Home Cart Sign in  
Chemical Structure| 179117-44-3 Chemical Structure| 179117-44-3

Structure of 179117-44-3

Chemical Structure| 179117-44-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 179117-44-3 ]

CAS No. :179117-44-3
Formula : C13H18BNO3
M.W : 247.10
SMILES Code : CC1(C)OB(OC1(C)C)C1=CC=C(C=C1)C(N)=O
MDL No. :MFCD05663887
InChI Key :NWEMAGLLVQDEKL-UHFFFAOYSA-N
Pubchem ID :2760588

Safety of [ 179117-44-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 179117-44-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 6
Fraction Csp3 0.46
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 71.01
TPSA ?

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

61.55 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

1.78
Log Po/w (WLOGP)?

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

1.08
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.

0.87
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

1.02
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.95

Water Solubility

Log S (ESOL):?

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

-2.61
Solubility 0.609 mg/ml ; 0.00247 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.

-2.69
Solubility 0.504 mg/ml ; 0.00204 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

-3.59
Solubility 0.0632 mg/ml ; 0.000256 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

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.

-6.54 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)

2.62

Application In Synthesis of [ 179117-44-3 ]

* 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.

  • Upstream synthesis route of [ 179117-44-3 ]

[ 179117-44-3 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 73183-34-3 ]
  • [ 619-56-7 ]
  • [ 179117-44-3 ]
YieldReaction ConditionsOperation in experiment
75% With (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; dichlorobis(trimethylphosphine)nickel In 1,4-dioxane at 100℃; for 12 h; Inert atmosphere; Sealed tube Under an argon atmosphere,To the reaction vessel, 1.4 mg (0.005 mmol) of dichlorobis (trimethylphosphine) nickel,77.4 mg (0.5 mmol) of 4-chlorobenzamide,152 mg (1.0 mmol) of cesium fluoride,140 mg (0.55 mmol) of 4,4,5,5,4 ', 4', 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolanyl)180 mg (1.05 mmol) of trimethyl (2,2,2-trifluoroethoxy) silane and 0.5 mL of 1,4-dioxane were added and sealed,And the mixture was stirred at 100 ° C. for 12 hours.After the reaction vessel was cooled to room temperature, 1 mL of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted three times with 8 mL of ethyl acetate, and the obtained organic phases were combined.The solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography (hexane: chloroform: ethyl acetate = 4: 1: 0 to 4: 1: 1)92 mg (white solid, yield 75percent) of 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzamide was obtained.
References: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 22, p. 3604 - 3610.
[2] Organic Letters, 2011, vol. 13, # 21, p. 5766 - 5769.
[3] Patent: JP5699037, 2015, B2, . Location in patent: Paragraph 0091; 0092.
  • 2
  • [ 698-67-9 ]
  • [ 73183-34-3 ]
  • [ 179117-44-3 ]
YieldReaction ConditionsOperation in experiment
79% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 95℃; A mixture of 2-70 (1.0 g, 5 mmol), (PinB)2 (2.28 g, 9 mmol), Pd(dppf)C12DCM (408 mg, 0.5 mmol), KOAc (980 mg, 10 mmol) and dioxane (5 mL) was degassed with N2 and stirred at 95 °C overnight. The resulting mixture was filtered and the filtrate was concentrated and purified via column chromatography on silica gel eluting with DCM/MeOH from 20/1 to 10/1 to give intermediate 2-71 (yellow solid, 975 mg, 79percent yield). LCMS (m/z):248 [M+Hj .
References: [1] Journal of the American Chemical Society, 2017, vol. 139, # 23, p. 7745 - 7748.
[2] Patent: WO2016/161145, 2016, A1, . Location in patent: Paragraph 00743.
[3] European Journal of Medicinal Chemistry, 2015, vol. 96, p. 382 - 395.
  • 3
  • [ 180516-87-4 ]
  • [ 179117-44-3 ]
YieldReaction ConditionsOperation in experiment
45% With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 3 h; Step 1
4-(4,4,5,5-Metramethyl-1,3,2-dioxaborolan-2-yl)benzamide
Procedure
To a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (200 mg, 0.746 mmol), EDCI (214 mg, 1.12 mmol), HOBt (151 mg, 1.12 mmol) and Et3N (151 mg, 1.49 mmol) in DCM (20 mL) was bubbled ammonia until saturation.
The mixture was stirred at room temperature for 3 h, then was filtered and the filtrate was concentrated to give residue which was purified by column chromatography (DCM:MeOH=50:1) to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (90 mg, 45percent) as a yellow solid. LC-MS: 248 [M+H]+, tR=1.421 min.
References: [1] Patent: US2012/252777, 2012, A1, . Location in patent: Page/Page column 96.
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 4036 - 4040.
  • 4
  • [ 3956-07-8 ]
  • [ 25015-63-8 ]
  • [ 179117-44-3 ]
References: [1] Patent: US6680401, 2004, B1, . Location in patent: Page column 19-20.
  • 5
  • [ 3956-07-8 ]
  • [ 73183-34-3 ]
  • [ 179117-44-3 ]
References: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 7, p. 1381 - 1385.
[2] European Journal of Organic Chemistry, 2014, vol. 2014, # 7, p. 1381 - 1385.
  • 6
  • [ 76-09-5 ]
  • [ 179117-44-3 ]
References: [1] Tetrahedron Letters, 2013, vol. 54, # 2, p. 166 - 169.
  • 7
  • [ 55-21-0 ]
  • [ 73183-34-3 ]
  • [ 188665-74-9 ]
  • [ 179117-44-3 ]
References: [1] Journal of the American Chemical Society, 2017, vol. 139, # 23, p. 7745 - 7748.
[2] Angewandte Chemie - International Edition, 2018, [3] Angew. Chem., 2018, vol. 130, p. 15988 - 15992,5.
  • 8
  • [ 586-76-5 ]
  • [ 179117-44-3 ]
References: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 4036 - 4040.
  • 9
  • [ 73183-34-3 ]
  • [ 179117-44-3 ]
References: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 4036 - 4040.
  • 10
  • [ 698-67-9 ]
  • [ 179117-44-3 ]
References: [1] Tetrahedron Letters, 2013, vol. 54, # 2, p. 166 - 169.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 179117-44-3 ]

