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Structure of 785051-54-9

Chemical Structure| 785051-54-9

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Product Details of [ 785051-54-9 ]

CAS No. :785051-54-9
Formula : C24H24BNO2
M.W : 369.26
SMILES Code : CC1(C)C(C)(C)OB(C2=CC=C(N3C4=C(C5=C3C=CC=C5)C=CC=C4)C=C2)O1
MDL No. :MFCD16294549
InChI Key :AHDSYMVAUJZCOP-UHFFFAOYSA-N
Pubchem ID :11850073

Safety of [ 785051-54-9 ]

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

Computational Chemistry of [ 785051-54-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 28
Num. arom. heavy atoms 19
Fraction Csp3 0.25
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 117.26
TPSA ?

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

23.39 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

5.98
Log Po/w (WLOGP)?

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

5.08
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.

3.92
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

3.97
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.79

Water Solubility

Log S (ESOL):?

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

-6.27
Solubility 0.0002 mg/ml ; 0.000000541 mol/l
Class?

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

Poorly soluble
Log S (Ali)?

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

-6.25
Solubility 0.000209 mg/ml ; 0.000000565 mol/l
Class?

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

Poorly 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

-8.2
Solubility 0.00000235 mg/ml ; 0.0000000064 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

Yes
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

No
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

No
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.

-4.31 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<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)

3.22

Application In Synthesis of [ 785051-54-9 ]

* 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 [ 785051-54-9 ]

[ 785051-54-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 785051-54-9 ]
  • [ 22034-13-5 ]
  • 4-(4-(9H-carbazol-9-yl)phenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 80℃; for 12h;Inert atmosphere; General procedure: To a solution of 4-bromobenzo[c] [1,2,5]thiadiazole (107 mg,0.50 mmol) and N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (124 mg, 0.50 mmol) in toluene-ethanol(30 mL/10 mL), Pd(PPh3)4 (57 mg, 0.05 mmol) and anhydrous K2CO3 (207 mg, 1.5 mmol) were added under an argon flow at room temperature. The mixturewas then heated to 80 °C for12 h. The mixture was quenched with water after cooling back to room temperature and extracted with dichloromethane. The combined extract was dried with anhydrous Na2SO4 and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel with CH2Cl2/petroleum (1:1) to afford NBT as an orange solid.
  • 2
  • [ 785051-54-9 ]
  • [ 66127-01-3 ]
  • C30H19N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With palladium diacetate; potassium carbonate; tricyclohexylphosphine; In ethanol; toluene; at 90 - 110℃;Inert atmosphere; Under nitrogen, palladium acetate (13mg, 0.059mmol), tricyclohexylphosphine (33mg, 0.118mmol) was added To <strong>[66127-01-3]<strong>[66127-01-3]3-bromo-1,10-phenanthrolin</strong>e</strong> (511mg, 1.97mmol), 9- (4- (4,4,5,5- tetramethyl-1,3,2-dioxaborolane - 2- Yl) phenyl) carbazole (800mg, 2.17mmol), aqueous potassium carbonate solution (2mL, 2M), ethanol (20mL), toluene (20 mL) mixed Co-solution and the reaction was heated to 90 ~ 110 C and stirred overnight. After cooling to room temperature, the reaction mixture was added to the distillation Water and the toluene layer was separated, the aqueous layer was extracted three times with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure After removal of the solvent was separated by a silica gel column, eluting with methylene chloride and ethyl acetate, to give a white solid, yield 91%(755mg).
  • 3
  • [ 785051-54-9 ]
  • [ 10016-52-1 ]
  • 9-(4-(8-bromodibenzo[b,d]furan-2-yl)phenyl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃; for 16.5h;Inert atmosphere; Example 1.9.13 9-(4-(8-bromodibenzo[b,d]furan-2-yl)phenyl)-9H-carbazole (Compound 13) A mixture of Compound 11 (2.00 g, 4.56 mmol), <strong>[10016-52-1]2,8-dibromodibenzo[b,d]furan</strong> (2.60 g, 7.98 mmol), tetrakis(triphenylphosphine) palladium(0) (0.26 g, 0.23 mmol), potassium carbonate (1.892 g, 13.70 mmol), 1,4-dioxane (60.00 mL), and water (12.00 mL) was degassed with bubbling argon for 1 hour. The reaction mixture was then heated to 80° C. and was stirred overnight (16.5 hours), maintaining an argon atmosphere. Consumption of the starting material was confirmed by thin-layer chromatography and the reaction was cooled to room temperature. The product was extracted with dichloromethane, dried, and purified by silica gel column chromatography with dichloromethane in hexanes as the eluent. The product fractions were then dried and the product was collected to yield Compound 13 (1.57 g, 70percent).
  • 4
  • [ 785051-54-9 ]
  • [ 19063-55-9 ]
  • C27H17NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 80℃; for 8h;Inert atmosphere; It mainly includes the following steps: taking the coumarin derivative (500 mg, 2.2 mmol) after bromination at the 6 position,A derivative of the pinacol borate (922 mg, 2.5 mmol) and K2CO3 (133 mg) were introduced at the 4-position of the carbazole phenyl group, and dissolved in a toluene-ethanol mixed solution (3:1, 80 ml).After passing nitrogen gas for 30 min, 15 mg of tetrakistriphenylphosphine palladium catalyst was added to the solvent, and the mixture was heated to 80 C, 1000 r / min, and reacted for 8 hours.After the reaction, it was cooled to room temperature, washed with a large amount of water, extracted with dichloromethane, and evaporated to remove excess solvent.The solid was dissolved in 100 mL of dichloromethane solution, washed with 40 mL of distilled water, and separated.The remaining water was removed with anhydrous sodium sulfate, separated, and dried.The crude product was separated and purified on a 200-300 mesh silica gel column using dichloromethane-hexane (yield: 1:4) to afford white compound C as shown in FIG.The coumarin-type organic nonlinear optical material compound C obtained by the above production method had a yield of 41%.
 

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