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[ CAS No. 50742-37-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 50742-37-5
Chemical Structure| 50742-37-5
Chemical Structure| 50742-37-5
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Quality Control of [ 50742-37-5 ]

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Product Details of [ 50742-37-5 ]

CAS No. :50742-37-5 MDL No. :MFCD01631862
Formula : C13H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :OWIFNISFRBVGIX-UHFFFAOYSA-N
M.W : 199.25 Pubchem ID :1094836
Synonyms :

Calculated chemistry of [ 50742-37-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.63
TPSA : 35.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 2.79
Log Po/w (MLOGP) : 2.69
Log Po/w (SILICOS-IT) : 2.68
Consensus Log Po/w : 2.55

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.266 mg/ml ; 0.00134 mol/l
Class : Soluble
Log S (Ali) : -2.61
Solubility : 0.494 mg/ml ; 0.00248 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.71
Solubility : 0.00393 mg/ml ; 0.0000197 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.49

Safety of [ 50742-37-5 ]

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:

Application In Synthesis of [ 50742-37-5 ]

* 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 [ 50742-37-5 ]

[ 50742-37-5 ] Synthesis Path-Downstream   1~57

  • 1
  • [ 50742-37-5 ]
  • 3-phenoxy-phenyldiazomethane [ No CAS ]
  • 2
  • [ 25145-23-7 ]
  • [ 50742-37-5 ]
  • [ 42336-92-5 ]
  • [ 183797-57-1 ]
  • 3
  • [ 50742-37-5 ]
  • [ 52314-67-7 ]
  • (1S,3S)-3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid 3-phenoxy-benzylamide [ No CAS ]
  • 4
  • [ 50742-37-5 ]
  • [ 52771-21-8 ]
  • (3-phenoxy-benzyl)-(3-trifluoromethoxy-benzyl)-amine [ No CAS ]
  • 5
  • [ 50742-37-5 ]
  • 2-(3-ethoxycarbonyloxycarbonyl-4-methoxy-benzyl)-butyric acid ethyl ester [ No CAS ]
  • [ 311771-19-4 ]
  • 6
  • [ 919995-76-9 ]
  • [ 50742-37-5 ]
  • 2-benzyl-<i>N</i>-<i>tert</i>-butoxy-<i>N</i>'-(3-phenoxy-benzyl)-malonamide [ No CAS ]
  • 7
  • [ 919995-77-0 ]
  • [ 50742-37-5 ]
  • <i>N</i>-<i>tert</i>-butoxy-2-(4-fluoro-benzyl)-<i>N</i>'-(3-phenoxy-benzyl)-malonamide [ No CAS ]
  • 8
  • [ 919995-79-2 ]
  • [ 50742-37-5 ]
  • <i>N</i>-<i>tert</i>-butoxy-2-(1-methyl-1<i>H</i>-benzoimidazol-2-ylmethyl)-<i>N</i>'-(3-phenoxy-benzyl)-malonamide [ No CAS ]
  • 9
  • [ 919995-78-1 ]
  • [ 50742-37-5 ]
  • <i>N</i>-<i>tert</i>-butoxy-2,<i>N</i>'-bis-(3-phenoxy-benzyl)-malonamide [ No CAS ]
  • 10
  • [ 919995-81-6 ]
  • [ 50742-37-5 ]
  • 2-isobutyl-<i>N</i>-(3-phenoxy-benzyl)-<i>N</i>'-trityloxy-malonamide [ No CAS ]
  • 11
  • [ 50742-37-5 ]
  • [ 608520-21-4 ]
  • <i>N</i>-<i>tert</i>-butoxy-<i>N</i>'-(3-phenoxy-benzyl)-malonamide [ No CAS ]
  • 12
  • [ 50742-37-5 ]
