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[ CAS No. 581-71-5 ] {[proInfo.proName]}

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Chemical Structure| 581-71-5
Chemical Structure| 581-71-5
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Product Details of [ 581-71-5 ]

CAS No. :581-71-5 MDL No. :MFCD00079346
Formula : C11H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QCUNDLUTTXSPFM-UHFFFAOYSA-N
M.W : 172.18 Pubchem ID :315482
Synonyms :

Calculated chemistry of [ 581-71-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.36
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.42
Log Po/w (XLOGP3) : 2.61
Log Po/w (WLOGP) : 2.36
Log Po/w (MLOGP) : 1.82
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 2.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.152 mg/ml ; 0.000881 mol/l
Class : Soluble
Log S (Ali) : -3.04
Solubility : 0.156 mg/ml ; 0.000906 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.44
Solubility : 0.0622 mg/ml ; 0.000361 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 581-71-5 ]

Signal Word:Danger Class:9
Precautionary Statements:P273-P280-P301+P312+P330-P305+P351+P338+P310 UN#:3077
Hazard Statements:H302-H318-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 581-71-5 ]

* 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 [ 581-71-5 ]

[ 581-71-5 ] Synthesis Path-Downstream   1~29

  • 2
  • [ 56679-88-0 ]
  • [ 581-71-5 ]
YieldReaction ConditionsOperation in experiment
99% With aluminum (III) chloride; In dichloromethane; at 20℃; for 8.0h; The compound was dissolved VII-1 (2mmol, 1equiv) 20mL of dichloromethane,An excess of AlCl3,In dry oxygen-free state holding 8h,The reaction was quenched with water and extracted with dichloromethane,After drying spin dry,A silica gel column (PE: EA = 8: 1),To give Compound VIII-1 (99%);
87% With boron tribromide; In dichloromethane; at 0 - 20℃; for 1.08333h;Inert atmosphere; Schlenk technique; Adapted from [5]. S10 (2.76 g, 14.82 mmol, (0316) 1.0 eq) was placed in a 50 ml_ 2 neck flask and purged with N2 gas. Anhydrous CH2CI2 (27.4 ml_) was added to the flask. A 100 ml_ schlenk flask was purged with N23 times before the addition of BBr3 (1.69 ml_, 17.78 mmol, 1.2 eq). Anhydrous CH2CI2 (27.8 ml_) was added to the BBr3 flask, which was then cooled to 0 C. The solution of S10 was then added slowly to the BBr3 solution over 5 minutes. Upon completion of the addition the flask was warmed to room temperature and stirred for one hour. The reaction was quenched with 150 ml_ of saturated NaHC03. The CH2CI2 was collected and the aqueous phase was extracted with EtOAc 3 times. The combined organic phases were rinsed with brine, dried over Na2S04, and filtered. The organic solvent was removed with a rotary evaporator and the crude product was purified using column chromatography (S1O2, 30% v/v EtOAc/hexanes) resulting in a bright yellow solid. Yield 2.21 g (87 %). (0317) Figure 45 shows 1HNMR (400 MHz, CDCI3, 25C) d (ppm) 10.33 (s, 1 H), 10.08 (0318) (d, J = 0.6 Hz, 1 H), 8.14 (s, 1 H), 7.89 - 7.84 (m, 1 H), 7.71 (d, J = 8.4 Hz, 1 H), 7.56 (d, J = 16.5 Hz, 1 H), 7.38 (d, J = 16.3 Hz, 1 H), 7.28 (s, 1 H) spectra of compound S1 1. (0319) Figure 46 shows 13C NMR (101 MHz, CDCI3, 25C) d (ppm) 196.80, 155.96, 138.33, 137.99, 130.41 , 129.50, 127.54, 126.82, 124.55, 122.43, 112.07 spectra of compound S1 1.
