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[ CAS No. 1988-15-4 ] {[proInfo.proName]}

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Chemical Structure| 1988-15-4
Chemical Structure| 1988-15-4
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Quality Control of [ 1988-15-4 ]

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Product Details of [ 1988-15-4 ]

CAS No. :1988-15-4 MDL No. :MFCD00995944
Formula : C12H19NO Boiling Point : -
Linear Structure Formula :- InChI Key :OIYNNJHEBQIVIJ-UHFFFAOYSA-N
M.W : 193.29 Pubchem ID :818538
Synonyms :

Calculated chemistry of [ 1988-15-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 62.03
TPSA : 46.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 3.14
Log Po/w (WLOGP) : 3.23
Log Po/w (MLOGP) : 2.67
Log Po/w (SILICOS-IT) : 2.63
Consensus Log Po/w : 2.8

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.2
Solubility : 0.121 mg/ml ; 0.000628 mol/l
Class : Soluble
Log S (Ali) : -3.78
Solubility : 0.032 mg/ml ; 0.000166 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.11
Solubility : 0.149 mg/ml ; 0.000771 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 1988-15-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1988-15-4 ]

* 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 [ 1988-15-4 ]

[ 1988-15-4 ] Synthesis Path-Downstream   1~23

  • 1
  • [ 1576-14-3 ]
  • [ 1988-15-4 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 2,6-Diisopropyl-4-nitrophenol With hydrogenchloride; tin In ethanol Reflux; Stage #2: With sodium hydroxide In water 4-Amino-propofol:; 4-Nitropropofol (0.368 g, 1.6 mmol) was dissolved in EtOH (2.8 mL) and concentrated HCI (7.5 mL.) An excess of tin granules (1.4 g) was added and the reaction mixture was heated to reflux. A colour change from pale yellow to colourless was observed. After one hr, the reaction mixture was filtered through a cellite pad. Solvent was removed under reduced pressure and the resultant residue was redissolved in water (50 ml). Aqueous sodium hydroxide was added dropwise until the solution was basic by universal indicator paper, (pH 12-15). The solution was then extracted with DCM (3 x 25 ml_). The organic extracts were combined, washed with brine, dried over sodium sulphate and the solvent removed to give 320 mg of analytically pure purple oil 98%. 1H NMR δ 6.45 (s, 2H), 4.75 (s, 1 H) 3.4 (br s, 2H) 3.1 (m, 2H) 1.3 (d, 12H). 13C NMR δ 140.45, 138.72, 136.48, 1 12.02, 27.70, 23.01. HRMS (Cl) C12H22N2O [M+NH4]+ requires 210.3093 found 210.3097. Anal C12H18NO requires C: 74.56% H: 9.91 % N: 7.24% found C: 74.36% H: 9.95% N: 7.23%.
35% With hydrogenchloride; iron; ammonium chloride In ethanol; water 74.74-2 Step 74-2: 2,6-Diisopropyl-4-aminophenol. Prepared according to the method of step 2 in Example 5, using iron powder (1.12g, 20.05mmol), EtOH (6.50mL), concentrated HCl (aqueous solution) (0.17mL), 25% NH4Cl (aqueous solution) (3.26mL) and 2, 6-Diisopropyl-4-nitrophenol (0.400g, 1.79mmol), purified by flash column chromatography (4:1 hexane:EtOAc), to obtain the title compound (0.090g, 35%), yellow viscous Oil, its color quickly turns black (the sample is stored in the refrigerator and freezer, and used within 24h).
With ammonium hydroxide; sodium dithionite
YieldReaction ConditionsOperation in experiment
2,6-Diisopropyl-4-nitroso-phenol, A., 50-60grad, wss. Na2S2O4;
4-Nitro-2,6-diisopropyl-phenol, Na2S, Aethylenglykol;
aus entspr. Sulfat, Na2S;
  • 3
  • [ 1988-15-4 ]
