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Chemical Structure| 103986-53-4 Chemical Structure| 103986-53-4

Structure of 103986-53-4

Chemical Structure| 103986-53-4

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Product Details of [ 103986-53-4 ]

CAS No. :103986-53-4
Formula : C11H11BO2
M.W : 186.02
SMILES Code : CC1=CC=C(B(O)O)C2=CC=CC=C12
MDL No. :MFCD01632204
InChI Key :JHVQEUGNYSVSDH-UHFFFAOYSA-N
Pubchem ID :2773511

Safety of [ 103986-53-4 ]

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

Computational Chemistry of [ 103986-53-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 10
Fraction Csp3 0.09
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 58.74
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.

0.0
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

2.44
Log Po/w (WLOGP)?

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

0.83
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.

1.64
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

0.81
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.14

Water Solubility

Log S (ESOL):?

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

-2.99
Solubility 0.189 mg/ml ; 0.00102 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.

-2.93
Solubility 0.217 mg/ml ; 0.00117 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

-3.35
Solubility 0.0827 mg/ml ; 0.000445 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.

-5.7 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

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)

1.57

Application In Synthesis of [ 103986-53-4 ]

* 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 [ 103986-53-4 ]

[ 103986-53-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 109179-31-9 ]
  • [ 103986-53-4 ]
  • C19H16O [ No CAS ]
  • C19H16O [ No CAS ]
  • 2
  • [ 103986-53-4 ]
  • [ 175205-81-9 ]
  • 2-[(5-methylnaphthalen-1-yl)-4-trifluoromethyl] pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
94.6% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 24h;Inert atmosphere; A mixture of 4-methyl-naphthalene-1-boronic acid (5.00 g,26.8 mmol), <strong>[175205-81-9]2-bromo-4-(trifluoromethyl)pyridine</strong> (6.68 g,29.5 mmol), tetrakis(triphenylphosphine)palladium (0.31 g,0.26 mmol, 1 molpercent), potassium carbonate (75 ml, 2Maqueous solution), and tetrahydrofuran (150 mL) washeaded under a nitrogen atmosphere at 80 C for 24 h.This reaction is the Suzuki coupling reaction. After thereaction, the mixture was cooled to room temperatureand the flask was left in an ice bath for 2 h. The compoundwas extracted by liquid?liquid separation (water anddichloromethane). The compound was purified by a celitesilicagel filter (solvent: toluene) and column chromatographyon silica gel (eluent: hexane/ethyl acetate, 15:1).Yield: 94.6percent (7.306 g); 1H NMR (CDCl3, 500 MHz):H (ppm) 8.52 (d, 1H), 8.38 (d, 1H), 8.33 (d, 1H), 8.18(d, 1H), 8.06 (s, 1H), 7.54 (s, 1H), 7.52 (d, 1H), 7.15(d, 1H), 7.09 (s, 1H), 2.26 (s, 1H).
  • 3
  • [ 36023-06-0 ]
  • [ 103986-53-4 ]
  • (±)-7-methoxy-8-(4-methylnaphthalen-1-yl)quinoline [ No CAS ]
  • 4
  • [ 103986-53-4 ]
  • [ 366496-33-5 ]
  • 10-fluoro-5-methyl-9-(4-methylnaphthalen-1-yl)-7H-benzo[c]carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With palladium diacetate; potassium carbonate; triphenylphosphine; In 1,2-dichloro-benzene; at 180℃; for 48.0h; General procedure: To a re-sealable pressure tube (13 x 100 mm) equipped with magnetic stir bar were added o-bromonitrobenzene 1 (0.25 mmol, 100 mol%), aryl boronic acid 2 (0.65 mmol, 260 mol%), Pd(OAc)2 (0.0125 mmol, 5 mol%), PPh3 (1.25 mmol, 500 mol %), K2CO3 (1 mmol, 400 mol%) and o-DCB (1.25 mL, 0.2 M concentration with respect to o-bromonitrobenzene 1. The mixture was heated at 180 C (oil bath temperature) for 48 h, at which point the reaction mixture was allowed to cool to ambient temperature. The reaction mixture was filtered through a pad of celite and the resulting liquor was concentrated in vacuo and purified by flash column chromatography (SiO2) under the conditions noted to furnish the corresponding product.
  • 5
  • [ 109179-31-9 ]
  • [ 103986-53-4 ]
  • 3-methyl-2-(4-methylnaphthalen-1-yl)benzaldehyde [ No CAS ]
  • 6
  • [ 109179-31-9 ]
  • [ 103986-53-4 ]
  • (R)-3-methyl-2-(4-methylnaphthalen-1-yl)benzaldehyde [ No CAS ]
  • 3-methyl-2-(4-methylnaphthalen-1-yl)benzaldehyde [ No CAS ]
  • 3-methyl-2-(4-methyl-2-((triisopropylsilyl)ethynyl)naphthalen-1-yl)benzaldehyde [ No CAS ]
 

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Technical Information

Categories

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[ 103986-53-4 ]

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