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[ CAS No. 2494-12-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 2494-12-4
Chemical Structure| 2494-12-4
Structure of 2494-12-4 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 2494-12-4 ]

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Product Details of [ 2494-12-4 ]

CAS No. :2494-12-4 MDL No. :MFCD00037174
Formula : C10H13NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :OFSAJYZMIPNPHE-UHFFFAOYSA-N
M.W : 195.22 Pubchem ID :100526
Synonyms :
NADA

Calculated chemistry of [ 2494-12-4 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 52.88
TPSA : 69.56 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.4
Log Po/w (XLOGP3) : -0.72
Log Po/w (WLOGP) : 0.78
Log Po/w (MLOGP) : 0.68
Log Po/w (SILICOS-IT) : 1.12
Consensus Log Po/w : 0.65

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.65
Solubility : 43.7 mg/ml ; 0.224 mol/l
Class : Very soluble
Log S (Ali) : -0.26
Solubility : 106.0 mg/ml ; 0.543 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.45
Solubility : 0.696 mg/ml ; 0.00356 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.21

Safety of [ 2494-12-4 ]

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

Application In Synthesis of [ 2494-12-4 ]

* 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 [ 2494-12-4 ]

[ 2494-12-4 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 2896-60-8 ]
  • [ 2494-12-4 ]
  • [ 136985-18-7 ]
YieldReaction ConditionsOperation in experiment
18.1% at 40℃; for 16h; 0.1 M potassium phosphate buffer pH 7.0, laccase;
  • 2
  • [ 1946-82-3 ]
  • [ 2494-12-4 ]
  • [ 146004-52-6 ]
  • [ 146004-53-7 ]
  • 3
  • [ 55174-61-3 ]
  • [ 2494-12-4 ]
YieldReaction ConditionsOperation in experiment
52% With boron tribromide In dichloromethane for 17h; Ambient temperature;
  • 4
  • [ 2494-12-4 ]
  • [ 76734-99-1 ]
YieldReaction ConditionsOperation in experiment
With Locusta migratoria; oxygen; edetate disodium Ambient temperature; 0.2M Na-acetate buffer, pH 5.5, overnight incubation;
  • 5
  • [ 6275-29-2 ]
  • [ 2494-12-4 ]
YieldReaction ConditionsOperation in experiment
90% With boron tribromide In dichloromethane at 0 - 20℃; for 20h;
52% With boron tribromide In dichloromethane for 17h; Ambient temperature;
45% With boron tribromide In dichloromethane at -78 - 18℃;
  • 6
  • [ 62-31-7 ]
  • [ 108-24-7 ]
  • [ 2494-12-4 ]
YieldReaction ConditionsOperation in experiment
77% With sodium acetate; In N,N-dimethyl-formamide; at 20℃; for 3.5h; General procedure: To a solution of catecholamine (5.28 mmol) in DMF (23 mL), was added NaOAc (0.43 g, 5.28 mmol) and Ac2O (500 ml, 5.29 mmol) and the mixture stirred for 3.5h at room temperature. The reaction was followed by thin layer chromatography (CH2Cl2/MeOH, 9:1); the spots were visualized using UV light and also a phosphomolydbic acid solution followed by heating. The solvent was evaporated and the crude mixture purified by flash chromatography on silica (CH2Cl2/MeOH, 9:1)
  • 7
  • [ 76734-99-1 ]
  • [ 2494-12-4 ]
  • [ 14522-07-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride at 40℃; for 1h;
  • 8
  • [ 2494-12-4 ]
  • [ 2497-02-1 ]
  • Nα-Acetyl-Nτ-<1-(3,4-dihydroxyphenyl)-2-N-acetylamino-ethyl>-histidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
8.1% With sodium phosphate at 40℃; for 16h; cuticle of larvae of the giant silkmoth Hyalophora cecropia;
  • 9
  • [ 2494-12-4 ]
  • [ 108-46-3 ]
  • [ 136985-27-8 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; potassium hexacyanoferrate(III) at 22℃; for 0.5h; Yield given;
  • 10
  • [ 2494-12-4 ]
  • 5-(2-acetamidoethyl)-2-hydroxy-1,4-benzoquinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With phosphate buffer pH 7.0; dihydrogen peroxide; horseradish peroxidase for 0.0833333h;
  • 11
