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[ CAS No. 58481-14-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 58481-14-4
Chemical Structure| 58481-14-4
Chemical Structure| 58481-14-4
Structure of 58481-14-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 58481-14-4 ]

CAS No. :58481-14-4 MDL No. :MFCD10574965
Formula : C9H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HZIKYLAZZZSYKF-UHFFFAOYSA-N
M.W :176.17 Pubchem ID :13415157
Synonyms :

Calculated chemistry of [ 58481-14-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.04
TPSA : 62.98 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) : -6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.83
Log Po/w (XLOGP3) : 1.12
Log Po/w (WLOGP) : 1.13
Log Po/w (MLOGP) : 0.04
Log Po/w (SILICOS-IT) : 1.51
Consensus Log Po/w : 1.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.78
Solubility : 2.91 mg/ml ; 0.0165 mol/l
Class : Very soluble
Log S (Ali) : -2.04
Solubility : 1.62 mg/ml ; 0.0092 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.59
Solubility : 0.454 mg/ml ; 0.00258 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 58481-14-4 ]

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 [ 58481-14-4 ]

* 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 [ 58481-14-4 ]
  • Downstream synthetic route of [ 58481-14-4 ]

[ 58481-14-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 557-21-1 ]
  • [ 14906-37-7 ]
  • [ 58481-14-4 ]
YieldReaction ConditionsOperation in experiment
85% With N,N-Dimethylcarbamoyl chloride In toluene for 2 h; Reflux; Inert atmosphere A reaction mixture of 4-(ethoxycarbonyl)pyridine-1-oxide28 (3.64 g, 21.82 mmol), DMCC (3.01 mL, 32.73 mmol) and Zn(CN)2(3.84 g, 32.73 mmol) in toluene (40 mL) was heated under reflux under an argon atmosphere for 2 h. The reaction mixture was cooled to room temperature and H2O (30 mL) was added, and stirring was continued for 15 min. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated under reduced pressure to yield a brown solid. This was then passed through a silica plug using EtOAc:Pet. Ether in a 2:1 ratio as the eluent yielding a yellow oil which solidified on ice. Orange solid (3.28 g, 85percent). m.p. 39-40 °C (lit. 42-44 °C);14 νmax (KBr) 2988, 2964, 2238, 1728, 1597, 1557, 1470, 1402, 1393, 1370, 1298, 1281, 1202, 1113, 1015, 990, 918, 890, 862, 763, 686 cm-1; δH (300 MHz, CDCl3) 8.90 (1 H, dd, J 4.9, 0.9 Hz, pyr-H), 8.25 (1 H, dd, J 1.5, 0.9 Hz, pyr-H), 8.10 (1 H, dd, J 4.9, 1.5 Hz, pyr-H), 4.47 (2 H, q, J 7.1 Hz, OCH2), 1.44 (3 H, t, J 7.1 Hz, CH3); δC (75 MHz, CDCl3) 163.1 (C=O), 151.9, 139.0, 134.7, 127.6, 126.1, 116.6 (CN), 62.6 (OCH2), 14.1 (CH3); HRMS (ESI): [M+H]+, found 177.0659. C9H9N2O2 requires 177.0659. NMR data is in agreement with literature data.14
Reference: [1] Tetrahedron, 2016, vol. 72, # 51, p. 8470 - 8478
  • 2
  • [ 773837-37-9 ]
  • [ 58481-14-4 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 28, p. 9499 - 9502
  • 3
  • [ 14906-37-7 ]
  • [ 7677-24-9 ]
  • [ 58481-14-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 2, p. 565 - 571
  • 4
  • [ 617-35-6 ]
  • [ 100-70-9 ]
  • [ 58481-14-4 ]
  • [ 97483-79-9 ]
Reference: [1] Heterocycles, 1987, vol. 26, # 3, p. 731 - 744
[2] Heterocycles, 1987, vol. 26, # 3, p. 731 - 744
  • 5
  • [ 617-35-6 ]
  • [ 100-70-9 ]
  • [ 58481-14-4 ]
  • [ 97483-79-9 ]
Reference: [1] Heterocycles, 1987, vol. 26, # 3, p. 731 - 744
[2] Heterocycles, 1987, vol. 26, # 3, p. 731 - 744
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