Home Cart Sign in  
Chemical Structure| 330793-01-6 Chemical Structure| 330793-01-6

Structure of 330793-01-6

Chemical Structure| 330793-01-6

*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 [ 330793-01-6 ]

CAS No. :330793-01-6
Formula : C17H26BNO4
M.W : 319.20
SMILES Code : CC(C)(C)OC(=O)NC1=CC=C(C=C1)B1OC(C)(C)C(C)(C)O1
MDL No. :MFCD02179439
InChI Key :HSJNIOYPTSKQBD-UHFFFAOYSA-N
Pubchem ID :2734617

Safety of [ 330793-01-6 ]

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

Computational Chemistry of [ 330793-01-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 23
Num. arom. heavy atoms 6
Fraction Csp3 0.59
Num. rotatable bonds 5
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 93.16
TPSA ?

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

56.79 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

3.47
Log Po/w (WLOGP)?

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

3.14
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.

1.86
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

2.06

Water Solubility

Log S (ESOL):?

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

-3.87
Solubility 0.0432 mg/ml ; 0.000135 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.

-4.34
Solubility 0.0144 mg/ml ; 0.0000452 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

-4.93
Solubility 0.00378 mg/ml ; 0.0000118 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

Yes
Log Kp (skin permeation)?

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

-5.78 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)

3.39

Application In Synthesis of [ 330793-01-6 ]

* 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 [ 330793-01-6 ]

[ 330793-01-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 73183-34-3 ]
  • [ 131818-17-2 ]
  • [ 330793-01-6 ]
YieldReaction ConditionsOperation in experiment
36% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere; A mixture of bis(pinacolato)diboron (10.5 g, 41.5 mmol), 4 (7.75 g, 28.5 mmol), Pd(dppf)Cl2 (0.79 g, 1.1 mmol) and potassium acetate (7.0 g, 71.4 mmol) in dry dioxane (100 mL) was added into a 250 mL round bottom flask. The mixture was stirred for 12 h at 110 C under the protection of argon. After being cooled to room temperature, it was filtered and the filtrate was concentrated on a rotary evaporator. The residue was subjected to column chromatography over silica gel (PE/EA 10:1) to give 5 (3.26 g, 36%) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 9.53(s, 1H), 7.56(d, J = 8.5 Hz, 2H), 7.47(d, J = 8.5 Hz, 2H), 1.48(s, 9H), 1.29(s, 12H).
With potassium acetate; In n-heptane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; b tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate A mixture of tert-butyl N-[(4-bromophenyl)carbamate (5.95 g, 0.0219 mol), diboron pinacol ester (6.67 g, 0.0263 mol), [1.1'-bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (1:1) (0.536 g, 0.00066 mol) and potassium acetate (6.47 g, 0.066 mol) in N,N-dimethylformamide (120 mL) was heated at 80 C. under an atmosphere of nitrogen for 16 hours. The mixture was allowed to cool to ambient temperature and the solvent removed under reduced pressure. Dichloromethane (100 mL) was added to the residue and the resulting solid was removed by filtration through a pad of Celite. The filtrate was concentrated to leave a yellow oil which was purified by flash chromatography on silica using ethyl acetate/n-heptane (7:93) as mobile phase. The resulting fractions were concentrated, the residue was triturated in n-heptane and the precipitate collected by filtration to yield tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (6.0 g, 0.0188 mol) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta 9.50(s, 1H), 7.55 (d, 2H), 7.46 (d, 2H), 1.47 (s, 9H), 1.27 (s, 12H).
With potassium acetate; In n-heptane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; b) tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate A mixture of tert-butyl N-[(4-bromophenyl)carbamate (5.95 g, 0.0219 mol), diboron pinacol ester (6.67 g, 0.0263 mol), [1.1'-bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (1:1) (0.536 g, 0.00066 mol) and potassium acetate (6.47 g, 0.066 mol) in N,N-dimethylformamide (120 mL) was heated at 80 C. under an atmosphere of nitrogen for 16 hours. The mixture was allowed to cool to ambient temperature and the solvent removed under reduced pressure. Dichloromethane (100 mL) was added to the residue and the resulting solid was removed by filtration through a pad of Celite. The filtrate was concentrated to leave a yellow oil which was purified by flash chromatography on silica using ethyl acetate/n-heptane (7:93) as mobile phase. The resulting fractions were concentrated, the residue was triturated in n-heptane and the precipitate collected by filtration to yield tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (6.0 g, 0.0188 mol) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta 9.50(s, 1H), 7.55 (d, 2H), 7.46 (d, 2H), 1.47 (s, 9H), 1.27 (s, 12H).
  • 2
  • [ 40000-20-2 ]
  • [ 330793-01-6 ]
  • [ 1334286-48-4 ]
  • 3
  • [ 78137-76-5 ]
  • [ 330793-01-6 ]
  • tert-butyl (4'-hydroxy-2'-nitro-[1,1'-biphenyl]-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 110℃; for 12h; General procedure: Palladium tetraphenylphosphine (115mg, 0.10mmol) and potassium carbonate solution (2M, 100muL) were added to a solution of 4-bromo-2-nitrophenol (150mg, 0.69mmol) and boronic ester (300mg, 0.82mmol) in dioxane (40mL) and the mixture was refluxed at 110°C for 12h. After 12h, the reaction mixture was concentrated to dryness and the residue so obtained was purified via column chromatography (SiO2, 100:1, CH2Cl2: acetone) to afford desired product as a yellow amorphous solid (136mg, 60percent).
72% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 110℃; for 12h;Reflux; tert-butyl (4'-hydroxy-2'-nitro-[1,1'-biphenyl]-4-yl)carbamate (32b): Palladium tetraphenylphosphine (0.10 mmol) and potassium carbonate solution (2M, 100 muL) were added to a solution of phenol (30b, 0.69 mmol) and boronic ester (0.82 mmol) in dioxane (10 mL) and the mixture was refluxed at 110 oC for 12 hours. After 12 hours, the reaction mixture was concentrated to dryness and the residue so obtained was purified via column chromatography (SiO2, 100:1, CH2Cl2:acetone) to afford desired product as a yellow amorphous solid (210 mg, 72percent). 1H NMR (500 MHz, chloroform-d) delta 7.40 (d, J = 8.3 Hz, 2H), 7.32 (d, J = 2.6 Hz, 1H), 7.28 (d, J = 5.0 Hz, 1H), 7.23? 7.17 (m, 2H), 7.07 (dd, J = 8.4, 2.6 Hz, 1H), 6.53 (s, 1H), 5.47 (s, 1H), 1.54 (s, 9H).13C NMR (126 MHz, CDCl3) delta 155.35, 153.00, 149.83, 138.39, 133.34, 132.05, 129.00, 128.64, 119.86, 118.99, 111.40, 81.16, 28.64. HRMS (ESI-) m/z [M-H+] calcd for C17H18N2O5 329.1137, found 329.1132
  • 4
  • [ 7597-22-0 ]
  • [ 330793-01-6 ]
  • [ 1197159-91-3 ]
  • 5
  • [ 25015-63-8 ]
  • [ 131818-17-2 ]
  • [ 330793-01-6 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 330793-01-6 ]

