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[ CAS No. 145498-86-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 145498-86-8
Chemical Structure| 145498-86-8
Chemical Structure| 145498-86-8
Structure of 145498-86-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 145498-86-8 ]

CAS No. :145498-86-8 MDL No. :MFCD22199644
Formula : C11H11NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :DAWBZAJVUJBYMZ-UHFFFAOYSA-N
M.W : 205.21 Pubchem ID :59838657
Synonyms :

Calculated chemistry of [ 145498-86-8 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.74
TPSA : 59.32 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) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 1.4
Log Po/w (WLOGP) : 1.55
Log Po/w (MLOGP) : 1.3
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 1.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.93 mg/ml ; 0.00941 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 1.15 mg/ml ; 0.00563 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.1
Solubility : 0.164 mg/ml ; 0.000798 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.94

Safety of [ 145498-86-8 ]

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 [ 145498-86-8 ]

* 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 [ 145498-86-8 ]
  • Downstream synthetic route of [ 145498-86-8 ]

[ 145498-86-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 143-33-9 ]
  • [ 71887-28-0 ]
  • [ 145498-86-8 ]
YieldReaction ConditionsOperation in experiment
95% With sodium iodide In N,N-dimethyl-formamide; acetonitrile for 10 h; Heating / reflux Into a 500 mL 3-neck round bottom flask was added 10 g (61.75 mmol) of 2-bromomethyl, 3-methoxy methyl benzoate, 4.0 g (81.6 mmol) of NaCN, 0.30 g (2 mmol) of NaI, 100 mL of CH3CN, and 50 mL of DMF. The reaction mixture was heated and refluxed for 10 hours. The precipitate (NaBr) was filtered off, and the solution was concentrated on an evaporator. 300 mL of water and 200 mL of ether were added and then shaken in a separatory funnel. The water was extracted twice with 100 mL of ether. The ether fractions were dried over MgSO4, and concentrated to yield methyl 3-methoxy-2-cyanomethylbenzoate (95-100percent yield). This ester (0.053 mmol, 10.51 g) was stirred vigorously in 100 mL of CH3OH. Ba(OH)2 H2O (0.079 mmol, 14.97 g) was added and the mixture stirred at room temperature overnight. The CH3OH was removed on a rotary evaporator. 150 mL of water, 200 mL of CH2Cl2, and 50 mL of 6N HCl were added, and then stirred in a flask to dissolve all residues. The mixture was transferred to a separatory funnel, acidified with 6N HCl to pH 1-2. The CH2Cl2 phase was separated and the aqueous phase extracted twice with 50 mL of CH2Cl2. The CH2Cl2 extracts were combined, dried over MgSO4 and charcoal, filtered, and evaporated to yield 8.8 g of a white solid, 2-cyanomethyl-3-methoxybenzoic acid, (87percent). Methyl 3-methoxy-2-cyanomethylbenzoate: 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.6 (d, 1H), 7.4 (t, 1H), 7.1 (d, 1H), 4.18 (s, 2H), 3.94 (s, 3H), 3.926 (s, 3H). TLC (1:1 ethyl acetate: hexane) 0.55. 2-Cyanomethyl-3-methoxybenzoic acid: 1H NMR (300 Mhz, CDCl3) δ (ppm): 7.55 (d, 1H), 7.45 (t, 1H), 7.3 (d, 1H), 4.121 (d, 2H), 3.91, (s, 3H). TLC (1:1 ethyl acetate: hexane
Reference: [1] Patent: US2006/20146, 2006, A1, . Location in patent: Page/Page column 32
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