  • [ 51-61-6 ]
  • [ 128459-09-6 ]
  • [ 2494-12-4 ]
YieldReaction ConditionsOperation in experiment
31% With sodium acetate In N,N-dimethyl-formamide for 4.5h; Ambient temperature;
  • 12
  • [ 2494-12-4 ]
  • [ 95-50-1 ]
  • 2-(2-acetylaminoethyl)dibenzo<b,e><1,4>dioxin [ No CAS ]
YieldReaction ConditionsOperation in experiment
With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; potassium carbonate 1.) dichloroethane, reflux, 16 h, 2.) DMF, room temperature, 15 h, 3.) CH3CN, irradiation, 3 h; Yield given. Multistep reaction;
  • 13
  • [ 2494-12-4 ]
  • N-acetyldopaminequinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; potassium chloride electrolysis;
With phenoloxidase from Lucilia cuprina pupae
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In methanol; chloroform-d1
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In d(4)-methanol at 18℃;
With silver(l) oxide In N,N-dimethyl-formamide at 0℃;
With mushroom tyrosinase In aq. phosphate buffer at 20℃; Enzymatic reaction; 2 4.2. General procedure for the enzymatic oxidation of catecholamines, followed by addition of the nitrogen nucleophile General procedure: Mushroom tyrosinase (0.2 mg, 1074 units) was added to a solution of catecholamine (20 mg) in 1 mL phosphate buffer (pH 7.4, 50 mM) at r.t. The color changed to yellow, indicating the formation of the corresponding o-quinone. The enzyme was removed from the reaction mixture using a 5 mL HitrapTM desalting column (GE Heathcare), eluted with water (20 mL). The yellow solution of catecholamine-quinone was then added dropwise to a solution of NAcHis (10 eq.) or Imid (10 eq.) in phosphate buffer (15 mL, pH 7.4, 50 mM), and the reaction mixture was stirred for 1 h. At the terminus of the reaction 1 mL of 88% formic acid was added, and the reaction mixture was carefully evaporated under reduced pressure. The resulting orange oil was dissolved in water and purified by reverse-phase (RP-18) modified silica gel column chromatography, using water (100 mL) and 50% MeOH (100 mL) as eluent. The fraction containing the product eluted with 50% MeOH and was purified by HPLC (see ESI).
With silver(l) oxide In acetone at 20℃; for 0.5h; 3.1 General procedure for oxidation nucleophilic trapping study General procedure: 5 equiv of Ag2O were added to a stirred solution of catecholamines in acetone at room temperature. After 30min (10min for NAΔDA), Ag2O was removed from the yellow reaction mixture via filtration. To the filtrate, 5 equiv of ethanethiol were added. Stirring was continued for 1h and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (5% MeOH/DCM) and/or semi-preparative reversed-phase HPLC/PDA method. All the purified compounds are brown oil unless specified otherwise

  • 14
  • [ 645-31-8 ]
  • [ 108-24-7 ]
  • [ 2494-12-4 ]
YieldReaction ConditionsOperation in experiment
With dmap In dichloromethane
In methanol; water; ethyl acetate at 20℃;
  • 15
  • [ 2494-12-4 ]
  • Kynuramine dihydrobromide [ No CAS ]
  • styelsamine B [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% Stage #1: N-acetyldopamine; Kynuramine dihydrobromide With cerium(III) chloride; silver(l) oxide In methanol; acetic acid at 40℃; for 1.5h; Stage #2: With hydrogenchloride In methanol; acetic acid at 90℃; for 0.5h; Further stages.;
  • 16
  • [ 2494-12-4 ]
  • [ 51-61-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Locusta migratoria, Na2EDTA, O2 / Ambient temperature; 0.2M Na-acetate buffer, pH 5.5, overnight incubation 2: 6M HCl / 3 h / 110 °C
Multi-step reaction with 2 steps 1: Locusta migratoria, Na2EDTA, O2 / Ambient temperature; 0.2M Na-acetate buffer, pH 5.5, overnight incubation 2: 1M HCl / 3 h / Heating
  • 17
  • [ 2494-12-4 ]
