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[ CAS No. 214360-47-1 ] {[proInfo.proName]}

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Chemical Structure| 214360-47-1
Chemical Structure| 214360-47-1
Structure of 214360-47-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 214360-47-1 ]

CAS No. :214360-47-1 MDL No. :MFCD04039011
Formula : C12H14BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QHAYLPAKZXKQSE-UHFFFAOYSA-N
M.W : 215.06 Pubchem ID :4198004
Synonyms :

Calculated chemistry of [ 214360-47-1 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 62.49
TPSA : 42.25 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) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.58
Log Po/w (WLOGP) : 1.33
Log Po/w (MLOGP) : 0.77
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 1.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.01
Solubility : 0.21 mg/ml ; 0.000977 mol/l
Class : Soluble
Log S (Ali) : -3.12
Solubility : 0.165 mg/ml ; 0.000766 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.6
Solubility : 0.0534 mg/ml ; 0.000248 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.86

Safety of [ 214360-47-1 ]

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 [ 214360-47-1 ]

* 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 [ 214360-47-1 ]
  • Downstream synthetic route of [ 214360-47-1 ]

[ 214360-47-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 214360-47-1 ]
  • [ 114772-40-6 ]
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374,17
[2] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374
  • 2
  • [ 126-30-7 ]
  • [ 214360-47-1 ]
YieldReaction ConditionsOperation in experiment
58% at 20℃; To a solution of TMP (3.28 mL, 19.4 mmol) in anhydrous THF (20 mL), n-BuLi (1.6 M in hexanes, 11.7 mL, 18.8 mmol) was added at -10 °C and the resulting mixture was stirred for 10 min. Then, B(Oi-Pr)3 (5.50 mL, 25 mmol) was added dropwise at -78 °C and stirred for additional 5 min before benzonitrile 1 (1.28 mL, 12.5 mmol) was added via a syringe in a single portion and the reaction mixture was stirred at -78 °C for 2 h. The solution was left to warm to rt while being stirred for 3 h and then quenched with saturated aqueous NH4Cl (60 mL). The resulting mixture was extracted with EtOAc (3 * 70 mL), the combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The intermediate product 2 was dissolved in anhydrous Tol (50 mL) and 2,2-dimethyl-1,3-propandiol (1.57 g, 15 mmol) was added and then stirred overnight at rt. The organic phase was washed with H2O (3 * 30 mL) and the aqueous extracts were washed with CH2Cl2 (3 * 30 mL). The CH2Cl2-phase was washed with H2O (1 * 30 mL), combined with Tol extract, dried (Na2SO4) and concentrated in vacuo. Recrystallization of the crude product from heptane afforded pure 3 (58percent, 2 steps) as a white crystalline solid: M.p. 109-111 °C; ESI-MS (m/z): 216.64 [MH]; 1Η ΝΜR (400 MHz, CDCl3): δ 7.88 (d, 1Η, J = 7.5 Hz), 7.68 (d, 1Η, J = 7.5 Hz), 7.54 (td, 1Η, J = 7.5 Hz, 1.0 Hz), 7.48 (td, 1Η, J = 7.5 Hz, 1.0 Hz), 3.83 (s, 4H), 1.05 (s, 6H) ppm; 13C NMR (160 MHz, CDCl3): δ 135.07, 133.64, 131.44, 130.47, 119.63, 116.56, 72.49, 31.84, 21.83 ppm.
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374,17
[2] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374
  • 3
  • [ 2042-37-7 ]
  • [ 201733-56-4 ]
  • [ 214360-47-1 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 10, p. 1671 - 1674
  • 4
  • [ 768-66-1 ]
  • [ 100-47-0 ]
  • [ 126-30-7 ]
  • [ 214360-47-1 ]
  • [ 74601-40-4 ]
Reference: [1] Organic Letters, 2001, vol. 3, # 10, p. 1435 - 1437
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