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CAS No. : | 101-86-0 | MDL No. : | MFCD00006989 |
Formula : | C15H20O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GUUHFMWKWLOQMM-NTCAYCPXSA-N |
M.W : | 216.32 | Pubchem ID : | 1550884 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 70.38 |
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) : | -4.23 cm/s |
Log Po/w (iLOGP) : | 2.95 |
Log Po/w (XLOGP3) : | 4.78 |
Log Po/w (WLOGP) : | 4.13 |
Log Po/w (MLOGP) : | 3.68 |
Log Po/w (SILICOS-IT) : | 4.57 |
Consensus Log Po/w : | 4.02 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.01 |
Solubility : | 0.0212 mg/ml ; 0.0000982 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.87 |
Solubility : | 0.00292 mg/ml ; 0.0000135 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.85 |
Solubility : | 0.00303 mg/ml ; 0.000014 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.53 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P501-P261-P272-P264-P280-P302+P352-P312-P337+P313-P305+P351+P338-P362+P364-P333+P313 | UN#: | N/A |
Hazard Statements: | H303-H315-H319-H317 | 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 |
---|---|---|
With sodium hydrogencarbonate; magnesium; In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water; | EXAMPLE 6 In a 2-liter three-necked flask equipped with a stirring device, a thermometer and a nitrogen substituting device, 13.2 g of magnesium and 300 milliliters of tetrahydrofuran were introduced and stirred violently. Then, a solution of 83.2 g of benzene bromide in 100 milliliters of tetrahydrofuran was added dropwise for 40 minutes. At that time, cooling was carried out with an ice bath if required. After the dropwise addition was ended, stirring was carried out at room temperature for 1 hour, and thereafter 108.2 g of alpha-n-hexyl cinnamaldehyde was added dropwise. After stirring for one day and one night, the solution was poured in ice water containing dilute hydrochloric acid, and extracted with 1 liter of ethyl acetate. After the solution was washed with an aqueous solution of sodium hydrogencarbonate and water, it was dried with anhydrous magnesium sulfate. After removing the solvent off by a rotary evaporator, 169.6 g of 1,3-diphenyl-2-n-hexyl-2-propen-1-ol was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With benzoic acid; L-proline; In neat (no solvent); at 125℃; for 1h;Inert atmosphere; | The aldol condensation was carried out by taking freshly distilled benzaldehyde (15.8 mmol) along with 40 mol% of the amino acid as a catalyst, 40 mol% of benzoic acid as co-catalyst and n-decane as an internal standard in a three-necked round bottom flask. The reaction was carried out under inert atmosphere at a desired temperature to minimize the oxidation of aldehydes used in the reaction. In order to improve the selectivity for the cross-aldol product and maximize atom efficiency of the reaction, 1-alkanaldehydes (7.9 mmol) were added to the reaction mixture under a controlled condition (1130 mul/h) using a syringe pump. The reaction mixture was colled down to room temperature after completion of the reaction (checked by GC). All the reactions were done in triplicate to ensure the reproducibility of the reaction. |
93.8% | With nitrogen; potassium hydroxide; In methanol; water; at 30℃; for 6h; | Methanol (128.2 g, 4.0 mol, 400 mol% / vs octanal, containing 0.04% of water, contained 0.05 g of water),andPotassium hydroxide in a mixture of water (2.6 g)(85% purity, 6.6 g, 0.10 mol, 10 mol% / vs octanal, containing 15% water, containing 0.99 g water) isA potassium hydroxide-methanol solution (137.1 g) was prepared.A reactor in which a thermometer, a mechanical stirrer, a condenser, and a nitrogen line were attached to a 500 mL four-neck separable flask was assembled.In the reactor, the potassium hydroxide-methanol solution (137.1 g) and benzaldehyde (formula (II-1), 180.4 g, 1.70 mol, 170 mol% / per octanal, containing 0.05% of water, contained water) Amount (0.09 g) was added.A 200 mL flask containing octanal (Formula (I-1)) was connected to the reactor with a dropping pump. Nitrogen