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Chemical Structure| 947-42-2 Chemical Structure| 947-42-2

Structure of 947-42-2

Chemical Structure| 947-42-2

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Product Details of [ 947-42-2 ]

CAS No. :947-42-2
Formula : C12H12O2Si
M.W : 216.31
SMILES Code : O[Si](C1=CC=CC=C1)(C2=CC=CC=C2)O
MDL No. :MFCD00002101
InChI Key :OLLFKUHHDPMQFR-UHFFFAOYSA-N
Pubchem ID :13693

Safety of [ 947-42-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H228-H315-H319
Precautionary Statements:P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313
Class:4.1
UN#:1325
Packing Group:

Computational Chemistry of [ 947-42-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 62.34
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.

1.94
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

2.6
Log Po/w (WLOGP)?

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

0.23
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.

1.88
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

0.8
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.49

Water Solubility

Log S (ESOL):?

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

-3.28
Solubility 0.114 mg/ml ; 0.000526 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.

-3.1
Solubility 0.172 mg/ml ; 0.000796 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

-3.88
Solubility 0.0288 mg/ml ; 0.000133 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

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.

-5.77 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<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)

3.72

Application In Synthesis of [ 947-42-2 ]

* 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 [ 947-42-2 ]

[ 947-42-2 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 186581-53-3 ]
  • [ 947-42-2 ]
  • [ 6843-66-9 ]
  • 2
  • [ 1185-55-3 ]
  • [ 947-42-2 ]
  • [ 476161-46-3 ]
  • [ 6843-66-9 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 23℃; for 24h; Diphenylsilanediol (60 g), tetrahydrofuran (THF, 30 g) and methyltrimethoxysilane (MTMOS, 180 g) were placed in a 500 mL 3-neck round bottom flask with a stir bar and reflux condenser. The reaction was allowed to proceed without ammonia catalyst for 24 hours at +23C. GC/MS showed that no desired reaction had taken place. Only some alkoxy/OH exchange between silanediol and MTMOS had occurred, to give methoxydiphenylsilanol and dimethoxydiphenylsilane.
  • 3
  • [ 1185-55-3 ]
  • [ 947-42-2 ]
  • [ 10175-48-1 ]
  • [ 6843-66-9 ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at -20℃; for 5h; Diphenylsilanediol (60 g), tetrahydrofuran (THF, 30 g) and methyltrimethoxysilane (MTMOS, 180 g) were placed in a 500 mL 3-neck round bottom flask with a stir bar and reflux condenser. The flask was cooled to -20C. l,8-Diazabicycloundec-7-ene (DBU, 0.5 g) was added into the solution. The reaction was allowed to proceed for 5 hours at -20C, after which GC/MS was run from the reaction mixture. It showed, that while low yields of the desired product was formed, over 80% of diphenylsilanediol was converted to dimethoxydiphenylsilane. DBU (pKb = 1.1) was clearly too strong base for this reaction and caused excessive side reactions
  • 4
  • [ 16066-09-4 ]
  • [ 947-42-2 ]
  • [ 188240-37-1 ]
YieldReaction ConditionsOperation in experiment
96% In a dry 100 L round bottom flask fitted with a magnetic stirrer, condenser, thermocouple probe with temperature control, heating mantle and nitrogen over-gas was placed 10.8 g (0.05 mole) DPSD and 20 g xylenes. The mixture was heated to 40 C. and stirred to dissolve the DPSD. Using a syringe, 0.1 ml of a 5% tris(pentafluorophenyl)boron in xylenes was added to yield a boron complex concentration of 100 ppm in the suspension. From an addition funnel was added 14.1 g (0.05 mole) <strong>[16066-09-4]1,1,1,3,5,7,7,7-octamethyltetrasiloxane</strong> (MD′D′M) at a rate that maintained a slow steady evolution of hydrogen gas. The addition continued for about 1 hour at 40-60 C. After complete addition of the MD′D′M, the reaction mixture was stirred at 60 C. for 1 hour. An FTIR analysis of the reaction mixture displayed no SiH (2150 cm-1). After a GC analysis indicated a large quantity of Diphenyl-DT2M2 and only a trace of octamethylcyclotetrasiloxane (D4), 0.1 g of magnesium oxide was added to neutralize the catalyst and the reaction mixture was stirred for 30 minutes. The mixture was filtered into a 100 ml round bottom flask, and the solvent was removed on a rotary evaporator at 90 C. and <5 mmHg to yield a residue of 21.6 g of residue that was 96% Diphenyl-DT2M2 (2 isomers) by GC analysis. A GPC analysis showed a trace of polymer.
  • 5
  • [ 2530-85-0 ]
  • [ 947-42-2 ]
  • C52H60O12Si5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With barium hydroxide; at 75℃; for 5h;Dean-Stark; Inert atmosphere; In a three-necked 1 L round flask equipped with a Deanstock with a mechanical stirrer and cooling tube, a thermometer connected to a thermostat, and a heating mantle,248.4 g (1 mol) of 3-methacryloxypropyltrimethoxysilane (KBM-503, Shinnets) and 216.3 g (1 mol) of diphenylsilanediol (SiSiB PC8228, Power Chemical) (x / y = 0.67) was added and 2 g of barium hydroxide was added as a catalyst, followed by reaction at 75 C. for 5 hours. At this time, a nitrogen tube was mounted in the reactor and nitrogen was continuously added to remove methanol generated during the reaction from the reactor to induce the reaction toward the forward reaction. After 5 hours, the temperature was lowered to 40 C. and distillation under reduced pressure was carried out at 1 MPa pressure to remove methanol remaining in the reaction, and a transparent viscous siloxane methacrylate oligomer including thiol and phenyl groups in the molecular structure was prepared. The liquid refractive index (nd 25) at 25 C of the obtained siloxane methacrylate oligomer was 1.581
 

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