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Structure of 19014-29-0

Chemical Structure| 19014-29-0

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Product Details of [ 19014-29-0 ]

CAS No. :19014-29-0
Formula : C12H12B2O5
M.W : 257.84
SMILES Code : OB(C1=CC=C(OC2=CC=C(B(O)O)C=C2)C=C1)O
MDL No. :MFCD00433207
InChI Key :DFPCWEXYGPRULG-UHFFFAOYSA-N
Pubchem ID :2832120

Safety of [ 19014-29-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501

Computational Chemistry of [ 19014-29-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 4
Num. H-bond acceptors 5.0
Num. H-bond donors 4.0
Molar Refractivity 72.61
TPSA ?

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

90.15 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

1.26
Log Po/w (WLOGP)?

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

-1.16
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.

-0.15
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

-2.18
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.45

Water Solubility

Log S (ESOL):?

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

-2.44
Solubility 0.945 mg/ml ; 0.00367 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.

-2.75
Solubility 0.457 mg/ml ; 0.00177 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

-2.44
Solubility 0.934 mg/ml ; 0.00362 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

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

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

No
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

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.98 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

0.0
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<0.0
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)

2.32

Application In Synthesis of [ 19014-29-0 ]

* 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 [ 19014-29-0 ]

[ 19014-29-0 ] Synthesis Path-Downstream   1~6

  • 1
  • C12H8Br2Mg2O [ No CAS ]
  • [ 19014-29-0 ]
  • 2
  • [ 19014-29-0 ]
  • [ 126-30-7 ]
  • [ 26076-43-7 ]
  • 3
  • [ 19014-29-0 ]
  • C28H16Br2OS2 [ No CAS ]
  • 4
  • [ 19014-29-0 ]
  • C64H40N2OS2 [ No CAS ]
  • 5
  • [ 19014-29-0 ]
  • C26H18BrNS [ No CAS ]
  • C64H44N2OS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 2.0h;Inert atmosphere; Under the protection of nitrogen gas to a three-necked flask of 250ml 4,4'- diphenylether hypo-3-boric acid 5.7g (22mmol), M37-220g (44mmol), tetrakis triphenylphosphine palladium 2g, 100ml toluene, ethyl alcohol 60ml, water 80ml and 16g of sodium carbonate is added, and the progress Circulating react for 2 hours. After the results gamcheuk and shown by TLC to stop the reaction when the complete reaction was cooled to room temperature fraction ( ) and washed with water and extract the award and merges the organic phase, dry, rotating dewatering (Spin Dry) through a yellow oil It gained the material.Column chromatography (dichloromethane / petroleum ether) to proceed to a white solid 13.0g was obtained to be 64% yield.
64% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 2.0h;Inert atmosphere; Reflux; In a 250 ml three-necked bottle under nitrogen protection,(22 mmol) of 4,4'-diphenyl ether diboric acid, 2 g of borate (22 mmol), M37-2 20 g (44 mmol), 2 g of tetrakis (triphenylphosphine palladium), 100 ml of toluene, 60 ml of ethanol, 16 g of sodium carbonate, , Reflux reaction for 2 hours, TLC showed complete reaction. The reaction was stopped, cooled to room temperature, partitioned, washed with water, extracted with water, and the organic phases were combined, dried and dried to give a yellow oil. Column chromatography (dichloromethane / petroleum ether) gave 13.0 g of a white solid in 64% yield.
  • 6
  • [ 7342-82-7 ]
  • [ 19014-29-0 ]
  • C28H18OS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 2.0h;Inert atmosphere; A 500ml three-necked flask equipped with a mechanical stirrer fitted under the protection of nitrogen gas4,4'-diphenylether hypo-boric acid 3-phenyl-carbazol--N-25.8g (100mmol),3-bromo-benzothiophene-51g (220mmol), tetrakistriphenylphosphinepalladium 3.5g, 150ml of toluene, ethyl alcohol 50ml, 100ml water and 53g of sodium carbonate for 2 hours dongan Circulating In response to the progress. TLC in gamcheuk and It presented the results to stop the reaction when the complete reaction and then cooled to room temperature, aliquots (Separated ), washed and extracted water with water, through the merging of the organic phase, dry, rotary dehydration (Spin dry) to obtain the oil-phase material as a yellow . a column chromatography (dichloromethane / petroleum ether), this 64% yield was obtained as a white solid 27.8g proceeds.
64% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 2.0h;Inert atmosphere; Reflux; To a 500 ml three-necked flask equipped with mechanical stirrer and nitrogen protection, 25.8 g (100 mmol) of 4,4'-diphenyl ether diboric acid, 3-boronic acid-N-phenylcarbazole, 51 g of 3-bromobenzothiophene (Toluene) palladium, 3.5 ml of toluene, 50 ml of ethanol, 53 ml of sodium carbonate and 100 ml of water were refluxed for 2 hours. TLC showed complete reaction. The reaction was stopped, cooled to room temperature, partitioned, washed with water, extracted with water, and the organic phases were combined, dried and dried to give a yellow oil. Column chromatography (dichloromethane / petroleum ether) gave 27.8 g of a white solid in 64% yield.
 

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