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CAS No. : | 61266-36-2 | MDL No. : | MFCD00168848 |
Formula : | C11H10O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QFLBWNWKBXCHKS-UHFFFAOYSA-N |
M.W : | 190.20 | Pubchem ID : | 4448596 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.18 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 51.63 |
TPSA : | 46.53 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.15 cm/s |
Log Po/w (iLOGP) : | 2.36 |
Log Po/w (XLOGP3) : | 1.84 |
Log Po/w (WLOGP) : | 0.9 |
Log Po/w (MLOGP) : | 1.88 |
Log Po/w (SILICOS-IT) : | 1.95 |
Consensus Log Po/w : | 1.78 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.36 |
Solubility : | 0.823 mg/ml ; 0.00433 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.44 |
Solubility : | 0.694 mg/ml ; 0.00365 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.39 |
Solubility : | 0.777 mg/ml ; 0.00408 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.25 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
16.7 g (95%) | With hydrogen;palladium-carbon; In methanol; | B. Preparation of methyl 4-(3-hydroxypropyl)benzoate STR17 To a 2-L stainless steel Parr bottle was charged 17.1 g (89.9 mmol) of <strong>[61266-36-2]methyl 4-(3-hydroxypropynyl)benzoate</strong> dissolved in 1 L MeOH, followed by the addition of 2.6 g of 5% Pd/C catalyst. This mixture was then hydrogenated at ambient temperature for 18 hours on a Parr shaker at 15 psi of hydrogen gas. The catalyst was filtered away, and washed with fresh MeOH. The filtrate was removed in vacuo, and the crude residue was flash chromatographed on silica gel eluding with 25% EtOAc/MeCl2. The correct fractions were combined and the solvents were removed in vacuo to give 16.7 g (95%) of methyl 4-(3-hydroxypropyl)benzoate as a colorless oil. Rf =0.36 (25% EtOAc/MeCl2) Mass (FD) M+=194 IR (KBr, cm-1)=1020, 1046, 1114, 1181, 1194, 1247, 1312, 1416, 1437, 1611, 1718, 2953, 3011, 3026, 3626 UV (EtOH) lambdamax =265, 203 (epsilon=25179, 16144) Anal. Calcd. for C11 H14 O3: C, 68.02; H, 7.27. Found: C, 67.95;H, 6.97. 1 H NMR (300 MHz, CDCl3) delta1.32 (t, J=5.5 Hz, 1H), 1.88-197 (m, 2H), 2.79 (t, J=7.7 Hz, 2H), 3.70 (q, J=6.1 Hz, 2H), 3.92 (s, 3H), 7.29 (d, J=8.0 Hz, 2H), 7.98 (d, J=8.2 Hz, 2H) |
With palladium on activated charcoal; hydrogen; | Compound 9 was prepared according to Scheme 7. [ Reaction of methyl 4-bromobenzoate (9. 1) with propargyl alcohol (9. 2) under Sonogashira conditions afforded compound 9. 3. Hydrogenation 9. 3 Obtaining compound 9. 4. Obtaining the acid after hydrolysis of the ester and subsequent treatment with acrylic acid under Dean and Stark conditions. The acid was reacted with intermediate 2 (3.6) to obtain diester 9. 7 and further reacted with diiodobenzene under Sonogashira conditions to obtain the target compound 9. 8 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; | Compound 9 was prepared according to Scheme 7. [ Reaction of methyl 4-bromobenzoate (9. 1) with propargyl alcohol (9. 2) under Sonogashira conditions afforded compound 9. 3. Hydrogenation 9. 3 Obtaining compound 9. 4. Obtaining the acid after hydrolysis of the ester and subsequent treatment with acrylic acid under Dean and Stark conditions. The acid was reacted with intermediate 2 (3.6) to obtain diester 9. 7 and further reacted with diiodobenzene under Sonogashira conditions to obtain the target compound 9. 