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Chemical Structure| 869340-02-3 Chemical Structure| 869340-02-3

Structure of 869340-02-3

Chemical Structure| 869340-02-3

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Product Details of [ 869340-02-3 ]

CAS No. :869340-02-3
Formula : C22H20Br2
M.W : 444.20
SMILES Code : BrC1=C2C=CC(C3=C42)=C(C(C)C)C=C(Br)C3=CC=C4C(C(C)C)=C1
MDL No. :MFCD27979119
InChI Key :NNVZVNMCMRPEND-UHFFFAOYSA-N
Pubchem ID :58536052

Safety of [ 869340-02-3 ]

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

Computational Chemistry of [ 869340-02-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 24
Num. arom. heavy atoms 16
Fraction Csp3 0.27
Num. rotatable bonds 2
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 114.71
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

4.46
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

8.67
Log Po/w (WLOGP)?

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

8.36
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.

7.2
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

8.25
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

7.39

Water Solubility

Log S (ESOL):?

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

-8.42
Solubility 0.0000017 mg/ml ; 0.0000000038 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.

-8.55
Solubility 0.00000126 mg/ml ; 0.0000000028 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

-9.81
Solubility 0.0000000682 mg/ml ; 0.0000000002 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

Low
BBB permeant?

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

No
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

No
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

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.

-2.85 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

1.0
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

1.0
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

2.0
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)

2.15

Application In Synthesis of [ 869340-02-3 ]

* 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 [ 869340-02-3 ]

[ 869340-02-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 869340-02-3 ]
  • [ 626-13-1 ]
  • C50H48N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With sodium t-butanolate;palladium diacetate; tri-tert-butyl phosphine; In toluene; at 110℃; for 8.0h; Under an atmospheric argon gas flow, 1,6-diisopropyl-3,8-dibromopyrene in an amount of 3.0 g (6.7 millimole), <strong>[626-13-1]m,m'-ditolylamine</strong> in an amount of 3.2 g (16.2 millimole), palladium acetate in an amount of 0.02 g (1.5 % by mole), tri-t-butylphosphine in an amount of 0.04 g (3 % by mole), sodium- t-butoxide in an amount of 1.6 g (16.6 millimole) and dried toluene in an amount of 75 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred with heating at a temperature of 110 C for 8 hours. After the completion of the reaction, the resultant solution was passed through a silicagel short column, and after concentrating under a reduced pressure, a precipitated crystal was separated by filtration. The crystal was washed with the use of 50 milliliter of toluene and 100 milliliter of methanol, and as a result, 4.5 g of pale yellow powder was obtained. The pale yellow powder was identified as a following Compound (5) from the result of 1H-NMR spectrum (refer to FIG. 6) and FD-MS measurement (the yield: 98 %). It was recognized that the peak absorption wavelength of the Compound (5) was 429 nanometers and the peak fluorescent wave length was 463 nanometers (toluene solution).
  • 2
  • [ 869340-02-3 ]
  • [ 19616-28-5 ]
  • C54H56N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% Intermediate M1 and toluene were added to a 500 mL three-necked flask equipped with magnetic stirring at room temperature to stir and dissolve, and nitrogen was replaced three times.Ethanol liquid nitrogen is cooled to -70 ° C, and n-butyl lithium is added dropwise.After about 10 minutes of dropwise addition, the temperature of the system rose to -60 °C.Stirring was continued for about 30 minutes, the temperature of the system was raised to -30 ° C, and the raw material 1,6-diisopropyl-3.8-dibromofluorene, Pd2 (dba) 3 was added.Tri-tert-butylphosphine was added, and the nitrogen was replaced 3 times, and transferred to an oil bath to heat the stirrer.The stirring was started, and the temperature was raised by heating in an oil bath to reflux for 6 hours.The TLC tracking reaction showed complete reaction of 1,6-diisopropyl-3.8-dibromofluorene (PE/DCM = 3:1, product Rf = 0.7) and the reaction was stopped. The reaction solution was cooled to room temperature, stirred with 100 mL of pure water for 10 minutes, and suction filtered, and the obtained solid was washed with purified water and toluene, respectively.The filtrate was separated, and the organic phase was washed with anhydrous sodium sulfate and filtered, filtered and evaporated.The combined 2 batches of solid were dissolved in 3 L of toluene, dried over anhydrous sodium sulfate and filtered with a short silica gel column.Dry the solvent under reduced pressure, using toluene,Recrystallization from ethanol gave 9 g of a yellow powdery solid. The yield was 43percent.
 

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