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[ CAS No. 38215-36-0 ] {[proInfo.proName]}

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Chemical Structure| 38215-36-0
Chemical Structure| 38215-36-0
Structure of 38215-36-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 38215-36-0 ]

CAS No. :38215-36-0 MDL No. :MFCD00041869
Formula : C20H18N2O2S Boiling Point : -
Linear Structure Formula :NSC7H4C9O2H4N(C2H5)2 InChI Key :VBVAVBCYMYWNOU-UHFFFAOYSA-N
M.W : 350.43 Pubchem ID :100334
Synonyms :
Chemical Name :3-(Benzo[d]thiazol-2-yl)-7-(diethylamino)-2H-chromen-2-one
UV :443 nm (in THF)
FL :493 nm (in THF) Materials Type :Dopant

Calculated chemistry of [ 38215-36-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 19
Fraction Csp3 : 0.2
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 104.92
TPSA : 74.58 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.65
Log Po/w (XLOGP3) : 4.89
Log Po/w (WLOGP) : 4.92
Log Po/w (MLOGP) : 3.47
Log Po/w (SILICOS-IT) : 5.48
Consensus Log Po/w : 4.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.39
Solubility : 0.00142 mg/ml ; 0.00000406 mol/l
Class : Moderately soluble
Log S (Ali) : -6.19
Solubility : 0.000225 mg/ml ; 0.000000643 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -7.58
Solubility : 0.0000092 mg/ml ; 0.0000000262 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.46

Safety of [ 38215-36-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 38215-36-0 ]

* 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 [ 38215-36-0 ]

[ 38215-36-0 ] Synthesis Path-Downstream   1~42

YieldReaction ConditionsOperation in experiment
3-Ethoxycarbonyl-7-diethylamino-cumarin, o-Aminothiophenol, Δ;
YieldReaction ConditionsOperation in experiment
In dichloromethane at 25℃; for 0.166667h; UV-irradiation;
  • 4
  • [ 38215-36-0 ]
  • 3-benzothiazol-2-yl-7-diethylamino-6-hydroxy-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dipotassium peroxodisulfate In water; acetonitrile at 30℃;
  • 5
  • [ 29182-45-4 ]
  • [ 17754-90-4 ]
  • [ 38215-36-0 ]
YieldReaction ConditionsOperation in experiment
72% With 2-chloro-1-methyl-pyridinium iodide; triethylamine In acetonitrile Heating;
  • 6
  • [ 38215-36-0 ]
  • [ 143-33-9 ]
  • [ 70546-25-7 ]
YieldReaction ConditionsOperation in experiment
79% With lead(IV) acetate In dimethyl sulfoxide at 40℃; for 2h;
  • 7
  • [ 29182-42-1 ]
  • [ 17754-90-4 ]
  • [ 38215-36-0 ]
YieldReaction ConditionsOperation in experiment
83% With piperidine; In ethanol; at 160℃; for 0.333333h;Microwave irradiation; Sealed tube; 4-(Diethylamino)salicylaldehyde (200 mg, 1.00 mmol, 1.0 equiv.) and <strong>[29182-42-1]2-(2-benzothiazolyl)acetic acid ethyl ester</strong> (229 mg, 1.03 mmol, 1.0 equiv.) were dissolved in absolute EtOH (8 mL, 0.13 M), transferred into a microwave vial and two drops of piperidine were added. The vial was tightly sealed with an aluminum/teflon crimp top and the mixture was then irradiated in a Biotage Initiator microwave reactor at 160 C for 20 min. Thereafter, solvents were evaporated under reduced pressure and the crude product was purified by flash-column chromatography on silica gel using EtOAc-PE as the mobile phase (orange solid, 291 mg, yield 83%).
