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[ CAS No. 94022-96-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 94022-96-5
Chemical Structure| 94022-96-5
Chemical Structure| 94022-96-5
Structure of 94022-96-5 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 94022-96-5 ]

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Product Details of [ 94022-96-5 ]

CAS No. :94022-96-5 MDL No. :MFCD00003540
Formula : C9H9F3O Boiling Point : -
Linear Structure Formula :- InChI Key :DBKIEXOOUXQPGC-UHFFFAOYSA-N
M.W : 190.16 Pubchem ID :587845
Synonyms :

Calculated chemistry of [ 94022-96-5 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.38
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 2.38
Log Po/w (WLOGP) : 3.39
Log Po/w (MLOGP) : 2.91
Log Po/w (SILICOS-IT) : 3.02
Consensus Log Po/w : 2.73

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.66
Solubility : 0.414 mg/ml ; 0.00218 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 0.681 mg/ml ; 0.00358 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.52
Solubility : 0.0574 mg/ml ; 0.000302 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 94022-96-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 94022-96-5 ]

* 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.

  • Downstream synthetic route of [ 94022-96-5 ]

[ 94022-96-5 ] Synthesis Path-Downstream   1~75

  • 1
  • [ 110-88-3 ]
  • [ 94022-96-5 ]
  • [ 117983-68-3 ]
  • 2
  • [ 124-63-0 ]
  • [ 94022-96-5 ]
  • [ 98440-42-7 ]
  • 3
  • Boc-(β-benzyl)-L-aspartic acid cesium salt [ No CAS ]
  • [ 94022-96-5 ]
  • Boc-Asp(Bzl) o-(trifluoromethyl)phenethyl ester [ No CAS ]
  • 4
  • [ 94022-96-5 ]
  • [ 94022-95-4 ]
  • 5
  • [ 94022-96-5 ]
  • 2-((1R,2S)-2-Trifluoromethyl-cyclohexyl)-ethanol [ No CAS ]
  • 2-((1S,2S)-2-Trifluoromethyl-cyclohexyl)-ethanol [ No CAS ]
  • 6
  • [ 94022-96-5 ]
  • [ 94022-98-7 ]
  • 7
  • [ 3970-21-6 ]
  • [ 94022-96-5 ]
  • 1-[2-(2-methoxy-ethoxymethoxy)-ethyl]-2-trifluoromethyl-benzene [ No CAS ]
  • 8
  • [ 94022-96-5 ]
  • 2-(trifluoromethyl)phenethyl azide [ No CAS ]
  • 10
  • [ 94022-96-5 ]
  • [ 21235-63-2 ]
YieldReaction ConditionsOperation in experiment
100% With Silicycle; In dichloromethane; To a 40ml scintillation vial was added 0.067ml of 2-[(trifluoromethyl)phenyl]ethanol (0.42 mmoles, 1eq) and 5ml dichloromethane. Then 3g of 21 wt% pyridinium chlorochromate/silica gel (Silicycle, 21wt%, 4eq) was added and the reaction was shaken on an orbital shaker overnight. The reaction was filtered, washed with 3ml diethyl ether and concentrated at room temperature at 200 mBar until approximately 3ml of volume remained. The resulting aldehyde was neither isolated nor analyzed the crude product was used in the next step below. (100% yield was assumed.) To a 40ml scintillation vial was added 66mg 4-(tetrahydro-1(2H)-pyridazinyl)-1- naphthalenecarbonitrile (B1) (0.278 mmoles, 1eq), 3ml ethanol, 1ml acetic acid, and the above aldehyde solution, which contains a solution of the above aldehyde in 3ml dichloromethane (0.42mmoles, 1.5eq). Then 400mg (polystyrylmethyl)trimethylammoniumcyanoborohydride resin (Novabiochem, 4.3mmol/g, 5eq) was added