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Chemical Structure| 134855-87-1 Chemical Structure| 134855-87-1

Structure of 134855-87-1

Chemical Structure| 134855-87-1

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Product Details of [ 134855-87-1 ]

CAS No. :134855-87-1
Formula : C8H11NO
M.W : 137.18
SMILES Code : OC1=CC=C(C(N)C)C=C1
MDL No. :MFCD00143209

Safety of [ 134855-87-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 134855-87-1 ]

* 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 [ 134855-87-1 ]

[ 134855-87-1 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 6298-96-0 ]
  • [ 134855-87-1 ]
  • 2
  • [ 134855-87-1 ]
  • 1-(1-benzoylamino-ethyl)-4-benzoyloxy-benzene [ No CAS ]
  • 3
  • [ 134855-87-1 ]
  • [ 98-88-4 ]
  • 1-(1-benzoylamino-ethyl)-4-benzoyloxy-benzene [ No CAS ]
  • 4
  • [ 34523-34-7 ]
  • sodium amalgam [ No CAS ]
  • methanolic acetic acid [ No CAS ]
  • [ 134855-87-1 ]
  • 7
  • [ 134855-87-1 ]
  • [ 50913-12-7 ]
  • C19H30N6O6 [ No CAS ]
  • 8
  • [ 2459-05-4 ]
  • [ 119072-55-8 ]
  • [ 134855-87-1 ]
  • [ 630-19-3 ]
  • C24H36N2O5 [ No CAS ]
  • 9
  • [ 2459-05-4 ]
  • [ 119072-55-8 ]
  • [ 134855-87-1 ]
  • [ 630-19-3 ]
  • (E)-ethyl 4-((1-(tert-butylamino)-3,3-dimethyl-1-oxobutan-2-yl)(1-(4-hydroxyphenyl)ethyl)amino)-4-oxobut-2-enoate [ No CAS ]
  • 10
  • [ 134855-87-1 ]
  • C14H22N6O4 [ No CAS ]
  • 11
  • [ 134855-87-1 ]
  • (R)-Nα-diphenylacetyl-NG-nitro-N-[(RS)-1-(4-hydroxyphenyl)ethyl]argininamide [ No CAS ]
  • 12
  • [ 134855-87-1 ]
  • (R)-Nα-diphenylacetyl-N-[(RS)-1-(4-hydroxyphenyl)-ethyl]argininamide acetate [ No CAS ]
  • 13
  • [ 134855-87-1 ]
  • <i>N</i>-[1-(4-hydroxy-phenyl)-ethyl]-benzamide [ No CAS ]
  • 14
  • [ 24424-99-5 ]
  • [ 134855-87-1 ]
  • [ 763932-69-0 ]
YieldReaction ConditionsOperation in experiment
64% With triethylamine; In tetrahydrofuran; for 15.08h; 16) l-(4-[(2S)-2-methoxypropyl]oxy}phenyl)ethanamineA. fert-butyl [l-(4-hydroxyphenyl)ethyl]carbamateTo l-(4-hydroxyphenyl)ethanamine (0.96 g, 7.0 mmol) in THF (20 mL) triethylamine (2.9 mL, 21 mmol) was added followed by the addition of di-tert-butyl dicarbonate (1.8 g, 8.4 mmol) in THF (20 mL) during 5 minutes. The resulting mixture was stirred for 15 hours, the volatiles removed under reduced pressure and the residue purified by silica gel column chromatography using a gradient of heptanes : ethyl acetate 9:1 to 1:1 affording 1.1 g of the tert-butyl [l-(4-hydroxyphenyl)ethyl]carbamate (64 %). 1H NMR (400 MHz, DMSO- d6) delta ppm 9.18 (s, 1 H) 7.18 (d, J=7.78 Hz5 1 H) 7.03 - 7.11 (m, J=8.41 Hz5 2 H) 6.63 - 6.72 (m, 2 H) 4.45 - 4.56 (m, 1 H) 1.35 (s, 9 H) 1.25 (d, J=7.03 Hz5 3 H) MS (ESI) m/z: 238 [M+H]
With sodium hydroxide; In ethanol; water; at 20℃; for 4.5h; To a solution of <strong>[134855-87-1]4-(1-aminoethyl)phenol</strong> (1.0 g) in ethanol (24 mL) were added di-t-butyl dicarbonate (4.77 g) and sodium hydroxyde (146 mg) at 0C and the solution was stirred at room temperature for 4.5 hours. The reaction solution was concentrated and water was added thereto. The solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (hexane: ethyl acetate=7:1) to give the title compound (2.18 g) having the following physical data. TLC:Rf 0.88 (chloroform:methanol=5:1); NMR (CDCl3): delta 1.36-1.50 (m, 13H), 4.79 (m, 1H), 7.10-7.18 (m, 2H), 7.26-7.32 (m, 2H).
  • 15
  • [ 34523-34-7 ]
  • [ 134855-87-1 ]
YieldReaction ConditionsOperation in experiment