  • 8
  • [ 38215-36-0 ]
  • iridium(III) chloride [ No CAS ]
  • di-μ-chlorido-bridged Ir(III) dimer of coumarin 6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In 2-ethoxy-ethanol; water for 27h; Inert atmosphere; 1.2 (2) Synthesis method of iridium complex: A mixture of iridium() chloride (0.151g, 0.428mmol) and coumarin 6 (0.304g, 0.867mmol) was heated to 110°C in 2-ethoxyethanol/water (12mL; 3:1v/v), After 27 hours of reaction in a nitrogen environment, the reaction was cooled to room temperature, the precipitate was filtered and washed with ethanol, and dried in vacuum to obtain an orange solid iridium()μ-chloro-bridged dimer complex (0.284g). The yield was 72%.Dimer complex (0.157g, 0.0847mmol) and 4'-p-dimethylaminophenyl-2,2':6',2"-terpyridine (0.067g, 0.19mmol) in dichloromethane/methanol ( 15mL; 4:1v/v) was heated to 60°C, filled with nitrogen and reacted for 21 hours. The reaction mixture was evacuated to remove the solvent. The obtained crude product was subjected to alumina column chromatography (solvent: methanol/dichloromethane) =1/99) Purified and recrystallized from methanol/ether to obtain orange-red crystal complex (0.1257g, 0.098mmol), yield 58%
69% In 2-methoxy-ethanol; water for 48h; Heating / reflux; 4 A mixture of 2-methoxyethanol and water (12 ml: 1 mL) was degassed with N2 for 10 min. To this solvent mixture was added IrCl3.xH2O (0.254 g, 0.853 mmol) followed by Coumarin 6 (0.750 g, 2.13 mmol) and the mixture was heated at reflux for 48 h under an atmosphere of N2. The reaction mixture was cooled to room temperature, poured into 500 ml of acetone and concentrated to dryness under reduced pressure. The residue was suspended in acetone (200 mL) and the insoluble orange product was collected by filtration and washed with acetone until the filtrate washes were colorless. Yield: 0.548 g, 69%. 1H NMR (400 MHz, CD2Cl2, 25° C.) δ 0.90 (t, 24H), 3.09 (m, 16H), 4.97 (d, 4H), 5.34 (m, 4H), 6.12 (d, 4H), 7.06 (m, 8H), 7.37 (m, 4H), 7.84 (m, 4H).
  • 9
  • (η5-cyclopentadienyl)Ru(3-(2-benzothiazolyl)-7-(diethylamino)coumarin)(1+) [ No CAS ]
  • [ 38215-36-0 ]
  • cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% In acetonitrile Irradiation (UV/VIS); photolysis; not isolated;
  • 10
  • [ 38215-36-0 ]
  • cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate [ No CAS ]
  • [ 120546-54-5 ]
YieldReaction ConditionsOperation in experiment
In 1,2-dichloro-ethane bubbling soln. of coumarin-311 in CH2Cl2 with N2 (30 min), addn. of Ru-complex under positive N2 pressure, bubbling with N2 (5 min), stirring (2 h, under N2); solvent removal (evapn.), washing (ether), redissolving in acetone, elution (diatomaceous earth column, acetone), elution (acetonitrile), evapn.; elem. anal.;
  • 11
  • [ 38215-36-0 ]
  • iridium(III) chloride hydrate [ No CAS ]
  • (3-(2'-benzothiazolyl)-7-(diethylamino)-2H-1-benzopyran-2-onato-N',C4)2Ir(μ-Cl)2Ir(3-(2'-benzothiazolyl)-7-(diethylamino)-2H-1-benzopyran-2-onato-N',C4)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 2-ethoxy-ethanol; water byproducts: HCl; under inert atmosphere; IrCl3*nH2O and 2-2.5 equiv. of ligand heated under reflux in 2-ethoxyethanol/H2O; according to M. Nonoyama, Bull. Chem. Soc. Jpn. 47 (1974) 767;
  • 12
  • [ 38215-36-0 ]
  • [ 10025-99-7 ]
  • [ 123-54-6 ]
  • [ 441072-44-2 ]
YieldReaction ConditionsOperation in experiment
10% With Na2CO3 In 2-ethoxy-ethanol; water K2PtCl4 was heated with 2-2.5 equiv. cyclometalating ligand in 3:1 mixt.2-ethoxyethanol and water to 80°C for 16 h, dimer was isolated a nd reacted with 3 equiv. chelating diketone and 10 equiv. Na2CO3 in 2-ethoxyethanol at 100°C for 16 h; solvent was removed under reduced pressure, residue was purified by chromy. andrecrystn. from CH2Cl2/MeOH; elem. anal.;
