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[ CAS No. 24463-15-8 ] {[proInfo.proName]}

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Chemical Structure| 24463-15-8
Chemical Structure| 24463-15-8
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Product Details of [ 24463-15-8 ]

CAS No. :24463-15-8 MDL No. :MFCD00029252
Formula : C17H12O Boiling Point : -
Linear Structure Formula :- InChI Key :NGDMLQSGYUCLDC-UHFFFAOYSA-N
M.W : 232.28 Pubchem ID :104977
Synonyms :

Calculated chemistry of [ 24463-15-8 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.06
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 76.27
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 : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 4.23
Log Po/w (WLOGP) : 3.92
Log Po/w (MLOGP) : 3.82
Log Po/w (SILICOS-IT) : 4.63
Consensus Log Po/w : 3.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.54
Solubility : 0.00675 mg/ml ; 0.0000291 mol/l
Class : Moderately soluble
Log S (Ali) : -4.37
Solubility : 0.01 mg/ml ; 0.0000431 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.42
Solubility : 0.0000883 mg/ml ; 0.00000038 mol/l
Class : Poorly soluble

Medicinal Chemistry

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

Safety of [ 24463-15-8 ]

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

Application In Synthesis of [ 24463-15-8 ]

* 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.

  • Upstream synthesis route of [ 24463-15-8 ]
  • Downstream synthetic route of [ 24463-15-8 ]

