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Chemical Structure| 83947-56-2 Chemical Structure| 83947-56-2

Structure of 83947-56-2

Chemical Structure| 83947-56-2

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Product Citations

Product Citations

Gruszczyński, Marcin ; Lewandowski, Dariusz ; Kuciński, Krzysztof ; Kubicki, Maciej ; Hreczycho, Grzegorz ;

Abstract: Nickel catalysis provides opportunities to modulate reaction pathways through changes in the coordination environment, yet strategies to deliberately redirect nickel reactivity remain limited. Here we show that ligand exchange at nickel allows a single catalytic system to produce different products from the same alkyne substrates. Aminophosphine-supported nickel catalysts promote selective hydroboration in the presence of pinacolborane, which functions both as a boron source and a reaction activator. The addition of forms a distinct ligand-coordinated nickel species that suppresses hydroboration and directs the reaction toward enyne formation. Our further studies identify coordination as a key step that directs the catalytic cycle, illustrating how simple additives can influence reaction outcomes. These results offer a straightforward strategy to access divergent reactivity in nickel catalysis and provide insight into the factors controlling catalytic pathway selection.

Keywords: Alkynes ; Nickel catalysis ; Ligand effects ; Hydroboration ; Enynes

Purchased from AmBeed: ; ; ; ;

Alternative Products

Product Details of [ 83947-56-2 ]

CAS No. :83947-56-2
Formula : C14H19BO2
M.W : 230.11
SMILES Code : CC1(C)C(C)(C)OB(/C=C/C2=CC=CC=C2)O1
English Name :E-Phenylethenylboronic acid, pinacol ester
MDL No. :MFCD03453666
InChI Key :ARAINKADEARZLZ-ZHACJKMWSA-N
Pubchem ID :5708413

Safety of [ 83947-56-2 ]

Computational Chemistry of [ 83947-56-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 17
Num. arom. heavy atoms 6
Fraction Csp3 0.43
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 72.32
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

3.55
Log Po/w (WLOGP)?

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

3.22
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.

2.19
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

2.39
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.27

Water Solubility

Log S (ESOL):?

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

-3.63
Solubility 0.0537 mg/ml ; 0.000233 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.

-3.62
Solubility 0.0549 mg/ml ; 0.000238 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

-4.09
Solubility 0.0186 mg/ml ; 0.0000807 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.

-5.18 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<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)

3.0

Application In Synthesis of [ 83947-56-2 ]

* 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 [ 83947-56-2 ]

[ 83947-56-2 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 292638-84-7 ]
  • [ 72824-04-5 ]
  • [ 83947-56-2 ]
  • [ 74213-48-2 ]
  • 2
  • [ CAS Unavailable ]
  • [ 25015-63-8 ]
  • [ 83947-56-2 ]
  • [ 143825-84-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran at 25℃; for 14h; Title compound not separated from byproducts.;
With Ru(at)TBAB at 85℃; for 23h; Inert atmosphere; stereoselective reaction; 2.3. General procedure for phenylacetylene hydroboration Pinacolborane (1.0 mmol) and then phenylacetylene (1.0 mmol)were added under argon to the M(at)OS (0.1 mol%) contained in a15 mL reaction tube. The mixture was stirred at 85°C for 23 h.The reaction mixture was then diluted in dichloromethane andfiltrated over a pad of silica. After washing twice with 10 mLof dichloromethane the filtrate was concentrated under vacuumto give the corresponding vinylborane as a mixture of isomers.Product distribution was determined by GC/MS. Conversion isdetermined using the relative areas in GC/MS and according tomesitylene as internal standard. The spectral data were in agree-ment with those reported in the literature.
With [Rh(CO)(2-pyridyldiphenylphosphine)(2-iodo-3,4,5,6-tetrafluorophenyldiphenylphosphine)]BARF In dichloromethane-d2 at 20℃; for 24h; Inert atmosphere; Overall yield = 88 %Spectr.;
With PhboxmiCo(CH2SiMe3) In hexane; toluene at 20℃; for 15h; Overall yield = 64 percent; regioselective reaction;
28 %Chromat. With C78H66N10(4+)*4F6P(1-); cobalt(II) chloride; sodium t-butanolate In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Schlenk technique; Glovebox;
1: 78 %Chromat. 2: 8 %Chromat. With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 25℃; Inert atmosphere; Glovebox; Schlenk technique;

