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[ CAS No. 5315-79-7 ] {[proInfo.proName]}

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Chemical Structure| 5315-79-7
Chemical Structure| 5315-79-7
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Product Details of [ 5315-79-7 ]

CAS No. :5315-79-7 MDL No. :MFCD00044543
Formula : C16H10O Boiling Point : -
Linear Structure Formula :- InChI Key :BIJNHUAPTJVVNQ-UHFFFAOYSA-N
M.W : 218.25 Pubchem ID :21387
Synonyms :

Calculated chemistry of [ 5315-79-7 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 72.17
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.13
Log Po/w (XLOGP3) : 4.64
Log Po/w (WLOGP) : 4.29
Log Po/w (MLOGP) : 3.84
Log Po/w (SILICOS-IT) : 4.28
Consensus Log Po/w : 3.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.81
Solubility : 0.00336 mg/ml ; 0.0000154 mol/l
Class : Moderately soluble
Log S (Ali) : -4.79
Solubility : 0.00353 mg/ml ; 0.0000162 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.01
Solubility : 0.000211 mg/ml ; 0.000000966 mol/l
Class : Poorly soluble

Medicinal Chemistry

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

Safety of [ 5315-79-7 ]

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 [ 5315-79-7 ]

* 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 [ 5315-79-7 ]