  • [ 98-60-2 ]
  • [ 63301-14-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate
  • 4
  • [ 1988-15-4 ]
  • [ 98-59-9 ]
  • [ 1988-12-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate
  • 5
  • [ 1988-15-4 ]
  • [ 98-68-0 ]
  • [ 75531-59-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate
  • 6
  • [ 1988-15-4 ]
  • [ 98-74-8 ]
  • [ 75531-64-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate
  • 7
  • [ 1988-15-4 ]
  • [ 933-01-7 ]
  • N-4-chlorophenylthio-2,6-diisopropyl-1,4-benzoquinonimine [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With triethylamine
With triethylamine In diethyl ether
  • 8
  • [ 1988-15-4 ]
  • [ 75531-74-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaHCO3 2: 25 percent / lead tetraacetate / acetic acid
  • 9
  • [ 1988-15-4 ]
  • [ 75531-77-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaHCO3 2: 29 percent / lead tetraacetate / acetic acid
  • 10
  • [ 1988-15-4 ]
  • [ 75531-75-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaHCO3 2: 34 percent / lead tetraacetate / acetic acid
  • 11
  • [ 1988-15-4 ]
  • [ 75531-81-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaHCO3 2: 31 percent / lead tetraacetate / acetic acid
  • 12
  • [ 79822-24-5 ]
  • [ 1988-15-4 ]
  • 5-[4-chloro-3-(3,5-diisopropyl-4-hydroxyphenylsulfamoyl)phenyl]-5-hydroxy-1-methyl-2-pyrrolidone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In water; ethyl acetate 1.c (c) (c) 5-(4-Chloro-3-(3,5-diisopropyl-4-hydroxyphenylsulfamoyl)-phenyl)-5-hydroxy-1-methyl-2-pyrrolidone A suspension of 29.1 g of 4-amino-2,6-diisopropylphenol in 450 ml of ethyl acetate is added in portions to a solution of 17.5 g of 5-(4-chloro-3-chlorosulfonylphenyl)-5-hydroxy-1-methyl-2-pyrrolidone and 22.7 g of triethylamine in 200 ml of ethyl acetate. The mixture is stirred at 50° C. for 3 hours, cooled, water is added, the organic phase is separated off, and the aqueous phase is extracted several times with ethyl acetate. The combined organic phases are washed with water and dried over sodium sulfate, and the solvent is distilled off. After addition of about 250 ml of methylene chloride to the amorphous red residue it is refluxed and crystallization is induced by scratching. The mixture is stirred at room temperature for 30 min, and the precipitate is filtered off and recrystallized from acetonitrile without prolonged standing. Colorless crystals of melting point 198°-200° C.
  • 13
  • [ 937-32-6 ]
  • [ 1988-15-4 ]
  • [ 1104591-06-1 ]
YieldReaction ConditionsOperation in experiment
25% With triethylamine In diethyl ether
  • 14
  • [ 13088-17-0 ]
  • [ 1988-15-4 ]
  • [ 1104591-45-8 ]
YieldReaction ConditionsOperation in experiment
51% Stage #1: 4-nitro-benzenesulfinyl chloride; 2,6-diisopropyl-4-aminophenol With triethylamine In diethyl ether for 0.166667h; Stage #2: With silver(l) oxide In acetone for 0.5h; Further stages.;
  • 15
  • [ 1988-15-4 ]
  • [ 103-71-9 ]
  • [ 1174550-03-8 ]
YieldReaction ConditionsOperation in experiment
29% In 1,4-dioxane at 100℃;
  • 16
  • [ 1988-15-4 ]
  • [ 100251-91-0 ]
YieldReaction ConditionsOperation in experiment
67% With hydrogenchloride In 1,4-dioxane; diethyl ether 4-Aminopropofol-hydrochloride:; 4-Amino propofol (310 mg, 1.6 mmol) was dissolved in Et2O (100 ml_). Concentrated HCI (5ml_) dissolved in 1 ,4-dioxane (25 ml_) was added dropwise with stirring. After 1 Hr the mixture is allowed to settle into two layers, the bottom layer is recovered and solvent removed under reduce pressure to a pink crystalline solid (250 mg, 67%) and is used without further analysis.