and the reaction was shaken on an orbital shaker overnight. The reaction was filtered and concentrated in vacuo. The residue was purified via preparative HPLC (Phenomenex column Luna C18, 75mm x 30mm, 5 micron), 50% acetonitrile/water (0.01% TFA) to 100% acetonitrile, to yield 36mg of the title compound as a yellow oil.1H NMR (400 MHz, METHANOL-D4) delta ppm 1.8 (m, 4 H), 2.6 (t, J=7.2 Hz, 2 H), 3.1 (t, J=7.2 Hz, 2 H), 3.4 (m, 2 H), 3.4 (m, 2 H), 7.0 (m, 1 H), 7.0 (m, J=8.1 Hz, 1 H), 7.1 (m, 2 H), 7.4 (m, 1 H), 7.4 (m, 1 H), 7.6 (m, 1 H), 7.8 (d, J=7.9 Hz, 1 H), 8.0 (d, J=8.6 Hz, 1 H), 8.3 (d, J=8.8 Hz, 1 H)
With pyridinium chlorochromate; In dichloromethane; at 20℃; for 1h; 2- (Trifluoromethyl) phenethyl alcohol (3. 00g, 15. 77MMOL) in dry dichloromethane (100ml) was added pyridinium chlorochromate (4.08g, 18. 93MMOL) in one portion at room temperature, under an atmosphere of nitrogen. The orange mixture turns black after 20 mins. The reaction was monitored by thin layer chromatography (100% diethyl ether; reactant r. f. 0.5, product r. F. 0.9). After 1 hr the solvent was evaporated in vacuo to give a black oil and this was taken up in diethyl ether (100ml) and filtered through a pad of silica and eluted with diethyl ether (100ml). The filtrate was taken and concentrated in vacuo to a yellow oil (1. 91G, 10. 09MMO1). The (2-trifluoromethylphenyl) acetaldehyde was taken to the next step without any purification. 8H (300 MHz, CDC13) 9.75 (1H, s), 7.87-7. 23 (4H, m), 3.94 (2H, s).
  • 11
  • (S)-2-(3,3-Dimethyl-2-oxo-pentanoylamino)-3-methyl-butyric acid [ No CAS ]
  • [ 94022-96-5 ]
  • (S)-2-(3,3-Dimethyl-2-oxo-pentanoylamino)-3-methyl-butyric acid 2-(2-trifluoromethyl-phenyl)-ethyl ester [ No CAS ]
  • 12
  • (1R,2R)/(1S,2S)-2-(1,4-Dioxa-7-azaspiro[4,4]non-7-yl)cyclohexanol [ No CAS ]
  • [ 94022-96-5 ]
  • (1R,2R)/(1S,2S)-1-[2-(2-trifluoromethyl)phenylethoxy]-2-[1,4-dioxa-7-azaspiro[4.4]non-7-yl]cyclohexane [ No CAS ]
  • 13
  • C11H21NO4S [ No CAS ]
  • [ 94022-96-5 ]
  • (1R,2R)/(1S,2S)-1-[(2-trifluoromethyl)phenethoxy]-2-(4-morpholinyl)cyclohexane [ No CAS ]
  • 14
  • [ 94022-96-5 ]
  • 5-trifluoromethyl-1H-2-benzopyran-1-one [ No CAS ]
  • 15
  • [ 94022-96-5 ]
  • [ 307494-54-8 ]
YieldReaction ConditionsOperation in experiment
1.47 g With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0℃; for 3h;Inert atmosphere; General procedure: A mixture of the substituted phenylethyl alcohol (10 mmol), Chloromethyl methyl ether (15mmol) and N,N-diisopropylethylamine (20 mmol) in dry dichloromethane (25 mL)was stirred under nitrogen atmosphere for 2.5 h at rt. The reaction mixture wasthen washed with water (2×50 mL), dried (NaSO4) and the solvent wasremoved in vacuo. The crude MOM acetal was dissolved in dried CH3CN (25mL) and added to cooled (0 oC) solution of Trimethylsilyltrifluoromethanesulfonate (TMSOTf) (10 mmol). The reaction was carried outunder nitrogen atmosphere for 3 h. Then the mixture was quenched by theaddition of l M NaHCO3 (20 mL ). The orgnic phase was washed withbrine (2×50 mL), dried (NaSO4) and evaporated under reducedpressure. Purification by FC afforded relevant substituted isochromans.