substitution in the reactor was performed, the reactor was placed in a 30 C. water bath, and agitation (500 rpm) in the reactor was started.After 5 minutes, dropping of octanal into the reactor was started. The above octanal at 25.6 g / hour for 3 hours,Thereafter, it was dropped to the reactor at 17.1 g / hour for 3 hours, and the octanal (128.2 g, 1.0 mol, water content 0 g) was dropped to the reactor over a total of 6 hours. The total amount of water contained in the raw materials used for the reaction was 3.73 g (20.7 mol% / vs octanal).After the addition of octanal was completed, stirring in the reactor was continued at 30 C. for 0.5 hours.Thereafter, acetic acid (5.0 g, 0.08 mol, 8.3 mol% / octanal) was added to the reactor to terminate the reaction in the reactor.The reaction result was calculated according to the following equation using the composition in the reaction product of each component obtained by quantitative analysis of the reaction product by GC (gas chromatography) using an internal standard method. In addition, tetradecane was used as an internal standard substance, and diethyl ether was used as a solvent. The calculated dimer formation rate and hexyl cinnamic aldehyde selectivity (vs. benzaldehyde) are shown in Table 1 below.Specifically, 0.3 mL of the reaction solution was sampled, taken into a screw tube, and precisely weighed.0.1 g of tetradecane was added to this reaction solution and precisely weighed.Furthermore, 1 mL of phosphate buffer and 3 mL of ether were added to it and shaken. The solution was allowed to stand for oil-water separation, and the upper layer was subjected to GC analysis.GC analysis is performed using a DB-1 column (GC column, 100% dimethylpolysiloxane, manufactured by Agilent Technologies, Inc.)And DB-WAX column (GC column, polyethylene glycol, manufactured by Agilent Technologies, Inc.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); isopropyl alcohol; at 82℃; for 6h;Inert atmosphere; Green chemistry; | <strong>[101-86-0]alpha-hexylcinnamaldehyde</strong> (216 mg, 1.0 mmol),Cat. [Ir] (1.1 mg, 0.002 mmol, 0.2 mol%) and isopropanol (5 mL) were sequentially added to a 25 mL Kelvin tube, protected with N2, and reacted at 82 C for 6 h. Cool to room temperature and remove the solvent by rotary evaporation.The pure target compound was obtained by column chromatography (developing solvent: petroleum ether / ethyl acetate), yield: 96% |
90% | With formic acid; C14H15Cl2IrN3O(1+)*Cl(1-); In ethanol; water; at 80℃; for 1h;pH 1.8; | In a 25 ml test tube reaction flask, 1.0 mmol of <strong>[101-86-0]alpha-hexylcinnamaldehyde</strong>, 0.001 mmol of bisazide chelate 1 (R1 is methoxy, R2 is chloro), 5.0 mmol of formic acid, 2 ml of water and The solvent was mixed with ethanol (volume ratio of 4:1), the pH of the solution was adjusted to about 1.8, and the reaction system was stirred at 80 C for 1.0 hour, the heating and stirring were stopped, and the mixture was cooled to room temperature. The reaction solution was extracted with ethyl acetate. The solvent was evaporated under reduced pressure, and then purified and purified by column chromatography to give the desired product. The column chromatography eluent was used as a petroleum ether: ethyl acetate mixed solvent in a volume ratio of 5:1. The yield is 90% and the semi-complete reduction is >99%. |
78% | General procedure: To a 25 mL Schlenk tube containing a solution of 1 in 2 mL of THF was added an aldehyde (1.0 mmol) and (EtO)3 SiH (0.20 g, 1.2 mmol). The reaction mixture was stirred at 50-55 C until there was no aldehyde left (monitored by TLC and GC-MS). The reaction was then quenched byMeOH (2mL) and a 10% aqueous solution of NaOH (5 mL) with vigorous stirring at 60 C for about 24 h.The organic product was extracted with diethyl ether (10 mL × 3), dried over anhydrous MgSO4, and concentrated under vacuum. The alcohol product was further purified using flash column chromatography (elute with 5-10% ethyl acetate in petroleum ether). The 1H NMR and 13C NMR spectra of the alcohol products are providedin Supporting information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With