  • [ 499-61-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Locusta migratoria, Na2EDTA, O2 / Ambient temperature; 0.2M Na-acetate buffer, pH 5.5, overnight incubation 2: 6M HCl / 3 h / 110 °C
  • 18
  • [ 2494-12-4 ]
  • [ 29477-54-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Locusta migratoria, Na2EDTA, O2 / Ambient temperature; 0.2M Na-acetate buffer, pH 5.5, overnight incubation 2: 6M HCl / 3 h / 110 °C
Multi-step reaction with 2 steps 1: Locusta migratoria, Na2EDTA, O2 / Ambient temperature; 0.2M Na-acetate buffer, pH 5.5, overnight incubation 2: 1M HCl / 3 h / Heating
  • 19
  • [ 2494-12-4 ]
  • [ 14522-07-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Locusta migratoria, Na2EDTA, O2 / Ambient temperature; 0.2M Na-acetate buffer, pH 5.5, overnight incubation 2: conc HCl / 1 h / 40 °C
  • 20
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 135851-75-1 ]
  • [ 2494-12-4 ]
  • [ 174499-67-3 ]
YieldReaction ConditionsOperation in experiment
15% With K2CO3; HCl In water; N,N-dimethyl-formamide N2-atmosphere; refluxing Ru-complex with excess of K2CO3 and acetamide (in DMF, 15 h), addn. of 6 M HCl, stirring with 1 equiv. of aq. NH4PF6 for 15 min; concn., extn. into CH2Cl2, chromy. (Al2O3, CH2Cl2/EtOH=9:1);
  • 21
  • [ 24589-78-4 ]
  • [ 2494-12-4 ]
  • N-acetyl-2-(3,4-bis(trimethylsilyloxy)phenyl)ethanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 50℃; for 1h;
  • 22
  • [ 2494-12-4 ]
  • [ 98-80-6 ]
  • [ 1220911-01-2 ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate at 70℃;
  • 23
  • [ 2494-12-4 ]
  • calf thymus DNA [ No CAS ]
  • [ 452094-39-2 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; mushroom tyrosinase In acetone at 37℃; for 10h; in air; Enzymatic reaction;
  • 24
  • [ 2494-12-4 ]
  • [ 145873-65-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: mushroom tyrosinase / aq. phosphate buffer / 20 °C / pH 7.4 / Enzymatic reaction 2: aq. phosphate buffer / 3 h / pH 7.4
  • 25
  • [ 2494-12-4 ]
  • [ 188987-95-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: mushroom tyrosinase / aq. phosphate buffer / 20 °C / pH 7.4 / Enzymatic reaction 2: aq. phosphate buffer / 3 h / pH 7.4 3: hydrogenchloride / water / 6 h / 90 °C
  • 26
  • [ 2494-12-4 ]
  • [ 1418130-96-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: mushroom tyrosinase / aq. phosphate buffer / 20 °C / pH 7.4 / Enzymatic reaction 1.2: pH 7.4 2.1: hydrogenchloride / water / 6 h / 90 °C
  • 27
  • [ 2494-12-4 ]
  • [ 2497-02-1 ]
  • [ 176226-41-8 ]
  • [ 145873-65-0 ]
YieldReaction ConditionsOperation in experiment
1: 6.4 mg 2: 0.5 mg Stage #1: N-acetyldopamine With mushroom tyrosinase In aq. phosphate buffer at 20℃; Enzymatic reaction; Stage #2: N-acetyl-L-histidine In aq. phosphate buffer 2 4.2. General procedure for the enzymatic oxidation of catecholamines, followed by addition of the nitrogen nucleophile General procedure: Mushroom tyrosinase (0.2 mg, 1074 units) was added to a solution of catecholamine (20 mg) in 1 mL phosphate buffer (pH 7.4, 50 mM) at r.t. The color changed to yellow, indicating the formation of the corresponding o-quinone. The enzyme was removed from the reaction mixture using a 5 mL HitrapTM desalting column (GE Heathcare), eluted with water (20 mL). The yellow solution of catecholamine-quinone was then added dropwise to a solution of NAcHis (10 eq.) or Imid (10 eq.) in phosphate buffer (15 mL, pH 7.4, 50 mM), and the reaction mixture was stirred for 1 h. At the terminus of the reaction 1 mL of 88% formic acid was added, and the reaction mixture was carefully evaporated under reduced pressure. The resulting orange oil was dissolved in water and purified by reverse-phase (RP-18) modified silica gel column chromatography, using water (100 mL) and 50% MeOH (100 mL) as eluent. The fraction containing the product eluted with 50% MeOH and was purified by HPLC (see ESI).
