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[ CAS No. 132274-70-5 ] {[proInfo.proName]}

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Chemical Structure| 132274-70-5
Chemical Structure| 132274-70-5
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Product Details of [ 132274-70-5 ]

CAS No. :132274-70-5 MDL No. :MFCD00103497
Formula : C10H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :OQORFMABOZEDBL-UHFFFAOYSA-N
M.W : 172.18 Pubchem ID :2776567
Synonyms :

Calculated chemistry of [ 132274-70-5 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.95
TPSA : 34.89 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) : -6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 1.69
Log Po/w (WLOGP) : 1.68
Log Po/w (MLOGP) : 1.07
Log Po/w (SILICOS-IT) : 1.67
Consensus Log Po/w : 1.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.47
Solubility : 0.588 mg/ml ; 0.00342 mol/l
Class : Soluble
Log S (Ali) : -2.04
Solubility : 1.58 mg/ml ; 0.00917 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.87
Solubility : 0.232 mg/ml ; 0.00135 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 132274-70-5 ]

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 [ 132274-70-5 ]

* 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 [ 132274-70-5 ]
  • Downstream synthetic route of [ 132274-70-5 ]

[ 132274-70-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 1126-00-7 ]
  • [ 68-12-2 ]
  • [ 132274-70-5 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With n-butyllithium In tetrahydrofuran; n-heptane at -78℃; for 2 h;
Stage #2: at -78 - 20℃; for 19 h;
Stage #3: With water In n-heptane; water
Example A: 1-Phenylpyrazole-5-carbaldehyd; Experimental procedure:; Under N2-atmosphere a solution of n-butyllithium in heptane (2.61 M, 5.3 mL, 13.9 mmol) is slowly added to a cooled (- 78 °C) solution of 1-phenyl-1H-pyrazole (2.0 g, 13.9 mmol) in abs. THF (60 mL). The reaction mixture was stirred for 2 h at -78 °C. Subsequently a Solution of abs. DMF (1.1 mL, 13.9 mmol) in abs. THF (8 mL) is slowly added at -78 °C. This mixture was stirred for 1 h at -78 °C, before it was slowly heated to room temperature and was stirred for a further 18 h. Then it was hydrolysed with water (10 mL) and subsequently extracted three times with CH2Cl2. The organic phases were dried (Na2SO4), filtered and the solvent was removed under vacuum. The crude product (2.48 g) was purified using flash-chromatography (OE= 6 cm, h = 12 cm, n-hexane:ethylacetate = 8:2, 30 mL, Rf = 0.24). Yellow Oil, that crystalized in the cold to a yellow solid, melting point: 31 °C, Yield: 2.15 g (90percent) C10H8N2O (172.2) MS (EI): m/z (rel.Int) = 172 [M+, 100], 144 [M - CO, 69]. IR (neat): ν (cm-1) = 3063 (C-H aromat.), 2923 (C-H aliphat.), 2854 (C-H), 1683 (C=O), 1596, 1517, 1499 (C=C), 763, 694 (C-H). 1H-NMR (CDCl3): δ (ppm) = 7.11 (d, J = 2.1 Hz, 1H, Pyrazole-4-CH), 7.46 - 7.56 (m, 5H, Phenyl-CH), 7.76 (d, J = 2.0 Hz, 1H, Pyrazole-3-CH), 9.88 (s, 1 H, CHO). 13C-NMR (CDCl3): δ (ppm) = 112.5 (1 C, Pyrazole-4-CH), 125.8 (2 C, Phenyl-CH, ortho), 129.4 (1 C, Phenyl-CH, para), 129.6 (2 C, Phenyl-CH, meta), 139.0 (1 C, Phenyl-C, quartaer), 140.3 (1 C, Pyrazole-5-C), 140.7 (1 C, Pyrazole-3-CH), 180.2 (1 C, CHO).
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 6, p. 2992 - 3001
[2] Patent: EP1982987, 2008, A1, . Location in patent: Page/Page column 13-14; 18-19
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 19, p. 6704 - 6713
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 10, p. 2749 - 2750
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