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Structure of 1607-57-4

Chemical Structure| 1607-57-4

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Product Details of [ 1607-57-4 ]

CAS No. :1607-57-4
Formula : C20H15Br
M.W : 335.24
SMILES Code : Br/C(C1=CC=CC=C1)=C(C2=CC=CC=C2)\C3=CC=CC=C3
MDL No. :MFCD00000135
InChI Key :VUQVJIUBUPPCDB-UHFFFAOYSA-N
Pubchem ID :15354

Safety of [ 1607-57-4 ]

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 [ 1607-57-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 21
Num. arom. heavy atoms 18
Fraction Csp3 0.0
Num. rotatable bonds 3
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 94.17
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.

3.52
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

6.56
Log Po/w (WLOGP)?

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

6.0
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.

5.88
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

5.77
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.55

Water Solubility

Log S (ESOL):?

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

-6.49
Solubility 0.000109 mg/ml ; 0.000000325 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.

-6.36
Solubility 0.000147 mg/ml ; 0.000000438 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

-8.34
Solubility 0.00000152 mg/ml ; 0.0000000045 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

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

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.

-3.69 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<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)

2.74

Application In Synthesis of [ 1607-57-4 ]

* 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 [ 1607-57-4 ]

[ 1607-57-4 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 1607-57-4 ]
  • [ 100-66-3 ]
  • [ 70592-05-1 ]
  • 1-(2-methoxyphenyl)-1,2,2-triphenylethylene [ No CAS ]
  • 2
  • [ 1607-57-4 ]
  • [ 5720-07-0 ]
  • [ 70592-05-1 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 12h;Inert atmosphere; Reflux; TPE-OMe and TPE-SMe were prepared and synthesized by Suzuki-Miyaura cross-coupling reaction using triphenyl bromide as raw material.The general synthesis method is as follows:In the mixture of bromotristyrene (3.35g, 10.8mmol) and substituted phenylboronic acid (10.00mmol) was added K2CO3 aqueous solution (2M, 15mL),Ethanol (15mL) and toluene (50mL) and Pd(PPh3)4 (0.10g, 0.10mmol),The reaction was refluxed for 12h under the protection of nitrogen.After cooling to room temperature, the reaction mixture was poured into water,It was extracted three times with dichloromethane, and the organic layer was washed with brine,Then dry on MgSO4.After removing the solvent under reduced pressure, pass through silica gel column chromatography,Petroleum ether is used as the eluent to obtain a white solid powder.
  • 3
  • [ 1607-57-4 ]
  • [ 182482-25-3 ]
  • C26H17F3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
6.3% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In water; toluene; at 120℃; for 39h;Inert atmosphere; under argon protection,Triphenylbromoethylene (168.1 mg, 0.47 mmol) was sequentially added to a 100 mL reaction flask.Tetrabutylammonium bromide (ie TBAB, 15.8 mg, 0.049 mmol),2-fluorophenylboronic acid (84.4 mg, 0.60 mmol), anhydrous potassium carbonate (207.8 mg, 1.50 mmol),Tetrakis(triphenylphosphine)palladium (29.9 mg, 0.026 mmol), 15 mL of toluene,5 mL water. Heat to reflux under stirring (oil bath temperature 120 C),Reaction for 35 h. After the reaction was monitored by TLC, the mixture was separated and the aqueous phase was extracted with dichloromethane (20 mL×2).The organic phases were combined, dried over anhydrous sodium sulfate, filtered and evaporated.Then, it was dissolved in 5 mL of dichloromethane and then subjected to thin layer chromatography (developing agent was n-hexane, specific shift value Rf=0.2), and the blue and white light band at 365 nm of ultraviolet light was scraped off, rinsed with dichloromethane, and the solvent was evaporated. ,A white solid 62.4 mg was obtained as Compound 1a, yield 37.6%,
  • 4
  • [ 479-79-8 ]
  • [ 1607-57-4 ]
  • 11-(1,2,2-triphenylvinyl)-11H-benzo[a]fluoren-11-ol [ No CAS ]
  • 5
  • [ 479-79-8 ]
  • [ 1607-57-4 ]
  • C37H24 [ No CAS ]
  • 7
  • [ 945865-80-5 ]
  • [ 1607-57-4 ]
  • C28H20O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; caesium carbonate; In water; toluene; for 24.0h;Inert atmosphere; 5-Bromoisophthalaldehyde (1) and diformylphenylboronic ester (2)were prepared according to the previously reported procedure [23].Bromotriphenylethylene (1.34 g, 4.0 mmol), 2 (1.28 g, 4.8 mmol), tetrabutylammoniumbromide (0.03 g, 0.1 mmol) and Cs2CO3 (1.30 g, 4.0mmol) were dissolved in the mixture of toluene (40 mL) and H2O (5 mL).The reaction mixture was degassed and stirred under nitrogen atmospherefor 0.5 h, and then a catalytic amount of Pd(PPh3)4 (0.11 g, 0.1mmol) was added and refluxed for another 24 h. After being cooled toroom temperature, the solvent was removed under a vacuum. The crudeproduct was purified by column chromatography to get pale powder ofTPE-2CHO with a yield of 1.25 g (81%). 1H NMR (400 MHz, CDCl3): δ9.87 (s, 2H), 8.10 (t, J = 1.52 Hz, 1H), 7.78 (d, J = 1.56 Hz, 2H),7.17-7.09 (m, 9H), 7.05-7.00 (m, 6H). 13C NMR (100 MHz, CDCl3): δ191.0, 146.2, 143.8, 142.5, 142.4, 142.1, 138.2, 137.6, 136.6, 131.3,131.2, 131.0, 128.2, 128.2, 128.1, 127.8, 127.3, 127.2, 127.1. FT-IR(KBr pellets) v 3463 (s), 3076 (w), 3024 (w), 2835 (w), 2715 (w),1699 (s), 1593 (m), 1490 (m), 1442 (m), 1380 (m), 1137 (m), 1074 (w),964 (w), 889 (w), 777 (w), 761 (w), 700 (s), 650 (w), 632 (w), 576 (w).Anal. Calculated for C28H20O2: C, 86.56; H, 5.15%. Found: C, 86.47; H,5.34%. Single crystals suitable for X-ray diffraction measurements wereobtained in CH2Cl2 for a week.
 

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