  • [ 608520-22-5 ]
  • <i>N</i>-<i>tert</i>-butoxy-2-isobutyl-<i>N</i>'-(3-phenoxy-benzyl)-malonamide [ No CAS ]
  • 13
  • [ 50742-37-5 ]
  • [ 608520-24-7 ]
  • [<i>tert</i>-butoxycarbamoyl-(3-phenoxy-benzylcarbamoyl)-methyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • 14
  • [ 919995-82-7 ]
  • [ 50742-37-5 ]
  • 2-benzyl-<i>N</i>-(3-phenoxy-benzyl)-<i>N</i>'-trityloxy-malonamide [ No CAS ]
  • 15
  • [ 50742-37-5 ]
  • <i>N</i>-hydroxy-2-isobutyl-<i>N</i>'-(3-phenoxy-benzyl)-malonamide [ No CAS ]
  • 16
  • [ 50742-37-5 ]
  • 2-benzyl-<i>N</i>-hydroxy-<i>N</i>'-(3-phenoxy-benzyl)-malonamide [ No CAS ]
  • 17
  • [ 50742-37-5 ]
  • 1,1,1-trifluoro-3-[(3-phenoxy-benzyl)-(3-trifluoromethoxy-benzyl)-amino]-propan-2-ol [ No CAS ]
  • 18
  • [ 50742-37-5 ]
  • (2,2,3,4,4-Pentamethyl-1-oxo-1λ5-phosphetan-1-yl)-(3-phenoxy-benzyl)-amine [ No CAS ]
  • 19
  • [ 50742-37-5 ]
  • (2,2,3,4,4-Pentamethyl-1-thioxo-1λ5-phosphetan-1-yl)-(3-phenoxy-benzyl)-amine [ No CAS ]
  • 20
  • [ 50742-37-5 ]
  • [ 104290-68-8 ]
  • 21
  • [ 75-44-5 ]
  • [ 50742-37-5 ]
  • C14H11NO2 [ No CAS ]
  • 22
  • [ 39515-51-0 ]
  • [ 50742-37-5 ]
  • 23
  • [ 808761-55-9 ]
  • [ 50742-37-5 ]
  • [ 864176-55-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In toluene; at 60℃; for 18h; Preparation 28 tert-Butyl {4-[([(3-phenoxybenzyl)aminolcarbonyl)amino)methyl]benzyl) carbamate A mixture of the compound from preparation 27 (500mg, 1.51 mmol), <strong>[50742-37-5]3-phenoxybenzylamine</strong> (EP 0313397, pg 16) (345mg, 1.59mmol) and triethylamine (0.64ml,4.53mmol) in toluene (20ml) was stirred at 60C for 18 hours. The cooled mixture was concentrated under reduced pressure and the resulting residue was purified by column chromatography on Isolute SCI gel using methanol as eluant to afford the title compound as a white solid, 342mg. 1H NMR (DMSO-d6, 400MHz) delta: 1.38(s, 9H), 4.17(s, 2H), 4.20(s, 4H), 6.82(dd, 1 H), 6.90(s, 1H), 7.00(m, 2H), 7.14(m, 4H), 7.22-7.40(m, 6H). LRMS: ES- 460 [M-H]-
YieldReaction ConditionsOperation in experiment
(b) 3-Phenoxybenzylamine A solution of the product from step (a) (6.5 g) in THF (75 ml) was added under N2 over 15 minutes to a stirred suspension of LAH (2.3 g) in THF (100 ml). After addition was complete, the mixture was refluxed for 5.5 hours, then cooled to -5 C., excess LAH destroyed by the careful addition of 15% w/v aqu. NaOH (100 ml), and the mixture taken up in water (150 ml) and ether (200 ml). The aqueous phase was separated, extracted with ether and the combined ether solutions washed with 2N aqu. NaOH (2*100 ml) and water (2*200 ml), dried over Na2 SO4 and evaporated in vacuo to give the desired product as a colourless oil (5.9 g). The 200 MHz 1 H NMR was consistent with the proposed structure.