  • 16
  • [ 94022-96-5 ]
  • [ 307494-66-2 ]
  • 17
  • [ 94022-96-5 ]
  • [ 307494-60-6 ]
  • 18
  • [ 94022-96-5 ]
  • [ 307494-55-9 ]
  • 19
  • [ 94022-96-5 ]
  • [ 307494-63-9 ]
  • 20
  • [ 94022-96-5 ]
  • 4-bromo-5-trifluoromethyl-isochroman-1-one [ No CAS ]
  • 21
  • [ 94022-96-5 ]
  • [ 307494-57-1 ]
  • 22
  • [ 94022-96-5 ]
  • 6aα,6bα,12bα,12cα-1,7-(bis)trifluoromethyl-tetrahydrocyclobuta[1,2-c;4,3-c']bis([2]benzothiopyran)-5,8-dione [ No CAS ]
  • 23
  • [ 94022-96-5 ]
  • 6aα,6bα,12bα,12cα-1,12-(bis)trifluoromethyl-tetrahydrocyclobuta[1,2-c;4,3-c']bis([2]benzothiopyran)-5,8-dione [ No CAS ]
  • 24
  • [ 94022-96-5 ]
  • (1R,2R)-2-[3-(2-Trifluoromethyl-phenyl)-propionyl]-cyclopropanecarboxylic acid [ No CAS ]
  • 25
  • [ 94022-96-5 ]
  • (1R,2R)-2-[3-(2-Trifluoromethyl-phenyl)-propionyl]-cyclopropanecarboxylic acid ethyl ester [ No CAS ]
  • 26
  • [ 94022-96-5 ]
  • (1R,2R)-2-[1-Amino-1-carboxy-3-(2-trifluoromethyl-phenyl)-propyl]-cyclopropanecarboxylic acid [ No CAS ]
  • 27
  • [ 94022-96-5 ]
  • (1R,2R)-2-{2,5-Dioxo-4-[2-(2-trifluoromethyl-phenyl)-ethyl]-imidazolidin-4-yl}-cyclopropanecarboxylic acid [ No CAS ]
  • 28
  • [ 94022-96-5 ]
  • N-<(2-diphenylmethylthio)-ethyl>-2-(2-trifluoromethylphenyl)-ethylamine [ No CAS ]
  • 29
  • [ 94022-96-5 ]
  • N-<2-<bis(4-fluorophenyl)methylthio>ethyl>-2-(2-trifluoromethylphenyl)-ethylamine [ No CAS ]
  • 30
  • [ 94022-96-5 ]
  • [ 117983-35-4 ]
  • 31
  • [ 94022-96-5 ]
  • [ 119744-50-2 ]
  • 32
  • [ 94022-96-5 ]
  • [ 119744-96-6 ]
  • 33
  • [ 94022-96-5 ]
  • 2-Amino-N-ethyl-N-[2-(2-trifluoromethyl-phenyl)-ethyl]-acetamide; hydrochloride [ No CAS ]
  • 34
  • [ 94022-96-5 ]
  • [ 119745-53-8 ]
  • 35
  • [ 94022-96-5 ]
  • (R)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-5-guanidino-pentanoic acid ({ethyl-[2-(2-trifluoromethyl-phenyl)-ethyl]-carbamoyl}-methyl)-amide; compound with acetic acid [ No CAS ]
  • 36
  • [ 94022-96-5 ]
  • (R)-5-Guanidino-2-[(S)-2-guanidino-3-(4-hydroxy-phenyl)-propionylamino]-pentanoic acid ({ethyl-[2-(2-trifluoromethyl-phenyl)-ethyl]-carbamoyl}-methyl)-amide; compound with acetic acid [ No CAS ]
  • 37
  • [ 94022-96-5 ]
  • (S)-2-Amino-succinic acid 4-benzyl ester 1-[2-(2-trifluoromethyl-phenyl)-ethyl] ester; compound with trifluoro-acetic acid [ No CAS ]
  • 38
  • [ 501031-26-1 ]
  • [ 94022-96-5 ]
  • [ 1972-28-7 ]
  • [ 501029-03-4 ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; In tetrahydrofuran; Example 67 3-(4-[2-(2-Trifluoromethyl-phenyl)-ethoxy]-indol-1-yl)-propionic acid (176) Prepared as described for Example 53 except the alkylation on the indole oxygen was completed in the following manner. 3-(4-Hydroxy-indol-1-yl)-propionic acid methyl ester (1.73 g, 7.89 mmol), triphenylphosphine (2.07 g, 7.89 mmol), and 2-(2-Trifluoromethyl-phenyl)-ethanol (1.25 mL, 7.89 mmol) were dissolved in tetrahydrofuran (35 mL). Diethyl azodicarboxylate (1.28 mL in 5 mL THF, 7.89 mmol) was added dropwise and the reaction stirred at room temperature overnight. The mixture was concentrated and purified by chromatography. Yield=290 mg, 10%. m.p.=126-129, THEORY: 63.66%; C, 4.81%; H, 3.71%; N. ACTUAL: 63.68%; C, 4.97%; H, 3.71%; N.
