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Structure of 23058-81-3

Chemical Structure| 23058-81-3

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Product Details of [ 23058-81-3 ]

CAS No. :23058-81-3
Formula : C12H17Br
M.W : 241.17
SMILES Code : CC(C1=CC(C(C)C)=CC(Br)=C1)C
MDL No. :MFCD12547791
Boiling Point : No data available
InChI Key :VRKJTEHREIEDIE-UHFFFAOYSA-N
Pubchem ID :11630091

Safety of [ 23058-81-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Computational Chemistry of [ 23058-81-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.5
Num. rotatable bonds 2
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 63.3
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.

3.34
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

4.87
Log Po/w (WLOGP)?

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

4.7
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.

4.81
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

4.5
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.44

Water Solubility

Log S (ESOL):?

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

-4.61
Solubility 0.00588 mg/ml ; 0.0000244 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.

-4.6
Solubility 0.00599 mg/ml ; 0.0000248 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

-4.9
Solubility 0.00302 mg/ml ; 0.0000125 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

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

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

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

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.

-4.31 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

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

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)

1.67

Application In Synthesis of [ 23058-81-3 ]

* 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 [ 23058-81-3 ]

[ 23058-81-3 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 75-77-4 ]
  • [ 23058-81-3 ]
  • [ 17911-15-8 ]
  • 2
  • 1-bromo-3-isopropenyl-5-isopropyl-benzene [ No CAS ]
  • [ 23058-81-3 ]
  • 3
  • [ 50-00-0 ]
  • [ 23058-81-3 ]
  • [ 23058-82-4 ]
  • 5
  • [ 99-62-7 ]
  • [ 23058-81-3 ]
  • 7
  • [ 23058-81-3 ]
  • [ 544-92-3 ]
  • [ 77212-90-9 ]
  • 9
  • [ 23058-81-3 ]
  • [ 906623-14-1 ]
  • [ 263397-82-6 ]
  • 10
  • [ 80058-84-0 ]
  • [ 23058-81-3 ]
YieldReaction ConditionsOperation in experiment
62% To a mixture of 4-bromo-2,6-bis(propan-2-yl)aniline (20.5 g, 80.02 mmol, 1.00 equiv) in 2N hydrochloric acid (210 mL) at -5° C. was added NaNO2 (13.8 g, 200.00 mmol, 2.50 equiv) in portions. The reaction was allowed stir at -5° C. for 10 min. Hypophosphorous acid (90 mL) was then added at -5° C. The reaction was warmed to room temperature and then stirred for 12 h. The resulting solution was extracted with 300 mL of ethyl acetate. The organic layer was concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:100) to give 12 g (62percent) of 1-bromo-3,5-bis(propan-2-yl)benzene as a light brown oil. 1H NMR (300 MHz, CDCl3): delta 7.18 (s, 2H), 6.98 (s, 1H), 2.89-2.80 (m, 2H), 1.23 (d, J=6.9 Hz, 12H) ppm.
52% 138 ml (2.59 mol) of96percent sulfuric acid was added dropwise to a solution of <strong>[80058-84-0]4-bromo-2,6-diisopropylaniline</strong> (as prepared above, purity ca. 90percent) in 2000 ml of95percent ethanol cooled to -1 ooc at such a rate to keep the reaction temperature below 7°C. After the addition was complete, the formed solution was stirred at roomtemperature for 1 h. Then, the reaction mixture was cooled in an ice-bath, and asolution of 103.1 g (1.49 mol) of sodium nitrite in 215 ml of water was addeddropwise over ca. 1 h. The formed solution was stirred at the same temperature for30 min. Further on, the cooling bath was removed, and 18 g of copper powder was added. Upon completion of the rapid evolution of nitrogen additional portions (ca. 5g each, ca. 70 gin total) of copper powder were added with 10 min intervals untilgas evolution ceased completely. The reaction mixture was stirred at roomtemperature overnight, then