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[ CAS No. 2198-53-0 ] {[proInfo.proName]}

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Chemical Structure| 2198-53-0
Chemical Structure| 2198-53-0
Structure of 2198-53-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2198-53-0 ]

CAS No. :2198-53-0 MDL No. :MFCD00008675
Formula : C10H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :NRPTXWYBRKRZES-UHFFFAOYSA-N
M.W : 163.22 Pubchem ID :16616
Synonyms :

Calculated chemistry of [ 2198-53-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.69
TPSA : 29.1 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) : -6.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.0
Log Po/w (XLOGP3) : 1.07
Log Po/w (WLOGP) : 2.07
Log Po/w (MLOGP) : 2.15
Log Po/w (SILICOS-IT) : 2.32
Consensus Log Po/w : 1.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.76
Solubility : 2.81 mg/ml ; 0.0172 mol/l
Class : Very soluble
Log S (Ali) : -1.27
Solubility : 8.71 mg/ml ; 0.0534 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.55
Solubility : 0.0461 mg/ml ; 0.000282 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 2198-53-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2198-53-0 ]

* 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.

  • Upstream synthesis route of [ 2198-53-0 ]
  • Downstream synthetic route of [ 2198-53-0 ]

[ 2198-53-0 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 2198-53-0 ]
  • [ 3176-66-7 ]
Reference: [1] Chemische Berichte, 1908, vol. 41, p. 663
[2] Patent: US2005/54697, 2005, A1, . Location in patent: Page/Page column 73
  • 2
  • [ 2198-53-0 ]
  • [ 39622-79-2 ]
Reference: [1] Bl. Johns Hopkins Hosp., 1952, vol. 91, p. 330,333
[2] Chemische Berichte, 1906, vol. 39, p. 74
  • 3
  • [ 2198-53-0 ]
  • [ 925-90-6 ]
  • [ 21436-98-6 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0℃; for 0.5 h;
Stage #2: With cerium(III) chloride In tetrahydrofuran; dichloromethane at -78℃; for 2 h;
Stage #3: With hydrogenchloride In ethyl acetate
General procedure: Tf2O (185μL, 1.1mmol) was added dropwise to a cooled (0°C) solution of amide (1.0mmol) and 2-fluoropyridine (103μL, 1.2mmol) in dichloromethane (4mL). After stirring at 0°C for 30min, the mixture was cannulated to a freshly prepared organocerium reagent/complex (3.0mmol) in THF (15mL) at −78°C and stirred for 2h. Aqueous HCl solution (3mol/L, 5mL) was added to quench the reaction and the mixture was allowed to warm to r.t. and stirred for 2h. Ammonium hydroxide solution (25percent, 5mL) was then added to the mixture. The organic layer was separated and the aqueous phase was extracted with diethyl ether (3× 10mL). The combined organic layers were washed with brine (3× 3mL) and concentrated under reduced pressure to about 1/3 volume. The residual organic phase was then extracted with aqueous HCl solution (3mol/L, 3× 5mL). The separated organic phase was washed with brine (5mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel to afford ketone. The aqueous phases were combined, washed with diethyl ether (5mL), basified with an ammonium hydroxide solution (25percent, 5mL) and back-extracted with diethyl ether (5× 20mL). The ether layers were combined, washed with brine (5mL), dried over anhydrous MgSO4, filtered, acidified with a solution of HCl in ethyl acetate (3mol/L, 5mL) and concentrated under reduced pressure to afford the desired amine hydrochloride salt.
Reference: [1] Chinese Chemical Letters, 2015, vol. 26, # 9, p. 1055 - 1058
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