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Chemical Structure| 214360-65-3 Chemical Structure| 214360-65-3

Structure of 214360-65-3

Chemical Structure| 214360-65-3

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Product Details of [ 214360-65-3 ]

CAS No. :214360-65-3
Formula : C13H16BF3O2
M.W : 272.07
SMILES Code : CC1(C)OB(OC1(C)C)C1=CC=C(C=C1)C(F)(F)F
MDL No. :MFCD05863924
InChI Key :GCQADNWXVSTJQW-UHFFFAOYSA-N
Pubchem ID :2760605

Safety of [ 214360-65-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H413
Precautionary Statements:P264-P270-P273-P301+P312-P330

Computational Chemistry of [ 214360-65-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 6
Fraction Csp3 0.54
Num. rotatable bonds 2
Num. H-bond acceptors 5.0
Num. H-bond donors 0.0
Molar Refractivity 67.92
TPSA ?

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

18.46 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

3.79
Log Po/w (WLOGP)?

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

4.16
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.

2.68
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

2.87
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.7

Water Solubility

Log S (ESOL):?

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

-4.02
Solubility 0.0262 mg/ml ; 0.0000963 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.

-3.87
Solubility 0.0366 mg/ml ; 0.000134 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

-4.88
Solubility 0.00356 mg/ml ; 0.0000131 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

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

Yes
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.

-5.27 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)

2.81

Application In Synthesis of [ 214360-65-3 ]

* 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 [ 214360-65-3 ]

[ 214360-65-3 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 98-08-8 ]
  • [ 25015-63-8 ]
  • [ 325142-82-3 ]
  • [ 214360-65-3 ]
YieldReaction ConditionsOperation in experiment
General procedure: [RuCl2(p-cymene)]2 (2.3 mg, 3.8 mumol) and TpMe2K (2.5 mg, 7.5 mumol)were placed in a resealable Schlenk tube. The tube was evacuated,backfilled with dinitrogen and then charged with the arene 2 (5 mmol).After stirring the mixture at room temperature for 1 h, pinacolborane(1; 36 muL, 0.25 mmol) was added. The reaction mixture was thenstirred at 120 C for 16 h. After the reaction, the mixture was analysedby GC and GC-MS. The volatile material was removed in vacuo, andthe residue was purified by Kugelrohr distillation.
  • 2
  • [ 98-08-8 ]
  • [ 73183-34-3 ]
  • [ 325142-82-3 ]
  • [ 214360-65-3 ]
YieldReaction ConditionsOperation in experiment
With bis(1,5-cyclooctadiene)nickel (0); 1,3-bis(mesityl)imidazolium chloride; sodium t-butanolate; at 140℃; for 24h;Inert atmosphere; Glovebox; Sealed tube; General procedure: A 20-mL glass vessel equipped with J. Young O-ring tap containing a magnetic stirring bar was dried with a heat-gun under reduced pressure and filled with nitrogen after cooling to room temperature. After adding bis(pinacolato)diboron (127.0 mg, 0.5 mmol), the vessel was introduced inside an argon-atmosphere glovebox. In the glovebox, Ni(cod)2 (13.8 mg, 0.05 mmol) and CsF (19.0 mg, 0.125 mmol) were added to the vessel, which was sealed with O-ring tap and then taken out of the glovebox. Then, PCyp3 (23.8 mg, 0.1 mmol) and benzene derivative 1 (3.0 mL) were added to the vessel under nitrogen atmosphere. The vessel was heated at 140 C for 24 h in an oil bath with stirring. After cooling the reaction mixture to room temperature, the mixture was concentrated and directly purified by preparative thin-layer chromatography (PTLC; hexane/ethyl acetate as the eluent) to afford the borylation product 2. Yields of 2 are calculated based on bis(pinacolato)diboron.
  • 3
  • [ 98-08-8 ]
  • 4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • [ 325142-82-3 ]
  • [ 214360-65-3 ]
  • 4
  • [ 98-08-8 ]
  • [ 73183-34-3 ]
  • [ 1073339-21-5 ]
  • [ 325142-82-3 ]
  • [ 214360-65-3 ]
  • 5
  • [ 98-08-8 ]
  • [ 73183-34-3 ]
  • [ 1197374-02-9 ]
  • [ 325142-82-3 ]
  • [ 214360-65-3 ]
  • 6
  • [ 76-09-5 ]
  • [ 98-08-8 ]
  • [ 22092-92-8 ]
  • [ 325142-82-3 ]
  • [ 214360-65-3 ]
YieldReaction ConditionsOperation in experiment
General procedure: In a glovebox, [Ir(OMe)(cod)]2 (33.1 mg, 0.050 mmol, 0.10 equiv), ICy?HCl (26.2 mg, 0.10 mmol,0.20 equiv), NaOt-Bu (19.2 mg, 0.20 mmol, 0.40 equiv) and benzene (1.0 mL) were added to a10 mL-sample vial with a Teflon-sealed screwcap, and stirred for 5 min at room temperature. 1g(113.1 mg, 1.0 mmol, 2.0 equiv) was added, and then the cap was screwed on to seal the vial. Thevial was stirred at 110 C for 18 h. The reaction mixture was cooled to room temperature. Pinacol(236 mg, 2.0 mmol, 4.0 equiv) in THF (2.0 mL) was added and the reaction mixture was stirred for1.5 h at room temperature under N2. The crude mixture was filtered through a pad of Celite andeluted with EtOAc. The filtrate was concentrated in vacuo and sampled for analysis by 1H NMRspectroscopy using 1,2-dichloroethane as an internal standard. The residue was purified by flashcolumn chromatography over silica gel eluting with hexane/EtOAc. Product-containing fractionswere concentrated in vacuo to give a pure borylated product.
 

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