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CAS No. : | 28752-82-1 | MDL No. : | MFCD00014130 |
Formula : | C10H10O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BXCJDECTRRMSCV-UHFFFAOYSA-N |
M.W : | 162.19 | Pubchem ID : | 101335 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 47.46 |
TPSA : | 26.3 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) : | -5.61 cm/s |
Log Po/w (iLOGP) : | 2.13 |
Log Po/w (XLOGP3) : | 2.36 |
Log Po/w (WLOGP) : | 2.06 |
Log Po/w (MLOGP) : | 1.66 |
Log Po/w (SILICOS-IT) : | 2.66 |
Consensus Log Po/w : | 2.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.44 |
Solubility : | 0.591 mg/ml ; 0.00364 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.55 |
Solubility : | 0.455 mg/ml ; 0.0028 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.93 |
Solubility : | 0.192 mg/ml ; 0.00118 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.48 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P362-P321-P332+P313-P337+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
99% | With potassium carbonate In acetonitrile for 12 h; Reflux | 2-hydroxybenzaldehyde 9 (0.5 ml, 4.69 mmol, Sigma-Aldrich catalogue id: S356) was dissolved in CH3CN (10 ml) and K2CO3 (0.97 ml, 7.03 mmol) and 3-bromoprop- 1 -ene (0.45 ml, 5.16 mmol, Sigma-Aldrich catalogue id: 337528) were added. Mixture was stirred at reflux for 12 hours. Solvent was then evaporated in vacuum and the residue dissolved in EtOAc (5 ml_). Water (10 ml) was added and the mixture stirred for 10 min at room temperature. Organic phase was then separated and the aqueous layer was extracted with EtOAc (2x10 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure to give title compound 10. Yield 99percent. 1H NMR (400 MHz, CDCI3) δ = 10.25 (1 H, s), 7.54-7.52 (1 H, m), 7.23- 7.19 (1 H, m), 6.72-6.66 (2H, m), 5.82-5.75 (1 H, m), 5.20-5.15 (1 H, d, J=17.6 Hz), 5.05-5.03(1 H, d, J=10.8 Hz), 4.33-4.31 (2H, m) ppm. 13C NMR (CDCI3) δ 188.9, 160.6, 135.6, 132.2, 127.8, 124.7, 120.5, 1 17.5, 1 12.7, 68.7 ppm, Liquid chromatography Mass Spectroscopy (LCMS) m/z (ES+) m/z: 347.0 [2M + Na]+, 185.0 [M + Na]+, 163.0 [M + H]+. Elemental analysis for Ci0H10O2: Calcd. C 74.06, H 6.21 ; Found C 74.36, H 6.52. |
96% | With potassium carbonate In acetonitrile for 2 h; Reflux | To a solution of 2-hydroxybenzaldehyde (15 g, 123 mmol, 1 equiv) and allylbromide (11.7 mL, 135 mmol, 1.1 equiv) in MeCN (250 mL) was added K2C03 (23.8 g, 172 mmol, 1.4 equiv). The yellow slurry was then heated to reflux. After 2 h, TLC indicated complete conversion. The now pale cream colored mixture was removed from heat and filtered. The filtrate was concentrated invacuo to provide 2-(allyloxy)benzaldehyde (19.15 g, 96percent) as a yellow oil. 1H NMR (400 MHz, CDCl3) 8 10.64- 10.49 (m, 1H), 7.86 (dd, J = 7.7, 1.9 Hz, 1H), 7.61 -7.49(m, 1H), 7.11-6.90(m,2H),6.10(ddt,J= 17.3, 10.5,5.2Hz, 1H),5.47(dq,J=17.3, 1.5 Hz, 1H), 5.36 (dq, J = 10.5, 1.4 Hz, 1H), 4.68 (dt, J = 5.1, 1.6 Hz, 2H). |
87% | Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25 h; Stage #2: at 60℃; for 12 h; |
General procedure: To the stirred solution of salicylic aldehyde (0.1 mol) (or 2-hydroxy-3-methoxybenzaldehyde (o-vanilin)) in DMF (40 mL), dry K2CO3 (0.12 mol) was added and the mixture was stirred for 15 min at 20 °C. Then corresponding alkyl halide (0.1 mol) was added, and the reaction mixture was stirred for 12 h at 60 °C. The cooled reaction mixture was poured into water (250 mL) and extracted by CH2Cl2 (40 mL). An organic layer was separated, washed with NH4OH 5percent (5×25 mL) and water (50 mL), and dried over Na2SO4. A solvent was removed in vacuo and the residue was crystallized by adding of cyclohexane (in case of the solid compounds, see p.p. 4.2.1–4.2.4), or distilled in vacuo 1 mm. Hg (in case of liquids, see p.p. 4.2.5–4.2.7). |
