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Chemical Structure| 3096-56-8 Chemical Structure| 3096-56-8

Structure of 3096-56-8

Chemical Structure| 3096-56-8

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Product Details of [ 3096-56-8 ]

CAS No. :3096-56-8
Formula : C13H7BrO
M.W : 259.10
SMILES Code : O=C1C2=C(C3=C1C=CC=C3)C=CC(Br)=C2
MDL No. :MFCD00010789
InChI Key :MTCARZDHUIEYMB-UHFFFAOYSA-N
Pubchem ID :725831

Safety of [ 3096-56-8 ]

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

Computational Chemistry of [ 3096-56-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 63.01
TPSA ?

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

17.07 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.41
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

4.32
Log Po/w (WLOGP)?

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

3.66
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.

3.27
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

4.31
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.59

Water Solubility

Log S (ESOL):?

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

-4.76
Solubility 0.0045 mg/ml ; 0.0000174 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.

-4.39
Solubility 0.0105 mg/ml ; 0.0000405 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

-5.93
Solubility 0.000304 mg/ml ; 0.00000117 mol/l
Class?

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

Moderately 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

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

No
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.

-4.81 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<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)

2.2

Application In Synthesis of [ 3096-56-8 ]

* 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 [ 3096-56-8 ]

[ 3096-56-8 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 689291-89-2 ]
  • [ 88284-48-4 ]
  • [ 3096-56-8 ]
  • 2
  • [ 589-87-7 ]
  • [ 172732-52-4 ]
  • [ 3096-56-8 ]
  • 3
  • [ 902518-11-0 ]
  • [ 3096-56-8 ]
  • C31H20BrNO [ No CAS ]
  • 4
  • [ 50548-45-3 ]
  • [ 3096-56-8 ]
  • C25H15BrO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
equipped with a pressure-equalizing dropping funnel 2L three-necked flask, metal magnesium (5.1g, 0.21mol), <strong>[50548-45-3]1-bromo-dibenzofuran</strong> (49.1g, 0.2mol) was dissolved in 450g of tetrahydrofuran, and placed in a constant pressure funnel, a nitrogen, three bottles heated to an inner temperature reaches 65 , through a pressure-equalizing dropping funnel was added <strong>[50548-45-3]1-bromo-dibenzofuran</strong> tetrahydrofuran, was added 1-bromo-time first one fifth of tetrahydrofuran dibenzofuran, after the initiation of the reaction, the remaining portion was slowly added dropwise, for 1.5 h addition was complete, the reaction at the reflux temperature IH, stand.2-bromo-fluorenone (51.8g, 0.2mol) was dissolved in 220g of tetrahydrofuran, and then slowly poured into the above three bottles, the reflux temperature of the reaction 3h, after the completion of the reaction, was cooled to 25 , the above reaction solution was slowly the mass was poured into 200g of 10percent concentration diluted hydrochloric acid, stirred for 15min, liquid separation, the organic phase was collected, the solvent removed under reduced pressure to give a crude product of compound 1, 82.1 g viscous liquid, the crude product of the above compound no purified, was used directly in the next reaction.
  • 5
  • [ 902518-11-0 ]
  • [ 3096-56-8 ]
  • 2-bromospiro[fluorenyl-9,8'-indolo[3,2,1-de]acridine] [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% Into a solution of the intermediate a (4.19) in purified THF (50 ml), a 2.5 M hexane solution of n-butyllithium (4.8 ml) was added dropwise gradually at -78 C. After stirring at the same temperature for 45 min, 2-bromo-9-fluorenone (2.59 g) was added. After stirring at the same temperature for one hour and further stirring at ordinary temperature for 2 h, the reaction was terminated by adding an aqueous solution of ammonium chloride. After extracting the organic substances with ethyl ether, the extract was dried over anhydrous magnesium sulfate, and then the ethyl ether was removed to obtain a yellow solid. After dispersing the obtained solid in ethanol, the dispersion was stirred. The solid collected by filtration was vacuum-dried to obtain 4.5 g of an intermediate, which was then dispersed in 40 ml of acetic acid. After adding 12 drops of concentrated sulfuric acid, the dispersion was refluxed for 3 h and then cooled to ordinary temperature. The precipitated solid was collected by filtration, washed with ethanol, and vacuum-dried to obtain the intermediate A (3.98 g, 82% yield). MS: [M+H]+=484
82% Into a solution of the intermediate a (4.19) in purified THF (50 ml), a 2.5 M hexane solution of n-butyllithium (4.8 ml) was added dropwise gradually at -78 C. After stirring at the same temperature for 45 min, 2-bromo-9-fluorenone (2.59 g) was added. After stirring at the same temperature for one hour and further stirring at ordinary temperature for 2 h, the reaction was terminated by adding an aqueous solution of ammonium chloride. After extracting the organic substances with ethyl ether, the extract was dried over anhydrous magnesium sulfate, and then the ethyl ether was removed to obtain a yellow solid. After dispersing the obtained solid in ethanol, the dispersion was stirred. The solid collected by filtration was vacuum-dried to obtain 4.5 g of an intermediate, which was then dispersed in 40 ml of acetic acid. After adding 12 drops of concentrated sulfuric acid, the dispersion was refluxed for 3 h and then cooled to ordinary temperature. The precipitated solid was collected by filtration, washed with ethanol, and vacuum-dried to obtain the intermediate A (3.98 g, 82% yield). MS: [M+H]+=484
82% Intermediate a (4.19 g)Was dissolved in purified THF (50 ml)A solution of n-butyllithium in hexane (4.8 ml) was slowly added dropwise at -78 C.After stirring at the same temperature for 45 minutes,2-Bromo-9-fluorenone (2.59 g) was added.After stirring at the same temperature for 1 hour, the temperature was raised to room temperature and further stirred for 2 hours,An aqueous solution of ammonium chloride was added to terminate the reaction.After organic matter was extracted with ethyl ether, the extract was dried over anhydrous magnesium sulfate,The ethyl ether was then removed to give a yellow solid.After dispersing the obtained solid in ethanol,Followed by stirring. The solid separated by filtration was dried under vacuum to obtain 4.5 g of an intermediate.The obtained intermediate was dispersed in 40 ml of acetic acid, 12 drops of concentrated sulfuric acid was added thereto, and the mixture was refluxed for 3 hours. After cooling to ambient temperature, the obtained solid was filtered off, washed with ethanol, and dried under vacuum to obtain 3.98 g (82% yield) of Intermediate A.
 

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