  • 25
  • [ 3622-35-3 ]
  • [ 50742-37-5 ]
  • [ 849810-93-1 ]
YieldReaction ConditionsOperation in experiment
62% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In tetrahydrofuran; at 20℃; for 17h; To a solution of <strong>[50742-37-5]3-phenoxybenzylamine</strong> described in Preparation Example 4 (33mg, 0.167mmol) and benzothiazole-6-carboxylic acid (30mg, 0.167mmol) in tetrahydrofuran (1 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (89mg, 0.20mmol) and triethylamine (28mul, 0.20mmol), and the solution was stirred at room temperature for 17 hours. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane : ethyl acetate), and the title compound (37mg, 62%) was obtained as a colorless oil. 1H-NMR Spectrum (CDCl3) delta(ppm) : 4.68(2H, d, J=6.0Hz), 6.50(1H, brs), 6.94(1H, dd, J=2.0, 8.0Hz), 7.02-7.04(3H, m), 7.11-7.15(2H, m), 7.31-7.37(3H, m), 7.88(1H, dd, J=1.6, 8.8Hz), 8.18(1H, d, J=8.8Hz), 8.49(1H, d, J=1.6Hz), 9.13(1H, s).
  • 26
  • [ 50742-37-5 ]
  • [ 1885-14-9 ]
  • [ 849806-49-1 ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 4h; Preparation Example 75. (3-Phenoxy-benzyl)-carbamic acid phenyl ester To a solution of phenyl chloroformate (0.29mL, 2.3mmol) in tetrahydrofuran (10mL) were added <strong>[50742-37-5]3-phenoxybenzylamine</strong> described in Preparation Example 4 (0.5g, 2.5mmol) and triethylamine (0.35mL, 2.5mmol) dropwise on an ice bath, and then, the solution was stirred at room temperature for 4 hours. The reaction solution was poured into brine, the solution was extracted with ethyl acetate and concentrated, and the title compound (0.7g, 2.2mmol, 88%) was obtained. 1H-NMR Spectrum (DMSO-d6) delta (ppm): 4.24 (2H, d, J=6.0 Hz), 6.87-7.49 (14H, m), 8.29 (1 H, t, J=6.0 Hz).
88% With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 4h; To a solution of phenyl chloroformate (0.29mL, 2.3mmol) in tetrahydrofuran (10mL) were added <strong>[50742-37-5]3-phenoxybenzylamine</strong> described in Preparation Example 4 (0.5g, 2.5mmol) and triethylamine (0.35mL, 2.5mmol) dropwise on an ice bath, and then, the solution was stirred at room temperature for 4 hours. The reaction solution was poured into brine, the solution was extracted with ethyl acetate and concentrated, and the title compound (0.7g, 2.2mmol, 88%) was obtained. 1H-NMR Spectrum (DMSO-d6) delta(ppm) : 4.24 (2H, d, J=6.0 Hz), 6.87-7.49 (14H, m), 8.29 (1 H, t, J=6.0 Hz).
  • 27
  • [ 50742-37-5 ]
  • [ 74240-76-9 ]
YieldReaction ConditionsOperation in experiment
58.7% In cyclohexanone; EXAMPLE 5 The procedure is carried out as described in Example 1(b) but with the use of 50 g (0.25 mol) of <strong>[50742-37-5]3-phenoxybenzylamine</strong> and 25 g (0.255 mol) of cyclohexanone. Distillation leaves 41 g (0.147 mol) of N-cyclohexylidene(<strong>[50742-37-5]3-phenoxybenzylamine</strong>), corresponding to a yield of 58.7% of theory; b.p. 135-136 C./4 Pa. Analysis for C19 H21 NO (molecular weight 279.38): calculated: C 81.69% H 7.58% N 5.01% O 5.73% found: C 80.81% H 7.56% N 5.02% O 6.12%. NMR spectrum tau [ppm]: 2.6-3.2(m), 5.51(s), 7.65(m), 8.33(m) in the ratio of 9:2:4:6.
