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Chemical Structure| 2039-85-2 Chemical Structure| 2039-85-2

Structure of 2039-85-2

Chemical Structure| 2039-85-2

3-Chlorostyrene

CAS No.: 2039-85-2

4.5 *For Research Use Only !

Cat. No.: A149871 Purity: 97% (stabilized with TBC)

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Product Details of [ 2039-85-2 ]

CAS No. :2039-85-2
Formula : C8H7Cl
M.W : 138.59
SMILES Code : C=CC1=CC(Cl)=CC=C1
MDL No. :MFCD00000598
InChI Key :BOVQCIDBZXNFEJ-UHFFFAOYSA-N
Pubchem ID :14905

Safety of [ 2039-85-2 ]

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

Computational Chemistry of [ 2039-85-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 41.54
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.

2.27
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

3.09
Log Po/w (WLOGP)?

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

2.87
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.

3.44
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

3.27
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.99

Water Solubility

Log S (ESOL):?

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

-3.07
Solubility 0.117 mg/ml ; 0.000845 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-2.76
Solubility 0.242 mg/ml ; 0.00175 mol/l
Class?

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

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

-3.43
Solubility 0.0515 mg/ml ; 0.000372 mol/l
Class?

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

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

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

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.

-4.95 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

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

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)

1.38

Application In Synthesis of [ 2039-85-2 ]

* 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 [ 2039-85-2 ]

[ 2039-85-2 ] Synthesis Path-Downstream   1~8

  • 3
  • [ 890315-75-0 ]
  • [ 2039-85-2 ]
  • [ 131274-22-1 ]
  • tert-butyl 2-(benzamido)-4-((E)-2-(3-chlorophenyl)vinyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tributyl-amine; citric acid;palladium diacetate; In N,N-dimethyl acetamide; ethyl acetate; Example 127 0.076 mL of 3-chlorostyrene, 0.19 mL of tributylamine, 2.9 mg of tri-tert-butylphosphine tetrafluoroborate and 4.5 mg of palladium acetate were added to 2.0 mL of N,N-dimethylacetamide solution containing 0.15 g of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature and stirred under nitrogen atmosphere at 110°C for 4 hours and 30 minutes. After the reaction mixture was cooled to room temperature, 0.025 mL of 3-chlorostyrene, 2.9 mg of tri-tert-butylphosphine tetrafluoroborate and 4.5 mg of palladium acetate were added at room temperature and stirred under nitrogen atmosphere at 110°C for 1 hour and 20 minutes. After the reaction mixture was cooled to room temperature, 10percent citric acid aqueous solution and ethyl acetate were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10percent citric acid aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane: ethyl acetate = 10:1] to obtain 86 mg of tert-butyl 2-(benzamido)-4-((E)-2-(3-chlorophenyl)vinyl)benzoate as white solid. 1H-NMR (CDCl3) delta: 1.56 (9H, s), 7.13=7.34 (5H, m), 7.40-7.45 (1H, m), 7.52-7.59 (4H, m), 8.01 (1H, d, J = 8.3 Hz), 8.06-8.11 (2H, m), 9.16 (1H, d, J = 1.7 Hz), 12.27 (1H, s).
  • 4
  • [ 2039-85-2 ]
  • [ 1593-60-8 ]
  • [ 1377813-87-0 ]
  • 5
  • [ 570-02-5 ]
  • [ 2039-85-2 ]
  • (E)-1-(3'-chlorostyryl)-2,4,6-trimethoxybenzene [ No CAS ]
  • 6
  • [ 2039-85-2 ]
  • [ 65130-47-4 ]
  • [ 16799-05-6 ]
  • 8
  • [ 67-56-1 ]
  • [ 2039-85-2 ]
  • [ 2905-65-9 ]
YieldReaction ConditionsOperation in experiment
73%Chromat. With tert.-butylhydroperoxide; oxygen; potassium carbonate; at 150℃; under 7500.75 Torr; for 48h;Autoclave; Green chemistry; General procedure: In the typical oxidation reaction, the substrate (0.25 mmol), catalyst(10 mol%), K2CO3 (20 mol%), TBHP (2.2 equiv.) and MeOH (4 mL) wereplaced in a round-bottomed flask. The mixture was then transferred tothe autoclave. The autoclave was closed and purged with oxygen for 3times. Finally, the autoclave was pressurized in oxygen atmosphere for48 h and stirred at 150 C. After the reaction was completed, the autoclavewas cooled to room temperature, the internal standard compound(biphenyl, 15 mg) and MeOH (2 mL) were added. The reaction solutionwas analyzed on GC and confirmed by GC-MS. Or the yield was determinedby 1HNMR using dibromomethane (10 mg) as the internalstandard.
 

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