  • 39
  • [ 395-45-9 ]
  • [ 79756-81-3 ]
  • [ 94022-96-5 ]
  • 40
  • [ 220605-36-7 ]
  • [ 94022-96-5 ]
  • [ 532984-12-6 ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 24h; 0.301 g (1 mmol) of (3R)-4-(4-toluenesulfonyl)thiomorpholine-3-carboxylic acid, 0.285 g (1.5 mmol) of (2-trifluoromethyl)-phenylethanol, 0.088 g (0.33 mmol) of CAS, 0.227 g (1.2 mmol) of DCC and 0.04 g (0.33 mmol) of DMAP were dissolved in 15 mL of CH2Cl2. The mixture was stirred for 24 h at room temperature. The solid was filtrated and the solvent was evaporated. The residual was dissolved in a suitable amount of ethyl acetate (20 ml) and then the mixture was filtered to remove insoluble substance. The ethyl acetate was added to 60 ml and then the liquid was washed with 10% NaHCO3 solution, saturated NaCl solution and dried over Na2SO4. After the drying agent was removed and part of ethyl acetate was evaporated, the crude product was purified by flash column chromatography (eluent: ethyl acetate:cyclohexane=1:3) to obtain the product as a oil (0.44 g).
  • 41
  • [ 585-76-2 ]
  • [ 94022-96-5 ]
  • [ 1203581-70-7 ]
  • 42
  • [ 585-76-2 ]
  • [ 94022-96-5 ]
  • [ 1203581-80-9 ]
  • 43
  • [ 533-58-4 ]
  • [ 94022-96-5 ]
  • [ 1300730-57-7 ]
YieldReaction ConditionsOperation in experiment
56% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 20℃; Example 26 l -iodo-2-(2-(trifluoromethyl)phenethoxy)benzene; [0347] To a stirred solution of the 2-iodophenol (220.0 mg, 1.0 mmol), the 2-(2- (trifluoromethyl)phenyl)ethanol (228.0 mg, 1.2 mmol), and triphenyl phosphine (314.0 mg, 1.2 mmol) in anhydrous THF (5 mL) at 0 C was added DEAD (40% in toluene, 1.20 mmol, 0.35 mL) dropwise. The yellow solution was allowed to warm to room temperature and stirring was continued overnite. After evaporating the solvent under reduced pressure the crude residue was dissolved in DCM (15 mL). The organic layer was washed with 10% NaOH (2 x 10 mL), water and brine. The organic phase was dried (Na2S04), filtered and evaporated under reduced pressure. The crude residue was purified by column chromatography on silica gel using hexanes EtOAc as the eluent. The compound was isolated in 56% yield as a white solid. NMR: 3.17 (t, 2H, J = 6.8 Hz), 4.22 (t, 2H, J = 6.8 Hz), 6.90-7.10 (m, 4H), 7.15-7.23 (ml H), 7.30-7.45 (m, 2H), 7.74 (dd, 1H, J= 7.6, 1.6 Hz).
  • 44
  • [ 1312023-07-6 ]
  • [ 94022-96-5 ]
  • [ 1666-13-3 ]
  • [ 1312023-23-6 ]
YieldReaction ConditionsOperation in experiment
76% With copper(I) trifluoromethanesolfonate toluene complex; In tetrahydrofuran; at 20℃; for 1h;Inert atmosphere; Molecular sieve; To a mixture of alcohol 1 (1 mmol), the O, Se acetal 2c (1.4 mmol) and activated 3 A molecular sieves (0.20 g) in dry THF (16 mL), copper(I) triflate toluene complex (0.5 mmol) was added at room temperature. The mixture was stirred under inert atmosphere and monitored by TLC. Reaction times ranged from 1 to 12 h. The reaction mixture was filtered through a celite pad and the filtrate poured into 20 mL of 4 N aqueous NH4OH, mixed, and separated. The aqueous phase was extracted with 10 mL of ethyl acetate and the combined organic phases were washed with 10 mL of brine, dried over sodium sulfate, and concentrated. Purification by silica gel column chromatography afforded the SEM-ether derivative 5.