85% | With potassium carbonate In acetone for 6 h; Reflux | K2CO3 (2.25g, 0.016 moles) was added to the stirred solution of 2-hydroxybenzaldehyde (1g, 0.008 moles) in acetone (8 ml) and followed by allyl bromide (0.99 g, 0.008moles). These contents were stirred under reflux conditions for 6 h. After completion of the reaction (TLC), the reaction mixture was filtered, the solvent was removed under reduced pressure, the crude reaction mixture was quenched with water and extracted with diethyl ether (3 x 20 ml), the layers were separated and the organic layer was dried over Na2SO4. Solvent was removed under reduced pressure; the crude product was purified by column chromatography (hexane) to afford the desired product 1aa as colourless solid in 85percent yield. The compound was well characterised by spectral data. |
84% | With 18-crown-6 ether; potassium carbonate; potassium iodide In acetonitrile at 75℃; for 18 h; Inert atmosphere | To a stirred solution of salicylaldehyde (20.0 g, 164 mmol) in acetonitrile (200 mL) was added allylbromide (27) (29.0 mL, 333 mmol), KI (544 mg, 3.28mmol), 18-crown-6 (432 mg, 1.64 mmol) and K2CO3 (66.0 g, 478 mmol) at rt after which the solution was refluxed at 75 °C for 18 h. The K2CO3 was filtered off and the solvent removed under reduced pressure. H2O (100 mL) was added and the aqueous layer extracted with EtOAc (2×100 mL). The organic layers were combined, washed with brine (50 mL), dried (Na2SO4) and the solvent removed under reduced pressure to yield the title compound as an orange oil (24.2 g, 84percent). TLC Rf=0.28 (Hexane/EtOAc 19:1). IR νmax (neat)/cm−1: 2861 w (C–H str), 1681 s (C=O str), 1598 s (C=C str), 1483 m (C=C str), 1457 m (C=C str). 1H NMR (400 MHz, CDCl3): δ 10.51 (1H, s, –CHO), 7.80 (2H, dd, J 7.5, 1.7 Hz, ArH), 7.50 (1H, ddd, J 8.5, 7.5, 2.0 Hz, ArH), 6.99 (1H, t, J 7.5 Hz, ArH), 6.95 (1H, d, J 8.5 Hz, ArH), 6.10–6.00 (1H, m, –CHCH2), 5.43 (1H, dq, J 17.4, 1.7 Hz, –CH2), 5.31 (1H, dq, J 10.6, 1.4 Hz, –CH2), 4.63 (1H, dt, J=5.1, 1.4 Hz, –CH2–). 13C NMR (125 MHz, CDCl3): δ 189.7, 160.9, 135.9, 132.4, 128.4, 125.1, 120.9, 118.1, 112.9, 69.2. HRMS (ESI+) m/z=163.0751 [M+H]+ found, C10H11O2+ required 163.0754. |
82.3% | With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 15 h; | The o-hydroxybenzaldehyde is first reacted with 3-bromopropene,To give intermediate O-A,And then under high temperature conditions for rearrangement reaction,To give 2-hydroxy-3-allylbenzaldehyde,As shown in Scheme 6,The specific preparation method is as follows: O-hydroxybenzaldehyde (290 g, 2.38 mol) was dissolved in 500 ml of DMF,K2CO3 (493 g, 3.57 mol) was added,Followed by the dropwise addition of 3-bromopropene (346 g, 2.86 mol)60 reaction 15h,Filter,The filtrate was poured into 500 mL of CH2Cl2,The organic phase was washed successively with 5percent aqueous NaOH,Saturated salt water and washed,Anhydrous Na2SO4 dried,Concentrated under reduced pressure,To give 317 g of a yellow oil,Yield 82.3percent.317 g (1.96 mol) of 2-allyloxybenzaldehyde was reacted at 200 ° C for 4 h,And distilled under reduced pressure to give 200 g of 3-allyl-2-hydroxybenzaldehyde as a yellow oil,Yield 63percent |