29.2 g (64.6%) With sodium hydroxide;palladium; In water; acetic acid; ethyl acetate; acetone; (b) 10.0 g of 10% w/w palladium-on-charcoal were added to a solution of 50.0 g (0.33 mole) of p-hydroxyacetophenone oxime [prepared as described in step (a) above] in 400 ml of acetic acid, and the mixture was subjected top catalytic hydrogenation for 8 hours. The catalyst was filtered off, the filtered solid was washed with 100 ml of acetic acid, and the filtrate and the washings were combined and concentrated by evaporation under reduced pressure. The residue was dissolved in 400 ml of water, washed with 400 ml of ethyl acetate and then adjusted to a pH value of 10.10 by the addition of a 20% w/v aqueous solution of sodium hydroxide, whilst cooling at a temperature between 5 and 10 C. the crystals which precipitated were collected by filtration, and washed, in turn, with 100 ml of cold water and 200 ml of acetone, to give 29.2 g (64.6%) of (R,S)-alpha-methyl-p-hydroxybenzylamine in the form of a colorless powder melting at 124-126 C.
With hydrogen;palladium 10% on activated carbon; In ethanol; under 760.051 Torr; First step, hydroxyamine hydrochloride (5.07 g) and NaOAc (12.05 g) were added to a solution of 4-hydroxyacetophenone (5 g) in EtOH (80 ml). The reaction mixture was stirred at 60C for 6 h. EtOH was removed under reduced pressure. H2O (40 ml) was added to the residue, and extracted with EtOAc (3 × 40 ml). The EtOAc of the combined organic layer was removed by rotary evaporation under reduced pressure to yield 4-hydroxyacetophenone oxime (4.53 g) as a pale yellowish solid. Second step, a solution of 4-hydroxyacetophenone oxime (4.53 g) in EtOH (50 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (502 mg). The reaction solution was filtered and the filtrate was concentrated to yield the 1-(4-hydroxyphenyl)-ethylamine (5.2 g) as a white solid. Third step, a mixture of 1-(4-hydroxyphenyl)-ethylamine (288 mg), 6-chloropurine riboside (200 mg) and triethylamine (3 ml) in PrOH (60 ml) was heated to 70C for 8h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (20 : 1) to yield N6-[(+/-)-1-(4-hydroxyphenyl)-ethyl] -adenosine(220 mg) as a white solid: positive ESIMS m/z 388 [M + H]+[Show Image] 410 [M + Na]+; negative ESIMS m/z 386 [M - H]-; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety delta 8.36 (1H, s, H-2), 8.17 (1H, s, H-8), 8.12 (1H, d, J= 8.4 Hz, -NH), 5.88 (1H, d, J= 5.7 Hz, H-1), 5.45 (2H, m, 2×-OH), 5.19 (1H, d, J = 4.5 Hz, -OH), 4.60 (1H, m, H-2'), 4.15 (1H, m, H-3'), 3.97 (1H, m, H-4'), 3.66 (1H, m, H-5a'), 3.55 (1H, m, H-5'b); the (+/-)-1-(4-hydroxyphenyl)-ethyl moiety delta 9.27 (1H, s, -OH), 7.23 (1H, d, J = 8.1 Hz, H-2", H-6"), 6.67 (1H, d, J = 8.1 Hz, H-3", H-5"), 5.42 (1H, m, H-7"), 1.49 (1H, d, J= 6.9 Hz, H-8"); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety delta 153.8 (s, C-6), 152.3 (d, C-2), 148.5 (s, C-4), 139.8 (d, C-8), 119.7 (s, C-5), 88.0 (d, C-1), 86.0 (d, C-4'), 73.6 (d, C-2'), 70.7 (d, C-3'), 61.8 (t, C-5'); the (+/-)-1-(4-hydroxyphenyl)-ethyl moiety delta 156.1 (s, C-4"), 135.3 (s, C-1), 127.3 (d, C-2", C-6"), 114.9 (d, C-3", C-5"), 48.3 (d, C-7"), 22.5 (q, C-8")o
5.2 g With palladium 10% on activated carbon; hydrogen; In ethanol; under 760.051 Torr; Second step, a solution of 4-hydroxyacetophenone oxime (4.53 g) in EtOH (50 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (502 mg). The reaction solution was filtered and the filtrate was concentrated to yield the 1-(4-hydroxyphenyl)-ethylamine (5.2 g) as a white solid.
5.2 g With palladium 10% on activated carbon; hydrogen; In ethanol; 4-hydroxyacetophenone oxime (4.53 g) was dissolved in EtOH (50 mL), Dissolved in 10% Pd / C (502 mg), hydrogenated under normal pressure,Pd / C was scraped off with the reaction solution, and the filtrate was steamed dry to obtain yellow liquid 4-hydroxybenzene (5.2 g).

