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CAS No. : | 56578-35-9 | MDL No. : | MFCD08460295 |
Formula : | C10H10O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DKOUYOVAEBQFHU-NSCUHMNNSA-N |
M.W : | 146.19 | Pubchem ID : | 5371802 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 46.51 |
TPSA : | 17.07 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) : | -5.59 cm/s |
Log Po/w (iLOGP) : | 1.9 |
Log Po/w (XLOGP3) : | 2.26 |
Log Po/w (WLOGP) : | 2.1 |
Log Po/w (MLOGP) : | 2.31 |
Log Po/w (SILICOS-IT) : | 2.95 |
Consensus Log Po/w : | 2.31 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.44 |
Solubility : | 0.529 mg/ml ; 0.00362 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.25 |
Solubility : | 0.813 mg/ml ; 0.00556 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.8 |
Solubility : | 0.231 mg/ml ; 0.00158 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.81 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H317-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 |
---|---|---|
94% | With catalyst: (S)-2-(C6H5)2((CH3)3SiO)C-pyrrolidine; NaBH4; lithium benzoate In methanol; dichloromethane 4-methylcinnamaldehyde, catalyst and Li salt added to Ni-complex in CH2Cl2/MeOH (1/5), mixt. stirred at room temp. for 24 h, MeOH and NaBH4 added, mixt. stirred at room temp. for 2.5 h; evapn. under vac., column chromy. (silica gel); dr = 5.7:1; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | Stage #1: 4-methyl-cinnamaldehyde With titanium(IV)isopropoxide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: maleic anhydride In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; | General procedure for preparation of compounds 2a-r General procedure: A mixture of corresponding aldehyde (6.0 mmol) and Ti(OiPr)4 (0.6 mmol) in dry THF (3 ml) was strirred at RT under Ar atmosphere for 30 min. Then cyklopent-4-ene-1,3-dione (0.192 g, 2.0 mmol) was added and the resultant solution was stirred at RT for 12 hrs. The reaction mixture was diluted with EtOAc (20 mL), washed with 5 % aqueous K2CO3 solution (3x20 mL), the organic layer was dried (Na2SO4) and solvents were removed under reduced pressure. The crude product was purified by column chromatography (hexane - hexane:ethyl acetate 93:7) and recrystallized from the mixture of hexane/ethyl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Stage #1: p-Tolylaceton With pyrrolidine; acetic acid In diethyl ether at 0℃; for 0.666667h; Inert atmosphere; Stage #2: 4-methyl-cinnamaldehyde In diethyl ether at 0℃; Inert atmosphere; | 1.2 General procedure methods General procedure: All reactions were set up under nitrogen atmosphere, unless otherwise noted. To a solution of pyrrolidine (81.8µl, 1 mmol) and acetic acid (57.2µl, 1 mmol) in ether (15 ml) prepared at 0°C was added dropwise a solution of benzylacetone (1 mmol) in ether (5 ml) over 10 min at the same temperature. After additional stirring for 30 min, a solution of cinnamaldehydes (2 mmol) in ether (5 ml) was added dropwise over 15 min and stirred at 0°C. The reaction progress was monitored by thin layer chromatography. After completion of the reaction dilute HCl was added to the reaction mixture. The organic phase was extracted with ether (2×30 ml), then washed with water (2×20 ml) and dried (Na2SO4). Then the solvent was removed and the product was purified by flash column using petroleum ether-ethyl acetate mixture as eluent to afford corresponded products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 1.2: 1 h / 0 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 3.1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / 0.17 h / 20 °C / Inert atmosphere 3.2: 4.17 h / 20 °C / Inert atmosphere 4.1: platinum(II) chloride; carbon monoxide; water / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: diethyl p-nitrobenzylphosphonate With sodium hydride In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: 4-methyl-cinnamaldehyde In tetrahydrofuran at 0℃; for 0.5h; | 2.1 Synthesis General procedure: Diphenylbutadiene derivatives utilized in this investigation were prepared by using Horner-Wadsworth-Emmons reaction [23] (Scheme 1a) in about 35-60% yields. In a typical procedure, triethyl phosphite (5.74 mmol) was added to the THF solution of benzyl bromide (2.3 mmol) and refluxed for 24 h under a N2 atmosphere. The reaction mixture was cooled to room temperature