  • 45
  • [ 56814-33-6 ]
  • [ 94022-96-5 ]
  • [ 1666-13-3 ]
  • [ 1312023-09-8 ]
YieldReaction ConditionsOperation in experiment
80% With N-iodo-succinimide; potassium carbonate; In ethyl acetate; at 20℃;Inert atmosphere; Molecular sieve; To a mixture of alcohol 1 (1 mmol), the O, Se acetal 2a (1.4 mmol), solid potassium carbonate (2.0 mmol) and activated 3 A molecular sieves (0.20 g) in dry ethyl acetate (16 mL), solid N-iodosuccinimide (1.4 mmol) was added in portion at room temperature. The mixture was stirred under inert atmosphere and monitored by TLC. Reaction times ranged from 0.5 to 2 h. The brown colored reaction mixture was quenched into 20 mL of 10% aqueous sodium thiosulfate pentahydrate solution, mixed, and separated. The aqueous phase was extracted with 10 mL of ethyl acetate and the combined organic phases were washed with 10 mL of brine, dried over sodium sulfate and concentrated. Purification by silica gel column chromatography afforded the MOM-ether derivative 3.
  • 46
  • [ 152407-19-7 ]
  • [ 94022-96-5 ]
  • [ 1666-13-3 ]
  • 1-[2-(2-methoxy-ethoxymethoxy)-ethyl]-2-trifluoromethyl-benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With N-iodo-succinimide; potassium carbonate; In ethyl acetate; at 20℃;Inert atmosphere; Molecular sieve; To a mixture of alcohol 1 (1 mmol), the O, Se acetal 2a (1.4 mmol), solid potassium carbonate (2.0 mmol) and activated 3 A molecular sieves (0.20 g) in dry ethyl acetate (16 mL), solid N-iodosuccinimide (1.4 mmol) was added in portion at room temperature. The mixture was stirred under inert atmosphere and monitored by TLC. Reaction times ranged from 0.5 to 2 h. The brown colored reaction mixture was quenched into 20 mL of 10% aqueous sodium thiosulfate pentahydrate solution, mixed, and separated. The aqueous phase was extracted with 10 mL of ethyl acetate and the combined organic phases were washed with 10 mL of brine, dried over sodium sulfate and concentrated. Purification by silica gel column chromatography afforded the MOM-ether derivative 3. The procedure adopted for the synthesis of MOM-derivatives 3 was employed for the synthesis of MEM-derivatives 4 with the sole exception that O, Se acetal 2b was used.
  • 47
  • [ 94022-96-5 ]
  • [ 1312023-07-6 ]
  • 48
  • [ 94022-96-5 ]
  • [ 152407-19-7 ]
  • 49
  • [ 1373155-07-7 ]
  • [ 94022-96-5 ]
  • 50
  • [ 94022-96-5 ]
  • [ 93378-90-6 ]
  • [ 1373155-07-7 ]
YieldReaction ConditionsOperation in experiment
80% With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -15℃;Molecular sieve; Inert atmosphere; General procedure: A mixture of alcohol 6 (1 mmol), N,Se acetal 5 (1.4 mmol) and activated 3-A molecular sieves (0.40 g) in dry dichloromethane (16 mL) was stirred for 0.5 h under argon atmosphere at room temperature. Solid N-iodosuccinimide (1.4 mmol) was added and then the mixture cooled to -15 C. After the addition of TMSOTf (12 muL, 0.07 mmol) the reaction mixture was stirred and monitored by TLC. Reaction times ranged from 1 to 2 h. The brown colored reaction mixture was then filtered through a celite path and the filtrate washed with 20 mL of 10% aqueous sodium thiosulfate pentahydrate solution. The aqueous phase was extracted with 10 mL of dichloromethane and the combined organic phases were washed with 10 mL of brine, dried over sodium sulfate, and then evaporated under vacuum. Purification by silica gel column chromatography afforded the phthalimidomethyl-ether derivative 7.