  • 16
  • [ 134855-87-1 ]
  • [ 159596-50-6 ]
  • [ 1105677-12-0 ]
  • 17
  • [ 134855-87-1 ]
  • [ 108-24-7 ]
  • N-[1-(4-hydroxy-phenyl)-ethyl]-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.05 g In tetrahydrofuran; at 20℃; for 0.5h; A mixture of acetic anhydride (0.825 ml), <strong>[134855-87-1]4-(1-aminoethyl)phenol</strong> (1 g) and THF (40 ml) was stirred at room temperature for 30 min. The mixture was extracted with water and ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.05 g). MS: [M+H]+ 180.2.
  • 18
  • [ 134855-87-1 ]
  • [ 1268607-91-5 ]
  • 19
  • [ 134855-87-1 ]
  • [ 1268609-69-3 ]
  • 20
  • [ 4316-94-3 ]
  • [ 134855-87-1 ]
  • [ 1268609-68-2 ]
YieldReaction ConditionsOperation in experiment
84% With triethylamine; In N,N-dimethyl-formamide; at 25℃; for 2.0h; 1. 4-[1-(6-Amino-5-nitropyrimidin-4-ylamino)-ethyl]-phenol. 4-Amino-5-nitro-6-chloropyrimidine (5.0 g, 29 mmol), <strong>[134855-87-1]4-(1-aminoethyl)phenol</strong> (4.3 g, 32 mmol) and Et3N (4.5 mL, 3.2 g, 32 mmol) were combined in anhydrous DMF (30 mL). After stirring 2 h at 25 C., the mixture was poured into dilute citric acid (150 mL; pH ca. 3) and the precipitated product was collected by suction filtration and washed with H2O. The solid was recrystallized from a refluxing mixture of H2O (100 mL) and EtOH (50 mL) to yield 6.6 g (84%).
84% With triethylamine; In N,N-dimethyl-formamide; at 25℃; for 2.0h; 4-Amino-5-nitro-6- chloropyrimidine (5.0 g, 29 mmol), 4-(l-aminoethyl)phenol (4.3 g, 32 mmol) and Et3N (4.5 mL, 3.2 g, 32 mmol) were combined in anhydrous DMF (30 mL). After stirring 2 h at 25 0C, the mixture was poured into dilute citric acid (150 mL; pH ca. 3) and the precipitated product was collected by suction filtration and washed with H2O. The solid was recrystallized from a refluxing mixture Of H2O (100 mL) and EtOH (50 mL) to yield 6.6 g (84%).
  • 22
  • [ 134855-87-1 ]
  • [ 2004-06-0 ]
  • N6-[1-(4-hydroxyphenyl)ethyl]adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In propan-1-ol; at 70℃; for 8.0h; First step, hydroxyamine hydrochloride (5.07 g) and NaOAc (12.05 g) were added to a solution of 4-hydroxyacetophenone (5 g) in EtOH (80 ml). The reaction mixture was stirred at 60C for 6 h. EtOH was removed under reduced pressure. H2O (40 ml) was added to the residue, and extracted with EtOAc (3 × 40 ml). The EtOAc of the combined organic layer was removed by rotary evaporation under reduced pressure to yield 4-hydroxyacetophenone oxime (4.53 g) as a pale yellowish solid. Second step, a solution of 4-hydroxyacetophenone oxime (4.53 g) in EtOH (50 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (502 mg). The reaction solution was filtered and the filtrate was concentrated to yield the 1-(4-hydroxyphenyl)-ethylamine (5.2 g) as a white solid. Third step, a mixture of 