  • 3
  • [ 1104636-68-1 ]
  • [ 83947-56-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
71% With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; water In tetrahydrofuran at 18℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;
  • 4
  • [ 57381-44-9 ]
  • C10H10BN2O4 [ No CAS ]
  • [ 83947-56-2 ]
  • (E)-5-(2-methoxypyridin-3-yl)-2-styrylbenzonitrile [ No CAS ]
  • 5
  • [ 468075-00-5 ]
  • [ CAS Unavailable ]
  • [ 83947-56-2 ]
  • [ CAS Unavailable ]
  • [ 1820862-09-6 ]
YieldReaction ConditionsOperation in experiment
69% With potassium phosphate; palladium diacetate; DavePhos In tetrahydrofuran; water at 90℃; for 16h; chemoselective reaction;
  • 6
  • [ 1195529-07-7 ]
  • [ 73183-34-3 ]
  • [ 83947-56-2 ]
YieldReaction ConditionsOperation in experiment
48% With isonicotinate tert-butyl ester at 110℃; for 15h; Schlenk technique; Inert atmosphere;
  • 7
  • [ 586-78-7 ]
  • [ 83947-56-2 ]
  • [ 1694-20-8 ]
YieldReaction ConditionsOperation in experiment
73% With palladium diacetate; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere; General Procedure I: Cross-Coupling Protocol General procedure: To an oven-dried, 25 mL round-bottomed flask, containing a magnetic stir-bar was added Pd(OAc)2 (0.05 equiv), t-Bu3PHBF4 (0.10 equiv), and K2CO3 (1.2 equiv). (E)-2-phenylethenylboronic acid pinacol ester (1.2 equiv) was weighed, dissolved in DMF ([0.2] with respect to the aromatic bromide), and then added to the solid reagents. The flask was capped witha septum, purged with argon for 10 min, and the aromatic bromide (1.0 equiv) was added by syringe. The flask was then placed in a preheated oil bath (90 °C) and allowed to stir under aballoon of argon. The reaction was determined to be complete by TLC and GC-MS analysis of a crude reaction aliquot. The reaction was then cooled to rt, poured into a separatory funnel containing H2O (10 mL), and extracted with EtOAc (3 × 10 mL). The three separate organic extracts were then sequentially washed with H2O (2 × 10 mL) and brine (20 mL). The organic extracts were combined, dried over Na2SO4 until flocculent, and filtered. Concentration of the filtrate and purification by flash chromatography (silica gel) provided the desired product.
  • 8
  • [ 623-00-7 ]
  • [ 83947-56-2 ]
  • [ 13041-79-7 ]
YieldReaction ConditionsOperation in experiment
76% With palladium diacetate; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 90℃; for 20h; Inert atmosphere; General Procedure I: Cross-Coupling Protocol General procedure: To an oven-dried, 25 mL round-bottomed flask, containing a magnetic stir-bar was added Pd(OAc)2 (0.05 equiv), t-Bu3PHBF4 (0.10 equiv), and K2CO3 (1.2 equiv). (E)-2-phenylethenylboronic acid pinacol ester (1.2 equiv) was weighed, dissolved in DMF ([0.2] with respect to the aromatic bromide), and then added to the solid reagents. The flask was capped witha septum, purged with argon for 10 min, and the aromatic bromide (1.0 equiv) was added by syringe. The flask was then placed in a preheated oil bath (90 °C) and allowed to stir under aballoon of argon. The reaction was determined to be complete by TLC and GC-MS analysis of a crude reaction aliquot. The reaction was then cooled to rt, poured into a separatory funnel containing H2O (10 mL), and extracted with EtOAc (3 × 10 mL). The three separate organic extracts were then sequentially washed with H2O (2 × 10 mL) and brine (20 mL). The organic extracts were combined, dried over Na2SO4 until flocculent, and filtered. Concentration of the filtrate and purification by flash chromatography (silica gel) provided the desired product.
  • 9
  • [ 611-15-4 ]
  • [ 83947-56-2 ]
  • [ 1294009-26-9 ]
YieldReaction ConditionsOperation in experiment