8 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With copper(l) iodide; C36H28Cl4N8O2Pd2; triethylamine; triphenylphosphine; In 2-methyltetrahydrofuran; at 20℃; for 0.25h;Schlenk technique; Green chemistry;Catalytic behavior; | A 20mL Schlenk tube with a magnetic stir bar was charged with 3-bromobenzoic acid 21 (0.5mmol), 4-methoxyphenylboronic acid 22 (0.6mmol), K2CO3 (1.25mmol), 5mL of solvent [H2O, H2O-MeOH (1:1)] and 50muL of solution (110-2-110-5M) of palladium complexes LPdCl2 in DMF under air atmosphere. The reaction mixture was placed in a preheated oil bath: at 100C for MeOH-H2O and at 35C or 100C for H2O; and stirred for the appropriate time and under conditions required (Table4). After this time, the mixture was cooled, diluted with 5mL of H2O, 5mL of Et2O and acidified by 1M HCl. The organic phase was separated, and the aqueous layer was extracted with Et2O (2×5mL). The combined organic layers were washed with brine (5mL), dried over Na2SO4, concentrated in vacuo and the yield was determined by 1H NMR analysis with 1,1,2,2-tetrachloroethane (0.5mmol) as internal standard (Table4). The pure product was obtained by a simple filtration of ether solution through silica gel pad and evaporation of solvent. |
With triethylamine;dichlorobis(triphenylphosphine)palladium[II]; In water; ethyl acetate; acetonitrile; | Step A: 4-(3-Hydroxy-prop-1-ynyl)-benzoic acid methyl ester. To a solution of methyl 4-iodobenzoate (20 g, 76 mmol), propargyl alcohol (5.55 g, 99.0 mmol) and triethylamine (20 mL) in acetonitrile (200 mL) was added dichlorobis(triphenylphosphine)palladium(II) (1.55 g, 2.21 mmol), followed by Cul (454 mg, 2.38 mmol). The reaction mixture was stirred at room temperature for 24 h. Water was added and the aqueous solution was washed with EtOAc (3*). The organic solutions were combined, dried (MgSO4), filtered and concentrated. Purification by medium pressure chromatography (9:1 hexanes:EtOAc to 4:1 hexanes:EtOAc) provided 4-(3-hydroxy-prop-1-ynyl)-benzoic acid methyl ester (12.65 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | (a) 1-(4-Methoxycarbonylphenyl)-1-propyn-3-ol; m.p. 81-83 C. (yield 92% of theory), with use of 4-bromobenzoic acid methyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18.0 g (95%) | With triphenylphosphine;palladium(II) chloride; In ethyl acetate; diethylamine; | A. Preparation of methyl 4-(3-hydroxypropynyl)benzoate STR16 In a 1-L round bottom flask under a nitrogen atmosphere were charged 26.2 g (0.1 mol) of methyl p-iodobenzoate, 6.1 mL (0.105 mol) of 2-propyn-1-ol, 0.085 g (0.50 mmol) of palladium chloride, 0.26 g (1.0 mmol) of triphenylphosphine, and 0.19 g (1.0 mmol) of copper (I) iodide dissolved in 250 mL of diethylamine. The reaction mixture was stirred at ambient temperature for 20 hours. The volatiles were removed in vacuo, and the crude residue was thoroughly triturated in 700 mL of ether. The inorganic salt was filtered away, and the filtrate was concentrated in vacuo. The crude solid was then flash chromatographed on silica gel eluding with a gradient of 100% MeCl2 to 25:75 EtOAc/MeCl2. The correct fractions were combined and this dark solution was decolorized with animal charcoal powder. The charcoal was then filtered away, and the filtrate was removed in vacuo to give 18.0 g (95%) of methyl 4-(3-hydroxypropynyl)benzoate as a pale yellow solid. Rf =0.46 (1:1 Hexane/EtOAc) m.p.=88-90 C. Mass (FD) M+=190 IR (KBr, cm)=694, 771, 862, 996, 1015, 1028, 1118, 1172, 1191, 1277, 1309, 1406, 1430, 1449, 1606, 1724, 3379 UV (EtOH) lambdamax =265, 203 (epsilon=25179, 16144) Anal. Calcd. for C11 H10 O3: C, 69.46; H, 5.30. Found: C, 69.73; H, 5.39. 