1-(4-hydroxyphenyl)-ethylamine (288 mg), 6-chloropurine riboside (200 mg) and triethylamine (3 ml) in PrOH (60 ml) was heated to 70C for 8h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (20 : 1) to yield N6-[(+/-)-1-(4-hydroxyphenyl)-ethyl] -adenosine(220 mg) as a white solid: positive ESIMS m/z 388 [M + H]+[Show Image] 410 [M + Na]+; negative ESIMS m/z 386 [M - H]-; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety delta 8.36 (1H, s, H-2), 8.17 (1H, s, H-8), 8.12 (1H, d, J= 8.4 Hz, -NH), 5.88 (1H, d, J= 5.7 Hz, H-1), 5.45 (2H, m, 2×-OH), 5.19 (1H, d, J = 4.5 Hz, -OH), 4.60 (1H, m, H-2'), 4.15 (1H, m, H-3'), 3.97 (1H, m, H-4'), 3.66 (1H, m, H-5a'), 3.55 (1H, m, H-5'b); the (+/-)-1-(4-hydroxyphenyl)-ethyl moiety delta 9.27 (1H, s, -OH), 7.23 (1H, d, J = 8.1 Hz, H-2", H-6"), 6.67 (1H, d, J = 8.1 Hz, H-3", H-5"), 5.42 (1H, m, H-7"), 1.49 (1H, d, J= 6.9 Hz, H-8"); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety delta 153.8 (s, C-6), 152.3 (d, C-2), 148.5 (s, C-4), 139.8 (d, C-8), 119.7 (s, C-5), 88.0 (d, C-1), 86.0 (d, C-4'), 73.6 (d, C-2'), 70.7 (d, C-3'), 61.8 (t, C-5'); the (+/-)-1-(4-hydroxyphenyl)-ethyl moiety delta 156.1 (s, C-4"), 135.3 (s, C-1), 127.3 (d, C-2", C-6"), 114.9 (d, C-3", C-5"), 48.3 (d, C-7"), 22.5 (q, C-8")o
220 mg With triethylamine; In propan-1-ol; at 70℃; for 8.0h; Third step, a mixture of 1-(4-hydroxyphenyl)-ethylamine (288 mg), 6-chloropurine riboside (200 mg) and triethylamine (3 ml) in PrOH (60 ml) was heated to 70 C. for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (20:1) to yield N6-[(+/-)-1-(4-hydroxyphenyl)-ethyl]-adenosine (220 mg) as a white solid: positive ESIMS m/z 388 [M+H]+ 410 [M+Na]+; negative ESIMS m/z 386 [M-H]-; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety delta 8.36 (1H, s, H-2), 8.17 (1H, s, H-8), 8.12 (1H, d, J=8.4 Hz, -NH), 5.88 (1H, d, J=5.7 Hz, H-1'), 5.45 (2H, m, 2*-OH), 5.19 (1H, d, J=4.5 Hz, -OH), 4.60 (1H, m, H-2'), 4.15 (1H, m, H-3'), 3.97 (1H, m, H-4'), 3.66 (1H, m, H-5a'), 3.55 (1H, m, H-5'b); the (+-)-1-(4-hydroxyphenyl)-ethyl moiety delta 9.27 (1H, s, -OH), 7.23 (1H, d, J=8.1 Hz, H-2", H-6"), 6.67 (1H, d, J=8.1 Hz, H-3", H-5"), 5.42 (1H, m, H-7"), 1.49 (1H, d, J=6.9 Hz, H-8"); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety delta 153.8 (s, C-6), 152.3 (d, C-2), 148.5 (s, C-4), 139.8 (d, C-8), 119.7 (s, C-5), 88.0 (d, C-1'), 86.0 (d, C-4'), 73.6 (d, C-2'), 70.7 (d, C-3'), 61.8 (t, C-5'); the (+-)-1-(4-hydroxyphenyl)-ethyl moiety delta 156.1 (s, C-4"), 135.3 (s, C-1"), 127.3 (d, C-2", C-6"), 114.9 (d, C-3", C-5"), 48.3 (d, C-7"), 22.5 (q, C-8").
220 mg With triethylamine; In propan-1-ol; at 70℃; for 8.0h; 4-hydroxybenzene(288 mg) was dissolved in n-propyl alcohol (60 mL), 6-chloropurine nucleoside (200 mg) and triethylamine (3 ml) were added, heated to 70 C. and reacted for 8 h. The solvent was evaporated with the reaction solution, chromatographed through a silica gel column and eluted with chloroform-methanol (20: 1) to give a white solidWas obtained to obtain N6-[1-(4-hydroxycyclohexylphenyl ketone)-ethyl]-adenosine (220 mg)