[ 5315-79-7 ] Synthesis Path-Downstream   1~85

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  • [ 77-78-1 ]
  • [ 34246-96-3 ]
YieldReaction ConditionsOperation in experiment
45% With sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 12h; A mixture of 1-formylpyrene (see preparation of 4, 0.69 g,3.0 mmol) and m-CPBA (1.04 g, 6.0 mmol) in CH2Cl2 (50 mL) wasstirred at reflux for 24 h under an argon atmosphere. To the solutionwere added THF (5 mL), MeOH (10 mL), and 25 % KOH aq (0.6 mL),and the resulting solution was stirred at room temperature for 3 h. Thesolution was concentrated in vacuo to give a black residue. The residuewas extracted with CH2Cl2 (100 mL) and sat. NaCl aq (50 mL). Theorganic layer was separated, dried over Na2SO4, filtered, and concentratedin vacuo, giving a residue that was subjected to silica gelcolumn chromatography (eluent: CHCl3) to give <strong>[5315-79-7]1-hydroxypyrene</strong>(0.36 g, 55 % yield, pink solid). Lit [96].A mixture of <strong>[5315-79-7]1-hydroxypyrene</strong> (0.17 g, 0.77 mmol), NaOH (0.5 g,5.0 mmol), Me2SO4 (0.26 g, 2.1 mmol) in H2O (15 mL) and THF (10 mL)was stirred at room temperature for 12 h. The mixture was extractedwith AcOEt (100 mL) and then Et2O (100 mL). The combined organiclayers were washed with sat. NaCl aq (50 mL), dried over Na2SO4, filtered,and concentrated in vacuo, giving a residue that was subjected tosilica gel column chromatography (eluent: CHCl3) to give 1-methoxypyrene(0.080 g, 45 % yield, brown solid). Lit [97].To a stirred nitrobenzene (120 mL) solution of 1-methoxypyrene(0.46 g, 2.0 mmol) was added dropwise nitrobenzene (40 mL) solutionof Br2 (0.4 mL, 7.2 mmol), and the resulting solution was stirred at 80 Cfor 12 h. After cooling to room temperature, conc. NaOH aq (10 mL)was added to quench excess Br2. The formed solid was washed withCHCl3 (100 mL) and collected by filtration to give 1,3,6-tribromo-8-methoxypyrene (0.85 g, 91 % yield, yellow solid).A mixture of 1,3,6-tribromo-8-methoxypyrene (0.93 g, 2.0 mmol),trimethylsilylacetylene (0.844 g, 8.6 mmol), PdCl2(PPh3)2 (0.071 g,0.10 mmol), CuI (0.033 g, 0.17 mmol), and PPh3 (0.068 g, 0.26 mmol)in THF (30 mL) and i-Pr2NH (25 mL) was stirred at 80 C for 12 h underan argon atmosphere. The resulting mixture was concentrated in vacuo,giving a residue that was subjected to silica gel column chromatography(eluent: hexane) followed by recycling preparative HPLC (GPC, eluent:CHCl3) to give 1-methoxy-3,6,8-tris(trimethylsilylethynyl)pyrene 0.24 g, 23 % yield). Yellow solid; mp 288 C; 1H NMR (400 MHz, CDCl3)8 0.37 (s, 9 H), 0.38 (s, 9 H), 0.40 (s, 9 H), 4.18 (s, 3 H), 7.66 (s, 1 H),8.27 (s, 1 H), 8.42 (d, J =9.3 Hz, 1 H), 8.48 (d, J =9.3 Hz, 1 H), 8.52 (d,J =9.3 Hz, 1 H), 8.53 (d, J =9.3 Hz, 1 H) ppm; 13C NMR (100 MHz,CDCl3) 8 0.0, 0.0, 0.0, 56.2, 100.3, 101.0, 103.0, 103.0, 103.5, 111.8,111.8, 116.8, 117.0, 119.2, 121.1, 122.5, 123.8, 123.9, 124.7, 125.0,126.6, 127.0, 132.5, 132.5, 134.3, 134.3, 153.5 ppm; IR (KBr) 887,1119, 1250, 2152, 2360, 2959 cm-1; MS (CI) m/z (relative intensity,%)=75 (100), 245 (12), 448 (14), 520 (M+, 85); HRMS (EI) calcd forC32H36OSi3: 520.1316, found: 520.2074.
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  • C16H8O(1+) [ No CAS ]
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  • [ 5315-79-7 ]
  • [ 111843-54-0 ]
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  • [ 5522-43-0 ]
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  • 1-hydroxy-2-nitropyrene [ No CAS ]
  • 13
  • [ 78751-40-3 ]
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YieldReaction ConditionsOperation in experiment
95.4% With water; sodium hydroxide; at 60℃; 1000 ml of water,80 g of sodium hydroxide (2 mol) and 245 g of acetoxypyrene obtained in Step 2 were added to a 2000 ml reaction flask,After the mixture is fully dissolved,The mixture was warmed to 60 C,After sufficient reaction (approximately 6 hours for this example)Cooling to about 30 C, and then dropping 500ml concentration of 35% concentrated hydrochloric acid,To be fully reacted,It will produce a large number of white solid,The mixture was filtered,dry,To give 196 g of solid 1-hydroxyprene as a white solid,The HPLC chromatogram of 1-hydroxypyrene shown in Figure 3 shows that the content of 1-hydroxypyrene is 99.28%The yield of 1-hydroxypyrene was 95.4%.
94% With water; sodium hydroxide; In ethanol; for 2.5h;Reflux; A solution of 0.19 g (0.73 mmol) of 1-acetoxypyrene 5 and 0.19 g (4.75 mmol) of NaOH in a mixture of 8.1 ml of EtOH and 5.4 ml of H2O was heated under reflux for 2.5 h. EtOH was distilled off in vacuo and the small portions of 2.7 ml of conc. HCl were added dropwise on cooling and stirring. The precipitate of 3 was filtered, washed with an excess of H2O and dried in a dessicator over NaOH. Yield 0.15 g (94%), mp 180-182 C (crystals from the reaction mass) (lit.,9(a),(b)179-181 C). IR (CHCl3, n/cm-1): 3594 (OH). MS, m/z (%): 218 (100,M+), 189 (82), 163 (6), 109 (9), 94 (32), 82 (4).