  • 51
  • [ 94022-96-5 ]
  • [ 1446491-75-3 ]
  • 52
  • [ 107-30-2 ]
  • [ 94022-96-5 ]
  • [ 1312023-09-8 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 20℃; for 2.5h;Inert atmosphere; General procedure: A mixture of the substituted phenylethyl alcohol (10 mmol), Chloromethyl methyl ether (15mmol) and N,N-diisopropylethylamine (20 mmol) in dry dichloromethane (25 mL)was stirred under nitrogen atmosphere for 2.5 h at rt. The reaction mixture wasthen washed with water (2×50 mL), dried (NaSO4) and the solvent wasremoved in vacuo. The crude MOM acetal was dissolved in dried CH3CN (25mL) and added to cooled (0 oC) solution of Trimethylsilyltrifluoromethanesulfonate (TMSOTf) (10 mmol). The reaction was carried outunder nitrogen atmosphere for 3 h. Then the mixture was quenched by theaddition of l M NaHCO3 (20 mL ). The orgnic phase was washed withbrine (2×50 mL), dried (NaSO4) and evaporated under reducedpressure. Purification by FC afforded relevant substituted isochromans.
  • 53
  • (E)-3-(4-methoxy-2-oxo-2H-pyran-6-yl)acrylic acid [ No CAS ]
  • [ 94022-96-5 ]
  • (E)-2-(trifluoromethyl)phenethyl 3-(4-methoxy-2-oxo-2H-pyran-6-yl)acrylate [ No CAS ]
  • 54
  • [ 3038-48-0 ]
  • [ 94022-96-5 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 4.5h;Reflux; General procedure: To a mixture of LiAlH4 (15 mmol) in anhydrous THF (25 mL) in an ice-bath was added dropwise a solution of phenylacetic acids (15 mmol) in THF (8 mL). This mixture was stirred at room temperature for 30 min, and then heated to reflux for 4 h. After it was cooled to room temperature, water (0.5 mL) was added, and then NaOH (15%, 0.5 mL) and water (1.5 mL) were added in sequence. After stirring for another 30 min, the mixture was filtered, dried over anhydrous Na2SO4 and concentrated to give crude products. Pure phenylethyl alcohols were obtained in 50-85% yield by column chromatography. Alternative method: To a solution of phenylacetic acids (15 mmol) in MeOH (30 mL) was added SOCl2 (30 mmol). This mixture was heated to reflux for 3 h before evaporation. The residue was dissolved in DCM (30 mL), washed with aqueous NaHCO3, water and brine, dried over anhydrous Na2SO4, and concentrated to give 100% yield of crude methyl phenylacetates which were used to next step without further purification. To a solution of the methyl phenylacetates in THF (30 mL) was added NaBH4 (60 mmol). When the mixture was heated to gently reflux, MeOH (1.0 mL) was added dropwise from a syringe over 5 min. After refluxing for another 6 h, the mixture was cooled to room temperature and poured into 30 mL ice water, and extracted with EtOAc (30 mL × 2). The combined organic phase was washed with brine, dried over anhydrous Na2SO4, and concentrated to give crude products. Pure phenylethyl alcohols were obtained in 70-85% yield by column chromatography.
  • 55
  • [ 4559-70-0 ]
  • [ 94022-96-5 ]
  • 2-(trifluoromethyl)phenethyl diphenylphosphinate [ No CAS ]
  • 56
  • [ 331-39-5 ]
  • [ 94022-96-5 ]
  • 2’-(trifluoromethyl)phenethyl (E)-3-(3,4-dihydroxy phenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With ytterbium(III) triflate; In nitromethane; at 120℃; General procedure: To a mixture of caffeic acid fine powder (1.0 g, 5.56 mmol), various phenethyl alcohols (5.56 mmol) in CH3NO2 (125 mL) was added Yb(OTf)3 (34.4 mg, 0.056 mmol). After 5 min of ultrasonic shake, the mixture was stirred on a 120 C oil bath for 40-120 min. The reaction mixture was cooled to room temperature, washed with 2% NaHCO3 (30 mL) and brine, dried over anhydrous Na2SO4, and concentrated to give crude products, which were purified by column chromatography to give the compounds 1-26 in 18-61% yields.