  • 28
  • [ 2494-12-4 ]
  • [ 2497-02-1 ]
  • [ 188987-95-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: mushroom tyrosinase / aq. phosphate buffer / 20 °C / pH 7.4 / Enzymatic reaction 1.2: pH 7.4 2.1: hydrogenchloride / water / 6 h / 90 °C
  • 29
  • [ 288-32-4 ]
  • [ 2494-12-4 ]
  • N-[2-(4,5-Dihydroxy-2-imidazol-1-yl-phenyl)-ethyl]-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
4 mg Stage #1: N-acetyldopamine With mushroom tyrosinase In aq. phosphate buffer at 20℃; Enzymatic reaction; Stage #2: 1H-imidazole In aq. phosphate buffer 2 4.2. General procedure for the enzymatic oxidation of catecholamines, followed by addition of the nitrogen nucleophile General procedure: Mushroom tyrosinase (0.2 mg, 1074 units) was added to a solution of catecholamine (20 mg) in 1 mL phosphate buffer (pH 7.4, 50 mM) at r.t. The color changed to yellow, indicating the formation of the corresponding o-quinone. The enzyme was removed from the reaction mixture using a 5 mL HitrapTM desalting column (GE Heathcare), eluted with water (20 mL). The yellow solution of catecholamine-quinone was then added dropwise to a solution of NAcHis (10 eq.) or Imid (10 eq.) in phosphate buffer (15 mL, pH 7.4, 50 mM), and the reaction mixture was stirred for 1 h. At the terminus of the reaction 1 mL of 88% formic acid was added, and the reaction mixture was carefully evaporated under reduced pressure. The resulting orange oil was dissolved in water and purified by reverse-phase (RP-18) modified silica gel column chromatography, using water (100 mL) and 50% MeOH (100 mL) as eluent. The fraction containing the product eluted with 50% MeOH and was purified by HPLC (see ESI).