80% With sodium hydroxide; In water; at 60℃; for 10h; The 1-acetoxyphosphonium (6.6 g, 25.16 mmol) obtained in the previous step was dissolved in 50 mL of a 1 M aqueous sodium hydroxide solution (2 g, 50 mmol) and reacted at 60 C. After the reaction was completed (about 10 hours), cooled to 0 C, Add about 20mL of 6M concentrated hydrochloric acid, precipitate a white solid, filter it, collect the solid, recrystallize with toluene, and add 1-hydroxypyrene seed crystals to induce crystallization during recrystallization to obtain high purity1-Hydroxyphosphonium (4.4 g, white solid, yield 80%, purity 99.87%)
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  • Formic acid pyren-1-yl ester [ No CAS ]
  • [ 5315-79-7 ]
YieldReaction ConditionsOperation in experiment
0.7 g With potassium hydroxide; In tetrahydrofuran; methanol; for 2h;Inert atmosphere; 1-hydroxypyrene was prepared from pyrene-1-carboxaldehyde 2 according to a known procedure by making changes in the purification procedure (Sehgal and Kumar, 1989). To a stirred solution of commercially available pyrene-1-carboxaldehyde 2(2.0 g, 8.6 mmol) in anhydrous CH2Cl2 (80 mL) m-chloroperbenzoic acid (m-CPBA, 2.2 g, 13 mmol) was added under an atmosphere of Ar. The resulting solution was refluxed under Ar atmosphere until TLC monitoring (SiO2, AcOEt/n-hexane 1/9, x2) showed the complete disappearance of the starting material (24 h). The reaction mixture was treated with 10% NaHCO3 until effervescence ceased and the organic solvent was evaporated under reduced pressure. The resulting brown residue was dissolved in a mixture of THF (20 mL) and MeOH (20 mL) and then 25% KOH solution (6 mL) was added. The solution was stirred under Ar until TLC monitoring (SiO2, AcOEt/n-hexane 1/9, x2) showed the complete disappearance of pyrene-1-carboxaldehyde 2 (2 h). Organic solvents were evaporated under reduced pressure and theresidue was taken up with 2% KOH solution and extracted with Et2O (320 mL) to remove unreacted aldehyde. The resulting aqueous phase was acidified (HCl 2 M) to pH = 2 at 0 C and extracted with CHCl3 (320 mL). The combined organic extracts were then dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by chromatography (Neutral Aluminium Oxide; MeOH/CHCl3 from 0.1/9.9 to 2.0/8.0) to afford compound 3 as a white solid with 37% yield (0.7 g, 3.2 mmol).1H NMR (CD3OD): 8.36 (d, J = 9.2, 1H), 8.00-7.73 (m, 7H), 7.48 (d,J = 8.4, 1H).
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  • [ 121633-88-3 ]
  • C80H76O8 [ No CAS ]
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  • 8-hydroxy-pyrene-trisulfonic acid-(1.3.6) [ No CAS ]
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  • sodium-<pyrene sulfonate-(1)> [ No CAS ]
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  • [ 7664-93-9 ]
  • [ 27928-00-3 ]
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  • 26
  • [ 5522-43-0 ]
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YieldReaction ConditionsOperation in experiment
85% .1), add 1-nitrosoguanidine 100g to a 1000ml reaction bottle,Add 500 ml of methanol and stir.1-nitrosoguanidine (solid) is suspended in the solution to form a suspension.2.2), light oxidation method:Air is introduced into the suspension obtained in step 2.1) at 20 to 25 C.The ventilation is 40L/min; the light intensity is 100Lux (for example, 100W fluorescent lamp) for photooxidation; after 5 hours of photooxidation, the solid will slowly disappear, the solution will slowly turn from yellow to black, and the light will be oxidized for 10 hours. The photooxidation was stopped; at this time, the 1-nitrosoguanidine content was less than 2% (i.e., less than 0.01 mol) by HPLC, and thus the reaction was completed.2.3), in the reaction obtained in step 2.2), add 1.00g of BHT (2,6-di-tert-butyl-4-methylphenol), concentrate to dry at 45-50 C, add 200ml of toluene, heat to 60 ~ 80 C to achieve dissolution, and then cool to 20 ~ 25 C, filtration, filter cake drying (60 C dry to constant weight),A 75 g of 1-hydroxyindole product was obtained. The content is 99.1%. The yield was 85%.
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  • 1-tetradecyl-1-pyrenyl ether [ No CAS ]
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  • [ 823-78-9 ]
  • 1-(3-bromobenzyloxy)pyrene [ No CAS ]
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  • [ 51760-23-7 ]
  • [ 572874-28-3 ]
  • [ 572874-27-2 ]
  • 1-[3-({3,5-bis[(dimethylamino)methyl]-4-(trimethylsilyl)phenyloxy}methyl)-5-bromobenzyloxy]pyrene [ No CAS ]
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  • [ 51760-23-7 ]
  • 1-[3-bromo-5-(bromomethyl)benzyloxy]pyrene [ No CAS ]
  • [ 572874-27-2 ]
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  • [ 1714-29-0 ]
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YieldReaction ConditionsOperation in experiment