  • 13
  • 3-benzothiazol-2-yl-7-diethylamino-chromene-2-thione [ No CAS ]
  • [ 38215-36-0 ]
YieldReaction ConditionsOperation in experiment
With mercury(II) diacetate aq. buffer;
With gold(III) chloride; TPEN at 20℃; for 0.5h; aq. acetate buffer;
  • 14
  • [ 17754-90-4 ]
  • [ 105-56-6 ]
  • [ 137-07-5 ]
  • [ 38215-36-0 ]
YieldReaction ConditionsOperation in experiment
60% With piperidine In ethanol for 7h; Reflux;
  • 15
  • [ 38215-36-0 ]
  • [ 773837-37-9 ]
  • [ 70546-25-7 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: Coumarin 6; sodium cyanide In dimethyl sulfoxide at 20℃; for 2h; Stage #2: With lead(IV) tetraacetate In dimethyl sulfoxide at 20℃; for 1h; 5.2.2. 3-Benzothiazol-2-yl-7-diethylamino-2-oxo-2H-chromene-4-carbonitrile (compound 12) The compound 3-benzothiazol-2-yl-7-diethylamino-chromen-2-one (compound 11, 1 g, 2.86 mmol) was dissolved in 10 mL of DMSO and the resulting solution was stirred at room temperature for 10 min. Sodium cyanide (0.29 mg, 5.7 mmol) was then added before the reaction mixture was stirred at room temperature for 2 h. The dark brown colored solution was then added with lead tetraacetate (1.27 g, 2.86 mmol) at room temperature and stirred for 1 h (Scheme 2). The resulting solution was poured drop-wise into 200 g of ice and a pinch of sodium chloride was added and stirred for 1 h at room temperature. The precipitation was collected, washed with 50 mL water and dried under vacuum to yield a pink solid as the pure product. The crude product containing a trace amount of the starting material was purified by treatment under reflux for overnight using 20 mL of a solvent mixture containing 20% ethyl acetate and 80% hexane to yield 750 mg of pure product (yield: 70%). mp 237-239 °C; IR (KBr): 2221 (m), 1712 (m), 1620 (m), 1558 (m), 1504 (s), 1420 (m); 1H NMR (300 MHz, CDCl3): δ 8.20 (d, J = 7.95 Hz, 1H), 7.87-7.98 (m, 2H), 7.34-7.55 (m, 2H), 6.78 (d, J = 6.78 Hz, 1H), 6.55 (s, 1H), 3.48 (t, J = 6.94 Hz, 4H), 1.27 (t, J = 7.02 Hz, 6H); HRMS calcd for C21H17N3O2S: 375.1041, found: 375.1035.
  • 16
  • [ 95-16-9 ]
  • [ 133590-13-3 ]
  • [ 38215-36-0 ]
YieldReaction ConditionsOperation in experiment
48% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane at 110℃; Inert atmosphere;
8 mg With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane at 110℃; for 6h;
  • 17
  • 7-diethylamino-3-(2,3-dihydro-1,3-benzothiazol-2-yl)coumarin [ No CAS ]
  • [ 38215-36-0 ]
YieldReaction ConditionsOperation in experiment
70% With dihydrogen peroxide In dichloromethane; water at 40℃; for 5h; Synthesis of 4. The weighed compound 1 (78.3 mg, 0.222 mmol) was dissolved in 5.0 mL of dichloromethane. Excess hydrogen peroxide (30% aq solution, 20 equiv) was added to the solution of 1. The solution was refluxed at 40 °C for 5 h. Resulting solution was cooled to rt, and evaporated in vacuum. Purification of the residue by column chromatography on silica gel with dichloromethane as an eluent afforded product 4 as a yellow solid in 70% yield
With copper(II) perchlorate In water; acetonitrile
With oxygen In tetrahydrofuran
With copper(II) ion In water; acetonitrile

  • 18
  • [ 17754-90-4 ]
  • [ 38215-36-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogenchloride; acetic acid / water 2: trichlorophosphate 3: methanol / 4 h / Reflux 4: copper(II) perchlorate / water; acetonitrile
Multi-step reaction with 2 steps 1: piperidine / 2.5 h / 65 °C 2: hydrogenchloride; water / 6 h / 95 °C
  • 19
  • [ 20571-42-0 ]
  • [ 38215-36-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trichlorophosphate 2: methanol / 4 h / Reflux 3: copper(II) perchlorate / water; acetonitrile
