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Chemical Structure| 134-52-1 Chemical Structure| 134-52-1

Structure of 134-52-1

Chemical Structure| 134-52-1

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Product Details of [ 134-52-1 ]

CAS No. :134-52-1
Formula : C12H10O2
M.W : 186.21
SMILES Code : OC1=CC(O)=CC=C1C2=CC=CC=C2
MDL No. :MFCD00029715
InChI Key :LYXCJGJSIWFKHZ-UHFFFAOYSA-N
Pubchem ID :11019578

Safety of [ 134-52-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315
Precautionary Statements:P280

Computational Chemistry of [ 134-52-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 55.92
TPSA ?

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

40.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.95
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

2.73
Log Po/w (WLOGP)?

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

2.76
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.

2.41
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

2.56
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.48

Water Solubility

Log S (ESOL):?

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

-3.28
Solubility 0.0971 mg/ml ; 0.000522 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.

-3.23
Solubility 0.109 mg/ml ; 0.000584 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

-3.77
Solubility 0.032 mg/ml ; 0.000172 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

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.

-5.5 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

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<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)

1.51

Application In Synthesis of [ 134-52-1 ]

* 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 [ 134-52-1 ]

[ 134-52-1 ] Synthesis Path-Downstream   1~11

  • 2
  • [ 134-52-1 ]
  • [ 79520-52-8 ]
  • [ 85630-06-4 ]
YieldReaction ConditionsOperation in experiment
General procedure: 2-naphthylboronic acid 13 (which was prepared according to L. J. Diorazio et al., Tetrahedron, 48, 1992, 8073) (1 g, 5.8 mmol), 1,3-dimethoxy-4-bromo-2-fluorobenzene 12 (1.37 g, 5.8 mmol) obtained from Example 2, anhydrous glyme (5 mL) and tetrakis (triphenylphosphine) palladium (0) (675 mg, 0.58 mmol, Lancaster Chemical) was stirred for 15 minutes. Subsequently, potassium carbonate (1.6 g in 7 mL of water) was added and refluxed for 24 hours. The reaction mixture was poured into 1:1 10% HCl and 200 mL ethyl acetate. The organic layer was washed with water (100 mL × 2)and washed with brine (100 mL × 1). After drying over sodium sulfate, the reaction mixture was filtered, the solvent was removed to obtain 1.15 g (71%) of the dimethyl ether intermediate. This intermediate (282 mg, 1 mmol) was dissolved in anhydrous dichloromethane (5 mL), cooled to -78C under an argon atmosphere. After addition of 1M boron tribromide (5 mL, 5 mmol) in dichloromethane, this solution was stirred at -78 C. for 30 minutes. Subsequently, the mixture was stirred at 4 C for 16 hours. The reaction mixture was poured into 100 mL of ice water, and extracted with ethyl acetate (100 mL). The organic layer was washed with water (100 mL × 2) and washed with brine (100 mL × 1). After drying over sodium sulfate, the mixture was filtered, solvent was removed, and the crude product was purified by silica gel chromatography (silica gel,10% CHCl 3 in hexane mobile phase) 220 mg (86%) of solid product was obtained. This compound was prepared using essentially the same procedure as used in Example 3, in place of 2-naphthylboronic acid 13, phenyl boronic acid 17 (Aldrich Chemical) and in place of 1,3-dimethoxy-4-bromo-2-fluorobenzene 12, 1,3-dimethoxy-4-bromobenzene 15 was used.
  • 4
  • 2.4-dibenzoyloxy-1-cyclohexyl-benzene [ No CAS ]
  • [ 134-52-1 ]
  • 5
  • [ 30728-32-6 ]
  • [ 134-52-1 ]
  • 6
  • [ 134-52-1 ]
  • [ 79-04-9 ]
  • [ 1346150-97-7 ]
YieldReaction ConditionsOperation in experiment
42% With aluminum (III) chloride; In nitrobenzene; at 20 - 40℃; for 3h;Cooling with ice; (b) Step 2 A solution of <strong>[134-52-1]biphenyl-2,4-diol</strong> (0.24 g, 1.3 mmol) in nitrobenzene (1.0 mL) was added with aluminum chloride (0.60 g, 4.5 mmol) at room temperature. Then, the reaction mixture was added with chloroacetyl chloride (0.60 g, 1.7 mmol) under ice cooling. The mixture was stirred at 40C for 3 hours, and then added with water, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (100:0 -> 90:10)) to obtain 6-hydroxy-5-phenylbenzofuran-3(2H)-one (0.12 g, 42%). 1H NMR (300 MHz, CDCl3) delta 4.62 (s, 2H), 6.58 (s, 1H), 7.38-7.48 (m, 3H), 7.48-7.56 (m, 2H), 7.58 (s, 1H), 12.00 (br s, 1H).
  • 7
  • [ 6626-15-9 ]
  • [ 98-80-6 ]
  • [ 134-52-1 ]
YieldReaction ConditionsOperation in experiment
61% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 20 - 95℃; for 6h;Inert atmosphere; Sealed tube; (a) Step 1 The synthesis was performed with reference to the known literature (). A solution of 4-bromoresorcinol (0.42 g, 2.2 mmol) in 1,2-dimethoxyethane (10 mL) was successively added with phenylboronic acid (0.37 g, 3.0 mmol), and 2 M aqueous sodium carbonate (3.5 mL), and the mixture was stirred at room temperature. After the inside of the reaction vessel was replaced with argon, the reaction mixture was added with tetrakis(triphenylphosphine)palladium(0) (0.14 g, 0.12 mmol), and the mixture was stirred at 95C for 6 hours in a sealed tube. The reaction mixture was added with ice water, the mixture was extracted with ethyl acetate, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (75:25)) to obtain biphenyl-2,4-diol (0.25 g, 61%). 1H NMR (300 MHz, DMSO-d6) delta 6.30 (dd, J = 2.2 Hz, J = 8.8 Hz, 1H), 6.40 (d, J = 2.2 Hz, 1H), 7.04 (d, J = 8.8 Hz, 1H), 7.20 (m, 1H), 7.33 (m, 2H), 7.47 (d, J = 7.3 Hz, 2H), 9.31 (s, 1H), 9.34 (s, 1H).
  • 8
  • [ 134-52-1 ]
  • [ 1346150-98-8 ]
  • 9
  • [ 134-52-1 ]
  • [ 1346150-99-9 ]
  • 10
  • [ 134-52-1 ]
  • (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxy-5-phenyl-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one dihydrochloride [ No CAS ]
  • 11
  • [ 134-52-1 ]
  • C15H7Cl3O7 [ No CAS ]
  • C27H15Cl3O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With methanesulfonic acid; at 130 - 135℃; for 2h; <strong>[134-52-1]4-phenyl-1,3-dihydroxybenzene</strong> 18 (182 mg, 1 mmol) obtained from Example 5, Ketone 32 (405 mg, 1 mmol, AB part 361893) and methanesulfonic acid (10 mL) were mixed, then, the mixture was stirred at 130 to 135 C for 2 hours. The reaction mixture was cooled, and mixed with ice water (50 mL). The precipitated dye was extracted with ethyl acetate (100 mL). The organic layer was washed with water (50 mL × 2) and washed with brine (50 mL × 1). After drying over sodium sulfate, the mixture was filtered, the solvent was removed, and the crude pigment was obtained. These dyes were crystallized from chloroform to give 450 mg (81%) of pure dye.
 

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