[ 24463-15-8 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 24463-15-8 ]
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YieldReaction ConditionsOperation in experiment
93% With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) triflate; 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole In acetonitrile at 25℃; for 1 h; General procedure: A round-bottom flask was charged with alcohol (2 mmol), CuOTf (0.1 mmol, 0.05 equiv) (S)-5-(pyrrolidin-2-yl)-1H-tetrazole (0.1 mmol, 0.05 equiv), TEMPO (0.1 mmol, 0.05 equiv), DMAP (0.15 mmol, 0.075 equiv) and CH3CN (5 ml). The reaction mixture was stirred at 25 °C open to air until the completion of the reaction, as monitored by TLC. After completion, CH3CN was evaporated under vacuum. The residue was then diluted with CH2Cl2 (5 ml) and filtered through a plug of silica gel to afford the desired product.
86% With C35H28Cl2N5PRu; potassium <i>tert</i>-butylate In toluene at 50℃; for 6 h; General procedure: using the complex 1 as catalyst in presence of a base following a general procedure. In a round-bottom flask, 1 mmol of substrate, 0.005mmol of catalyst (3.6mg) and 0.010 mmol of tBuOK (1.1mg) were mixed in 10mL toluene. The reaction mixture was heated at 50°C in aerobic condition with continuous stirring for 6h and then the solvent was evaporated with a rotary evaporator under reduced pressure. The crude product, thus obtained, was purified on preparative silica gel GF-254 TLC plate using ethyl acetate: hexane (1:10) solvent mixture as eluent. The oxidized products were characterized by NMR spectroscopy (See Figs. S4–S32).
80% With 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide; Oxone; cetyltrimethylammonim bromide In water at 20℃; for 2 h; Green chemistry General procedure: The alcohol (2 mmol) was added to a solution of IBS (0.02 mmol, 0.01 eq), oxone (2.2 mmol, 1.1 equiv.) and 3 wtpercent CTAB solution (5 mL). The mixture was stirred at room temperature. The reaction was monitored by TLC. After completion, the solution was extracted with CH2Cl2 (3 × 10 mL). The combined organic phase was then filtered through a pad of silica gel and evaporated under vacuum to afford the desired product.
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  • 2
  • [ 24463-15-8 ]
  • [ 16640-68-9 ]
  • [ 3029-19-4 ]
  • [ 103698-30-2 ]
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  • 3
  • [ 24463-15-8 ]
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  • [ 3029-19-4 ]
  • [ 74833-81-1 ]
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  • 4
  • [ 220196-58-7 ]
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  • [ 91385-15-8 ]
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  • 5
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  • [ 142-08-5 ]
  • [ 822-89-9 ]
  • [ 3029-19-4 ]
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Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 52, p. 9747 - 9750
  • 6
  • [ 67-56-1 ]
  • [ 220196-58-7 ]
  • [ 3029-19-4 ]
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  • [ 91385-15-8 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 2001, # 10, p. 1927 - 1932
  • 7
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YieldReaction ConditionsOperation in experiment
88% With sodium tetrahydroborate In tetrahydrofuran; methanol Pyrene-aldehyde (1 g, 4.3 mmol) anddry tetrahydrofuran (20 mL) were placed in a round bottom flask.Sodium borohydride (165 mg, 4.3 mmol) was added in small portions,together with small portions of methanol to help the solubilization(total volume of added methanol = 10 mL). An orangesolution was obtained. The reaction was quenched with a 2percent concentratedhydrochloric acid solution. The solvent was removedunder reduced pressure. The white powder obtained was dissolvedin dichloromethane, washed with water and the organic phase wasdried with magnesium sulphate. The solvent was removed underreduce pressure. The resulting solid was subjected to silica gel columnchromatography (eluent = dichloromethane). Yield = 88percent.1H NMR (300 MHz, CDCl3, 300 K): d (ppm) = 1.87 (s, 1H); 5.39 (s,2H); 7.9–8.4 (m, 9H). 13C NMR {1H} (75 MHz, CDCl3, 300 K): d(ppm) = 6403; 123.15; 124.87; 124.93; 125.13; 125.42; 125.45;126.14; 126.19; 127.54; 127.63; 128.07; 128.97; 130.95; 131.42;131.44; 133.94. ESI-MS: m/z = 254.97 [M+Na]+, 214.99 [MOH]+(Calcd. for C17H12O:: 232.09 (exact mass); 232.28 (FW)). UV–Vis(DCM): kmax (nm) = 314; 327; 344.
81% With sodium tetrahydroborate In methanol at 0 - 20℃; 1-pyrenecarboxaldehyde (0.35 g, 1.50 mmol) was dissolved in15 mL methanol, and NaBH4 (0.08 g, 2.10 mmol) was added slowly into the reaction mixture at 0 °C for 30 min. After stirring at room temperature overnight, 20 mL 5percent HCl was added in the reaction to quench the excess NaBH4, and the solution changed to milk-white suspension. The organic solvent was removed and then the solid was extracted with ethyl acetate (3 × 15 mL). The organic fractions were washed with saturated NaHCO3 aqueous solution. The collected organic solution was dried with sodium sulfate and was concentrated to give compound 8 in an 81percent yield. 1H NMR (400MHz, CDCl3) δ 8.30–7.96 (m, 9 H, Ar–H),5.33 (s, 2 H, CH2). TOF-MS: m/z 231.1[M–H].
75% With sodium tetrahydroborate In tetrahydrofuran; ethanol at 0 - 20℃; for 5 h; To a solution of pyrene aldehyde 13 (1.0 g, 4.34 mmol) in THF/Ethanol (10 mL: 30 mL) at 0 °C, NaBH4 (0.83 g, 21.71 mmol) was slowly added in five portions. The reaction mixture was slowly raised to rt and stirred for 5 h. It was then poured into ice-water (100 mL) containing 10 mL of Conc. HCl. The reaction mixture was extracted with CHCl3 (3 x 25 mL). The combined organic layer was washed with water and dried (Na2SO4). Removal of solvent under reduced pressure afforded pyrenyl methanol 15 (0.76 g, 75percent) as a pale yellow solid. mp 124-125 °C (Lit. 123-124 °C); 1H-NMR (300 MHz, CDCl3): δ 8.24 (d, J = 9.3 Hz, 1 H, ArH), 8.13 (t, J = 7.5 Hz, 2 H, ArH), 8.06-8.01 (m, 2 H, ArH), 7.99-7.918 (m, 4 H, ArH), 5.28 (s, 2 H, OCH2), 2.03 (s, 1 H, OH) ppm. 13C-NMR (75 MHz, CDCl3): δ 133.7 (C), 131.2 (2C), 131.1 (C), 130.7 (C), 128.7 (C), 127.8 (C-H), 127.4 (C-H), 127.3 (C-H), 125.9 (C-H), 125.9 (2C-H), 125.2 (C-H), 125.2 (C-H), 124.6 (C), 122.9 (C-H), 63.7 (Ar-CH2) ppm.
54 %Chromat. With sodium hydroxide In isopropyl alcohol at 82℃; for 2 h; General procedure: In a typical procedure, a 5 mg (0.77 molpercent) of RuO2/MWCNT and 80 mg (2 mmol) of NaOH were stirred with 5 mL of i-PrOH taken in an ace pressure tube equipped with a stirring bar. Then the substrate (1 mmol) was added to the stirring solution and then the mixture was heated at 82°C. The completion of the reaction was monitored by GC. After the reaction, the catalyst was separated out from the reaction mixture by simple centrifugation and the products and unconverted reactants were analyzed by GC without any purification. Selectivity of the product for each reaction was alsocalculated. Finally, the separated RuO2/MWCNT was washed well with diethyl ether followed by drying in an oven at 60°C for 5 h and it was reused for the subsequent transfer hydrogenation of carbonyl compounds to investigate the reusability of the RuO2/MWCNT.

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  • 11
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  • 12
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  • 13
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  • 14
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  • 16
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  • 18
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