Multi-step reaction with 2 steps 1.1: oxone||potassium monopersulfate triple salt; hydrogen bromide / dichloromethane / 2 h / 20 °C 1.2: 2 h / 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; caesium carbonate / 1,4-dioxane / 6 h / 110 °C
  • 20
  • [ 57597-64-5 ]
  • [ 38215-36-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol / 4 h / Reflux 2: copper(II) perchlorate / water; acetonitrile
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 6 - 8 h / 24.84 °C / Inert atmosphere; Glovebox 2: oxygen / tetrahydrofuran
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 6 - 8 h / 24.84 °C / Inert atmosphere; Glovebox 2: arsenic triiodide; triethylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere; Glovebox
Multi-step reaction with 2 steps 1: ethanol / 6 h / 20 °C / Inert atmosphere 2: toluene / Irradiation
Multi-step reaction with 3 steps 1: ethanol / 6 h / 20 °C / Inert atmosphere 2: acetic anhydride / 12 h / 20 °C / Inert atmosphere 3: toluene / Irradiation
Multi-step reaction with 3 steps 1: ethanol / 6 h / 20 °C / Inert atmosphere 2: formic acid / 6 h / 20 - 80 °C 3: toluene / Irradiation

  • 21
  • 7-diethylamino-3-(2,3-dihydro-1,3-benzothiazol-2-yl)coumarin [ No CAS ]
  • [ 38215-36-0 ]
  • [ 1423156-59-5 ]
  • [ 4636-73-1 ]
YieldReaction ConditionsOperation in experiment
With arsenic triiodide; triethylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Glovebox;
  • 22
  • [ 137-07-5 ]
  • [ 38215-36-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 6 - 8 h / 24.84 °C / Inert atmosphere; Glovebox 2: oxygen / tetrahydrofuran
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 6 - 8 h / 24.84 °C / Inert atmosphere; Glovebox 2: arsenic triiodide; triethylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere; Glovebox
Multi-step reaction with 2 steps 1: ethanol / 6 h / 20 °C / Inert atmosphere 2: toluene / Irradiation
Multi-step reaction with 3 steps 1: ethanol / 6 h / 20 °C / Inert atmosphere 2: acetic anhydride / 12 h / 20 °C / Inert atmosphere 3: toluene / Irradiation
Multi-step reaction with 3 steps 1: ethanol / 6 h / 20 °C / Inert atmosphere 2: formic acid / 6 h / 20 - 80 °C 3: toluene / Irradiation

  • 24
  • [ 38215-36-0 ]
  • iridium(III) chloride trihydrate [ No CAS ]
  • di-μ-chlorido-bridged Ir(III) dimer of coumarin 6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% In 2-ethoxy-ethanol; water at 110℃; for 24h;
72% In 2-ethoxy-ethanol; water at 20℃; for 27h; Inert atmosphere; 1.2.1; 2-3 (1) Iridium (III) chloride (0.151g, 0.428mmol) and a mixture of coumarin 6 (0.304 g, 0.867 mmol) in 2-ethoxyethanol/water (12 mL; 3: 1 v / v), after 27 hours of reaction in a nitrogen atmosphere, the reaction was reduced to room temperature. The precipitate was filtered and washed with ethanol, an orange solid iridium (III) μ-chloro-bridged dimer complex (0.284 g) was obtained after drying in a vacuum, with a yield of 72%;
71% In 2-ethoxy-ethanol; water at 110℃; for 24h; Inert atmosphere;
69% In 2-ethoxy-ethanol; water at 110℃; for 44h; Inert atmosphere;
69% In 2-ethoxy-ethanol; water at 110℃; for 44h; Inert atmosphere;

  • 25
  • [ 38215-36-0 ]
  • C88H56N4(4+)*4Cl(1-) [ No CAS ]
  • 2C20H18N2O2S*C88H56N4(4+)*4Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In [D3]acetonitrile at 20℃; for 0.0833333h;
  • 26
  • 7-diethylamino-3-(2,3-dihydro-1,3-benzothiazol-2-yl)coumarin [ No CAS ]
  • [ 38215-36-0 ]
  • [ 57597-64-5 ]
YieldReaction ConditionsOperation in experiment
In toluene Irradiation;
Multi-step reaction with 2 steps 1: acetic anhydride / 12 h / 20 °C / Inert atmosphere 2: toluene / Irradiation
  • 27
  • 7-diethylamino-3-(3-acetyl-2,3-dihydro-1,3-benzothiazol-2-yl)coumarin [ No CAS ]
  • [ 38215-36-0 ]
  • [ 57597-64-5 ]
YieldReaction ConditionsOperation in experiment
