Home Cart Sign in  
Chemical Structure| 286961-15-7 Chemical Structure| 286961-15-7

Structure of 286961-15-7

Chemical Structure| 286961-15-7

*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 [ 286961-15-7 ]

CAS No. :286961-15-7
Formula : C19H26BNO4
M.W : 343.23
SMILES Code : O=C(N1CCC(B2OC(C)(C)C(C)(C)O2)=CC1)OCC3=CC=CC=C3
MDL No. :MFCD11521562
InChI Key :QDSFHRPYZPQWEJ-UHFFFAOYSA-N
Pubchem ID :11290836

Safety of [ 286961-15-7 ]

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

Computational Chemistry of [ 286961-15-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 25
Num. arom. heavy atoms 6
Fraction Csp3 0.53
Num. rotatable bonds 5
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 101.93
TPSA ?

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

48.0 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

2.85
Log Po/w (WLOGP)?

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

3.05
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.

1.98
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

1.84
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.95

Water Solubility

Log S (ESOL):?

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

-3.61
Solubility 0.084 mg/ml ; 0.000245 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.

-3.52
Solubility 0.104 mg/ml ; 0.000304 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

-4.53
Solubility 0.0101 mg/ml ; 0.0000294 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.

-6.37 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<0.0
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)

3.95

Application In Synthesis of [ 286961-15-7 ]

* 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 [ 286961-15-7 ]

[ 286961-15-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1121057-75-7 ]
  • [ 501-53-1 ]
  • [ 286961-15-7 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In dichloromethane; at 20℃; for 2h; Example 2: Tetrahydropyridine 2 was prepared in 3 steps starting with the deprotection of 1 using Method 3. The resulting HCl amine salt was dissolved in dichloromethane (0.2 M). Benzyl chloroformate (1.2 equiv) was added followed by triethylamine (3.0 equiv). The reaction was allowed to stir at room temperature for 2h after which point it was diluted with IN HCl and extracted with excess dichloromethane. The organic layer was dried over MgSpsi4 and concentrated to provide the desired carbamate in quantitative yield, which was converted directly to boronic acid 2 using Method 2. [M-H]- = 260.1 m/z. Activity: B
  • 2
  • [ 34259-99-9 ]
  • [ 286961-15-7 ]
  • benzyl 4-(1,3-thiazol-4-yl)-3,6-dihydropyridine-1(2H)-oarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 90℃; for 2.5h;Inert atmosphere; Sealed tube; Aqueous sodium carbonate solution (2M) and 1,4-dioxane were both degassed by passing astream of nitrogen through a fritted glass tube into the liquids for 15 mm. Benzyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1 (2H)-carboxylate (250 mg, 0.73mmol), <strong>[34259-99-9]4-bromo-1,3-thiazole</strong> (119 mg, 0.73 mmol), [1,1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (32 mg, 0.044 mmol), degassed aqueous sodium carbonate solution (2M, 1.1 mL, 2.2 mmol) and degassed 1,4-dioxane (3 mL) were placed into a nitrogen flushed tube, sealed and heated under pressure at 90 °C for 2.5 h. The cooled reaction mixture was diluted with H20 and extracted with EtOAc. The organic phasewas passed through a phase separator and concentrated onto flash silica (15 mL). The resulting powder was purified by column chromatography (normal phase, [Biotage SNAP cartridge KP-sil 50 g, 40-63 jim, 60 A], 40 mL per mm, 65percent Et20 in isohexane isochratic) to give benzyl 4-(1 ,3-thiazol-4-yl)-3,6-dihydropyridine-1 (2H)-oarboxylate (173 mg, 79percent).LCMS (Method C): mlz 301 (M+H) (ES?), at 1.46 mi UV active.
  • 3
  • [ 261953-36-0 ]
  • [ 286961-15-7 ]
  • benzyl 4-(1H-indazol-6-yl)-5,6-dihydropyridine-1(2H)carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; at 74℃;Inert atmosphere; A reaction mixture of 6-iodo-1H-indazole (1 g, 4.10 mmcl), benzyl 4-(4,4,5,5-tetramethyl-1 ,3,2-diox-aborolan-2-yI)-5,6-dihydropyridine-1(2H)-carboxylate (1.41 g, 4.10 mmol),PdCI2(dppf)-CH2CI2 adduct (0.335 g, 0.410 mmol) and sodium carbonate (1.30 g, 12.3 mmol)was bubbled with nitrogen and stirred at 74 C (oil bath) overnight. Then the reactionmixture was filtered, concentrated to remove solvent and diluted with ethyl acetate (180 mL) and water (50 mL). Separated organic part was dried over anhydrous Na2504, fitered and concentrated. Purification via ISCO system (ethyl acetate/petroleum ether) afforded the title product.LC-MS (ESI) [mobile phase: from 95% water (0.05% TFA) and 5% CH3CN to 5% water (0.05%TFA) and 95% CH3CN in 5.0 mm]: m/z 334 [M + H] Rt 3.50 mm.
  • 4
  • [ 286961-15-7 ]
  • [ 364793-86-2 ]
  • benzyl-4-(3-(2-morpholinoethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,2-dimethoxyethane; water; at 120.0℃; for 0.75h;Sealed tube; Inert atmosphere; Microwave irradiation; General procedure: The boronic acid pinacol ester (1 equiv.), aryl halide (1 equiv.) and Pd(dppf)Cl2·CH2Cl2 adduct (0.1 equiv.) were dissolved in a mixture of DME and aqueous sodium carbonate (1M) in a microwave vial. The vial was sealed, evacuated and backfilled with N2. The reaction mixture was heated in the microwave at 120C for 45min and monitored by LCMS. The reaction mixture was concentrated in vacuo to give the crude material which was purified by Biotage column chromatography (see individual compounds for details of the eluent used).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 286961-15-7 ]

Organoborons

Chemical Structure| 286961-14-6

A130704 [286961-14-6]

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Similarity: 0.89

Chemical Structure| 1035235-26-7

A296628 [1035235-26-7]

tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Similarity: 0.82

Chemical Structure| 905273-91-8

A267611 [905273-91-8]

tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate

Similarity: 0.82

Chemical Structure| 2126812-29-9

A129545 [2126812-29-9]

Benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate

Similarity: 0.82

Chemical Structure| 885693-20-9

A119303 [885693-20-9]

tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Similarity: 0.81

Aryls

Chemical Structure| 2126812-29-9

A129545 [2126812-29-9]

Benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate

Similarity: 0.82

Chemical Structure| 330794-35-9

A114471 [330794-35-9]

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate

Similarity: 0.79

Chemical Structure| 956136-85-9

A205601 [956136-85-9]

tert-Butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylate

Similarity: 0.79

Chemical Structure| 1048976-83-5

A183372 [1048976-83-5]

1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine

Similarity: 0.75

Chemical Structure| 889865-34-3

A629658 [889865-34-3]

tert-Butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)piperidine-1-carboxylate

Similarity: 0.74

Amides

Chemical Structure| 286961-14-6

A130704 [286961-14-6]

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Similarity: 0.89

Chemical Structure| 1035235-26-7

A296628 [1035235-26-7]

tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Similarity: 0.82

Chemical Structure| 905273-91-8

A267611 [905273-91-8]

tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate

Similarity: 0.82

Chemical Structure| 2126812-29-9

A129545 [2126812-29-9]

Benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate

Similarity: 0.82

Chemical Structure| 885693-20-9

A119303 [885693-20-9]

tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Similarity: 0.81