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[ CAS No. 55490-87-4 ] {[proInfo.proName]}

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Chemical Structure| 55490-87-4
Chemical Structure| 55490-87-4
Structure of 55490-87-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 55490-87-4 ]

CAS No. :55490-87-4 MDL No. :MFCD00176107
Formula : C18H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :RDMANBWYQHJIFZ-UHFFFAOYSA-N
M.W :254.29 Pubchem ID :41459
Synonyms :

Calculated chemistry of [ 55490-87-4 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 14
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 80.66
TPSA : 47.58 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 4.78
Log Po/w (WLOGP) : 4.31
Log Po/w (MLOGP) : 3.02
Log Po/w (SILICOS-IT) : 4.28
Consensus Log Po/w : 3.74

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.88
Solubility : 0.00335 mg/ml ; 0.0000132 mol/l
Class : Moderately soluble
Log S (Ali) : -5.51
Solubility : 0.000785 mg/ml ; 0.00000309 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.01
Solubility : 0.000246 mg/ml ; 0.000000966 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.37

Safety of [ 55490-87-4 ]

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 [ 55490-87-4 ]

* 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 [ 55490-87-4 ]
  • Downstream synthetic route of [ 55490-87-4 ]

[ 55490-87-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 642-31-9 ]
  • [ 109-77-3 ]
  • [ 55490-87-4 ]
YieldReaction ConditionsOperation in experiment
80% at 95℃; for 6 h; General procedure: The mixture of aromatic aldehyde (10.0 mmol), malononitrile or ethylcyanoacetate (11.0 equiv), pyridine (10.0 mmol) was stirred at 95 oC for 6 h. The progress of reaction was monitored by using TLC. After the completion of reaction, water (10 mL) was added to the reaction mixture and extracted with dichloromethane (3 X 10 mL) and the combined organic layer was dried over anhydrous sodium sulphate and solvent was evaporated under vacuum. The crude products were purified by column chromatography using hexane as eluent and characterized as b-cyanostyrenes 1a-m.
59 %Spectr. With Er(1,3,5-benzenetricarboxylate)(1,2-ethanediamine)0.75(H2O)0.25 In cyclohexane at 40℃; for 2 h; General procedure: The amine‐grafted MOF‐catalyzed Knoevenagel condensationreactions of aldehydes and active methylene compoundswere conducted in magnetically stirred round bottom flasks fitted with a reflux condenser. In a typical reaction, a mixture of cyclohexane (10 mL), benzaldehyde (1 mmol), and malononitrile(1.1 mmol) was added to a 50 mL flask containing catalyst2 (6 mg, 1 molpercent). The concentration of the catalyst wascalculated with respect to the molar ratio of the terminal aminogroup to the aldehyde. For comparison, the amounts of theother catalysts were also calculated based on the molaramounts of the amino groups available for the reaction (8 and27 mg for 3 and 4, respectively). The resulting mixture wasstirred at 40 °C for 2 h. The catalyst was then separated fromthe reaction mixture by centrifugation, and washed with ethylacetate (5 × 2 mL) to remove any physically adsorbed reagents.The catalyst was then dried at room temperature for 6 h andreused in the next run. The filtrate was concentrated underreduced pressure to give the crude Knoevenagel product as aresidue, which was purified by flash column chromatographyover silica gel to give the pure product. The pure product wascharacterized by 1H NMR using 1,3,5‐trimethylbenzene as aninternal standard.
Reference: [1] Journal of Chemical Research, 2012, vol. 36, # 6, p. 328 - 332
[2] Journal of the Chinese Chemical Society, 2013, vol. 60, # 1, p. 35 - 44
[3] Synthetic Communications, 2018, vol. 48, # 17, p. 2169 - 2176
[4] Journal of the American Chemical Society, 2017, vol. 139, # 14, p. 4995 - 4998
[5] Journal of the American Chemical Society, 2008, vol. 130, # 12, p. 3937 - 3941
[6] Chemical Communications, 2013, vol. 49, # 86, p. 10136 - 10138
[7] CrystEngComm, 2016, vol. 18, # 14, p. 2463 - 2468
[8] Angewandte Chemie - International Edition, 2016, vol. 55, # 41, p. 12778 - 12782[9] Angew. Chem., 2016, vol. 128, # 41, p. 12970 - 12974,5
[10] Journal of Physical Chemistry, 1991, vol. 95, # 15, p. 5737 - 5742
[11] Heterocycles, 1999, vol. 51, # 5, p. 1101 - 1107
[12] Journal of Molecular Catalysis A: Chemical, 2014, vol. 390, p. 198 - 205
[13] Monatshefte fur Chemie, 2014, vol. 145, # 7, p. 1165 - 1171
[14] European Journal of Inorganic Chemistry, 2015, vol. 2015, # 6, p. 1022 - 1032
[15] Inorganic Chemistry, 2015, vol. 54, # 11, p. 5169 - 5181
[16] Journal of Materials Chemistry A, 2015, vol. 3, # 33, p. 17320 - 17331
[17] Chinese Journal of Catalysis, 2015, vol. 36, # 11, p. 1949 - 1955
[18] New Journal of Chemistry, 2015, vol. 39, # 12, p. 9772 - 9781
[19] RSC Advances, 2016, vol. 6, # 19, p. 16087 - 16099
[20] Research on Chemical Intermediates, 2016, vol. 42, # 4, p. 2919 - 2935
[21] Crystal Growth and Design, 2016, vol. 16, # 5, p. 2874 - 2886
[22] Journal of Materials Chemistry A, 2018, vol. 6, # 2, p. 342 - 348
[23] Journal of Molecular Structure, 2017, vol. 1147, p. 682 - 696
[24] New Journal of Chemistry, 2018, vol. 42, # 12, p. 9847 - 9856
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