  • 28
  • [ 50742-37-5 ]
  • [ 78-84-2 ]
  • [ 74672-19-8 ]
YieldReaction ConditionsOperation in experiment
97.8% In toluene; (b) Production of N-isobutylidene-(<strong>[50742-37-5]3-phenoxybenzylamine</strong>) STR6 38 g (0.528 mol) of isobutyraldehyde is added dropwise within 30 minutes, with stirring, to a solution of 99.5 g (0.5 mol) of <strong>[50742-37-5]3-phenoxybenzylamine</strong> in 100 ml of toluene. After completion of the dropwise addition, stirring is continued for 20 minutes at room temperature, and the water which has formed (about 8.5 g) is separated in a separating funnel. The toluene with the unreacted isobutyraldehyde and residual water is then removed by rotation in a water-jet vacuum, and the residue is distilled in an oil-pump vacuum to yield 124 g (0.49 mol) of N-isobutylidene-(<strong>[50742-37-5]3-phenoxybenzylamine</strong>) as a colourless, mobile liquid, corresponding to a yield of 97.8% of theory; b.p. 85 C./4 Pa; nD20 =1.5666. Analysis for C17 H19 NO (molecular weight 253.35): calculated: C 80.60%; H 7.56%; N 5.53%; O 6.31%. found: C 79.91%; H 7.62%; N 5.41%; O 6.52%. MS spectrum: molecular peak 253, masses of the fragments 184, 183, 168, 153, 77. NMR spectrum tau [ppm]: 2.47(d), 2.6-3.2(m), 5.50(s), 7.51(m), 8.97(d) in the ratio of 1:9:2:1:6.
  • 29
  • [ 50742-37-5 ]
  • [ 96-22-0 ]
  • [ 74240-72-5 ]
YieldReaction ConditionsOperation in experiment
93.6% EXAMPLE 3 The procedure is carried out as described in Example 1(b) except that 50 g (0.25 mol) of <strong>[50742-37-5]3-phenoxybenzylamine</strong> and 30 g (0.348 mol) of diethyl ketone are used. There is obtained after distillation 62.5 g (0.234 mol) of N-3-pentylidene-(<strong>[50742-37-5]3-phenoxybenzylamine</strong>), corresponding to a yield of 93.6% of theory; b.p. 128 C./5 Pa. Analysis for C18 H21 NO (molecular weight 267.37): calculated: C 80.86%; H 7.92%; N 5.24%; O 5.98%. found: C 80.97%; H 7.88%; N 5.36%; O 5.92%. MS spectrum: molecular peak 267, masses of the fragments 238, 183, 85, 83. NMR spectrum tau [ppm]: 2.6-3.3(m), 5.51(s), 7.70(m), 8.90(m) in the ratio of 9:2:4:6.
  • 30
  • [ 676326-53-7 ]
  • [ 50742-37-5 ]
  • [ 849810-85-1 ]
YieldReaction ConditionsOperation in experiment
50% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 48h; Reference Example H-1 Quinazoline-6-carboxylic acid 3-phenoxybenzylamide To a solution of quinazoline-6-carboxylic acid obtained in Preparation Example H-3 (9mg, 0.052mmol) in N,N-dimethylformamide (3mL) were added <strong>[50742-37-5]3-phenoxybenzylamine</strong> described in Preparation Example 4 (11 mg, 0.052mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (28mg, 0.062mmol) and triethylamine (17mul, 0.125mmol), and the solution was stirred for 2 days at room temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate, and concentrated. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate), and the title compound (11 mg, 0.031 mmol, 50%) was obtained. 1H-NMR Spectrum (CD3OD) delta (ppm) : 4.62 (2H, s), 6.88 (1H, dd, J=8.0, 1.2Hz), 6.98 (2H, dd, J=1.2, 8.0Hz), 7.09 (1H, s), 7.07 (1H, dd, J=7.6, 8.0Hz), 7.15 (1H, d, J=7.6Hz), 7.29-7.35 (3H, m), 8.10 (1H, d, J=8.8Hz), 8.40 (1H, dd, J=2.0, 8.8Hz), 8.57 (1 H, d, J=2.0Hz), 9.32 (1 H, s), 9.61 (1 H, s).
