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Chemical Structure| 90-93-7 Chemical Structure| 90-93-7

Structure of 90-93-7

Chemical Structure| 90-93-7

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Product Details of [ 90-93-7 ]

CAS No. :90-93-7
Formula : C21H28N2O
M.W : 324.46
SMILES Code : O=C(C1=CC=C(N(CC)CC)C=C1)C2=CC=C(N(CC)CC)C=C2
MDL No. :MFCD00009044
InChI Key :VYHBFRJRBHMIQZ-UHFFFAOYSA-N
Pubchem ID :66663

Safety of [ 90-93-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 90-93-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 24
Num. arom. heavy atoms 12
Fraction Csp3 0.38
Num. rotatable bonds 8
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 103.96
TPSA ?

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

23.55 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.73
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

5.34
Log Po/w (WLOGP)?

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

4.61
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.

3.66
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

4.25
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.32

Water Solubility

Log S (ESOL):?

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

-5.06
Solubility 0.00284 mg/ml ; 0.00000875 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.

-5.59
Solubility 0.00084 mg/ml ; 0.00000259 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

-6.68
Solubility 0.0000678 mg/ml ; 0.000000209 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

Yes
Log Kp (skin permeation)?

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

-4.49 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

0.0 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<2.0
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)

2.14

Application In Synthesis of [ 90-93-7 ]

* 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 [ 90-93-7 ]

[ 90-93-7 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 90-93-7 ]
  • [ 135-91-1 ]
  • 2
  • [ 90-93-7 ]
  • [ 1066-26-8 ]
  • [ 228415-25-6 ]
  • [ 135-91-1 ]
YieldReaction ConditionsOperation in experiment
General procedure: Preparation methods of 3,3-diaryl-3H-naphtho[2,1-b]pyrans were generally based on condensation reactions taking place in the apolar solvent as toluene under acid catalysis, which starting from suitable naphthols and propargyl alcohols.[26], [27] and [28]The propargyl alcohol (2) was prepared from the diaryl ketone (1) as outlined in Scheme 1. 10 mmol diaryl ketone (1) was dissolved in 50 mL dry THF and was added dropwise to a solution of 50 mmol sodium acetylide in THF below 0 C. The mixture was then allowed to stir at room temperature for about 3 h until none of the diaryl ketone (1) remained by TLC examination of the reaction mixture. The reaction mixture was poured into iced water for separation. The organic phase was collected and followed by washing with water (3×50 mL) and then dried (anhyd Na2SO4). The propargyl alcohol was then obtained in the yield of about 80% after the short flash chromatography and was used for subsequent procedure directly.273 mmol propargyl alcohol (2), 3 mmol 2-naphthol derivative (3), and 1.0 g p-toluenesulfonic acid (TsOH) were dissolved in 50 mL toluene. The reaction mixture was refluxed for about 2 h until TLC examination indicated that none of the propargyl alcohol remained. The mixture was cooled to room temperature and washed with 1 mol L-1 NaOH solution (2×50 mL) and water. After drying with anhyd Na2SO4, removal of the toluene by vacuum evaporation gave a dark gum. The pure naphthopyran product was obtained by elution from silica using 10% ethyl acetate/hexane.
  • 3
  • [ 135-91-1 ]
  • [ 90-93-7 ]
YieldReaction ConditionsOperation in experiment
25.3 g With dihydrogen peroxide; chloranil; Aliquat 336; In chlorobenzene; at 20 - 25℃; 4,4'-bis(dialkylamino)diphenylmethane (30 g), cobalt complex (3) (0.9 g), tetrachlorophenylhydrazine (0.9 g),Trioctylmethylammonium chloride (1g) and chlorobenzene (100ml) were added to a 250ml four-neck bottle.Add 30% hydrogen peroxide (13.2g) dropwise, add at room temperature, control the temperature 20~25 C, drop,The spot plate is monitored until there is no remaining reaction material.After the end of the reaction, the temperature was lowered, and the temperature was lowered to 5 C, and 30 ml of a 20% sodium hydrogen sulfite solution was added to wash, and the mixture was allowed to stand for liquid separation.The organic phase is distilled off under reduced pressure.The crude tetraethylmethanolone was obtained in an amount of 29 g.The crude product was recrystallized from 29 g of n-heptane.Obtained a pale yellow tetraethylmethanol ketone solid (25.3 g),The content is 99.1%.
  • 4
  • [ 90-93-7 ]
  • [ 15424-38-1 ]
  • C62H69N5(2+)*2Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.2% A mixture of 4,4′-bis(diethylamino)-benzophenone (3.0g, 9.3mmol), toluene (30mL), and phosphorus (V) oxychloride (4.2mL, 15.2mmol) was vigorously stirred at 25C for 1h. Subsequently, n-phenyl-9-anthramine (1.0g, 3.7mmol) was added to the mixture. The resulting solution was stirred for 24h at 105C and then cooled to room temperature. The settled mixture was extracted using CH2Cl2 and NaCl brine. The collected organic layers were dried over anhydrous MgSO4 and evaporated. The crude dye mixture was refluxed in an acetone/ethyl acetate (1:3, v/v) binary solvent at 80C for 3h. The final solid product was filtered out and dried at 80C under vacuum for 1 day. Yield: 2.73g, 77.2%; 1H NMR (DMSO-d6, ppm): δ=10.1 (1H, s), 8.22 (2H, d), 7.31 (26H, m), 3.60 (16H, d), 1.20 (24H, t); 13C NMR (DMSO-d6, ppm): δ=12.70, 44.81, 45.46, 112.65, 113.94, 114.54, 114.63, 124.83, 125.58, 126.08, 126.33, 126.77, 127.50, 127.75, 129.55, 130.21, 130.46, 130.96, 131.19, 131.84, 132.71, 133.57, 137.00, 138.97, 139.94, 146.9, 153.82, 154.77, 155.33, 168.85, 169.83, 175.85; MALDI-TOF: m/z 882.57 (100%, [M + H]+); Elemental analysis: Calcd. for C62H69N5Cl2: C,77.96; H, 7.28; N, 7.33%. Found: C, 77.77; H, 7.42; N, 7.52.
  • 5
  • [ 90-93-7 ]
  • [ 15424-38-1 ]
  • C62H69N5O12S4(2+)*2Cl(1-) [ No CAS ]
 

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