  • 30
  • [ 120-20-7 ]
  • [ 2494-12-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / 1 h / 20 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 20 h / 0 - 20 °C
  • 31
  • [ 51-61-6 ]
  • [ 72-89-9 ]
  • [ 2494-12-4 ]
YieldReaction ConditionsOperation in experiment
With 5,5'-dithiobis-(2-nitrobenzoic acid); Drosophila melanogaster arylalkylamine N-acetyltransferase A from E. coli In aq. buffer Enzymatic reaction;
With dipyridin-4-yl disulfide; wild-type arylalkylamine N-acyltransferase from Tribolium castaneum In aq. buffer Enzymatic reaction;
  • 32
  • [ 2494-12-4 ]
  • methyl 6-(2-acetylaminoethyl)-4-hydroxybenzothiazole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: silver(l) oxide; sodium sulfate; formic acid / methanol / 0.25 h / 20 °C / Darkness 2: iron(III) chloride hexahydrate / water / 72 h / 20 °C
  • 33
  • [ 2494-12-4 ]
  • [ 18598-63-5 ]
  • C14H20N2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-acetyldopamine With formic acid; sodium sulfate; silver(l) oxide In methanol at 20℃; for 0.25h; Darkness; Stage #2: L-cysteine methyl ester hydrochloride In methanol Methyl 6-(2-acetylaminoethyl)-4-hydroxy-benzothiazole-2-carboxylate General procedure: Silver(I) oxide (256 mg, 1.1 mmol) and sodium sulfate (251 mg, 1.8 mmol) were added to asolution of N-acetyldopamine 8 (60 mg, 0.3 mmol) and formic acid (42 μL, 1.1 mmol) inmethanol (4 mL) and the black suspension was stirred for 15 min in the dark at rt then filteredthrough a pad of Celite. The filter cake was washed with methanol (2 × 6 mL) and thecombined red filtrates were immediately added dropwise to a solution of cysteine methylester hydrochloride (57 mg, 0.3 mmol) in methanol (2 mL). After addition had completed thepale green solution was concentrated to give the cysteine adduct as a pale yellow/green foamthat was used directly without purification; (Found: [M+H+], 329.1160. C14H21N2O5S+requires 329.1166.); The above foam was dissolved in water (0.7mL) and a solution ofiron(III) chloride hexahydrate (442 mg, 1.6 mmol) in water (1.8 mL) was slowly addeddropwise with vigorous stirring. The mixture was stirred for 72 h at rt, then diluted with water(10 ml) and extracted with ethyl acetate (3 × 10 mL). The combined organic extracts werewashed with water (30 mL) and brine (30 mL), dried (Na2SO4) and concentrated. The residuewas subjected to flash column chromatography on silica gel, eluting with ethanol-ethylacetate (1:9) to give the title compound as yellow solid
  • 34
  • [ 2494-12-4 ]
  • N-(2-(ethylthio)-3,4-dihydroxyphenethyl)acetamide [ No CAS ]
  • N-(3-(ethylthio)-4,5-dihydroxyphenethyl)acetamide [ No CAS ]
  • N-(2,5-bis(ethylthio)-3,4-dihydroxyphenethyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: silver(l) oxide / acetone / 0.5 h / 20 °C 2: acetone / 1 h / 20 °C
  • 35
  • [ 2494-12-4 ]
  • C12H15NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: silver(l) oxide / acetone / 0.5 h / 20 °C 2: [(2)H6]acetone / 0.05 h
  • 36
  • [ 67-56-1 ]
  • [ 2494-12-4 ]
  • 4-methoxykynuramine dihydrobromide [ No CAS ]
  • 5-methoxycystodytine J [ No CAS ]
  • 5-methoxycystodytin K [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 47% 2: 26% Stage #1: methanol; N-acetyldopamine With acetic acid; sodium sulfate; silver(l) oxide for 0.5h; Inert atmosphere; Darkness; Stage #2: 4-methoxykynuramine dihydrobromide With cerium(III) chloride heptahydrate at 70℃; for 72h; Inert atmosphere;
  • 37
  • [ 2494-12-4 ]