73% With boron tribromide; In dichloromethane; at 0 - 20℃; for 20.0h;Inert atmosphere; The starting material <strong>[56679-88-0]3-methoxy-2-naphthaldehyde</strong> was prepared accordingto the procedure described by Legouin et al. [31]. The crude product was purified by flash columnchromatography on silica gel using dichloromethane to aord pure product as a pale yellow solid (0.59 g,56%). The NMR data are consistent with that reported in literature [31]. HRMS-ESI calculated forC12H10O2 [M + H]+ 186.0681, found 186.0645. Next a flame-dried 50 mL round-bottom flask equippedwith a magnetic stirrer, nitrogen inlet was charged with a solution of <strong>[56679-88-0]3-methoxy-2-naphthaldehyde</strong>(0.21 g, 1.5 mmol) in dry dichloromethane (20 mL) and cooled to 0 C. BBr3 (6.0 mL, 1.0 M solutionin dichloromethane) was added under a nitrogen atmosphere and was stirred at 0 C for 15 min,and at room temperature for 20 h. The reaction mixture was poured into ice and 1.0 M HCl (10 mL).The mixture was stirred for 20 min and extracted with dichloromethane (2 30 mL), dried overanhydrous magnesium sulphate and evaporation of solvent under reduced pressure gave a crudeproduct purified by flash column chromatography on silica gel, using dichloromethane to aordspure product as a pale yellow solid (0.14 g, 73%). The NMR data are consistent with that reported inliterature except that the two signals at 10.32 ppm must be assigned as the OH resonance and thatat 10.08 ppm as the resonance of the aldehyde proton. HRMS-ESI calculated for C11H8O2 [M + H]+172.0524, found 172.0538.
  • 3
  • [ 581-71-5 ]
  • [ 74-95-3 ]
  • [ 66943-05-3 ]
  • 3-hydroxy-4-(1,4,7,10-tetraoxa-13-azacyclopentadec-13-ylmethyl)naphthalene-2-carbaldehyde [ No CAS ]
  • 4
  • [ 13041-60-6 ]
  • [ 581-71-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 87 percent / LiAlH4 / tetrahydrofuran / 6 h / 20 °C 2: 82 percent / pyridinium chlorochromate; sodium acetate; molecular sieves 4 Angstroem / CH2Cl2 / 0.67 h 3: 80 percent / BBr3 / CH2Cl2 / 1 h / 20 °C
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2.25 h / 20 °C / Inert atmosphere; Glovebox; Cooling with ice; Schlenk technique 2: pyridinium chlorochromate; potassium acetate / dichloromethane / 2.08 h / 0 - 20 °C / Schlenk technique; Inert atmosphere; Molecular sieve 3: boron tribromide / dichloromethane / 0 - 20 °C / Inert atmosphere; Schlenk technique
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2.25 h / 20 °C / Schlenk technique; Inert atmosphere; Cooling with ice 2: potassium acetate; pyridinium chlorochromate / dichloromethane / 2.08 h / 0 - 20 °C / Schlenk technique; Inert atmosphere; Molecular sieve 3: boron tribromide / dichloromethane / 1.08 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
  • 5
  • [ 581-71-5 ]
  • [ 2567-29-5 ]
  • C24H18O2 [ No CAS ]
  • 6
  • [ 581-71-5 ]
  • [ 68220-26-8 ]
  • C18H12ClFO2 [ No CAS ]
  • 7
  • [ 996-98-5 ]
  • [ 581-71-5 ]
  • [ 5970-45-6 ]
  • Zn(2+)*(C10H6(OH)CHNNC(O))2(2-)*4H2O={Zn(C10H6(OH)CHNNC(O))2(H2O)2}*2H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With acetic acid In ethanol; water addn. of the hydrazine in hot H2O to an ethanolic soln. of the acetate containing a trace of acetic acid with stirring for 10 min, reflux, 1 h, hot filtration, washing (H2O, C2H5OH, ether), suspension in ethanol, addn. of the naphthaldehyde, reflux, 20h; hot filtration, washing (hot ethanol, ether), drying in an air oven at ca 70°C, elem. anal.;
  • 8
  • [ 996-98-5 ]
  • [ 581-71-5 ]
  • uranyl(VI) acetate dihydrate [ No CAS ]
  • UO2(2+)*(C10H6(OH)CHNNC(O))2(2-)*4H2O={UO2(C10H6(OH)CHNNC(O))2(H2O)2}*2H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With acetic acid In ethanol; water addn. of the hydrazine in hot H2O to an ethanolic soln. of the acetate containing a trace of acetic acid with stirring for 10 min, reflux, 1 h, hot filtration, washing (H2O, C2H5OH, ether), suspension in ethanol, addn. of the naphthaldehyde, reflux, 6 h; hot filtration, washing (hot ethanol, ether), drying in an air oven at ca 70°C, elem. anal.;