  • 31
  • [ 50742-37-5 ]
  • [ 311770-42-0 ]
  • [ 311771-19-4 ]
  • 32
  • [ 50742-37-5 ]
  • [ 311770-45-3 ]
  • C29H33NO5 [ No CAS ]
  • 33
  • C15H16N6O4 [ No CAS ]
  • [ 50742-37-5 ]
  • C26H23N7O4 [ No CAS ]
  • 34
  • [ 50742-37-5 ]
  • [ 215453-28-4 ]
  • C30H25N3O2 [ No CAS ]
  • 35
  • [ 50742-37-5 ]
  • [ 100-52-7 ]
  • [ 179056-63-4 ]
YieldReaction ConditionsOperation in experiment
Typical procedure: To a stirred solution of the amine (1.0 equiv) and the aldehyde (1.0 equiv) in dichloroethane (0.2 M) was added acetic acid (5.0 equiv). The solution was stirred for 18 h, then sodium triacetoxyborohydride (1.2 equiv) was added and the mixture was stirred for 1 h. The appropriate isocyanate (1.5 equiv) was added and the mixture was stirred for an additional 4 h before being quenched with a saturated aqueous solution of sodium bicarbonate. The layers were separated and the aqueous layer was extracted three times with dichloromethane. The organic layers were combined and dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude was purified on silica gel.
  • 36
  • [ 50742-37-5 ]
  • [ 100-52-7 ]
  • [ 1283596-10-0 ]
  • 37
  • [ 50742-37-5 ]
  • [ 107-13-1 ]
  • [ 1038222-56-8 ]
  • 38
  • [ 1347758-05-7 ]
  • [ 50742-37-5 ]
  • [ 1347757-08-7 ]
  • 39
  • [ 1422682-36-7 ]
  • [ 50742-37-5 ]
  • [ 1422682-27-6 ]
  • 40
  • [ 393870-46-7 ]
  • [ 50742-37-5 ]
  • [ 1456712-11-0 ]
YieldReaction ConditionsOperation in experiment
24% With pyridine; In toluene; at 20℃; Example 17 - 3-[(Z)-2-Chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-N-[(3-phenoxyphenyl) methyl]cyclopropanecarboxamide 55 A solution of 3-[(Z)-2-chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-cyclopropanecarbonyl chloride (100mg, 1.1 eq) in toluene (6ml_) was added dropwise to a solution of (3- phenoxyphenyl)methanamine (170mg, 1 eq) and pyridine (68muIota_, 1 eq) in toluene (6ml_). The reaction mixture was stirred overnight at room temperature after which time TLC analysis showed the reaction had gone to completion. The reaction mixture was diluted with ethyl acetate (15ml_) and washed with water (2 x 10ml_) and brine (10ml_) before being dried over MgS04 and the solvent removed in vacuo. The residue was purified by flash chromatography (solvent 9: 1 hexane/ethyl acetate) to afford the product as a clear oil (86mg, 24 %). 1 H NMR deltaEta (CDCIs, 300 MHz): 7.22 (m, 3H), 7.04 (m, 2H), 6.94 (m, 3H), 6.84 (m, 2H), 5.78 (s, 1 H), 4.33 (ddd, J= 20.7, 15.0, 5.7 Hz, 2 H), 1.99 (m, 2 H), 1.21 (s, 3H), 1.19 (s, 3H); ESI-MS 424.2 [MH]+..