  • 5,12-dimethoxydiplamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: silver(l) oxide; acetic acid; sodium sulfate / 0.5 h / Inert atmosphere; Darkness 1.2: 72 h / 70 °C / Inert atmosphere 2.1: N-Bromosuccinimide / dichloromethane / 72 h / Inert atmosphere; Reflux; Irradiation 3.1: tetrabutylammomium bromide / water; dichloromethane / 0.25 h / Inert atmosphere
  • 38
  • [ 2494-12-4 ]
  • 5,12-dimethoxyvaramine B [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: silver(l) oxide; acetic acid; sodium sulfate / 0.5 h / Inert atmosphere; Darkness 1.2: 72 h / 70 °C / Inert atmosphere 2.1: N-Bromosuccinimide / dichloromethane / 72 h / Inert atmosphere; Reflux; Irradiation 3.1: tetrabutylammomium bromide / water; dichloromethane / 0.25 h / Inert atmosphere 4.1: sodium dithionite; water / dichloromethane / 0.17 h / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere
  • 39
  • [ 2494-12-4 ]
  • 5-methoxy-10-thiomethylarnoamsolidine B [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: silver(l) oxide; acetic acid; sodium sulfate / 0.5 h / Inert atmosphere; Darkness 1.2: 72 h / 70 °C / Inert atmosphere 2.1: N-Bromosuccinimide / dichloromethane / 72 h / Inert atmosphere; Reflux; Irradiation 3.1: tetrabutylammomium bromide / water; dichloromethane / 0.25 h / Inert atmosphere 4.1: sodium dithionite; water / dichloromethane / 0.17 h / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride / water / 20 h / Inert atmosphere; Reflux
  • 40
  • [ 2494-12-4 ]
  • N-(4,11-dimethoxy-5-(methylthio)-6,7-dihydropyrido[4,3,2-mn]pyrrolo[3,2,1-de]acridin-7-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: silver(l) oxide; acetic acid; sodium sulfate / 0.5 h / Inert atmosphere; Darkness 1.2: 72 h / 70 °C / Inert atmosphere 2.1: N-Bromosuccinimide / dichloromethane / 72 h / Inert atmosphere; Reflux; Irradiation 3.1: tetrabutylammomium bromide / water; dichloromethane / 0.25 h / Inert atmosphere 4.1: sodium dithionite; water / dichloromethane / 0.17 h / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 24 h / 70 °C / Inert atmosphere; Sealed tube
  • 41
  • [ 2494-12-4 ]
  • (±)-syn-N-(4,11-dimethoxy-5-(methylsulfinyl)-6,7-dihydropyrido[4,3,2-mn]pyrrolo[3,2,1-de]acridin-7-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: silver(l) oxide; acetic acid; sodium sulfate / 0.5 h / Inert atmosphere; Darkness 1.2: 72 h / 70 °C / Inert atmosphere 2.1: N-Bromosuccinimide / dichloromethane / 72 h / Inert atmosphere; Reflux; Irradiation 3.1: tetrabutylammomium bromide / water; dichloromethane / 0.25 h / Inert atmosphere 4.1: sodium dithionite; water / dichloromethane / 0.17 h / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 24 h / 70 °C / Inert atmosphere; Sealed tube 6.1: dihydrogen peroxide / water; acetonitrile / 4 h / 20 °C / Inert atmosphere
  • 42
  • [ 2494-12-4 ]
  • (±)-anti-N-(4,11-dimethoxy-5-(methylsulfinyl)-6,7-dihydropyrido[4,3,2-mn]pyrrolo[3,2,1-de]acridin-7-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: silver(l) oxide; acetic acid; sodium sulfate / 0.5 h / Inert atmosphere; Darkness 1.2: 72 h / 70 °C / Inert atmosphere 2.1: N-Bromosuccinimide / dichloromethane / 72 h / Inert atmosphere; Reflux; Irradiation 3.1: tetrabutylammomium bromide / water; dichloromethane / 0.25 h / Inert atmosphere 4.1: sodium dithionite; water / dichloromethane / 0.17 h / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 24 h / 70 °C / Inert atmosphere; Sealed tube 6.1: dihydrogen peroxide / water; acetonitrile / 4 h / 20 °C / Inert atmosphere
  • 43
  • [ 2494-12-4 ]