1 H NMR (300 MHz, CDCl3) delta 1.76 (t, J=6.2 Hz, 1H), 3.94 (s, 3H), 4.54 (d, J=6.2 Hz, 2H), 7.51 (d, J=8.2 Hz, 2H), 8.00 (d, J=8.3 Hz, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With copper(I) iodide; In water; diethylamine; | b. Methyl 4-(3-hydroxypropynyl)benzoate Methyl 4-iodobenzoate (9.0 g, 34.4 mmol) was dissolved in 90 ml of diethylamine. The solution was stirred vigorously and, sequentially, 121 milligrams of bis(triphenylphosphine) palladium chloride and 65 milligrams of cuprous iodide were added, each in a single portion, followed by 1.93 grams of propargyl alcohol. The resultant mixture was stirred for about 20 hours at room temperature in an argon atmosphere. At the end of this period, diethylamine was removed by concentration in vacuo. The residue was diluted with 200 ml of water and extracted three times with 100 ml of benzene and 75 ml of ethyl acetate. The organic extracts were combined, dried over Na2 SO4, and concentrated in vacuo, yielding a brown solid. This crude residue was purified by flash chromatography. Elution with a 2 to 1 (V:V) mixture of hexane and ethyl acetate yielded 5.44 grams (83% yield) of a pale yellow solid melting at 81 to 82 C. The following analyses were obtained for this material, indicating that it was methyl 4-(3-hydroxy propynyl) benzoate: NMR (CDCl3) delta=7.98 (2H, d, J=8.3 Hz), 7.49 (2H, d, J=8.3 Hz), 4.52 (2H, s), 3.92 (3H,s) Anal. (C11 H10 O3) C,H |
83% | With copper(I) iodide; In water; diethylamine; | b. Methyl 4-(3-hydroxypropynyl)benzoate Methyl 4-iodobenzoate (9.0 g, 34.4 mmol) was dissolved in 90 ml of diethylamine. The solution was stirred vigorously and, sequentially, 121 milligrams of bis(triphenylphosphine) palladium chloride and 65 milligrams of cuprous iodide were added, each in a single portion, followed by 1.93 grams of propargyl alcohol. The resultant mixture was stirred for about 20 hours at room temperature in an argon atmosphere. At the end of this period, diethylamine was removed by concentration in vacuo. The residue was diluted with 200 ml of water and extracted three times with 100 ml of benzene and 75 ml of ethyl acetate. The organic extracts were combined, dried over Na2 SO4, and concentrated in vacuo, yielding a brown solid. This crude residue was purified by flash chromatography. Elution with a 2 to 1 (V:V) mixture of hexane and ethyl acetate yielded 5.44 grams (83% yield) of a pale yellow solid melting at 81 to 82 C. The following analyses were obtained for this material, indicating that it was methyl 4-(3-hydroxy propynyl) benzoate: NMR (CDCl3) delta=7.98 (2H, d, J=8.3 Hz), 7.49 (2H, d, J=8.3 Hz), 4.52 (2H, s), 3.92 (3H,s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere; | General procedure: To the solution of 3-phenyl-2-propyn-1-ol (1.32 g, 10.0 mmol),NEt3 (7.0 mL, 50.0 mmol) and 4-(dimethylamino)pyridine (DMAP) (127.5 mg, 1.05 mmol) in methylene chloride(CH2Cl2) (50 mL) at 0C was added pivaloyl chloride (1.35 mL,11.0 mmol) slowly under Ar and the mixure was warmed toroom temperature. After stirring for 2 h, the mixture wasquenched with water and extracted with chloroform (CHCl3).The combined extracts were washed with 1.0 M aqueoussolution of HCl and 3.0 M aqueous solution of NaOH, driedover Na2SO4 and concentrated under reduced pressure. Theobtained residue was purified by silica gel column chromatography(hexane/CH2Cl2=75/25) to give 11a (1.89 g, 88%) asa colorless oil. |
Tags: 61266-36-2 synthesis path| 61266-36-2 SDS| 61266-36-2 COA| 61266-36-2 purity| 61266-36-2 application| 61266-36-2 NMR| 61266-36-2 COA| 61266-36-2 structure
[ 16819-43-5 ]
4,4'-(1,2-Ethynediyl)dibenzoic Acid
Similarity: 0.88
[ 16819-43-5 ]
4,4'-(1,2-Ethynediyl)dibenzoic Acid
Similarity: 0.88
[ 393522-78-6 ]
Methyl 4'-(hydroxymethyl)-[1,1'-biphenyl]-4-carboxylate
Similarity: 0.73
[ 143726-85-6 ]
tert-Butyl 4-(hydroxymethyl)benzoate
Similarity: 0.70
[ 84851-56-9 ]
Methyl 4-(1-hydroxyethyl)benzoate
Similarity: 0.70
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