2 mL), water (2 mL),And reacted in an oil bath at 100 C for 1 h; after the reaction is completed, 10 ml of saturated brine is added.And acidified with dilute hydrochloric acid to weak acidity; extracted with ethyl acetate (3×10 mL), and dissolved under reduced pressure,Purification by column chromatography gave the title compound 2-carboxymethylbiphenyl as a white solid.Yield 98%, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; | EXAMPLE 1 1-Biphenylylacetoxy-3-(2-methoxyphenoxy)-propan-2-ol (Compound Ia) A suspension of 20 g of 2-(2,3-epoxypropoxy)-1-methoxybenzene, 70 g of biphenylylacetic acid, 100 cc of 1N sodium hydroxide, is kept under reflux for one hour. After cooling to room temperature, the suspension is extracted three times with 75 cc each of ether. The combined ether extracts are then washed with 8% sodium carbonate and then water up to neutrality. After drying and evaporation of the solvent under vacuum, a dense oil is obtained which solidifies after stirring a few hours with diisopropyl ether. The product is recrystallized from diethyl ether/diisopropyl ether in a ratio of 1:1. Yield: 37 g (85%); m.p.: 70 C.; Empirical formula: C24 H24 O5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Use of Iron Oxide-Pd Complexes in Solid Phase Suzuki Cross-Coupling ReactionsThe reaction scheme is presented in FIG. 4. A typical solid-phase Suzuki cross-coupling reaction was as follows. First, a solid phase polystyrene resin (1% divinylbenzene crosslinked, 200-400 mesh) was loaded with aryl halogens (J. Org. Chem. 2006, 71, 537). Then, the aforementioned resin (1.22 g) loaded with an aryl halogen (1 mmol) was added to a mixed suspension of the arylboronic acid (2 mmol) and K2CO3 (2 mmol) in 20 mL of DMF containing Iron Oxide-Pd (4 nm) (30 mg, 0.87 mol %). The mixture was heated to 80 C. and was maintained at this temperature for 6 days. Iron Oxide-Pd was magnetically concentrated using an external permanent magnet. To this end, the mixture was vigorously shaken. A permanent magnet was then applied externally. Magnetic nanoparticles were concentrated on the sidewalls of the tube (horizontal direction) while some resins were suspended in solution or precipitate at the bottom of the tube (vertical). The suspended and precipitated resins, as well as the solution, were transferred out of the tube using a pipette. This process usually needed to be repeated more than eight times to ensure that most of nanoparticles were removed from resins. Iron Oxide-Pd was then washed with methanol (10×200 mL). Afterwards, magnetic nanoparticles were further washed with water (5×100 mL) and methanol (5×100 mL). The nanoparticles were then air-dried and used directly for a new round of Suzuki reaction.The resins and excessive arylborate were separated via filtration. The beads were recovered as the filter and subsequently washed with methanol (5×100 mL) and water (5×100 mL). The cleavage of the Suzuki product out of the resins was achieved by adding the solid-phase beads (1.18 g) and NaOH (2 mmol) to a mixture of ethanol (15 mL) and water (15 mL). The mixture was heated to reflux and stirred at this temperature for 2 days. After cooling down to ambient temperature, resins were filtered off and the filtrate was neutralized with 1 M HCl to pH 7. Solvents were removed in vacuo and the residues were extracted with ethyl acetate (10×50 mL). The combined organic solutions were dried over anhydrous Na2SO4 and subjected to HPLC and NMR analyses. A simple recrystallization step was also employed using EtOH/H2O to improve the purity of the Suzuki product. The structures of isolated Suzuki products were determined by 1H NMR, IR and high-resolution MS. HPLC analyses of isolated products after recrystallization showed that high purity (>99%) was obtained. A UV detector with a fixed wavelength of 254 nm was employed for signal detection. A typical HPLC analysis program used a solvent gradient starting from 40% H2O in CH3CN to 10% H2O in CH3CN in 6 min followed by 10% H2O in CH3CN for additional 9 min with a flow rate of 0.5 mL/min.The yields of the solid-phase cross-coupling products were summarized in Table 3. The Iron Oxide-Pd nanocomplex effectively catalyzed these reactions. TABLE 3 Suzuki Cross-Coupling of Aryl Halogens (on Resins) and Arylboronic Acids (in Solution) under Iron Oxide-Pd (4 nm). Suzuki productb entryYa borateyield (%)c purity (%)d 1 o-I 78 >99 2 o-I 63 >99 3 o-I 71 >99 4 o-I 77 >99 5 o-Br 62 >99 aSee FIG. 4, Y = substitution on phenyl ring.bSuzuki products were cleaved from resins and purified via recrystallization steps.cAverage of at least two runs.dPurity was determined by HPLC analyses and the structures of Suzuki products were confirmed by 1H NMR and MS. |
Tags: 14676-52-9 synthesis path| 14676-52-9 SDS| 14676-52-9 COA| 14676-52-9 purity| 14676-52-9 application| 14676-52-9 NMR| 14676-52-9 COA| 14676-52-9 structure
A207319 [7500-53-0]
2,2'-(1,2-Phenylene)diacetic acid
Similarity: 0.97
A273748 [30981-98-7]
2,3-Dimethylbenzeneacetic acid
Similarity: 0.97
A325355 [13612-34-5]
2-(2,5-Dimethylphenyl)acetic acid
Similarity: 0.97
A207319 [7500-53-0]
2,2'-(1,2-Phenylene)diacetic acid
Similarity: 0.97
A273748 [30981-98-7]
2,3-Dimethylbenzeneacetic acid
Similarity: 0.97
A325355 [13612-34-5]
2-(2,5-Dimethylphenyl)acetic acid
Similarity: 0.97
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