  • (±)-syn-pseudocerosine methyl ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: silver(l) oxide; acetic acid; sodium sulfate / 0.5 h / Inert atmosphere; Darkness 1.2: 72 h / 70 °C / Inert atmosphere 2.1: N-Bromosuccinimide / dichloromethane / 72 h / Inert atmosphere; Reflux; Irradiation 3.1: tetrabutylammomium bromide / water; dichloromethane / 0.25 h / Inert atmosphere 4.1: sodium dithionite; water / dichloromethane / 0.17 h / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 24 h / 70 °C / Inert atmosphere; Sealed tube 6.1: dihydrogen peroxide / water; acetonitrile / 4 h / 20 °C / Inert atmosphere 7.1: neat (no solvent) / 5 h / 45 °C / Inert atmosphere; Sealed tube 7.2: Alltech C18 SPE cartridge
  • 44
  • [ 2494-12-4 ]
  • (±)-anti-pseudocerosine methyl ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: silver(l) oxide; acetic acid; sodium sulfate / 0.5 h / Inert atmosphere; Darkness 1.2: 72 h / 70 °C / Inert atmosphere 2.1: N-Bromosuccinimide / dichloromethane / 72 h / Inert atmosphere; Reflux; Irradiation 3.1: tetrabutylammomium bromide / water; dichloromethane / 0.25 h / Inert atmosphere 4.1: sodium dithionite; water / dichloromethane / 0.17 h / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 24 h / 70 °C / Inert atmosphere; Sealed tube 6.1: dihydrogen peroxide / water; acetonitrile / 4 h / 20 °C / Inert atmosphere 7.1: neat (no solvent) / 8 h / 45 °C / Inert atmosphere; Sealed tube 7.2: Alltech C18 SPE cartridge
  • 45
  • [ 2494-12-4 ]
  • C21H21N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: silver(l) oxide; acetic acid; sodium sulfate / 0.5 h / Inert atmosphere; Darkness 1.2: 72 h / 70 °C / Inert atmosphere 2.1: N-Bromosuccinimide / dichloromethane / 6 h / Inert atmosphere; Reflux; Irradiation 3.1: tetrabutylammomium bromide / water; dichloromethane / 1 h / Inert atmosphere 4.1: sodium dithionite; water / dichloromethane / 0.17 h / Inert atmosphere
  • 46
  • [ 2494-12-4 ]
  • N-(2-(5-bromo-10-methoxy-4-oxo-4H-pyrido[2,3,4-kl]acridin-6-yl)ethyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: silver(l) oxide; acetic acid; sodium sulfate / 0.5 h / Inert atmosphere; Darkness 1.2: 72 h / 70 °C / Inert atmosphere 2.1: N-Bromosuccinimide / dichloromethane / 6 h / Inert atmosphere; Reflux; Irradiation
  • 47
  • [ 2494-12-4 ]
  • 5-methoxydiplamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: silver(l) oxide; acetic acid; sodium sulfate / 0.5 h / Inert atmosphere; Darkness 1.2: 72 h / 70 °C / Inert atmosphere 2.1: N-Bromosuccinimide / dichloromethane / 6 h / Inert atmosphere; Reflux; Irradiation 3.1: tetrabutylammomium bromide / water; dichloromethane / 1 h / Inert atmosphere
  • 48
  • [ 2494-12-4 ]
  • 5-methoxyvaramine B [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: silver(l) oxide; acetic acid; sodium sulfate / 0.5 h / Inert atmosphere; Darkness 1.2: 72 h / 70 °C / Inert atmosphere 2.1: N-Bromosuccinimide / dichloromethane / 6 h / Inert atmosphere; Reflux; Irradiation 3.1: tetrabutylammomium bromide / water; dichloromethane / 1 h / Inert atmosphere 4.1: sodium dithionite; water / dichloromethane / 0.17 h / Inert atmosphere 5.1: hexane; tetrahydrofuran; methanol / 0.5 h / 20 °C / Inert atmosphere
  • 49
  • [ 2494-12-4 ]
  • [ 74-88-4 ]
  • [ 6275-29-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide for 24h; Inert atmosphere;
  • 50
  • [ 62-31-7 ]
  • [ 75-36-5 ]
  • [ 2494-12-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran; methanol Inert atmosphere;
  • 51
  • [ReOCl3(PPh3)2] [ No CAS ]
  • [ 2494-12-4 ]
  • 2-{Bis-[(diphenylphosphanyl)-methyl]-amino}-phenol [ No CAS ]
  • C42H39N2O5P2Re [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 16h; Inert atmosphere; Schlenk technique;
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