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[ CAS No. 49763-96-4 ] {[proInfo.proName]}

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Chemical Structure| 49763-96-4
Chemical Structure| 49763-96-4
Structure of 49763-96-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 49763-96-4 ]

CAS No. :49763-96-4 MDL No. :
Formula : C14H18O3 Boiling Point : -
Linear Structure Formula :- InChI Key :IBLNKMRFIPWSOY-FNORWQNLSA-N
M.W : 234.29 Pubchem ID :5311454
Synonyms :
BCX2600

Calculated chemistry of [ 49763-96-4 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.43
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 67.53
TPSA : 38.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.13
Log Po/w (XLOGP3) : 4.16
Log Po/w (WLOGP) : 2.73
Log Po/w (MLOGP) : 2.25
Log Po/w (SILICOS-IT) : 3.15
Consensus Log Po/w : 3.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.98
Solubility : 0.0247 mg/ml ; 0.000106 mol/l
Class : Soluble
Log S (Ali) : -4.68
Solubility : 0.00489 mg/ml ; 0.0000209 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.93
Solubility : 0.275 mg/ml ; 0.00117 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.23

Safety of [ 49763-96-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 49763-96-4 ]

* 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 [ 49763-96-4 ]

[ 49763-96-4 ] Synthesis Path-Downstream   1~6

  • 2
  • [ 49763-96-4 ]
  • [ 2419-68-3 ]
  • 3
  • [ 1076-38-6 ]
  • [ 49763-96-4 ]
  • [ 2482649-33-0 ]
YieldReaction ConditionsOperation in experiment
78% With 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; for 0.166667h; Green chemistry;
  • 4
  • [ 2419-68-3 ]
  • [ 49763-96-4 ]
YieldReaction ConditionsOperation in experiment
With methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate at 0 - 20℃; One-Pot Process for synthesis of Siripentol (1) A solution of 3, 4-dihydroxy benzaldehyde13 (72 mmol), methylene diiodide (72 mmol), KOH(144 mmol) and ethanol (100 mL). The mixturestirred and boiled at 70°C for 4 h; after completionof reaction Cool, filter and distill filtrate to get crude2. Add DCM and water (30:30 ml). Stirr for 10-15minute. remove aq. Layer and concentrate organiclayer. Then in the same flask add 3,3,dimethyl2-butanone (99 mmol), potassium carbonate(110 mmol) and add PTC i.e. TBAB (0.70 mmoland heat for 1 h at 100°C. Reaction completiondetected on TLC. Add DCM and water (50:50 mL)and remove aq. Layer and concentrate the DCMlayer under reduced pressure to get residue 4. Thenadd a solution of CeCl3.7H2O (18 mmol) in MeOH(30 mL). Cool to 0 to 5°C. Dissolve NaBH4 (72 mmol)in MeOH (50 mL) and add dropwise in 5 minutes.After the addition of NaBH4 solution over then removethe cooling and stir the reaction mixture at R.T. After30 minute. TLC shows (Hexane: Ethyl acetate=8:2) complete conversion of starting material. Forwork-up add 50 mL, 2 N HCl stirred for 30 minute.Cool to 10°C and precipitate is formed filtered anddried to get pure Stiripentol 1 (90.62%). 74- 75°C(lit.11: 74°C); HPLC Purity:>99%; PMR (DMSO-d6,dppm):0.98 (singlet, 9H), 1.54 (singlet, 1H) 3.9 (m,1H), 5.98 (singlet, 2H), 6.17 (dd, 1H), 6.51 (doublet,1H), 6.78 (doublet, 1H), 6.84 (doublet, 1H), 6.96(doublet, 1H); 13C NMR, 100 MHz,DMSO-d6): d25.96, 33.23, 33.50, 34.98, 79.17, 100.73,108.16,108.95,121.14, 136.31,145.58, 147.57
With methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate at 0 - 20℃; regioselective reaction; One-Pot Process for synthesis of Siripentol (1) A solution of 3, 4-dihydroxy benzaldehyde13 (72 mmol), methylene diiodide (72 mmol), KOH(144 mmol) and ethanol (100 mL). The mixturestirred and boiled at 70°C for 4 h; after completionof reaction Cool, filter and distill filtrate to get crude2. Add DCM and water (30:30 ml). Stirr for 10-15minute. remove aq. Layer and concentrate organiclayer. Then in the same flask add 3,3,dimethyl2-butanone (99 mmol), potassium carbonate(110 mmol) and add PTC i.e. TBAB (0.70 mmoland heat for 1 h at 100°C. Reaction completiondetected on TLC. Add DCM and water (50:50 mL)and remove aq. Layer and concentrate the DCMlayer under reduced pressure to get residue 4. Thenadd a solution of CeCl3.7H2O (18 mmol) in MeOH(30 mL). Cool to 0 to 5°C. Dissolve NaBH4 (72 mmol)in MeOH (50 mL) and add dropwise in 5 minutes.After the addition of NaBH4 solution over then removethe cooling and stir the reaction mixture at R.T. After30 minute. TLC shows (Hexane: Ethyl acetate=8:2) complete conversion of starting material. Forwork-up add 50 mL, 2 N HCl stirred for 30 minute.Cool to 10°C and precipitate is formed filtered anddried to get pure Stiripentol 1 (90.62%). 74- 75°C(lit.11: 74°C); HPLC Purity:>99%; PMR (DMSO-d6,dppm):0.98 (singlet, 9H), 1.54 (singlet, 1H) 3.9 (m,1H), 5.98 (singlet, 2H), 6.17 (dd, 1H), 6.51 (doublet,1H), 6.78 (doublet, 1H), 6.84 (doublet, 1H), 6.96(doublet, 1H); 13C NMR, 100 MHz,DMSO-d6): d25.96, 33.23, 33.50, 34.98, 79.17, 100.73,108.16,108.95,121.14, 136.31,145.58, 147.57
  • 5
  • [ 139-85-5 ]
  • [ 49763-96-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium hydroxide / ethanol / 4 h / 70 °C 2: tetrabutylammomium bromide; potassium carbonate / 1 h / 100 °C 3: sodium tetrahydroborate; cerium(III) chloride heptahydrate; methanol / 35 min / 0 - 20 °C
Multi-step reaction with 3 steps 1: potassium hydroxide / ethanol / 4 h / 70 °C 2: tetrabutylammomium bromide; potassium carbonate / 1 h / 100 °C 3: sodium tetrahydroborate; cerium(III) chloride heptahydrate; methanol / 35 min / 0 - 20 °C
  • 6
  • [ 49763-96-4 ]
  • [ 7144-49-2 ]
  • [ 2914988-43-3 ]
YieldReaction ConditionsOperation in experiment
71 % With TBADT In water at 20℃; Irradiation;
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