Organoborons

Chemical Structure| 376584-62-2

A137391 [376584-62-2]

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one

Similarity: 0.89

Chemical Structure| 1004294-80-7

A181496 [1004294-80-7]

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one

Similarity: 0.89

Chemical Structure| 138500-88-6

A813793 [138500-88-6]

(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine

Similarity: 0.88

Chemical Structure| 1313399-38-0

A122995 [1313399-38-0]

2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one

Similarity: 0.87

Chemical Structure| 128376-64-7

A188411 [128376-64-7]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.86

Aryls

Chemical Structure| 138500-88-6

A813793 [138500-88-6]

(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine

Similarity: 0.88

Chemical Structure| 380151-86-0

A173594 [380151-86-0]

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.86

Chemical Structure| 128376-64-7

A188411 [128376-64-7]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.86

Chemical Structure| 380151-85-9

A117333 [380151-85-9]

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.85

Chemical Structure| 909391-56-6

A929818 [909391-56-6]

N,N-Dimethyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine

Similarity: 0.83

Amides

Chemical Structure| 376584-62-2

A137391 [376584-62-2]

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one

Similarity: 0.89

Chemical Structure| 1004294-80-7

A181496 [1004294-80-7]

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one

Similarity: 0.89

Chemical Structure| 1313399-38-0

A122995 [1313399-38-0]

2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one

Similarity: 0.87

Chemical Structure| 1221239-09-3

A513662 [1221239-09-3]

2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one

Similarity: 0.84

Chemical Structure| 935660-75-6

A193200 [935660-75-6]

N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide

Similarity: 0.83

Amines

Chemical Structure| 138500-88-6

A813793 [138500-88-6]

(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine

Similarity: 0.88

Chemical Structure| 909391-56-6

A929818 [909391-56-6]

N,N-Dimethyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine

Similarity: 0.83

Chemical Structure| 935660-75-6

A193200 [935660-75-6]

N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide

Similarity: 0.83

Chemical Structure| 590418-05-6

A179400 [590418-05-6]

2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Similarity: 0.81

Chemical Structure| 129636-11-9

A158780 [129636-11-9]

N,N-Dimethyl-1-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine

Similarity: 0.79