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Structure of 4181-05-9

Chemical Structure| 4181-05-9

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Product Details of [ 4181-05-9 ]

CAS No. :4181-05-9
Formula : C19H15NO
M.W : 273.33
SMILES Code : C1=CC(=CC=C1N(C2=CC=CC=C2)C3=CC=CC=C3)C=O
MDL No. :MFCD00145131
InChI Key :UESSERYYFWCTBU-UHFFFAOYSA-N
Pubchem ID :77846

Safety of [ 4181-05-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 4181-05-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 21
Num. arom. heavy atoms 18
Fraction Csp3 0.0
Num. rotatable bonds 4
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 86.51
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

20.31 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.95
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

5.2
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

4.97
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

4.13
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.92
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.23

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-5.18
Solubility 0.0018 mg/ml ; 0.00000659 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-5.37
Solubility 0.00116 mg/ml ; 0.00000423 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-6.71
Solubility 0.0000527 mg/ml ; 0.000000193 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

Yes
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-4.28 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.74

Application In Synthesis of [ 4181-05-9 ]

* 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.

  • Downstream synthetic route of [ 4181-05-9 ]

[ 4181-05-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 700-46-9 ]
  • [ 4181-05-9 ]
  • [ 1620483-87-5 ]
  • 2
  • [ 4181-05-9 ]
  • [ 1671-88-1 ]
  • C31H23N7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With acetic acid; In methanol; at 85℃; for 6h; 1.20 mmol of monoformaldehyde triphenylamine and 1.00 mmol of 3,5-dipyridyl-4-amino-1,2,4-triazole are added to a 100 ml three-necked round bottom flask containing 20 ml of methanol.Under magnetic stirring,Slowly heated to 85 C,When all the ingredients are completely dissolved,Slowly add 3 drops of glacial acetic acid.The reaction was stopped after stirring for 6h at 85 C.The resulting reaction solution was cooled to room temperature,That is bright yellow precipitate precipitation,filter,Washed three times with methanol,After drying that L1,Yield 65%.
  • 3
  • [ 784-04-3 ]
  • [ 4181-05-9 ]
  • C35H25NO [ No CAS ]
  • 4
  • [ 5027-32-7 ]
  • [ 109-63-7 ]
  • [ 4181-05-9 ]
  • C86H64B2F4N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% In a 100 mL flask, the mixture of 1 ,1 ,2,2-tetraacetylethane (500 mg, 2.523 mmol, 1 eq) and BF3 Et20 (666 μΙ_, 5.297 mmol, 2.1 eq) in 3ml_ ethyl acetate was heated for 30min at 50-60C in air. Dissolved 4-(N,N-Diphenylamino)-benzaldehyde (2.90 g, 10.597 mmol, 4.2 eq) and B(n-OBu)3 (2.439 g, 10.597 mmol, 4.2 eq) into 40mL ethyl acetate, then the solution was injected into the first mixture. Kept the reaction at 50-60C for another 30 min. First portion of morpholine (176 μΙ_, 2.018 mmol, 0.8eq) was added dropwise into the reaction. After 6 h heating, second portion of morpholine (176 μΙ_, 2.018 mmol, 0.8eq) was added, and the reaction was kept heating at 50-60C overnight. All the solvents were evaporated. The crude product could be obtained by flash column chromatography (silica, CH2CI2). Further purification was done by many times' precipitation in CH2CI2/petroleum ether, giving dark green powder (712 mg, 22% yield). 1H NMR (400 MHz, CD2CI2, ppm): 58.02 (d, 3J= 15.2 Hz, 1 H), 7.41 (d, 3J= 9.2 Hz, 2H), 7.32 (m, 4H), 7.14 (m, 6H), 6.69 (d, 3J= 9.2 Hz, 2H), 6.58 (d, 3J= 15.2 Hz, 1 H); (0310) 13C NMR (400 MHz, CDCI3, ppm): Not soluble enough. (0311) HRMS (ESI+) [M - H]- calcd for found m/z= 1373.5201.
  • 5
  • [ 36997-31-6 ]
  • [ 4181-05-9 ]
  • (N'<SUP>1</SUP>E,N'<SUP>3</SUP>E,N'<SUP>5</SUP>E)-N'<SUP>1</SUP>,N'<SUP>3</SUP>,N'<SUP>5</SUP>-tris(4-(diphenylamino)benzylidene)benzene-1,3,5-tricarbohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With hydrazine hydrate; acetic acid; In ethanol; dimethyl sulfoxide; at 80.0℃; for 24.0h; Add 25ml of ethanol to a 50ml round bottom flask, 1,3,5-Benzenetrihydrazide (0.67g, 2.66mmol) is stirred and dissolved; Take another 250ml round bottom flask and add 50ml DMSO, 4-Diphenylaminobenzaldehyde (2.6g, 9.56mmol) is stirred and dissolved, After dissolving, add the trimellitic hydrazide solution to the 4-diphenylaminobenzaldehyde solution, Add 2 drops of glacial acetic acid, stir and reflux for 24h at 80C. After the reaction is completed, the reaction solution is cooled to room temperature, A large amount of solid precipitated and filtered under reduced pressure. The filter cake was washed 3 times with ethanol and dried, The pure target compound (1) N'1, N'3, N'5-tris((E)-4-(diphenylamino)benzylidene)<strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong> is obtained. Yield 83%,
 

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