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[ CAS No. 51649-83-3 ] {[proInfo.proName]}

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Chemical Structure| 51649-83-3
Chemical Structure| 51649-83-3
Structure of 51649-83-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 51649-83-3 ]

CAS No. :51649-83-3 MDL No. :MFCD00005051
Formula : C20H13NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :YOAWSYSKQHLFPM-UHFFFAOYSA-N
M.W : 347.32 Pubchem ID :103924
Synonyms :
6-Aminofluorescein
Chemical Name :6-Amino-3',6'-dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one

Calculated chemistry of [ 51649-83-3 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.05
Num. rotatable bonds : 0
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 93.15
TPSA : 102.01 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 2.74
Log Po/w (WLOGP) : 3.15
Log Po/w (MLOGP) : 1.94
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 2.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.23
Solubility : 0.0204 mg/ml ; 0.0000586 mol/l
Class : Moderately soluble
Log S (Ali) : -4.54
Solubility : 0.0101 mg/ml ; 0.0000291 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.79
Solubility : 0.000567 mg/ml ; 0.00000163 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.44

Safety of [ 51649-83-3 ]

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 [ 51649-83-3 ]

* 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 [ 51649-83-3 ]

[ 51649-83-3 ] Synthesis Path-Downstream   1~34

  • 1
  • [ 2307-00-8 ]
  • [ 108-46-3 ]
  • [ 3326-34-9 ]
  • [ 51649-83-3 ]
YieldReaction ConditionsOperation in experiment
With ethanol; nickel Hydrogenation;
With palladium on activated charcoal; hydrazine hydrate
  • 3
  • 7,8-Dihydromorphine-3-carboxymethyl ether hydrochloride [ No CAS ]
  • [ 541-41-3 ]
  • [ 51649-83-3 ]
  • 7,8-Dihydromorphine-3-(fluorescein-6-ylamino-carbonylmethyl) Ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
In <i>N</i>-methyl-acetamide; triethylamine 8 7,8-Dihydromorphine-3-(fluorescein-6-ylamino-carbonylmethyl) Ether EXAMPLE 8 7,8-Dihydromorphine-3-(fluorescein-6-ylamino-carbonylmethyl) Ether 7,8-Dihydromorphine-3-carboxymethyl ether hydrochloride (0.1 mmol) was dissolved in 0.3 ml of dimethylformamide. The solution was cooled in an ice bath and 0.014 ml triethylamine and 0.0105 ml of ethyl chloroformate were added. The solution was stirred for 11/2 hours, and half of it was allowed to react with 6-aminofluorescein at room temperature overnight. The product was purified by chromatography on a silica gel thin layer plate, developing with chloroform/methanol/acetic acid, then on a second plate developed with chloroform/methanol.
  • 4
  • [ 51649-83-3 ]
  • [ 219122-41-5 ]
YieldReaction ConditionsOperation in experiment
319 mg (85%) 1.b b) b) 4-amino-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid ethyl ester (compound of formula B) Such a compound was obtained with the same method as used for the synthesis of a) but starting from 6-aminofluorescein (which is the spiro-lacton form of 4-amino-2-(6'-hydroxy-3'-oxo-3H-xanthen-9'-yl)-benzoic acid) with yield 319 mg (85%). 1H NMR ((CD3)2SO, ppm): 0.83 (t, 3H, J=7.5 Hz), 3.83 (q, 2H, J=7.5 Hz), 5.85 (br.s, 2H), 6.47 (m, 1H), 6.78 (m, 1H), 7.02 (m, 2H), 7.07 (m, 2H), 7.34 (m, 2H), 7.92 (m, 1H).
  • 5
  • [ 51649-83-3 ]
  • 6-azidofluorescein [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 6'-amino-3,6-dihydroxyspiro<xanthene-9,1'-isobenzofuran>-3'-one With hydrogenchloride; sodium nitrite In water for 0.333333h; Stage #2: With sodium azide In water at 0℃; for 48h;
  • 6
  • [ 27402-68-2 ]
  • [ 51649-83-3 ]
YieldReaction ConditionsOperation in experiment
975 mg With sodium hydrogensulfide; sodium sulfide nonahydrate In water for 24h; Reflux;
  • 7
  • [ 610-27-5 ]
  • [ 51649-83-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 200 °C 1.2: 2 h / Reflux 2.1: sodium hydroxide / methanol / Heating 3.1: sodium sulfide nonahydrate; sodium hydrogensulfide / water / 24 h / Reflux
  • 8
  • [ 108-46-3 ]
  • [ 51649-83-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 200 °C 2: sodium sulfide nonahydrate; sodium hydrogensulfide / water / 24 h / Reflux
Multi-step reaction with 3 steps 1.1: 200 °C 1.2: 2 h / Reflux 2.1: sodium hydroxide / methanol / Heating 3.1: sodium sulfide nonahydrate; sodium hydrogensulfide / water / 24 h / Reflux
  • 9
  • [ 53299-21-1 ]
  • [ 51649-83-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol / Heating 2: sodium sulfide nonahydrate; sodium hydrogensulfide / water / 24 h / Reflux
  • 10
  • [ 51649-83-3 ]
  • [ 1394015-42-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: calcium carbonate / acetone / 3 h / 20 °C / Reflux 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h 2.2: 20 °C / Darkness