  • 23
  • [ 134855-87-1 ]
  • [ 134855-88-2 ]
  • [ 99-93-4 ]
  • 25
  • [ 134855-87-1 ]
  • [ 221670-72-0 ]
  • [ 134855-88-2 ]
YieldReaction ConditionsOperation in experiment
87.9% With ammonia; sodium acetate; zinc; In ethanol; for 3.0h;Reflux; General procedure: The acetophenone oxime (VI-1, 3.12 g, 23.11 mmol) was dissolved in 140 ml of absolute ethanol,(7.51 g, 115.56 mmol) and sodium acetate (1.78 g, 23.11 mmol), respectively,Stir evenly. Add 70ml of ammonia, heating reflux 1h, stop the reaction. Desolate out part of the ethanol,Add 100ml water dilution, 1M dilute hydrochloric acid PH to 2 ~ 3, 50ml ether washing once,15% NaOH solution adjusted to 12 ~ 13, ethyl acetate extraction (80 × 4), combined organic phase,Dried over anhydrous MgSO4 and desolved to give 2.24 g of a yellow liquid, 80.0% yield.
  • 27
  • [ 134855-87-1 ]
  • N-(1-(4-((4-(3-(cyclopropylmethoxy)phenoxy)-2,6-difluorobenzyl)oxy)phenyl)ethyl)acetamide [ No CAS ]
  • 28
  • [ 134855-87-1 ]
  • N-(1-(4-((4-(3-(cyclopropylmethoxy)phenoxy)-2-fluorobenzyl)oxy)phenyl)ethyl)acetamide [ No CAS ]
  • 29
  • [ 134855-87-1 ]
  • [ 221670-72-0 ]
  • 30
  • [ 134855-87-1 ]
  • [ 221670-72-0 ]
  • [ 99-93-4 ]
  • 31
  • [ 134855-87-1 ]
  • [ 1730-25-2 ]
  • C11H15NO [ No CAS ]
  • 32
  • [ 3383-21-9 ]
  • [ 134855-87-1 ]
  • 4-(6,8-di-tert-butyl-2H-benzo[b][1,4]oxazin-3-yl)phenol [ No CAS ]
  • 33
  • [ 3383-21-9 ]
  • [ 134855-87-1 ]
  • C22H29NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 20℃;Inert atmosphere; General procedure: To a stirred solution of ortho-benzoquinone (0.825 mmol, 1.0equiv) in acetonitrile (4.0 mL), was added dropwise a solution ofprimary amine (0.825 mmol, 1.0 equiv) in acetonitrile (4.25 mL)over 5 min under an argon atmosphere. The deep green colouredsolution was stirred at room temperature for 2e8 h. Aftercompletion of the reaction, as indicated by TLC, the reactionmixture was cooled to 0C. To this, triethylamine (0.34 mL,2.48 mmol, 3 equiv) and iodine granules (0.419 g, 1.65 mmol, 2 eq),were added. The resulting mixture was stirred vigorously for10e60 min under argon atmosphere. Upon completion, the reac-tion mixture was diluted with water and extracted with EtOAc(3 5 mL). The combined organic layer was washed with aqueoussaturated sodium thiosulfate (1 10 mL) and brine (2 10 mL),respectively, dried over Na2SO4, ltered, and concentrated in vacuo.The crude residue was puried by silica gel column chromatog-raphy eluting with pentane:EtOAc (95:5e80:20 v:v) to afford thedesired benzo[1,4]oxazine product.
 

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