  • 17
  • [ 1988-15-4 ]
  • [ 407-25-0 ]
  • 4-trifluoroacetamide-propofol [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With pyridine In ethyl acetate at 60℃; for 0.5h; 4-Triflouroacetamide-propofol:; 4-Aminopropofol (200 mg, 1.04 mmol) was dissolved in EtOAc (40 ml_). Pyridine (0.25 ml_, 3mmol) was added followed by triflouroacetic anhydride (0.2 ml_, 1 mmol). The reaction mixture was heated to 60° C for 30 mins. Upon cooling, solvent was removed under reduced pressure, the residue was redissolved in DCM (50 ml_), washed successively with water and brine and dried over sodium sulphate. After removal of solvent, 4-triflouroacetamidopropofol was recovered as a pale pink crystalline solid (205 mg, 75%). 1H NMR δ 7.16 (s, 2H), 6.3 (br s, 1 H), 5.0 (1 H, s), 3.2 (m, 2H), 1.3 (d, J = 6.9 Hz, 12H). 13C NMR δ 155.18, 144.28, 138.05, 130.51 , 117.03, 1 15.85, 27.78, 23.12. HRMS (El): C14H18F3NO2 [M+H]+ requires 306.2751 , found 306.2747. Anal. Ci4H18F3NO2 requires C: 58.12, H: 6.27, N: 4.84, found C: 58.1 1 , H: 6.25, N: 4.83.
  • 18
  • [ 1988-15-4 ]
  • [ 108-24-7 ]
  • [ 1988-14-3 ]
YieldReaction ConditionsOperation in experiment
In methanol at 20℃; for 0.5h; 5 5.3.5
N-(3,5-Di-iso-propyl-4-hydroxyphenyl)-acetamide 5 General procedure: Anhydride method-To a solution of phenols 16a-c or naphthols 20a,b (5 mmol) in CH3OH (20 mL), the proper anhydride was added (10 mmol). After stirring for 0.5 h at rt the reaction was quenched with ice, the precipitate filtered and washed with H2O. The crude residue was then purified by CC (petroleum ether (40-70°)/Et2O: 7/3) followed by crystallization to afford products 1-3, 5-6, 12-13. White needles. IR (KBr-DRIFTS): 3450, 3283, 1636; 1H NMR (DMSO-d6): δ (ppm) 1.13 (d, J=6.8, 12H, 4* CH3), 1.98 (s, 3H, CH3CO), 3.29 (spt, J=6.8, 2H, 2* CH3CHCH3), 7.21 (s, 2H, H-C(6), H-C(2)), 7.80 (s, 1H, OH), 9.60 (s, 1H, NH); 13C NMR (DMSO-d6): δ (ppm) 167.3 (C=O), 146.2 (C(4)), 135.4 (C(5), C(3)), 132.0 (C(1)), 114.5 (C(6), C(2)), 26.1 (2* CH3CHCH3), 23.7 (CH3CO), 22.8 (4* CH3); mp: 168.6-169.5 °C (EtOH/H2O) (lit. 45 165-166 °C). Anal. Calcd for C14H21NO2: C, 71.46; H, 8.99; N, 5.95. Found: C, 71.33; H, 8.98; N, 6.11.
  • 19
  • [ 2078-54-8 ]
  • [ 1988-15-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,6-diisopropylphenol With hydrogenchloride; sodium hydroxide; sodium carbonate; sodium nitrite; 4-aminobenzene sulfonic acid In water at 0℃; for 1h; Stage #2: With sodium dithionite In water at 80℃; 5.2 General procedure for the preparation of compounds 16a-d and 20a,b General procedure: To a vigorously stirred solution of sulfanilic acid (7.8 g, 45 mmol) in H2O (50 mL) and anhydrous Na2CO3 (2.2 g, 21 mmol), a solution of 5 M NaNO2 (13.5 mL, 67.5 mmol) was added dropwise maintaining the temperature at 10-15 °C. The reaction mixture was then cooled and poured into a solution of 12 M HCl (9.0 mL, 0.11 mol) at 0 °C and stirred at 0 °C for 20 min until the amine has been diazotized. (0037) To a solution of NaOH (9.0 g, 0.22 mol) in H2O (50 mL) phenols 15a-d or naphthols 19a,b (42 mmol) were added. To this stirred solution, cooled to 5 °C, the diazo solution was added in small portions; the colour of the mixture changed to red. Stirring was continued at 0 °C for 1 h. The reaction mixture was then warmed to 80 °C and Na2S2O4 (20 g, 0.11 mol) was added in small quantities until the colour of the solution changed from red to yellow. Compounds 16a-d, 20a,b precipitated, the reaction mixture was filtered