  • 11
  • [ 463-71-8 ]
  • [ 51649-83-3 ]
  • [ 18861-78-4 ]
YieldReaction ConditionsOperation in experiment
350 mg With calcium carbonate In acetone at 20℃; for 3h; Reflux;
  • 12
  • [ 51649-83-3 ]
  • [ 814-68-6 ]
  • [ 172531-40-7 ]
YieldReaction ConditionsOperation in experiment
85% In acetone at 0 - 20℃; for 3h;
  • 13
  • [ 54-47-7 ]
  • [ 51649-83-3 ]
  • C28H21N2O10P [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In ethanol for 4h; Reflux; 2.4.1 General synthesis General procedure: 7-Amino-4-methyl-coumarin (B) (0.040g, 2.28×10-4mol) or 6-Aminofluorescein (C) (0.080g, 2.30×10-4mol) was dissolved in absolute ethanol, followed by the addition of pyridoxal-5′-phosphate (A) (0.056g, 2.28×10-4mol; 0.057g, 2.30×10-4mol). The solution was stirred and kept under refluxing for 4h. At the end, light orange (compound 1) and orange (compound 2) powders were obtained, and were washed several times with cold ethanol, diethylether and dried under vacuum.
  • 14
  • [ 51649-83-3 ]
  • 1-(2-(4-(2-((2-((3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-6-yl)amino)-2-oxoethyl)(methyl)ammonio)ethyl)phenoxy)-1,1,2,2-tetrafluoroethyl)-3,3-dimethyl-2,3-dihydro-1H-1λ3-benzo[d][1,2]iodaoxol-2-ium bis(trifluoroacetate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / tetrahydrofuran / 0.25 h / 0 °C 1.2: 0.25 h 2.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
  • 15
  • [ 51649-83-3 ]
  • [ 598-21-0 ]
  • 2-bromo-N-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-6-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% Stage #1: 6'-amino-3,6-dihydroxyspiro<xanthene-9,1'-isobenzofuran>-3'-one With sodium hydrogencarbonate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: 2-Bromoacetyl bromide In tetrahydrofuran for 0.25h;
  • 16
  • recombinant superfolder green fluorescent protein with incorporated 5-hydroxytriptophane in 151 position [ No CAS ]
  • [ 51649-83-3 ]
  • recombinant superfolder green fluorescent protein with incorporated 5-hydroxytriptophane in 151 position selecively labeled with 6-diazoflurescein [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6'-amino-3,6-dihydroxyspiro<xanthene-9,1'-isobenzofuran>-3'-one With hydrogenchloride; sodium nitrite In water Cooling with ice; Stage #2: recombinant superfolder green fluorescent protein with incorporated 5-hydroxytriptophane in 151 position In aq. phosphate buffer for 0.166667h; Cooling with ice;
  • 17
  • recombinant fab fragment of the anti-Her2 antibody with incorporated 5-hydroxytriptophane in 169 position [ No CAS ]
  • [ 51649-83-3 ]
  • recombinant superfolder green fluorescent protein with incorporated 5-hydroxytriptophane in 151 position selecively labeled with 6-diazoflurescein [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6'-amino-3,6-dihydroxyspiro<xanthene-9,1'-isobenzofuran>-3'-one With hydrogenchloride; sodium nitrite In water Cooling with ice; Stage #2: recombinant fab fragment of the anti-Her2 antibody with incorporated 5-hydroxytriptophane in 169 position for 0.25h; Cooling with ice;
  • 18
  • [ 51649-83-3 ]
  • C20H12N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6'-amino-3,6-dihydroxyspiro<xanthene-9,1'-isobenzofuran>-3'-one With hydrogenchloride In water Stage #2: With sodium nitrite In water for 0.00277778h; Cooling with ice; Preparation of fluorescein-diazonium (7): 6-aminofluorescein was dissolved in 10 mM MCl at a concentration of 10 mM. Separately a 60 mM sodium nitrite solution was prepared and both solutions were cooled on ice. 20 μL NaNO2 (60 mM) was added to 100 μL of fluorescein (10 mM) and vortexed for 10 sec then kept on ice to generate a 8.3 mM fluorescein diazonium solution. This solution was further diluted to 1 mM with water and used for the labeling studies.
  • 19
  • [ 14468-88-3 ]
  • [ 51649-83-3 ]
  • 4-azido-N-(3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthen]-6-yl)butanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
113 mg With sodium hydrogencarbonate In tetrahydrofuran at 0 - 20℃;
  • 20
  • [ 108-24-7 ]
  • [ 51649-83-3 ]
  • 6-aminofluorescein diacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With caesium carbonate In acetonitrile at 20℃; for 0.5h;
  • 21
  • [ 51649-83-3 ]
  • C24H18N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: caesium carbonate / acetonitrile / 0.5 h / 20 °C 2.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 4 °C 2.2: 4 °C
  • 22
  • [ 51649-83-3 ]
  • C38H41N3O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / acetonitrile / 0.5 h / 20 °C 2.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 4 °C 2.2: 4 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.02 h / 20 °C