In toluene Irradiation;
  • 28
  • 7-diethylamino-3-(3-formyl-2,3-dihydro-1,3-benzothiazol-2-yl)coumarin, [ No CAS ]
  • [ 38215-36-0 ]
  • [ 57597-64-5 ]
YieldReaction ConditionsOperation in experiment
In toluene Irradiation;
  • 29
  • [ 38215-36-0 ]
  • C138H168O6 [ No CAS ]
  • C138H168O6*0.05C20H18N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 20℃;
  • 30
  • [ 38215-36-0 ]
  • [ 517-51-1 ]
  • C138H168O6 [ No CAS ]
  • C138H168O6*0.05C42H28*0.05C20H18N2O2S [ No CAS ]
  • 31
  • [ 38215-36-0 ]
  • dimethyl [3-(benzo[d]thiazol-2-yl)-7-(diethylamino)-2-oxo-2H-chromen-4-yl]phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 20 °C / Cooling with ice 1.2: 1 h / 20 °C 2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / methanol; ethyl acetate / 0.08 h / 70 °C
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C / Cooling with ice 1.2: 1 h / 20 °C 2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / methanol; ethyl acetate / 0.08 h / 70 °C
  • 32
  • [ 38215-36-0 ]
  • [3-(benzo[d]thiazol-2-yl)-7-(diethylamino)-2-oxo-2H-chromen-4-yl]phosphonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2.5 h / 20 - 55 °C 1.2: 1 h / 20 °C 2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / methanol; ethyl acetate / 0.08 h / 75 °C 3.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2.5 h / 55 °C / Cooling with ice 1.2: 1 h / 20 °C 2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / ethyl acetate / 0.08 h / 75 °C 3.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C
  • 33
  • [ 38215-36-0 ]
  • [ 13086-84-5 ]
  • di-tert-butyl [3-(benzo[d]thiazol-2-yl)-7-(diethylamino)-2-oxo-2H-chromen-4-yl]-phosphonate [ No CAS ]
  • 34
  • [ 38215-36-0 ]
  • [ 13086-84-5 ]
  • C28H37N2O5PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a stirred suspension of NaH (34 mg of 60 wt. % in mineral oil, 0.858 mmol) in dry DMF (1.5 mL), cooled in ice-water bath, di(tert-butyl) phosphite (173 μL, 0.858 mmol) was added in one portion. The resulting suspension was stirred for 2 h at rt and for 30 min at 55 C. The resulting thin white suspension was added to a stirred suspension of Coumarin 6 (100 mg, 0.286 mmol) in DMF (0.8 mL). The solids dissolved immediately and clear light-orange solution formed. The mixture was stirred at rt for 1 h and then poured into sat. aq. NaHCO3 (50 mL), extracted with EtOAc (4*15 mL), the combined extracts were dried over Na2SO4, filtered and evaporated. The residue was redissolved in EtOAc (20 mL), heated up to 75 C., and a solution of DDQ (65 mg, 0.286 mmol) in EtOAc (3 mL) was added quickly dropwise. The mixture was stirred at 75 C. for 5 min, cooled down to rt and evaporated. The product was isolated by column chromatography (30 g SiO2, gradient 20% to 50% EtOAc/hexane) and lyophilized from 1,4-dioxane. Bright yellow-orange solid, yield 130 mg (84%). 1H NMR (400 MHz, acetone-d6): δ 8.25 (br.s, 1H), 8.08-8.03 (m, 1H), 7.99 (ddd, J=8.1, 1.2, 0.6 Hz, 1H), 7.55-7.47 (m, 1H), 7.47-7.41 (m, 1H), 6.84 (dd, J=9.4, 2.7 Hz, 1H), 6.58 (dd, J=2.7, 1.5 Hz, 1H), 3.57 (q, J=7.2 Hz, 4H), 1.45 (s, 18H), 1.26 (t, J=7.1 Hz, 6H). 31P NMR (162 MHz, acetone-d6): 5 0.60. 13C NMR (101 MHz, acetone-d6): δ 209.9, 163.7 (d, J=7.0 Hz), 160.4, 157.5 (d, J=13.4 Hz), 154.1, 152.1, 138.2, 132.1 (d, J=2.0 Hz), 126.3, 125.7, 123.9, 122.3, 110.9, 109.8, 107.2 (d, J=7.9 Hz), 97.6 (d, J=2.6 Hz), 85.2 (d, J=7.3 Hz), 67.6, 45.2, 12.8. MS (ESI): m/z (positive mode, rel. int., %)=543.2 (55) [M+H]+, 565.2 (35) [M+Na]+, 581.2 (100) [M+K]+. HRMS (C28H36N2O5PS): m/z (positive mode)=543.2077 (found [M+H]+), 543.2077 (calc.). UV/Vis (MeCN): λmax (ε)=434 nm (39000 M-1cm-1); fluorescence (MeCN): λexcit=470 nm, λem=658 nm, φfl=0.29. Standard: Abberior Star520SX tert-butyl ester, φfl=0.27 (MeCN).