24% With pyridine; In toluene; at 20℃; Example 17 3-[(Z)-2-Chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-N-[(3-phenoxyphenyl)methyl]cyclopropanecarboxamide 55 A solution of 3-[(Z)-2-chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-cyclopropanecarbonyl chloride (100 mg, 1.1 eq) in toluene (6 mL) was added dropwise to a solution of <strong>[50742-37-5](3-phenoxyphenyl)methanamine</strong> (170 mg, 1 eq) and pyridine (68 muL, 1 eq) in toluene (6 mL). The reaction mixture was stirred overnight at room temperature after which time TLC analysis showed the reaction had gone to completion. The reaction mixture was diluted with ethyl acetate (15 mL) and washed with water (2*10 mL) and brine (10 mL) before being dried over MgSO4 and the solvent removed in vacuo. The residue was purified by flash chromatography (solvent 9:1 hexane/ethyl acetate) to afford the product as a clear oil (86 mg, 24%). 1H NMR deltaH (CDCl3, 300 MHz): 7.22 (m, 3H), 7.04 (m, 2H), 6.94 (m, 3H), 6.84 (m, 2H), 5.78 (s, 1H), 4.33 (ddd, J=20.7, 15.0, 5.7 Hz, 2H), 1.99 (m, 2H), 1.21 (s, 3H), 1.19 (s, 3H); ESI-MS 424.2 [MH]+.
  • 41
  • [ 1087410-86-3 ]
  • [ 50742-37-5 ]
  • [ 1376394-75-0 ]
  • 42
  • [ 329-98-6 ]
  • [ 50742-37-5 ]
  • [ 1376376-07-6 ]
  • 43
  • [ 50742-37-5 ]
  • [ 124-63-0 ]
  • [ 1089332-95-5 ]
  • 44
  • [ 50742-37-5 ]
  • [ 1939-99-7 ]
  • [ 1376376-07-6 ]
  • 45
  • [ 558-25-8 ]
  • [ 50742-37-5 ]
  • [ 1089332-95-5 ]
  • 46
  • [ 51517-01-2 ]
  • [ 50742-37-5 ]
  • [ 1376394-75-0 ]
  • 47
  • [ 611-35-8 ]
  • [ 50742-37-5 ]
  • N-(3-phenoxybenzyl)quinolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.08 g With tri-n-propylamine; In pentan-1-ol; for 66h;Reflux; (3-Phenoxyphenyl)methanamine (2.02 g, 10.2 mmol) was taken up in 60 mL of 1-pentanol, and then 15 mL of volatile material was removed by distillation. The mixture was cooled below boiling, and tripropylamine (3.80 mL, 19.9 mmol) and 4-chloroquinoline (1.65 g, 10.2 mmol) were added. Heating at reflux was resumed. After 66 hr, volatile material was removed by evaporation. The mixture was partitioned between DCM (150, 100 mL) and 5% Na2C03 (80 mL). The combined organic phases were dried over Na2S04, filtered, and concentrated to give a solid. Recrystallization from EA/Hex gave 2.08 g of colorless solid. R 0.34 (10% MeOH/DCM); mp 163.0-164.0 C; 1H NMR (CDC13) delta 8.54 (d, 1H, J=5.5 Hz), 8.00 (m, 1H), 7.76 (d, 1H, J=8.1 Hz), 7.64 (m, 1H), 7.43 (m, 1H), 7.34-7.29 (m, 3H), 7.11 (m, 1H), 7.05 (s, 1H), 7.02-6.99 (m, 2H), 6.94 (dd, 1H, J=2.2, 8.0 Hz), 6.42 (d, 1H, J=5.5 Hz), 5.46 (br s, 1H, NH) 4.51 (m, 2H, AB); 13C NMR (CDC13) delta 158.2, 156.9, 151.3, 149.5, 148.7, 139.9, 130.5, 130.3, 130.0, 129.3, 125.0, 123.8, 122.2, 119.5, 119.3, 118.9, 118.0, 117.8, 99.7, 47.4.