filtered through glass frit (G3), diluted with two-foldvolume of water, and crude product was extracted with 4 x 200 ml of dichloromethane. The combined extract was dried over K2C03, evaporated todryness, and then distilled in vacuum (b.p. up to 120°C/5 mm Hg) to give ayellowish liquid. This product was additionally purified by flash-chromatography onsilica gel 60 ( 40-63 )lm; eluent: hexane) and distilled once again (b.p. 85-99°C/5mm Hg) to give 120.0 g (52percent) of 1-bromo-3,5-diisopropylbenzene as a colorless liquid.1H NMR (CDCh): b 7.19 (d, J = 1.2 Hz, 2H), 6.99 (br.t, 1H), 2.86 (sept, J = 6.9 Hz,2H), 1.24 (d, J= 6.9 Hz, 12H). 13CeH} NMR (CDCh): b 151.04, 126.85, 123.70,122.34, 34.06, 23.87
  • 12
  • [ 23058-81-3 ]
  • (3,5-Diisopropyl-benzyl)-(2-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine [ No CAS ]
  • 13
  • [ 23058-81-3 ]
  • 3,5-Diisopropyl-benzylamine [ No CAS ]
  • 14
  • [ 62655-20-3 ]
  • [ 23058-81-3 ]
  • 15
  • [ 23058-81-3 ]
  • Allyl-3,5-diisopropylphenylether [ No CAS ]
  • 16
  • [ 23058-81-3 ]
  • [ 26674-24-8 ]
  • 17
  • [ 23058-81-3 ]
  • [ 26489-82-7 ]
  • 18
  • [ 23058-81-3 ]
  • [ 23250-48-8 ]
  • 19
  • [ 23058-81-3 ]
  • [ 33513-42-7 ]
  • [ 112538-48-4 ]
  • 20
  • [ 23058-81-3 ]
  • [ 184760-75-6 ]
  • [ 1155315-10-8 ]
  • 21
  • [ 23058-81-3 ]
  • [ 97634-16-7 ]
  • [ 1155315-15-3 ]
  • 22
  • [ 23058-81-3 ]
  • [ 1826-67-1 ]
  • [ 19789-39-0 ]
  • 23
  • [ 23058-81-3 ]
  • [ 1312366-30-5 ]
  • 24
  • [ 23058-81-3 ]
  • C26H39O2P [ No CAS ]
  • 25
  • [ 23058-81-3 ]
  • [ 1241937-93-8 ]
  • 26
  • [ 23058-81-3 ]
  • [ 82495-67-8 ]
  • [ 1203710-16-0 ]
YieldReaction ConditionsOperation in experiment
74% Production Example 5 1,2-Bis(bis(3,5-diisopropylphenyl)phosphino)benzene 3,5-Diisopropylbromobenzene (3.04 g, 12.60 mmol) was added dropwise to magnesium (0.48 g, 19.75 mmol) and THF (7 mL) in an argon atmosphere. After the dropwise addition, the mixture was heated under reflux for 1 hour. The reaction mixture was cooled to ambient temperature and filtered, and the thus-obtained THF solution of 3,5-diisopropylphenylmagnesium bromide, and 1,2-bis(dichlorophosphino)benzene (0.45 g, 1.61 mmol) were reacted as in Production Example 1. The reaction was allowed to proceed overnight at 60 C. After purification, the title compound was obtained as a yellow oily substance (1.18 g, yield 74%). 1H NMR (CDCl3) δ 1.11 (s, 24H), 1.14 (s, 24H), 2.69-2.79 (m, 8H), 6.86-6.89 (m, 8H), 6.94 (brs, 12H), 7.01-7.09 (m, 2H), 7.22-7.26 (m, 2H); 13C NMR (CDCl3) δ 23.9 (8C), 24.0 (8C), 34.0 (8C), 124.4 (4C), 128.6 (2C), 129.4 (dd, J=9.9 Hz, 8C), 133.8 (t, J=2.8, 2.9 Hz, 2C), 137.5 (dd, J=2.9 Hz, 4C), 144.6 (dd, J=10.2, 10.3 Hz, 2C), 148.2 (dd, J=3.2, 3.4 Hz, 8C); 31P NMR (CDCl3) δ -12.8.
  • 27
  • [ 37031-29-1 ]
  • [ 23058-81-3 ]
  • C53H74O4 [ No CAS ]
  • 28
  • [ 23058-81-3 ]
  • C57H73O4P [ No CAS ]
  • 29
  • [ 23058-81-3 ]
  • [ 1231646-15-3 ]
  • 30
  • [ 23058-81-3 ]
  • [ 1231646-17-5 ]
  • 31
  • [ 23058-81-3 ]
  • 2-methylfuryl-4-(3,5-diisopropylphenyl)-5-methylindene [ No CAS ]
  • 32
  • [ 23058-81-3 ]
  • [ 1231646-23-3 ]
  • 33
  • [ 5419-55-6 ]
  • [ 23058-81-3 ]
  • [ 263397-82-6 ]
YieldReaction ConditionsOperation in experiment
5.9 g To the solution of <strong>[23058-81-3]3,5-diisopropylbromobenzene</strong>(5.76 g, 23.9 mmol) and tetramethylethylenediamine(3.6 mL, 23.9 mmol) in diethyl ether(30 mL), solution of n-butyllithium in n-hexane(14.5 mL, 23.9 mmol) was dropped at -60C. Reaction solution was stirred for 1.5 hours at -60C, and further was stirred for 30 minutes at 0C, then, solution of triisopropyl borate (6.6 mL) in diethyl ether(5 mL) was dropped at -60C. Reaction solution was stirred for 30 minutes at -60C, and further, was stirred overnight at room temperature, then, diluted hydrochloric acid (50 mL) was added. Resulting solid part was filtered to obtain the crude product of 3,5-diisopropylphenylboronic acid (5.9 g).
  • 34
  • [ 23058-81-3 ]
  • [ 1361146-90-8 ]
  • 35
  • [ 37031-29-1 ]
  • [ 23058-81-3 ]
  • [ 1361146-89-5 ]
 

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