  • 57
  • [ 106-95-6 ]
  • [ 94022-96-5 ]
  • allyl (2-(trifluoromethyl)phenethyl) ether [ No CAS ]
  • 58
  • [ 94022-96-5 ]
  • 1-(2-(3-fluoropropoxy)ethyl)-2-(trifluoromethyl)benzene [ No CAS ]
  • 59
  • [ 94022-96-5 ]
  • (3-(2-(trifluoromethyl)phenethoxy)propyl)trimethoxysilane [ No CAS ]
  • 60
  • [ 50-00-0 ]
  • [ 21742-00-7 ]
  • [ 94022-96-5 ]
YieldReaction ConditionsOperation in experiment
71% General procedure: Phenethyl alcohol (3a) A two neck Schlenk flask equipped with a magnetic stirring bar and septum was heated with heat gun (~400 C) for 10 min under high vacuum. After cooling to room temperature, the flask was flushed with argon (3 times). Zn-dust (654 mg, 2.0 equiv, 10.0 mmol) was added followed by THF (20 mL). 1,2-Dibromoethane (5 mol%) was added and the reaction mixture was heated until ebullition occurs. After cooling to rt, chlorotrimethylsilane (1 mol%) was added and the mixture was heated again till ebullition occurs. The flask was again cooled to rt and benzyl chloride (633 mg, 5.0 mmol, 1 equiv) was added as a solution in THF (10 mL) and it was heated at 70 C for 2 h and cooled to rt. Paraformaldehyde (450 mg, 3.0 equiv. 15.0 mmol) was slowly added at rt and the flask was again heated at 70 C for 6 h. The solution was cooled to rt and saturated NH4Cl solution was added. The phases were separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layer was washed with water (20 mL), brine (10 mL) and then dried over Na2SO4. The solvents were evaporated under reduced pressure and the residue was purified by silica gel column chromatography using cyclohexane or cyclohexane/ethyl acetate as an eluent to obtain phenethyl alcohol (3a) (510 mg, 83%) as a colourless liquid.
  • 61
  • [ 94022-96-5 ]
  • 1-(tert-butylperoxy)-5-(trifluoromethyl)isochroman [ No CAS ]
  • 62
  • [ 545-06-2 ]
  • [ 94022-96-5 ]
  • 2-(trifluoromethyl)phenethyl 2,2,2-trichloroacetimidate [ No CAS ]
  • 63
  • [ 94022-96-5 ]
  • C11H7Cl3F3NO [ No CAS ]
  • 65
  • [ 39900-63-5 ]
  • [ 94022-96-5 ]
  • 5-methoxy-2-(2-(trifluoromethyl)phenethoxy)benzonitrile [ No CAS ]
  • 66
  • [ 39900-63-5 ]
  • [ 94022-96-5 ]
  • (E)-ethyl 3-(3-(2-(2-cyano-4-methoxyphenoxy)ethyl)-4-(trifluoromethyl)phenyl)acrylate [ No CAS ]
  • 67
  • [ 395-45-9 ]
  • [ 94022-96-5 ]
  • 68
  • [ 94022-96-5 ]
  • (R)-5-isobutyl-1-phenyl-N-((1-(2-(trifluoromethyl)phenethyl)pyrrolidin-3-yl)methyl)-1H-pyrazole-3-carboxamide [ No CAS ]
  • 69
  • [ 98-59-9 ]
  • [ 94022-96-5 ]
  • [ 267643-69-6 ]
  • 70
  • [ 94022-96-5 ]
  • C9H6F4O3S [ No CAS ]
  • 71
  • [ 94022-96-5 ]
  • 1-phenyl-5-(2-(trifluoromethyl)phenyl)-1H-1,2,3-triazole [ No CAS ]
  • 72
  • [ 94022-96-5 ]
  • 2-(trifluoromethyl)styryl acetate [ No CAS ]
  • 2-(trifluoromethyl)styryl acetate [ No CAS ]
  • 73
  • [ 98-07-7 ]
  • [ 94022-96-5 ]
  • [ 98-87-3 ]
  • 1-chloro-2-(2-trifluoromethylphenyl)ethane [ No CAS ]
  • 74
  • [ 67-56-1 ]
  • [ 94022-96-5 ]
  • C10H11F3O [ No CAS ]
  • 75
  • 5-methyl-3-(trifluoromethyl)benzo[d]isothiazole 1,1-dioxide [ No CAS ]
  • [ 94022-96-5 ]
  • C18H15F6NO3S [ No CAS ]
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