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[ CAS No. 936250-18-9 ] {[proInfo.proName]}

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Chemical Structure| 936250-18-9
Chemical Structure| 936250-18-9
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Product Details of [ 936250-18-9 ]

CAS No. :936250-18-9 MDL No. :MFCD06795674
Formula : C14H18BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :DROXVQHBOYMKPQ-UHFFFAOYSA-N
M.W : 259.11 Pubchem ID :17998911
Synonyms :

Calculated chemistry of [ 936250-18-9 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 73.97
TPSA : 51.48 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.67
Log Po/w (WLOGP) : 1.89
Log Po/w (MLOGP) : 0.73
Log Po/w (SILICOS-IT) : 1.75
Consensus Log Po/w : 1.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.16
Solubility : 0.178 mg/ml ; 0.000685 mol/l
Class : Soluble
Log S (Ali) : -3.4
Solubility : 0.102 mg/ml ; 0.000395 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.23
Solubility : 0.0152 mg/ml ; 0.0000587 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.04

Safety of [ 936250-18-9 ]

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

Application In Synthesis of [ 936250-18-9 ]

* 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 [ 936250-18-9 ]
  • Downstream synthetic route of [ 936250-18-9 ]

[ 936250-18-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 73183-34-3 ]
  • [ 936250-18-9 ]
YieldReaction ConditionsOperation in experiment
95% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In tetrahydrofuran for 18 h; Inert atmosphere; Reflux Under a N2 atmosphere, an oven dried 100 mL flask was charged with 2-(3-iodophenoxy)acetonitrile 42 (1.16 g, 4.48 mmol), bis(pinacolato)diboron 43 (4.55 g, 17.92 mmol), potassium acetate (1.76 g, 17.92 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (32.8 mg, 1 molpercent).
Dry THF (50 mL) was added to the mixture, and the flask was heated at reflux for 18 h under N2 atmosphere.
The solvent was then evaporated under reduced pressure, ethyl acetate (30 mL) was added and the mixture was sonicated for 10 min and filtered.
The filtrate was triturated with MgSO4 and charcoal (0.5 g), and filtered through a short pad of celite.
The filtrate was then concentrated under reduced pressure and the resulting residue was recrystallised from a mixture of ethyl acetate/hexane (3:2) to give the boronic ester 40 as a pink solid (1.1 g, 95percent), mp: 40-41 °C; IR (cm-1): ν 2980 (m, C-H aliphatic), 2152 (m, CN), 1128 (w, C-O).
1H NMR (CDCl3), δ: 7.43 (d, 1H, J = 7.6 Hz, phenoxy_6 H), 7.39 (s, 1H, phenoxy_2 H), 7.08 (t, 1H, J = 7.9 Hz, phenoxy_5 H), 6.96 (d, 1H, J = 8.0 Hz, phenoxy_4 H), 4.76 (s, 2H, CH2), 1.26 (s, 12H, 4xCH3).
13C NMR, δ: 157.1 (phenoxy C1), 132.6 (phenoxy C3), 131.4 (phenoxy C5), 124.7 (phenoxy C4), 114.8 (CN), 114.6 (phenoxy C2), 94.6 (phenoxy C6), 83.7 (dioxaborolan C4, C5), 53.9 (CH2), 25.2 (4xCH3) ppm. ESI-MS m/z 259 (M+). HRMS (ESI) calcd for C14H19BNO3 (MH+), 260.1458; found, 260.1462.
Reference: [1] Tetrahedron, 2018, vol. 74, # 12, p. 1294 - 1306
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  • [ 626-02-8 ]
  • [ 936250-18-9 ]
Reference: [1] Tetrahedron, 2018, vol. 74, # 12, p. 1294 - 1306
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