  • 48
  • [ 88467-12-3 ]
  • [ 50742-37-5 ]
  • 49
  • [ 13826-35-2 ]
  • [ 50742-37-5 ]
  • 50
  • N-(3-phenoxybenzyl)phthalimide [ No CAS ]
  • [ 50742-37-5 ]
YieldReaction ConditionsOperation in experiment
3.25 g With hydrazine hydrate; In isopropyl alcohol; for 7h;Reflux; Hydrazine monohydrate (3.50 mL, 72.1 mmol) was added to a mixture of N-(3-phenoxybenzyl)phthalimide (6.28 g, 19.1 mmol) and 200 mL of IPA while using mechanical stirring. The mixture was heated at reflux for 7 hr. After standing overnight, a precipitate had formed. The mixture was concentrated by evaporation, and the residue was partitioned between isopropyl acetate and 5% Na2C03 and brine. The organic phases were dried over Na2S04, filtered, and concentrated. SPE, washing with 50% isopropyl acetate/Hex and then eluting with 3% MeOH/DCM + 2% TEA gave fractions that contained ninhydrin (+) product. The combined product fractions were washed with 5% Na2C03, dried over Na2S04, filtered, and concentrated to give 3.25 g of yellow oil. R 0.28 (10% MeOH/DCM); 1H NMR (CDC13) delta 7.36- 7.25 (m, 3H), 7.12-6.95 (m, 5H), 6.87 (ddd, 1H, J=1.0, 2.5, 8.2 Hz), 3.82 (br s, 2H), 2.15 (br s, 2H, NH2).
  • 51
  • [ 5190-68-1 ]
  • [ 50742-37-5 ]
  • N-(3-phenoxybenzyl)quinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.29 g With triethylamine; In isopropyl alcohol; for 5.5h;Reflux; (3-Phenoxyphenyl)methanamine (1.55 g, 7.79 mmol) was taken up in 60 mL of IPA, and 15 mL of volatile material was removed by distillation. The mixture was cooled, and TEA (1.50 mL, 10.7 mmol) and 4-chloroquinazoline (1.20 g, 7.32 mmol) in 15 mL of IPA were added. The mixture was heated at reflux for 5.5 hr, and then stirred at room temperature overnight. Then, the volatile components were evaporated, and the residue was partitioned between DCM (3x70 mL) and 5% Na2C03 (40 mL). The combined organic phases were dried over Na2S04, filtered, and concentrated. SPE, eluting with 25% and then 55% EA/Hex, gave product fractions that were combined and concentrated to yield an orange solid. Recrystallization from EA/Hex gave a pink solid, and then from MeOH gave 1.29 g of a light pink solid. R 0.19 (50% EA/Hex); mp 146.5- 148.0 C; 1H NMR (CDC13) delta 8.66 (s, 1H), 7.83 (d, 1H, J=8.5 Hz), 7.77 (d, 1H, J=8.1 Hz), 7.71 (m, 1H), 7.42 (m, 1H), 7.30 (m, 3H), 7.10 (m, 2H), 7.04 (br s, 1H), 6.99 (m, 2H), 6.90 (m, 1H), 6.44 (m, IH, NH), 4.84 (m, 2H, AB); C NMR (CDC13) delta 159.5, 157.9, 157.0, 155.5, 149.6, 140.4, 132.9, 130.3, 130.0, 128.7, 126.3, 123.7, 122.6, 120.9, 119.2, 118.3, 117.9, 115.1, 45.1.