  • 9
  • [ 581-71-5 ]
  • [ 30159-70-7 ]
  • 10
  • [ 581-71-5 ]
  • [ 29182-42-1 ]
  • [ 1312774-03-0 ]
  • 11
  • [ 216369-04-9 ]
  • [ 581-71-5 ]
  • [ 949574-56-5 ]
YieldReaction ConditionsOperation in experiment
In ethanol Reflux; General procedure of the preparation of chiral phosphine-Schiff base type ligands L1-L13 General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields.
  • 12
  • [ 581-71-5 ]
  • (Sa)-3,3'-diformyl-2,2'-dihydroxy-1,1'-binaphthalene [ No CAS ]
  • [ 121314-69-0 ]
YieldReaction ConditionsOperation in experiment
45 % ee With C17H22FeN2; copper(l) chloride In acetonitrile at 15℃; for 96h; Overall yield = 35 %;
  • 13
  • [ 581-71-5 ]
  • [ 3964-52-1 ]
  • (E)-3-(((3-chloro-4-hydroxyphenyl)imino)methyl)naphthalen-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% In methanol; for 2h;Reflux; To a stirring methanolic solution (20 ml) of 2-hydroxynaphthaldehyde (2 mmol), a methanolic solution (20 ml) of 4-amino-2-chloro phenol (2 mmol) was added dropwise. The contentof resulting mixture was refluxed for 2 h leading to the isolation of microcrystalline solid product. The product was filtered and washed with methanol and then finally dried under vacuo over anhydrous calcium chloride (Scheme 1). Ligand (L1): Yield: 73%, Colour: yellow, m.p. >300 C, Anal. Calc. forC17H12NO2Cl (%) C, 68.58; H, 4.06; N, 4.70. Found: C, 68.54; H, 4.03; N,4.62. IR (KBr, cm-1) 1630 nu(HC=N), 3437 nu(OH), 1318 nu(C-O). ESI-MS (m/z+), 298.89.
  • 14
  • N-[3-(triisopropylsilyloxy)naphthalen-2-yl]methoxy}benzenesulfonamide [ No CAS ]
  • [ 581-71-5 ]
  • [ 30159-70-7 ]
  • 15
  • N-[(3-hydroxynaphthalen-2-yl)methoxy]benzenesulfonamide [ No CAS ]
  • [ 98-10-2 ]
  • [ 581-71-5 ]
  • [ 599-71-3 ]
  • [ 30159-70-7 ]
  • [ 16722-50-2 ]
  • nitrosyl hydride [ No CAS ]
  • 22
  • 1,1,1-trifluoro-N-[3-(triisopropylsilyloxy)naphthalen-2-yl]methoxy}-methanesulfonamide [ No CAS ]
  • [ 581-71-5 ]
  • [ 30159-70-7 ]
  • 23
  • 1,1,1-trifluoro-N-[(3-hydroxynaphthalen-2-yl)methoxy]methanesulfonamide [ No CAS ]
  • [ 581-71-5 ]
  • [ 421-85-2 ]
  • [ 30159-70-7 ]
  • [ 48022-83-9 ]
  • nitrosyl hydride [ No CAS ]
  • 24
  • N-[(3-hydroxynaphthalen-2-yl)methoxy]methanesulfonamide [ No CAS ]
  • [ 581-71-5 ]
  • [ 3144-09-0 ]
  • [ 43633-03-0 ]
  • [ 50695-55-1 ]
  • [ 30159-70-7 ]
  • nitrosyl hydride [ No CAS ]
  • 25
  • [ 423165-07-5 ]
  • [ 581-71-5 ]
  • [ 1443256-99-2 ]
  • C31H40F2N6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.56% With ammonium hydroxide; In methanol; water; for 2h;Cooling with ice; General procedure: To an aqueous solution of active hydrogen containing amide, few drops of aqueous ammonia solution (1 eq.) and secondary amine (1 eq.) were added in drops in an ice-cold solution under constant stirring for dissolution. Aromatic aldehydes dissolved in methanol, added dropwise to the above mixture and stirring was continued for 2 h. The formation of compounds were observed within 30 min. Reaction was monitored by TLC, after completion of reaction, the product was filtered and washed with distilled water and dried at 45-50 C.
  • 26
  • [ 581-71-5 ]
  • [ 55896-93-0 ]