67 %Chromat. With bis(cyclopentadienyl)dihydrozirconium In toluene at 130℃; Inert atmosphere; Glovebox;
  • 10
  • [ 2039-85-2 ]
  • [ 83947-56-2 ]
  • [ 871125-84-7 ]
YieldReaction ConditionsOperation in experiment
79 %Chromat. With bis(cyclopentadienyl)dihydrozirconium In toluene at 130℃; Inert atmosphere; Glovebox;
  • 11
  • [ 405-99-2 ]
  • [ 83947-56-2 ]
  • [ 504433-86-7 ]
YieldReaction ConditionsOperation in experiment
72 %Chromat. With bis(cyclopentadienyl)dihydrozirconium In toluene at 130℃; Inert atmosphere; Glovebox;
  • 12
  • [ 2039-82-9 ]
  • [ 83947-56-2 ]
  • [ 1242770-51-9 ]
YieldReaction ConditionsOperation in experiment
20 %Chromat. With bis(cyclopentadienyl)dihydrozirconium In toluene at 130℃; Inert atmosphere; Glovebox;
  • 13
  • [ 160233-76-1 ]
  • [ 83947-56-2 ]
  • [ 2446617-56-5 ]
YieldReaction ConditionsOperation in experiment
100% With trans-bis(triphenylphosphine)palladium dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere; S-14.1 Step 1 : Synthesis of (E)-6-styrylquinoline-4-carboxylic acid. To a solution of 6- bromoqumolme-4-carboxyiic acid (0.2 g, 0.8 mmol, 1.0 equiv) and (E)-2-styryl)-4,4,5,5- tetramethyl-l,3,2-dioxaborolane (0.22 g, 0.96 mmol, 1.2 equiv) in dioxane (10 ml) and water (2 ml) was added in K2CO3 (0.169 g, 1 .6 mmol, 2.0 equiv) and the mixture was purged with N2 gas for 10 min, followed by the addition of Pd(PPh2)Ck (0.028 g, 0.04 mmol. 0.05 equiv). The resulting reaction mixture was heated at 100° C for overnight. Product formation was confirmed by LCMS After the completion of reaction the reaction mixture was diluted with water (30 mL) and washed with ethyl acetate (50 mL x 2). Aqueous layer was separated and dried over lyophiiizer to obtain (E)-6-styrylquinoline-4-carboxylic acid (0.300 g, Quant. Yield) as a yellow solid. LCMS 276.0 [M+H]+
  • 14
  • [ 50-00-0 ]
  • [ 841-77-0 ]
  • [ 83947-56-2 ]
  • [ 16699-20-0 ]
YieldReaction ConditionsOperation in experiment
78 % Stage #1: 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane With hydrogenchloride; sodium periodate; water In tetrahydrofuran at 20℃; Stage #2: formaldehyd; diphenylmethylpiperazine at 90℃;
  • 15
  • [ 99275-47-5 ]
  • [ 83947-56-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(tert-butyloxycarbonyl)-5-methoxyindole With n-butyllithium In tetrahydrofuran; pentane at 0 - 20℃; Inert atmosphere; Stage #2: 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane In tetrahydrofuran; pentane at -78 - 20℃; Inert atmosphere;
  • 16
  • [ 155444-28-3 ]
  • [ 83947-56-2 ]
  • [ 3084049-46-4 ]
YieldReaction ConditionsOperation in experiment
With copper diacetate; sodium hydride In toluene at 110℃; Sealed tube; Molecular sieve;
  • 17
  • [ 1061357-86-5 ]
  • [ 83947-56-2 ]
  • [ 3079282-31-5 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 2-methyltetrahydrofuran; water at 75℃; Inert atmosphere; Synthesis of the Compound of the Invention 2,5-Dibromo-4-iodopyridine (15 g, 1 Eq, 41.4 mmol) was dissolved in 2-MeTHF (150 mL), (E)-4,4,5,5-tetramethyl-2-styryl-1,3,2-dioxaborolane (10.6 g, 1.114 Eq, 46.1 mmol), water (100 mL, 1.5 mol, 3.6 Eq, 150 mmol), K3PO4 (1.5 M) and Pd(dppf)Cl2.DCM (1.64 g, 0.05 Eq, 2.1 mmol) were added to the mixture degassed with nitrogen gas, and heated to 75°C for 20 hours. After cooling to room temperature, the reaction mixture was filtered and transferred to a separatory funnel. The organic layer was drained and the aqueous layer was re-extracted with 2-MeTHF (250 mL). The combined organic layers were then dried over anhydrous Mg2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using 5-20% MTBE/iso-hexane as eluent to give (E)-2,5-dibromo-4-styrylpyridine (12.2 g, 29 mmol, 70%, 80% purity).
 

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