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Structure of 612088-55-8

Chemical Structure| 612088-55-8

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Product Details of [ 612088-55-8 ]

CAS No. :612088-55-8
Formula : C14H24BF4P
M.W : 310.12
SMILES Code : CC([PH+](C(C)(C)C)C1=CC=CC=C1)(C)C.F[B-](F)(F)F
MDL No. :MFCD08704553
InChI Key :HRDPEVWZXUWEFR-UHFFFAOYSA-O
Pubchem ID :11220595

Safety of [ 612088-55-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 612088-55-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 20
Num. arom. heavy atoms 6
Fraction Csp3 0.57
Num. rotatable bonds 3
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 85.22
TPSA ?

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

13.59 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

5.68
Log Po/w (WLOGP)?

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

7.1
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.

5.18
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

3.64
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.32

Water Solubility

Log S (ESOL):?

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

-5.37
Solubility 0.00134 mg/ml ; 0.00000431 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-5.73
Solubility 0.000577 mg/ml ; 0.00000186 mol/l
Class?

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

Moderately 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

-4.94
Solubility 0.00357 mg/ml ; 0.0000115 mol/l
Class?

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

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
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

No
Log Kp (skin permeation)?

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

-4.16 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

1.0
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

1.0
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

2.0
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

2.0 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)

3.69

Application In Synthesis of [ 612088-55-8 ]

* 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 [ 612088-55-8 ]

[ 612088-55-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 677-22-5 ]
  • [ 644-97-3 ]
  • [ 612088-55-8 ]
YieldReaction ConditionsOperation in experiment
86% In a round-bottomed flask, 60.6 mg of copper(I)bromide-dimethyl sulphide complex and 51.2 mg of lithium bromide are initially charged under protective gas. 20 ml of hexane, 4 ml of dichlorophenylphosphine and another 19 ml of hexane are subsequently added.The reaction solution is cooled to 0 C. 32.4 ml of a 2 M solution of tert-butylmagnesium chloride in ether are then slowly added dropwise.The mixture is subsequently allowed to slowly adjust to room temperature and is then stirred at room temperature for a further two hours.For workup, the mixture is cautiously admixed with 75 ml of degassed 2 M HBF4.Another 5 ml of 8 M HBF4 are then additionally added and stirred for 15 min.Filtration with suction is then effected and the filter cake is washed with a little cold water.The residue is dried under reduced pressure to constant weight. Yield: 7.9 g (86% of theory) purity >99%. 1H NMR (CDCl3, ppm): 7.9 (m, broad); 7.80 (t); 7.69 (2H, td); 6.92 (d, 485 Hz); 1.53 (d, 17 Hz,); 31P NMR (CDCl3, ppm): 44.93 (s)
  • 2
  • [ 32673-25-9 ]
  • imidazolium tetrafluoroborate [ No CAS ]
  • [ 612088-55-8 ]
  • 3
  • [ 1191-15-7 ]
  • [ 644-97-3 ]
  • [ 75-65-0 ]
  • [ 612088-55-8 ]
YieldReaction ConditionsOperation in experiment
95% Under argon protection, add 1 L of toluene to the dry reactor, then add phenylphosphine dichloride (178 g, 1 mol), and add 1.0 M of diisobutylaluminum hydride solution in 3 L at 0-10 C. Then, the temperature is raised to 20-40 o C for 6 hours, and then the reaction is quenched by adding 2 L of 1 N sodium hydroxide solution, and then liquid separation, extraction, and the organic layer is dried over anhydrous magnesium sulfate, and the organic phase is transferred to another dry reaction. After the addition, tert-butanol (148 g, 2 mol) and 47% by mass of boron trifluoride diethyl ether solution (1.8 kg, 6 mol) were added in sequence, and reacted at 20-40 C for 12 hours, and then quenched by adding water. A precipitate formed and suction filtered, and the solid was dried in vacuo to give 294 g of di-tert-butylphenylphosphonium tetrafluoroborate in a yield of 95%
 

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