  • 52
  • [ 75-15-0 ]
  • [ 50742-37-5 ]
  • 1-(isothiocyanatomethyl)-3-phenoxybenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% General procedure: To a solution of phenethylamine (200 mg, 1.65 mmol) and Et3N (0.64 mL, 4.95 mmol) in anhydrousTHF (2.5 mL) cooled with an ice bath, a solution of CS2 (0.12 mL, 1.98 mmol) was slowly dropped in.The reaction solution was stirred at room temperature for 0.5 h, after which AcCl (0.14 mL, 1.98 mmol)was dropped in at 0 C, and after 5 min the mixture was warmed to room temperature for 15-30 min.When the starting amine was finished, as verified by checking thin layer chromatography (T.L.C.),1MHCl (aq., 2 mL) was added to quench the reaction. The solution was extracted by EtOAc three times.All organic phases were combined and washed with brine, dried over Na2SO4, and finally filtered andconcentrated under reduced pressure. The residue was purified by column chromatography on silicagel (EtOAc/petroleum = 1/1) to provide phenethyl isothiocyanate (PEITC) (253 mg, 94%).
  • 53
  • [ 50742-37-5 ]
  • [ 421551-82-8 ]
  • 3-oxo-2-(3-phenoxybenzyl)isoindoline-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
123 mg With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 10 - 50℃;Inert atmosphere; C) 3-oxo-2-(3-phenoxybenzyl)isoindoline-5-carbonitrile Under nitrogen atmosphere, a mixture of <strong>[421551-82-8]methyl 2-(bromomethyl)-5-cyanobenzoate</strong> (100 mg), 1-(3-phenoxyphenyl)methanamine (94 mg), DIEA (0.082 mL) and THF (7 mL) was stirred at 50C for 6 hr, and then overnight at room temperature, and the reaction mixture was concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (123 mg). MS (API+), found: 341.2 (M+1)
  • 54
  • [ 50742-37-5 ]
  • [ 311770-42-0 ]
  • 2-[4-methoxy-3-(3-phenoxy-benzylcarbamoyl)-benzyl]-butyric acid [ No CAS ]
  • 55
  • [ 50742-37-5 ]
  • [ 311770-45-3 ]
  • C27H29NO5 [ No CAS ]
  • 56
  • [ 1453186-96-3 ]
  • [ 50742-37-5 ]
  • 8-isopropyl-2-(methylthio)-N-(3-phenoxybenzyl)pyrazolo[1,5-a][1,3,5]triazin-4-amine [ No CAS ]
  • 57
  • [ 6025-60-1 ]
  • [ 50742-37-5 ]
  • 4-(3-phenoxyphenyl)pyrrolo[1,2-a]quinoxaline [ No CAS ]
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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • Acetal Formation • Amides Can Be Converted into Aldehydes • Amine Synthesis from Nitriles • Amine Synthesis from Nitriles • Amines Convert Acyl Chlorides into Amides • Amines Convert Esters into Amides • Azide Reduction by LiAlH4 • Azide Reduction by LiAlH4 • Basicity of Amines • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Chichibabin Reaction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Deprotonation of Methylbenzene • Diazotization Reaction • DIBAL Attack Nitriles to Give Ketones • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Enamine Formation • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Grignard Reagents Transform Esters into Alcohols • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hofmann Elimination • Hofmann Rearrangement • Hydride Reductions • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Leuckart-Wallach Reaction • Mannich Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitration of Benzene • Nitrosation of Amines • Nomenclature of Ethers • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Peptide Bond Formation with DCC • Petasis Reaction • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Ethers • Preparation of LDA • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reductive Amination • Reductive Amination • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Ring Opening of Azacyclopropanes • Ring Opening of Azacyclopropanes • Ring Opening of Oxacyclobutanes • Ring Opening of Oxacyclopropane • Specialized Acylation Reagents-Vilsmeier Reagent • Strecker Synthesis • Sulfonation of Benzene • Synthesis of 2-Amino Nitriles • Synthesis of Alcohols from Tertiary Ethers • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • The Nucleophilic Opening of Oxacyclopropanes • Ugi Reaction • Vilsmeier-Haack Reaction
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; ;