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Chemical Structure| 84563-54-2 Chemical Structure| 84563-54-2

Structure of 84563-54-2

Chemical Structure| 84563-54-2

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Product Details of [ 84563-54-2 ]

CAS No. :84563-54-2
Formula : C21H26F3IO3S
M.W : 542.39
SMILES Code : CC(C1=CC=C([I+]C2=CC=C(C(C)(C)C)C=C2)C=C1)(C)C.O=S([O-])(C(F)(F)F)=O
MDL No. :MFCD02683471
InChI Key :VGZKCAUAQHHGDK-UHFFFAOYSA-M
Pubchem ID :2734848

Safety of [ 84563-54-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P301+P330+P331-P305+P351+P338-P310
Class:8
UN#:3261
Packing Group:

Computational Chemistry of [ 84563-54-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 29
Num. arom. heavy atoms 12
Fraction Csp3 0.43
Num. rotatable bonds 5
Num. H-bond acceptors 6.0
Num. H-bond donors 0.0
Molar Refractivity 118.63
TPSA ?

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

65.58 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

8.01
Log Po/w (WLOGP)?

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

4.8
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.

5.95
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

6.85
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.12

Water Solubility

Log S (ESOL):?

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

-8.23
Solubility 0.00000323 mg/ml ; 0.0000000059 mol/l
Class?

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

Poorly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-9.24
Solubility 0.000000312 mg/ml ; 0.0000000006 mol/l
Class?

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

Poorly 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

-8.21
Solubility 0.00000331 mg/ml ; 0.0000000061 mol/l
Class?

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

Poorly 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

Yes
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

No
Log Kp (skin permeation)?

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

-3.92 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

2.0
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.

0.17

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

3.0 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<2.0
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)

3.86

Application In Synthesis of [ 84563-54-2 ]

* 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 [ 84563-54-2 ]

[ 84563-54-2 ] Synthesis Path-Downstream   1~2

YieldReaction ConditionsOperation in experiment
With procetonato-copper(II); In ethanol; ethyl acetate;Conversion of starting material; Examples:Gel times in comparison to halonium salt based ternary redox systemsPreparation of solution 1: At room temperature in a 100 ml round bottom flask 0.083 g of procetonato-Copper(II) were dissolved in an appropriate amount of ethyl acetate. 9.917 g of Bis[2-(3,4-epoxycyclohexyl)-ethyl]-methyl-phenyl-silane were added and after a brief homogenization the solvent was removed under vacuo (0.01 mbar) at 50 C. The amount of procetonato-copper(II) is adjusted so that there are 0.25 %-mol of procetonato-copper(II) within the complete resulting mixture of procetonato-copper(II) together with the reducing agent (see below: preparation of Solution 2) and the iodonium salt (see below: preparation of Solution 3).Preparation of solution 2: As described above for procetonato-copper(II) (see above: preparation of solution 1) as respective reducing agents benzoin (solvent ethyl acetate, Solution 2a) and ascorbyl palmitate (solvent ethanol, Solution 2b) are dissolved within bis[2-(3,4-epoxycyclohexyl)-ethyl]-methyl-phenyl-silane so that there is 1.00 %-mol of the reducing agent within the complete resulting mixture of the reducing agent together with procetonato-copper(II) (see above: preparation of solution 1) and the iodonium salt (see below preparation of solution 3).Preparation of solution 3: As described above for the reducing agents (see above: preparation of solution 2) as respective iodonium salts (4-cumyl)-(4-tolyl)-iodonium tetrakis(pentafluorophenyl)borate (solvent ethyl acetate, solution 3a), (4-ocytyloxy-phenyl)-phenyl-iodonium hexafluorostibonate (solvent ethyl acetate, solution 3b), (4-methoxy-phenyl)-phenyl-iodonium hexafluorostibonate (solvent ethanol, solution 3c), [3-(2-hydroxy-tetradecyloxy)-phenyl]-phenyl-iodonium hexafluorostibonate (solvent ethanol, Solution 3d) and bis(4-tert-butylphenyl)-iodonium trifluoromethansulfonate (solvent ethanol, solution 3e) were dissolved in bis[2-(3,4-epoxycyclohexyl)-ethyl]-methyl-phenyl-silane so that there is 1.00 %-mol of the iodonium salt within the complete resulting mixture of the iodonium salt together with procetonato-copper(II) (see above: preparation of solution 1) and the reducing agent (see above: preparation of solution 2).Preparation of Solution 4: As described above for procetonato-copper(II) (see above: preparation of solution 1) but without added solvent, a Pt(0) complex was dissolved in Bis[2-(3,4-epoxycyclohexyl)-ethyl]-methyl-phenyl-silane so that the resulting mixture contained 500 ppm of platinum metal of the Pt(0) complex together with the iodonium salt (see above preparation of solution 3). The Pt(0) complex was prepared from hexachloroplatinum acid by reduction with 1,1,3,3-Tetramethyl-1,3-divinyldisiloxane in the presence of a vinyl terminated poly(dimethylsiloxane) containing 1.3 %-weight of platinum metal as described e.g. within U.S. Pat Nos. 3,715,334, 3,775,352 and 3,814,730 for similar platinum complexes. Preparation of the example mixtures:i. Example mixtures with a ternary initiator system: First 1.00 g of Solution 3 was added to 1.00 g of Solution 1. Then 1.00 g of Solution 2 was added. The resulting mixture was then homogenized by vigorously stirring by hand with a spatula made of polyethylene.ii. Example mixture with a binary initiator system: 1.00 g of solution 4 was added to 1.00 g of Solution 3. The resulting mixture was then homogenized by vigorously stirring by hand with a spatula made of polyethylene.
  • 2
  • [ 84563-54-2 ]
  • [ 10406-06-1 ]
  • 4-(tert-butyl)phenyl 5-bromo-1H-indole-3-carboxylate [ No CAS ]
 

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