  • 35
  • [ 38215-36-0 ]
  • [ 868-85-9 ]
  • C22H25N2O5PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: Dimethyl phosphite With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Cooling with ice; Stage #2: Coumarin 6 In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h;
Stage #1: Dimethyl phosphite With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Cooling with ice; Stage #2: Coumarin 6 In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; 1 Dimethyl [3-(benzo[d]thiazol-2-yl)-7-(diethylamino)-2-oxo-2H-chromen-4-yl]phosphonate (1) To a stirred suspension of NaH (17 mg of 60 wt. % in mineral oil, 0.429 mmol) in dry DMF (0.5 mL), cooled in ice-water bath, dimethyl phosphite (40 μL, 0.429 mmol) was added in one portion. The resulting suspension was warmed up to rt and stirred for 30 min, turning into a clear solution, which was added to a stirred suspension of Coumarin 6 (50 mg, 0.143 mmol) in DMF (0.5 mL). The orange solid dissolved immediately and clear red-orange solution formed. The mixture was stirred at rt for 1 h, and the resulting pale orange solution was poured into water (30 mL) and brine (10 mL), extracted with EtOAc (4*15 mL), the combined extracts were dried over Na2SO4, filtered and evaporated. The residue was taken up in EtOAc (20 mL) and MeOH (5 mL), heated up to 70° C., and a solution of DDQ (32 mg, 0.143 mmol) in EtOAc (2 mL) was added quickly dropwise. The mixture was stirred at 70° C. for 5 min, cooled down to rt and evaporated. The crude product was purified by column chromatography twice (16 g SiO2, gradient 50% to 100% EtOAc/hexane, and 17 g SiO2, gradient 50% to 80% EtOAc/hexane) and lyophilized from 1,4-dioxane. Bright yellow solid, yield 34 mg (52%). 1H NMR (400 MHz, CDCl3): δ 8.18 (d, J=9.3 Hz, 1H), 8.08 (ddd, J=8.1, 1.3, 0.7 Hz, 1H), 7.92 (ddd, J=8.0, 1.3, 0.7 Hz, 1H), 7.48 (ddd, J=8.2, 7.2, 1.3 Hz, 1H), 7.41 (ddd, J=8.3, 7.3, 1.2 Hz, 1H), 6.65 (dd, J=9.4, 2.7 Hz, 1H), 6.52 (dd, J=2.7, 1.7 Hz, 1H), 3.67 (s, 3H), 3.64 (s, 3H), 3.44 (q, J=7.1 Hz, 4H), 1.23 (t, J=7.1 Hz, 6H). 13C NMR (101 MHz, CDCl3): 5 162.2 (d, J=7.1 Hz), 160.0 (d, J=19.9 Hz), 156.6 (d, J=14.3 Hz), 152.8, 151.5, 142.3 (d, J=172.0 Hz), 137.1, 130.5 (d, J=2.7 Hz), 126.1, 125.6, 123.6, 121.7, 119.5 (d, J=6.4 Hz), 109.7, 107.2 (d, J=9.9 Hz), 97.4 (d, J=2.5 Hz), 67.2, 53.6, 53.5, 45.1, 12.6. 31P NMR (162 MHz, CDCl3): δ 13.37. MS (ESI): m/z (positive mode, rel. int., %)=459.1 (100) [M+H]+, 497.1 (45) [M+K]+. HRMS (C22H23N2O5PS): m/z (positive mode)=459.1138 (found [M+H]+), 459.1138 (calc.). UV/Vis (MeCN): λmax (ε)=439 nm (24000 M-1cm-1); fluorescence (MeCN): λexcit=470 nm, λem=651 nm, φfl=0.20. Standard: Abberior Star520SX tert-butyl ester, φfl=0.27 (MeCN).