85.4% With potassium hydroxide; In water; at 220℃; for 18h; A method for preparing 1-hydroxyfluorene includes the following steps: Add 9.50g to 100mL reaction kettleBy purchasing a purity of 95%1-bromofluorene(33.8mmol),330mg copper oxide (3.38mmol)And 11.4 g of potassium hydroxide (203 mmol),Then, 70 mL of a mixed solvent of polyethylene glycol-400 and water (volume ratio V / V = 4: 1) was added.After stirring well, the reaction kettle was heated to 220 C.After the reaction has fully proceeded (the reaction in this example is about 18 hours),After cooling to room temperature, ethyl acetate (50 mL) and water (200 mL) were added to the reaction mixture for dilution, the temperature was lowered to 0 C, and 1M hydrochloric acid was slowly added to adjust the pH to 2-3.The layers were allowed to stand and separated, and ethyl acetate was added to the aqueous layer for extraction (2x150mL). The organic layers were combined, washed with 1M hydrochloric acid (3x50mL) and water (2x50mL), and the layers were allowed to stand. The organic layer was dried over anhydrous sodium sulfate and filtered. Concentrated to dryness under reduced pressure.To the crude product, a mixed solvent of petroleum ether and ethyl acetate (300 mL volume ratio V / V = 3: 1) was added for dilution, followed by filtration through celite, and the black insoluble matter was filtered off. The filtrate was concentrated under reduced pressure to obtain a dark brown solid. Dichloromethane (40 mL) was added to the crude product, and heated to reflux to form a suspension,After slowly cooling to room temperature, cooling at 0 C for 30 minutes, filtering, collecting the filter cake, drying,Get1-hydroxypyrene 6.30g(Off-white solid, yield 85.4%, purity 97%).
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  • 1-pyrenyl-1-hexadecylcarboxylate [ No CAS ]
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  • 4-(pyren-1-yloxymethyl)-benzoic acid methyl ester [ No CAS ]
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  • [ 150550-99-5 ]
  • C41H32O7 [ No CAS ]
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  • [ 150551-01-2 ]
  • C73H60O15 [ No CAS ]
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  • C39H26O7(2-)*2K(1+) [ No CAS ]
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  • C69H48O15(4-)*4K(1+) [ No CAS ]
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  • 1-[3-(trimethylsilyl)benzyloxy]pyrene [ No CAS ]
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  • [ 5315-79-7 ]
  • 1,3-bis[(1-pyrenyloxy)methyl]-5-(trimethylsilyl)benzene [ No CAS ]
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  • [ 129-00-0 ]
  • nickel [ No CAS ]
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  • [ 129986-84-1 ]
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  • [ 129986-94-3 ]
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  • [ 5315-79-7 ]
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  • [ 5315-79-7 ]
  • ethyl-(8-nitro-pyren-1-yl)-ether [ No CAS ]
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  • [ 5315-79-7 ]
  • ethyl-(6-nitro-pyren-1-yl)-ether [ No CAS ]
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  • PhCH3 [ No CAS ]
  • [ 5315-79-7 ]
  • [ 100-39-0 ]
  • [ 584-08-7 ]
  • [ 123689-56-5 ]
YieldReaction ConditionsOperation in experiment
25.9% In acetone; 8A. 1-Benzyloxyprene To a RB flask equipped with overhead stirrer, condenser and N2 inlet line with bubbler was added <strong>[5315-79-7]1-hydroxypyrene</strong> (Cambridge Chemical, Inc., 5.0 g, 23 mmol), benzyl bromide (Aldrich, 15.64 g, 92 mmol, 10.94 mL), K2 CO3 (Mallinckrodt, 12.72 g, 92 mmol) and acetone (100 mL). The mixture was refluxed overnight, cooled and then poured into H2 O (250 mL) and extracted with EtOAc (3*100 mL). The EtOAc layers were combined and washed successively with 1N NaOH (100 mL), H2 O (100 mL) and saturated NaCl solution (2*100 mL). The solution was then dried (K2 CO3) and the solvent removed by rotary evaporation to give the crude product. This material was purified by passing it through a plug of SiO2 using PhCH3 as the eluding solvent. The solvent was then removed from the appropriate fractions by rotary evaporation and the solid recrystallized from CH2 Cl2 /hexane to give 1.78 g (25.9% yield) of 1-benzyloxypyrene, mp 105-106, (C,H).
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  • heptakis(2,3-di-O-benzyl)-6(B),6(C),6(E),6(F),6(G)-penta-O-benzyl-β-cyclodextrin [ No CAS ]
  • C207H200O35 [ No CAS ]
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  • [ 107-30-2 ]
  • [ 115560-65-1 ]
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  • [ 108-24-7 ]
  • pyrene-1,2-diyl diacetate [ No CAS ]
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  • [ 476488-97-8 ]
  • [ 476489-02-8 ]
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  • [ 952677-14-4 ]
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  • [ 1252934-31-8 ]
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  • C16H8(2)H2O [ No CAS ]
  • C16H8(2)H2O [ No CAS ]
  • C16H8(2)H2O [ No CAS ]
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  • C23H22O3 [ No CAS ]
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  • [ 1241385-36-3 ]
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