  • ethyl naphtho[2,3-e][1,2]oxathiine-3-carboxylate 2,2-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With pyridine In 1,2-dichloro-ethane at 85℃; for 1h; Sealed tube; Sulfocoumarin-3-carboxylates; General Procedure General procedure: To a heavy-walled reaction tube containing a magnetic stir bar weresequentially added 2-hydroxyaryl aldehyde 1 (0.5 mmol), 1,2-dichlo-roethane (3 mL), pyridine (98 μL, 1.2 mmol), and sulfonyl chloride 2(112 mg, 0.6 mmol, dropwise addition). The resulting solution quicklyturned brown in color. The tube was quickly sealed with a screw capand placed in a preheated (85 °C) oil bath. After stirring for 1 h, themixture was cooled to room temperature and washed with 2 M HCl (8mL) to remove the pyridine. The aqueous phase was washed with di-chloromethane (5 mL). The combined organic phase was washed withsaturated NaHCO 3 solution (15 mL), dried over Na 2 SO 4 , and concen-trated under vacuum. The residue was submitted to column chroma-tography over silica gel with PE/EtOAc as eluent to afford the pureproducts 3.
  • 27
  • [ 581-71-5 ]
  • [ 84405-44-7 ]
  • [ 62-53-3 ]
  • 2-(3-hydroxynaphthalen-2-yl)-1-phenyl-(5,10-dibromophenanthro[9,10-d]imidazole) [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With ammonium acetate; acetic acid; at 120℃; for 12h;Schlenk technique; Inert atmosphere; Adapted from [3]. S5 (1.00 g, 2.73 mmol, 1.0 eq) was added to a 50 ml_ schlenk flask with ammonium acetate (1.05 g, 13.66 mmol, 5.0 eq). The system was purged with N2 gas three times. Then acetic acid (13.7 ml_) was added to the vessel followed by aniline (0.50 ml_, 5.45 mmol, 2.0 eq) and S1 1 (0.47 g, 2.73 mmol, 1.0 eq). The reaction vessel was then heated to reflux for 12 h. Upon cooling to room temperature the reaction was quenched with water and the resulting precipitate was collected via vacuum filtration and rinsed with water. The brown solid was dissolved in CH2CI2 and rinsed once with brine, then passed through a silica plug with hot CH2CI2. The CH2CI2 was then removed in a rotary evaporator and the residue was recrystallized from ethyl acetate resulting in a light cocoa colored solid. Yield 0.830 g (51 %). (0321) Figure 47 shows 1HNMR (400 MHz, CDCI3, 25C) d (ppm) 13.15 (s, 1 H), 8.82 (d, J = 2.1 Hz, 1 H), 8.52 (d, J = 9.0 Hz, 1 H), 8.45 (d, J = 8.9 Hz, 1 H), 7.91 - 7.87 (m, 1 H), 7.83 (t, J = 7.6 Hz, 2H), 7.74 (dd, J = 8.8, 2.2 Hz, 1 H), 7.69 - 7.66 (m, 2H), 7.64 - 7.59 (m, 2H), 7.43 (s, 1 H), 7.37 (d, J = 16.3 Hz, 1 H), 7.26 (s, 1 H), 7.15 (d, J = 1 1.7 Hz, 3H) spectra for compound S12. (0322) Figure 48 shows 13C NMR (101 MHz, CDC ) d (ppm) 155.51 , 148.75, 138.56, 135.23, 134.63, 131.38, 131.23, 129.72, 129.05, 128.86, 128.59, 127.86, 127.84, 127.78, 127.22, 126.94, 126.80, 126.80, 125.98, 125.78, 125.42, 125.04, 124.1 1 , 123.81 , 123.46, 122.46, 121.39, 1 14.94, 11 1.96 spectra for compound S12.
  • 28
  • [ 581-71-5 ]
  • [ 30478-88-7 ]
  • 3'-bromo-2,2'-dihydroxy-[1,1'-binaphthalene]-3-carbaldehyde [ No CAS ]
  • [ 141779-46-6 ]
  • [ 111795-43-8 ]
  • 29
  • [ 91-95-2 ]
  • [ 581-71-5 ]
  • copper dichloride [ No CAS ]
  • C56H34Cu2N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% In ethanol at 60℃; for 6h; 1 Preparation Example 1: Synthesis of Compound A 3,3'-diaminobenzidine (10.0 g, 46.7 mmol) was dissolved in ethanol (100 ml) and then stirred at room temperature for 10 minutes. Thereafter, 2-hydroxy-3-naphthaldehyde (35.4 g, 205.5 mmol) and copper (II) chloride (13.2 g, 98.1 mmol) were dissolved in ethanol (100 ml), and then slowly added dropwise and stirred at about 60° C. for 6 hours. Made it. After the reaction was finished, it was cooled to room temperature and filtered. The filtrate was collected, put into methanol (50 ml), stirred at room temperature for 1 hour, and filtered. The filtrate was dried to obtain compound A (29.8 g, 67%).
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