and further cooled to 0 °C using an ice bath. Sodium hydride (11.5mmol) was added to this mixture and stirred for 5 min. Aldehyde (2.3 mmol) was subsequently added drop wise to the pale/dark pink colored solution and stirring was continued for additional 30 min. In the case of methyl substituted aldehydes, corresponding (E) geometric isomer of α-methyl cinnamaldehyde (Aldrich) was used. Thin Layer Chromatography (TLC) was utilized to monitor the progress of the reaction and the reaction was quenched by adding water. The organic layer was extracted using dichloromethane and concentrated under reduced pressure. The crude reaction mixture so obtained was purified by column chromatography using silica gel, 5% ethyl acetate in petroleum ether. Starting materials, 4-methylcinnamaldehyde required for the synthesis of ( 2) and nitro cinnamaldehyde required for synthesis of (3) and (5), were obtained by DDQ oxidation of 4-allyl toluene [40] (Scheme 1b) and by simple nitration using a nitrating mixture generated by mixing KNO3 with H2SO4 of α-methyl-cinnamaldehyde (scheme 1c), respectively. Characterization data for all the synthesized dienes were given in the Supplementary information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (S)-2-(((tert-butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine; palladium diacetate; triethylamine In acetonitrile at 30℃; for 48h; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | Stage #1: (E)-tert-butyl 3-(2-ethoxy-2-oxoethylidene)-2-oxoindoline-1-carboxylate; 3-Methyl-2,4-pentanedione With 3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-(((1S)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione In tetrachloromethane at 0℃; for 24h; Stage #2: 4-methyl-cinnamaldehyde With morpholine In tetrachloromethane at 0℃; for 24h; | General Procedure for the Synthesis of Spirocyclohexane Oxindoles General procedure: A suspension of oxoindole derivative (2, 0.20 mmol) and cat. 6a (0.01 mmol, 5 mol %) in anhydrous CCl4 (0.2 mL, 1 M) was cooled to 0 oC before added with 1,3-dicarbonyl compound (1, 0.4 mmol). The reaction mixture was stirred vigurously for 24 hours at 0 oC, then α,β-unsaturated aldehyde (3, 0.6 mmol) and morpholine (cat. 7e, 50 mol %) were added successfully. After 24 hours, the reaction mixture was purified on silica gel to afford the desired product directly. The racemic samples were prepared by using the mixture of quinine and quinidine (1:1, 20 mol %), morpholine (50 mol %) as the catalyst combination. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: 7-methoxy-1H-indole; 4-methyl-cinnamaldehyde With trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In diethyl ether at -50℃; for 1h; Inert atmosphere; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at -50 - 25℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydride / mineral oil; tetrahydrofuran; dimethyl sulfoxide / 12.5 h / 0 - 20 °C / Inert atmosphere 2: triethylamine; toluene-4-sulfonic acid / 1,3,5-trimethyl-benzene / 1 h / 200 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With copper(I) bromide In ethanol at 60℃; for 8h; | 2-p-TolylH-imidazo[1,2-a]pyridine-3-carbaldehyde (5) To the mixture of 2-amino pyridine (3) (13 g, 0.138 mmol)and (E)-3-p-tolylacrylaldehyde (4) (24. 2 g, 0.166 mmol) taken in ethanol, 10 mol% CuBr (1.98 g, 0.0138 mmol) was added and the reaction mixture was stirred at 60 °C for 8 h. After completion of the reaction (monitored by TLC), the reaction mixture was filtered using the Whatman paper. The filtrate was dried on rotavapor and was then extracted with water and ethyl acetate. Ethyl acetate layer was dried over anhydrous sodium sulfate and evaporated on vacuum rotavapor to give crude product. The crude product was purified by column chromatography using n-hexane and ethyl acetate to provide pure colorless product 5 as yellow color solid, in 23.8 g with 61% yield. mp: 168-169 °C; 1H NMR(300 MHz, CDCl3): δ 2.47 (s, 3H), 7.08 (d, 2H, J = 8.1 Hz),7.13 (t, 1H), 7.56 (t, 1H), 7.81 (d, 2H, J = 8.1 Hz), 7.85 (d,1H, J = 8.0 Hz), 9.68 (d, 1H, J = 8.0 Hz), 10.12 (s, 1H); 13CNMR (75 MHz, CDCl3): δ 21.7, 115.3, 117.8, 120.3, 128.8,129.5, 130.1, 130.8, 141.0, 147.9, 158.9, 179.6; MS (ESI):m/z 237 [M + H]+; Anal. Calcd for C15H12N2O: C, 76.25;H, 5.12; N, 11.86. Found: C, 76.03; H, 4.99; N, 11.71. |
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