  • 23
  • [ 51649-83-3 ]
  • C30H23N3O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: caesium carbonate / acetonitrile / 0.5 h / 20 °C 2.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 4 °C 2.2: 4 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.02 h / 20 °C 4.1: manganese(IV) oxide / dichloromethane / 0.17 h / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 6 h / 20 °C
  • 24
  • [ 51649-83-3 ]
  • C38H39N3O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / acetonitrile / 0.5 h / 20 °C 2.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 4 °C 2.2: 4 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.02 h / 20 °C 4.1: manganese(IV) oxide / dichloromethane / 0.17 h / 20 °C
  • 25
  • [ 51649-83-3 ]
  • C26H19N3O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: caesium carbonate / acetonitrile / 0.5 h / 20 °C 2.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 4 °C 2.2: 4 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.02 h / 20 °C 4.1: manganese(IV) oxide / dichloromethane / 0.17 h / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 6 h / 20 °C 6.1: sodium hydroxide; water / dimethyl sulfoxide / 0.5 h / 20 °C
  • 26
  • [ 51649-83-3 ]
  • C34H35N3O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / acetonitrile / 0.5 h / 20 °C 2.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 4 °C 2.2: 4 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.02 h / 20 °C 4.1: manganese(IV) oxide / dichloromethane / 0.5 h / 20 °C 4.2: 1 h / 20 °C
  • 27
  • [ 51649-83-3 ]
  • C35H37N3O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: caesium carbonate / acetonitrile / 0.5 h / 20 °C 2.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 4 °C 2.2: 4 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.02 h / 20 °C 4.1: manganese(IV) oxide / dichloromethane / 0.5 h / 20 °C 4.2: 1 h / 20 °C 5.1: cesium fluoride / N,N-dimethyl-formamide / 0.75 h / 20 °C
  • 28
  • [ 51649-83-3 ]
  • C27H21N3O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: caesium carbonate / acetonitrile / 0.5 h / 20 °C 2.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 4 °C 2.2: 4 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.02 h / 20 °C 4.1: manganese(IV) oxide / dichloromethane / 0.5 h / 20 °C 4.2: 1 h / 20 °C 5.1: cesium fluoride / N,N-dimethyl-formamide / 0.75 h / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
  • 29
  • [ 51649-83-3 ]
  • [ 518-45-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: caesium carbonate / acetonitrile / 0.5 h / 20 °C 2.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 4 °C 2.2: 4 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.02 h / 20 °C 4.1: manganese(IV) oxide / dichloromethane / 0.17 h / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 6 h / 20 °C 6.1: sodium hydroxide; water / dimethyl sulfoxide / 0.5 h / 20 °C 7.1: recombinant human prostate-specific membrane antigen; sodium chloride / dimethyl sulfoxide / 37 °C / pH 7.4 / Enzymatic reaction
  • 30
  • [ 51649-83-3 ]
  • [ 70672-06-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: caesium carbonate / acetonitrile / 0.5 h / 20 °C 2.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 4 °C 2.2: 4 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.02 h / 20 °C 4.1: manganese(IV) oxide / dichloromethane / 0.5 h / 20 °C 4.2: 1 h / 20 °C 5.1: cesium fluoride / N,N-dimethyl-formamide / 0.75 h / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 7.1: recombinant human prostate-specific membrane antigen; sodium chloride / dimethyl sulfoxide / 37 °C / pH 7.4 / Enzymatic reaction
  • 31
  • [ 51649-83-3 ]
  • C20H11NO5(2-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium hydroxide In dimethyl sulfoxide at 25℃;
  • 32
  • [ 955094-26-5 ]
  • [ 51649-83-3 ]
  • N-(3’,6’-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9’-xanthen]-5-yl)-3-(2-(2-(3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido)ethoxy)ethoxy)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With triethylamine In N,N-dimethyl-formamide for 48h;
  • 33
  • [ 32315-10-9 ]
  • [ 1008-78-2 ]
  • [ 51649-83-3 ]
  • C29H18N4O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% Stage #1: bis(trichloromethyl) carbonate; 6'-amino-3,6-dihydroxyspiro<xanthene-9,1'-isobenzofuran>-3'-one With sodium hydrogencarbonate In acetone at 0℃; for 0.5h; Stage #2: 5-amino-3-phenyl-1,2,3-oxadiazol-3-ium chloride In acetone at 0 - 20℃; for 8h;
  • 34
  • [ 1008-78-2 ]
  • [ 51649-83-3 ]
  • C17H20N2O [ No CAS ]
  • C21H13N2O6(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / acetone / 0.5 h / 0 °C 1.2: 8 h / 0 - 20 °C 2.1: dimethyl sulfoxide / 20 °C
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