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Chemical Structure| 873-63-2 Chemical Structure| 873-63-2

Structure of 873-63-2

Chemical Structure| 873-63-2

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Product Details of [ 873-63-2 ]

CAS No. :873-63-2
Formula : C7H7ClO
M.W : 142.58
SMILES Code : ClC1=CC(CO)=CC=C1
MDL No. :MFCD00004632
Boiling Point : No data available
InChI Key :ZSRDNPVYGSFUMD-UHFFFAOYSA-N
Pubchem ID :70117

Safety of [ 873-63-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335-H412
Precautionary Statements:P261-P273-P305+P351+P338

Computational Chemistry of [ 873-63-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 37.58
TPSA ?

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

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.93
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

1.94
Log Po/w (WLOGP)?

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

1.68
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.

2.14
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

2.33
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.0

Water Solubility

Log S (ESOL):?

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

-2.37
Solubility 0.603 mg/ml ; 0.00423 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.

-1.99
Solubility 1.46 mg/ml ; 0.0103 mol/l
Class?

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

Very 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

-2.82
Solubility 0.217 mg/ml ; 0.00152 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

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

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.

-5.79 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)

1.0

Application In Synthesis of [ 873-63-2 ]

* 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 [ 873-63-2 ]

[ 873-63-2 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 201230-82-2 ]
  • [ 873-63-2 ]
  • [ 54109-03-4 ]
  • 2
  • [ 2905-65-9 ]
  • [ 873-63-2 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 1h;Inert atmosphere; General procedure: To a solution of methyl phenyl acetates (1.0 eq.) in dry THF (5mL) was added LiAlH4 (2 eq.) at 0C under N2 atmosphere, and the resulting mixture was stirred at room temperature for 1h [23]. After complete consumption of starting material, the reaction mixture was quenched with Na+/K+ tartrate solution (∼10mL), and the mixture was filtered after being stirred at room temperature overnight. The collected filtrate was dried and concentrated to afford crude alcohol intermediate, which was oxidized by PCC (2 eq.) for 2h in CH2Cl2 (5-10mL) [24,25]. The reaction mixture was filtered through short silica column to remove brown side-product. The collected filtrate was concentrated in vacuo for next step without any purification.
  • 3
  • [ 67-56-1 ]
  • [ 873-63-2 ]
  • [ 2905-65-9 ]
YieldReaction ConditionsOperation in experiment
93% With carbon tetrabromide; oxygen; at 20℃; for 20h;Irradiation; General procedure: Typical procedure: A solution of 4-tert-butylbenzyl alcohol (1a, 0.3 mmol) and CBr4 (0.09 mmol) in dry MeOH (4 mL) in a pyrex test tube, purged with an O2-balloon, was stirred and irradiated externally with four 22 W fluorescent lamps for 20 h. The reaction mixture was concentrated in vacuo. Purification of the crude product by PTLC (toluene) provided methyl 4-tert-butylbenzoate (2a) (Rf = 0.40, 54.0 mg, 94%).
90% With Au#Co; oxygen; potassium carbonate; at 80℃; under 750.075 Torr; for 10h;Autoclave; 20 mg of Au-Co composite particle support (0.1 mol%), 13.8 mg of K2CO3 (10 mol%), 142.5 mg of m-chlorobenzyl alcohol (1 mmol),4 mL of methanol was sequentially added to a pressure vessel with a 25 mL glass lining. After replacing the oxygen three times, the pressure was increased to 0.1 MPa, and the reaction was carried out at 80 C for 10 hours. After cooling to room temperature, the gas was slowly depressurized, the catalyst was filtered, and the filtrate was concentrated by steaming. After residue column chromatographyYellowish liquid productMethyl m-chlorobenzoate 164.7mg,The yield was 90%.
86% With 1H-imidazole; tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In water; at 80℃; for 7h;Green chemistry; General procedure: To a mixture of benzyl alcohol (108 mg, 1.0 mmol) and TBHP(180 mg, 2.0 mmol) in water (3 ml), the catalyst TBAI (73.8 mg,0.2 mmol), imidazole (136 mg, 2.0 mmol), and MeOH (2 ml)were added, and the mixture was stirred at 80 C for 8 h. Theprogress of the reaction was monitored by TLC. After completionof reaction, the reaction mixture was cooled to room temperature.Then MeOH was distilled out, and the organic productwas extracted with ethyl acetate (3 × 10 ml), repeatedly washedwith distilled water (4 × 5 ml) to remove the unreacted TBHP,dried with anhydrous sodium sulfate, and the solvent was evaporatedunder reduced pressure to afford methyl benzoate (112mg, yield 82%).
  • 4
  • [ 873-63-2 ]
  • [ 98-80-6 ]
  • [ 69605-90-9 ]
YieldReaction ConditionsOperation in experiment
66% With C20H16Cl2N2Pd; potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 6h; General procedure: A 50 mL round bottom flask was charged with a mixture of aryl chloride (0.5 mmol), arylboronic acid (0.75 mmol), K2CO3 (1.5 mmol), Pd catalyst (0.2 mol %), solvent (6 mL) and the mixture was stirred for required times at appropriate temperature. After completion, the reaction mixture was diluted with water (20 mL) and extracted with ether (20 mL ×3). Combined extract was washed with brine (20 mL ×3) and dried over Na2SO4. After evaporation of the solvent under reduced pressure, the residue was chromatographed (silica gel, ethyl acetate/hexane 1:9) to obtain the desired product. The products were confirmed by comparing the melting points, 1H NMR and mass spectral data with authentic samples.
60% With 2Na(1+)*C26H18N2O8PdS2(2-); cetyltrimethylammonim bromide; potassium carbonate; In water; at 100℃; for 8h; General procedure: The Suzuki reaction was performed in a 50 mL round-bottomed flask, aryl halide (0.5 mmol), arylboronic acid (0.65 mmol), K2CO3 (1 mmol), Complex 1 (0.2-1 mol%) and water (4 mL) were charged and stirred for the required time at room temperature for aryl bromides or at 100 C for aryl chlorides. After completion, the mixture was cooled down to room temperature, diluted with water (10 mL) and extracted with diethyl ether (3 × 15 mL). The organic layer was washed with brine (3 × 15 mL), dried over anhydrous Na2SO4. The crude products were chromatographed on silica gel (ethyl acetate/hexane).
  • 5
  • [ 2947-61-7 ]
  • [ 57772-50-6 ]
  • [ 873-63-2 ]
  • N-(3-chlorobenzyl)-8-methyl-3-(p-tolyl)quinolin-2-amine [ No CAS ]
 

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