80% | With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 4 h; | It was prepared from2-allyloxybenzaldehyde, by addition of chloroform followed by reaction withethyl chloroformate.(a) 2-Allyloxybenzaldehyde: Itwas prepared by the allylation of salicylaldehyde with allyl bromide accordingto the method reported in literature3 with some modifications. A solution of allylbromide (3.6 g, 0.03 mol) in 5 mL dry THF was added dropwise to astirred mixture of salisylaldehyde (2.44 g, 0.02 mol) and sodium hydride [1.0 g(60 percent in oil), 0.04 mol] in 40 mL dry THF and 5 mL DMF at room temperature 25C. After completion of reaction (4 h), the reaction mixture was filtered toremove the inorganic solid residue. The solid on the filter paper was washedwith more THF (3 × 10 mL). The combined organic filtrate was evaporared on arotavapor. The concentrated reaction product was diluted with 30 mL diethylether and washed successively with 5 percent aq NaOH solution (3 × 10 mL) followed bywater (3 × 10 mL). The organic layer was dried over anhydrous sodium sulphatefor 4-5 h and filtered. Evaporation of the filtrate under reduced pressure on arotavapor afforded 2-allyloxybenzaldehyde (2.58 g, 80 percent) as a light yellow liquid. |
78.9% | With potassium carbonate; potassium iodide In acetonitrileReflux | In a 50 ml round-bottom flask by adding salicyldehyde (0.61g, 5 . 0mmoL), 35.0 ml acetonitrile, 3-bromopropylene (0.72g, 6 . 0mmol), potassium carbonate (2.07g, 15 . 0mol), a catalytic amount of potassium iodide, reflux reaction. After the end of the detection reaction TLC, solvent evaporation to dryness, separating by silica gel column, to obtain 0.64g oily, yield 78.9percent. 1 HNMR (300MHz, CDCl 3): δ 10.54 (s, 1H), 6.98-7.84 (m, 4H), 6.07 (m, 1H), 5.46 (dd, 1H, J = 16.8,1 . 5Hz,), 5.34 (d, 1H, J = 10.8,1 . 5Hz), 4.66 (d, 2H, J = 5.2Hz). |
70% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12 h; | General procedure: The bromoalkene (11.0 mmol) was added to a suspension of K2CO3 (14.4 mmol) and 3,5-di-tert-butyl-2-hydroxybenzaldehyde (11.0 mmol) in DMF (50 mL) and stirred at room temperature for 12 h. The mixture was diluted with CH2Cl2 (25 mL) and washed twice with water, dried using Na2SO4 (anhydrous) and concentrated under reduced pressure. The crude product was purified by flash chromatography (SiO2: hexane/EtOAc, 15:1 unless indicated otherwise). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | at 200℃; for 4 h; | The o-hydroxybenzaldehyde is first reacted with 3-bromopropene,To give intermediate O-A,And then under high temperature conditions for rearrangement reaction,To give 2-hydroxy-3-allylbenzaldehyde,As shown in Scheme 6,The specific preparation method is as follows: O-hydroxybenzaldehyde (290 g, 2.38 mol) was dissolved in 500 ml of DMF,K2CO3 (493 g, 3.57 mol) was added,Followed by the dropwise addition of 3-bromopropene (346 g, 2.86 mol)60 reaction 15h,Filter,The filtrate was poured into 500 mL of CH2Cl2,The organic phase was washed successively with 5percent aqueous NaOH,Saturated salt water and washed,Anhydrous Na2SO4 dried,Concentrated under reduced pressure,To give 317 g of a yellow oil,Yield 82.3percent.317 g (1.96 mol) of 2-allyloxybenzaldehyde was reacted at 200 ° C for 4 h,And distilled under reduced pressure to give 200 g of 3-allyl-2-hydroxybenzaldehyde as a yellow oil,Yield 63percent |
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