p-toluene sulfonic acid impregnated on MCM-41; In neat (no solvent); at 125℃; for 13h;Inert atmosphere; Green chemistry; | General procedure: In a three necked round bottom flask, benzaldehyde(39.5 mmol), n-decane (0.01 g) as an internal standard andPTSA-MCM-41 (100 mg) were taken under inter gas atmosphereto which 1-heptanal (7.9 mmol) was added at a rate of 1130 L/hby using syringe pump, while keeping the reaction temperature at125C. The controlled addition of 1-heptanal is important in orderto minimize its self-condensation and maximize the yield of mainproduct jasminaldehyde. The reaction was monitored on GC. Allthe reactions were done in triplicate to ensure the reproducibilityof the reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With copper(II) bis(trifluoromethanesulfonate); In toluene; at 70℃; for 6h;Schlenk technique; Inert atmosphere; | General procedure: 3. Typical Procedure for N-substituted 1, 4-dihydropyridines via three-component reaction Ethyl propiolate 3a (0.6 mmol, 60 muL), alpha-methyl cinnamaldehyde 1a (0.3 mmol, 42 S3 muL), aniline 2a (0.36 mmol, 33 muL), Cu(OTf)2 (0.015 mmol, 5.4 mg) and 2.0 mL toluene were added to a Schlenk tube in argon atmosphere. Then the mixture was stirred at 70 oC under argon atmosphere with TLC monitoring until the complete consumption of 1a. The reaction mixture was washed with brine, and then extracted with ethyl acetate three times. The organic layers were combined, dried over Na2SO4, and concentrated in vacuo, the residue was purified by triethylamine treated silica gel column chromatography to afford the desired product 4aaa (88.1 mg, 92% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium hydroxide; at 20℃; | A method of synthesizing oxazolidin-4-one in this example was carried out in a 10 ml round bottom flaskAlpha-n-hexylcinnamaldehyde(Formula 5f) (0.1 mmol, 21.6 mg),Tetrafluoropropanol (1 ml),N-benzyloxy-alpha-methyl-alpha-bromopropionamide(Structural formula such as 1a) (0.2 mmol, 54.2 mg)Sodium bicarbonate (0.1 mmol, 8.4 mg). At room temperature until the aldehyde reaction was complete (TLC monitoring), after which the mixture was subjected to distillation under reduced pressure followed by column chromatography using petroleum ether and ethyl acetate as the eluent to give the compound of formula 6f-5.5- dimethyl-3-benzyloxy-2- (2-substituted-1-phenyl-1-octene-yl) oxazolidin-4-one(Colorless liquid, 34.0 mg, yield 84%). The reaction equation is: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In ethanol; at 60 - 70℃; for 8h; | General procedure: alpha-Hexylcinnamaldehyde, 1.1 g (0.0051 mol),was added dropwise with stirring to a solution of 0.76 g (0.005 mol) of o-hydroxybenzohydrazide in10 mL of ethanol, and the mixture was stirred for 8 h at 60-70C, the progress of the reaction being monitored by TLC. When the reaction was complete, the mixture was cooled, and the finely crystalline solid was filtered off and washed with a small amount of cold ethanol. Yield 1.20 g (69%), mp 157-158C (from 1,4-dioxane). 1H NMR spectrum, delta, ppm: 0.80 t (3H, 26-H,2J = 6.4 Hz), 1.21-1.32 m (6H, 23-H, 24-H, 25-H),1.48-1.55 m (2H, 22-H), 2.56 t (2H, 21-H, 3J =7.8 Hz), 6.80 s (1H, 14-H), 6.89-6.93 m (2H, 4-H,6-H), 7.26-7.32 m (2H, 3-H, 5-H), 7.38 d (2H, 17-H,19-H, 3J = 4.3 Hz), 7.40 d (2H, 16-H, 20-H, 3J = 4.3 Hz),7.41 s (1H, N=CH), 7.83 d (1H, 18-H, 3J = 7.3 Hz).13C NMR spectrum, deltaC, ppm: 14.47 (C26), 22.61 (C25),26.24 (C22), 28.52 (C23), 29.46 (C24), 31.46 (C21),116.39 (C2), 117.79 (C4), 119.41 (C6), 128.41 (C18),128.96 (C3), 129.15 (C17, C19), 129.43 (C16, C20),134.28 (C5, C15), 136.61 (C=CH), 137.87 (C=CH),139.62 (N=CH), 159.65 (C1), 165.15 (C=O). