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[ CAS No. 149557-18-6 ] {[proInfo.proName]}

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Chemical Structure| 149557-18-6
Chemical Structure| 149557-18-6
Structure of 149557-18-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 149557-18-6 ]

CAS No. :149557-18-6 MDL No. :MFCD03427190
Formula : C9H13BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :SRSWMXFANVKOFH-UHFFFAOYSA-N
M.W : 180.01 Pubchem ID :3691230
Synonyms :

Calculated chemistry of [ 149557-18-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.37
TPSA : 49.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.69
Log Po/w (WLOGP) : 0.16
Log Po/w (MLOGP) : 0.65
Log Po/w (SILICOS-IT) : -0.09
Consensus Log Po/w : 0.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.44 mg/ml ; 0.00797 mol/l
Class : Soluble
Log S (Ali) : -2.35
Solubility : 0.807 mg/ml ; 0.00448 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.22
Solubility : 1.07 mg/ml ; 0.00597 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.02

Safety of [ 149557-18-6 ]

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 [ 149557-18-6 ]

* 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 [ 149557-18-6 ]

[ 149557-18-6 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 149557-18-6 ]
  • [ 84447-29-0 ]
  • [ 190970-23-1 ]
YieldReaction ConditionsOperation in experiment
73% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 60℃; Inert atmosphere;
  • 2
  • [ 149557-18-6 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 2h; 2.55 4.2.55 Suzuki-Miyaura coupling: typical procedures. General procedure: To a solution of 20b (51.5 mg, 0.118 mmol) in dioxane (1.0 mL) and water (0.5 mL) was added 3-methoxyphenylboronic acid (26.9 mg, 0.127 mmol), potassium carbonate (48.9 mg, 0.354 mmol), dichlorobis(triphenylphosphine)palladium (4.1 mg, 0.0059 mmol), and the mixture was heated at 100 °C for 2 h. The reaction mixture was partitioned between AcOEt and water. The organic layer was washed water, brine, dried with Na2SO4, and evaporated.
  • 3
  • [ 149557-18-6 ]
  • [ 2218486-78-1 ]
  • [ 2218469-76-0 ]
YieldReaction ConditionsOperation in experiment
66.5% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane for 2h; Heating; 4.2. General method for preparation of compounds 6a-r, (exemplified by 6a) General procedure: The building block 4 (100.0 mg, 0.21 mmol) was dissolved in dioxane (5 mL), then followed by the additions of 2-fluoro-3-methoxyphenylboronic acid (71.4 mg, 0.42 mmol), Pd(dppf)Cl2(20 mg), and Na2CO3 (66.8 mg, 0.63 mmol). The reaction mixture was heated at 100 C for 2 h before cooled to rt. After concentrated,the residue was dissolved in EtOAc (50 mL) and washed with H2O(10 mL 2), and brine (10 mL 2), dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel using petroleum ether-EtOAc (4:1) to give 6a (76.0 mg,69.9%) as a white solid.
  • 4
  • [ 149557-18-6 ]
  • [ 2411685-27-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
84% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water Reflux; Inert atmosphere;
  • 5
  • [ 122862-27-5 ]
  • [ 149557-18-6 ]
  • [ 2501944-26-7 ]
YieldReaction ConditionsOperation in experiment
48% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene; acetonitrile at 110℃; for 60h; Inert atmosphere; 4 AMBMP analog 5 was synthesized according to scheme I. 4.6- dichloropyrimidine-2-amine was reacted with equivalent amount of benzo[d][l,3]dioxol-5- ylmethanamine in t-butanol. The reaction product was further reacted with equivalent amount of (3-( propoxy)phenyl)boronic acid, in the presence of Pd(PPh3)4 in a column. The product obtained was subjected to purification using silica gel chromatography on Combiflash Rf 200 by employing hexane-EtOAc step gradient (95:5 80:20) over 30 min. Fractions corresponding to the product peak were combined and concentrated using rotavap to afford AMBMP analog 5 in 48% yield. The product was characterized by NMR.
  • 6
  • [ 149557-18-6 ]
  • [ 608-30-0 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In lithium hydroxide monohydrate; toluene at 100℃; Schlenk technique; Inert atmosphere;
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