  • 36
  • [ 38215-36-0 ]
  • [ 333-27-7 ]
  • C21H21N2O2S(1+)*CF3O3S(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene at 10 - 87℃; for 3h; 1 Coumarin 6(Tokyo Chemical Industry Co., Ltd. product) 14.4 parts were mixed with 737 parts of toluene and stirred at 87°C.To the mixture was added 10.1 parts of methyl trifluoromethanesulfonate.The mixture was stirred at 87[deg.] C. for 3 hours.The mixture was stirred at 10°C.The mixture was filtered and the resulting residue was washed 6 times with 433 parts of toluene.The residue was dried under reduced pressure at 60°C to obtain 20.8 parts of a compound represented by the formula (X-1).
In toluene at 10 - 87℃; for 3h; 1 Example 1 14.4 parts of coumarin 6 (manufactured by Tokyo Chemical Industry Co., Ltd.) and 737 parts of toluene were mixed and stirred at 87 ° C. To this mixture was added 10.1 parts of methyl trifluoromethanesulfonate. The mixture was stirred at 87 ° C. for 3 hours.The mixture was stirred at 10 ° C. The mixture was filtered, and the obtained residue was washed six times with 433 parts of toluene. The residue was dried under reduced pressure at 60 ° C.To obtain 20.8 parts of a compound represented by the formula (I-2).
  • 37
  • [ 38215-36-0 ]
  • 4C57H66N2O12*2Pt(2+)*4NO3(1-) [ No CAS ]
  • 4C57H66N2O12*2Pt(2+)*4NO3(1-)*2C20H18N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water-d2 at 80℃; for 1h;
  • 38
  • [ 56278-50-3 ]
  • [ 17754-90-4 ]
  • [ 38215-36-0 ]
YieldReaction ConditionsOperation in experiment
With piperidine In ethanol Synthesis of 6a, 6b and 6c (Fig. 1) General procedure: Aldehydes 5a-5c (1 mmol) and 7-(diethylamino)-2-oxobenzo[d]thiazole-2-carbonitrile (1mmol)were stirred in absoluteethanol (5 mL) for a period of 4-5 h in presence of piperidine(0.01 ml). Reaction was monitored by TLC. On completion ofreaction, solution was mixed with ice water (20 mL) containing0.025 mL of conc. HCl. The precipitate was filtered and washedwith water, dried under vacuum to give compounds 6a-6c.
With piperidine In ethanol at 20℃; for 2h;
  • 39
  • [ 38215-36-0 ]
  • [ 14568-13-9 ]
  • C22H24Cl2N2O3PtS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93.5% In methanol for 12h; Reflux; 4.1.1 Synthesis of Pt1-Pt11 General procedure: The reaction of H-QC1-H-QC11 with cis-Pt(DMSO)2Cl2 (1.0mmol) in a 2/1M ratio in refluxing CH3OH (10.0mL) for 12.0h afforded reddish-brown complexes Pt1-Pt11 in good yield (86.2%-94.0%).
  • 40
  • 3-(benzo[d]thiazol-2-yl)-N,N-diethyl-2-imino-2H-chromen-7-amine [ No CAS ]
  • [ 38215-36-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water at 95℃; for 6h;
  • 41
  • [ 56278-50-3 ]
  • [ 38215-36-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: piperidine / 2.5 h / 65 °C 2: hydrogenchloride; water / 6 h / 95 °C
  • 42
  • [ 38215-36-0 ]
  • iridium(III) chloride n-hydrate [ No CAS ]
  • di-μ-chlorido-bridged Ir(III) dimer of coumarin 6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In 1,2-dimethoxyethane; water at 110℃; for 27h; Inert atmosphere; 1.2 (2) Synthesis method of iridium complex Iridium(III) chloride hydrate (0.151g, 0.428mmol)The mixture with coumarin 6 (0.304g, 0.867mmol) was heated to 110°C in ethylene glycol ether/water (12mL; 3:1v/v),After 27 hours of reaction in a nitrogen environment, the reaction was lowered to room temperature. The precursor was precipitated by adding water, filtered with suction, washed with ethanol, and dried in vacuum to obtain an orange solid iridium()μ-chloro-bridged dimer complex (0.284g) with a yield of 72%.
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