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | In ethanol; at 60 - 70℃; for 8h; | General procedure: alpha-Hexylcinnamaldehyde, 1.1 g (0.0051 mol),was added dropwise with stirring to a solution of 0.76 g (0.005 mol) of o-hydroxybenzohydrazide in10 mL of ethanol, and the mixture was stirred for 8 h at 60-70C, the progress of the reaction being monitored by TLC. When the reaction was complete, the mixture was cooled, and the finely crystalline solid was filtered off and washed with a small amount of cold ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; In toluene; at 120℃; for 12h;Inert atmosphere; | Under nitrogen atmosphere, 2-aminobenzamide (136 mg, 1 mmol), [Cp*IrCl2]2 (8 mg, 0.01 mmol, 1 mol%), toluene (1.0 mL), <strong>[101-86-0]alpha-hexylcinnamaldehyde</strong> (216 mg, 1 mmol) were successively Add to 25mL Schlenk reaction flask. The mixture was reacted at 120C for 12 hours and then cooled to room temperature. The solvent was removed in vacuo under reduced pressure and then purified by column chromatography (developer: ethyl acetate/petroleum ether) to give the pure target compound in a yield of 88%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A suspension of sodium hydride (2.24 g, 55% dispersion in mineral oil, 51 .3 mmol, 1.1 eq., washed twice with hexane) in 1 ,2-dimethoxyethane (DME, 100 ml) was treated dropwise with a solution of diethylcyanomethyl phosphonate (8.2 ml, 51 .1 mmol, 1 .1 eq.) in DME (10 ml). The resulting mixture was stirred for 1 h at 20 C, treated dropwise with a solution of alpha-hexyl- cinnamic aldehyde (10 g, 46.2 mmol) in DME (20 ml), stirred at 60 C for 3 h, cooled to 20 C, poured into 2N aq. HCI/ice (200 ml), and extracted twice with MTBE (75 ml). The combined organic phases were washed three times with water (75 ml), four times with aqueous saturated NaCI solution (75 ml), dried (MgS04), and concentrated. The crude yellow/orange oil (12.3 g) was distilled using a ball-to-ball distillation apparatus (Kugelrohr, 160-200 C oven temperature, 0.06-0.07 mbar) and the fraction distilled at 180-200 C (0.06-0.07 mbar, 7.31 g, 86:10:4 mixture of isomers, light yellow solid) was distilled again using the same apparatus (190-220 C oven temperature, 0.06 mbar) giving pure 4-benzylidenedec-2-enenitrile (5.95 g, 54%, 83:13:4 mixture of isomers) as a white solid.Compound 16:1H-NMR (CDCI3, 400 MHz): d 7.42-7.36 (m, 2H), 7.35-7.28 (m, 3H), 7.10 {dd, J = 0.8, 16.4, 1 H), 6.73 (br. s, 1 H), 5.41 (br. d, J = 16.4, 1 H), 2.45-2.39 (m, 2H), 1 .56-1.46 (m, 2H), 1 .42-1 .24 (m, 6H), 0.89 (, J = 6.8, Me).13C-NMR (CDCI3, 100 MHz): d 154.79 (d), 139.42 (d), 138.50 (s), 135.91 (s), 129.1 1 (d, 2 C), 128.58 (d, 2 C), 128.28 (d), 1 18.70 (s), 94.94 (d), 31 .44 (i), 29.47 (i), 28.55 (i), 26.63 (i), 22.57 (f), 14.01 (q). MS (El): m/z 240 [M + H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With bismuth (III) nitrate pentahydrate; In ethanol; at 100℃; for 12h; | General procedure: To a 100 mL round bottom flask fitted with a condenser containing magnetic stir bar, 1a (0.5mmol), 2a (1.2 equiv, 0.6 mmol), Bi(NO2)3? 5H2O (10 mol%), and ethanol (5 mL) were added.The resultant mixture was stirred at 60 C under open-air condition for 12 h. The reactionmixture was cooled to rt, and subjected to crystallization (EtOH) to get analytically pure 2-phenyl-3H-quinazolin-4-one 3a (91%); 1H NMR (400 MHz, DMSO-d6) delta 12.55 (s, 1H), 8.28 - 8.10(m, 3H), 7.83 (ddd, J = 8.5, 6.4, 1.7 Hz, 1H), 7.75 (d, J = 8.2 Hz, 1H), 7.67 - 7.47 (m, 4H); 13C NMR(100 MHz, DMSO-d6) delta 162.7, 152.8, 149.2, 135.0, 133.2, 131.8, 129.1, 128.2, 127.9, 127.0,126.3, 121.4; Mass (ESI) m/z: = 222.1(M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With bismuth (III) nitrate pentahydrate; In ethanol; at 100℃; for 12h; | General procedure: To a 100 mL round bottom flask fitted with a condenser containing magnetic stir bar, 1a (0.5mmol), 2a (1.2 equiv, 0.6 mmol), Bi(NO2)3? 5H2O (10 mol%), and ethanol (5 mL) were added.The resultant mixture was stirred at 60 C under open-air condition for 12 h. The reactionmixture was cooled to rt, and subjected to crystallization (EtOH) to get analytically pure 2-phenyl-3H-quinazolin-4-one 3a (91%); 1H NMR (400 MHz, DMSO-d6) delta 12.55 (s, 1H), 8.28 - 8.10(m, 3H), 7.83 (ddd, J = 8.5, 6.4, 1.7 Hz, 1H), 7.75 (d, J = 8.2 Hz, 1H), 7.67 - 7.47 (m, 4H); 13C NMR(100 MHz, DMSO-d6) delta 162.7, 152.8, 149.2, 135.0, 133.2, 131.8, 129.1, 128.2, 127.9, 127.0,126.3, 121.4; Mass (ESI) m/z: = 222.1(M+). |
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