Multi-step reaction with 2 steps 1: nitric acid / hexane / 1 h / 0 - 20 °C 2: hydrogenchloride; iron; ammonium chloride / water; ethanol
  • 20
  • [ 1240390-28-6 ]
  • [ 1988-15-4 ]
  • [ 216854-23-8 ]
  • C22H32N6O2*(x)ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 2,4-dichloro-pyrimidine-5-carboxylic acid amide; 2,6-diisopropyl-4-aminophenol With triethylamine In 1,4-dioxane; N,N-dimethyl-formamide at 50℃; for 2h; Stage #2: tert-butyl (S)-piperidin-3-yl-carbamate With triethylamine In 1,4-dioxane; N,N-dimethyl-formamide at 50℃; for 1h; Stage #3: With hydrogenchloride In 1,4-dioxane; diethyl ether at 20℃; 74.74-3 Step 74-3: (S)-2-(3-Aminopiperidin-1-yl)-4-((4-hydroxy-3,5-diisopropylphenyl)amino)pyrimidine-5-carboxamide . Combine 2,6-diisopropyl-4-aminophenol (0.085g, 0.44mmol), 2,4-dichloropyrimidine-5-carboxamide (0.084g, 0.44mmol), triethylamine (0.13mL, 0.93 mmol) was dissolved in anhydrous dioxane (5.0 mL) and DMF (1.0 mL). The mixture was heated at 50°C for 2 h, and then cooled to room temperature. Tert-butyl (S)-piperidin-3-yl carbamate (0.088 g, 0.44 mmol) and triethylamine (0.13 mL, 0.93 mmol) were added, and the reaction mixture was heated at 50° C. for 1 h. The reaction mixture was diluted with EtOAc (15 mL) and washed successively with water (3×10 mL) and brine (10 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to obtain a crude product, which was purified by silica flash column chromatography (1:4 hexane: EtOAc), and the product was obtained by two replacements. The intermediate was dissolved in Et2O (10.0 mL), and 4M HCl in dioxane (5.0 mL) was added dropwise, and the mixture was stirred at room temperature overnight. Hexane (15 mL) was added, the precipitate was filtered and dried to obtain the hydrochloride salt of the title compound as a pale yellow powder (0.154 g, 80%).
  • 21
  • [ 1988-15-4 ]
  • [ 74-88-4 ]
  • 1,3-diisopropyl-2-methoxy-5-nitrobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.315 g Stage #1: 2,6-diisopropyl-4-aminophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; Cooling with ice; 75.75-1 Step 75-1: 1,3-Diisopropyl-2-methoxy-5-nitrobenzene. 2,6-Diisopropyl-4-aminophenol (0.287g, 1.29mmol) was added to the flask, which was then flushed with N2 for 15 minutes. Anhydrous DMF (5.0 mL) was added, and the mixture was cooled to 0°C. Sodium hydride (60% dispersion in mineral oil, 0.154 g, 3.85 mmol) was added and the reaction mixture was stirred for 30 minutes. Methyl iodide (0.24 mL, 3.86 mmol) was added dropwise, the cooling bath was removed, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc (40 mL) and washed successively with water (7×30 mL) and brine (20 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to obtain a crude product without further purification (0.315 g, quantitative).
  • 22
  • [ 1988-15-4 ]
  • [ 3883-87-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C / Cooling with ice 2.1: ammonium chloride; zinc / water; tetrahydrofuran / 2.5 h / 0 - 20 °C
  • 23
  • [ 1988-15-4 ]
  • C23H34N6O2*(x)ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C / Cooling with ice 2.1: ammonium chloride; zinc / water; tetrahydrofuran / 2.5 h / 0 - 20 °C 3.1: triethylamine / N,N-dimethyl-formamide; 1,4-dioxane / 2 h / 50 °C 3.2: 50 °C 3.3: 6 h / 20 °C
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