Organoborons

Chemical Structure| 1190423-36-9

A221252 [1190423-36-9]

tert-Butyl (tert-butoxycarbonyl)(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)carbamate

Similarity: 0.93

Chemical Structure| 470478-90-1

A319256 [470478-90-1]

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

Similarity: 0.92

Chemical Structure| 540752-87-2

A753614 [540752-87-2]

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

Similarity: 0.91

Chemical Structure| 262444-42-8

A190537 [262444-42-8]

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

Similarity: 0.86

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: 0.84

Aryls

Chemical Structure| 470478-90-1

A319256 [470478-90-1]

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

Similarity: 0.92

Chemical Structure| 540752-87-2

A753614 [540752-87-2]

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

Similarity: 0.91

Chemical Structure| 262444-42-8

A190537 [262444-42-8]

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

Similarity: 0.86

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: 0.84

Chemical Structure| 1912446-60-6

A243569 [1912446-60-6]

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

Similarity: 0.82

Amides

Chemical Structure| 1190423-36-9

A221252 [1190423-36-9]

tert-Butyl (tert-butoxycarbonyl)(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)carbamate

Similarity: 0.93

Chemical Structure| 470478-90-1

A319256 [470478-90-1]

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

Similarity: 0.92

Chemical Structure| 540752-87-2

A753614 [540752-87-2]

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

Similarity: 0.91

Chemical Structure| 262444-42-8

A190537 [262444-42-8]

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

Similarity: 0.86

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: 0.84

Amines

Chemical Structure| 1190423-36-9

A221252 [1190423-36-9]

tert-Butyl (tert-butoxycarbonyl)(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)carbamate

Similarity: 0.93

Chemical Structure| 262444-42-8

A190537 [262444-42-8]

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

Similarity: 0.86

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: 0.84

Chemical Structure| 380430-49-9

A298015 [380430-49-9]

(4-Boc-Aminophenyl)boronic acid

Similarity: 0.82

Chemical Structure| 380430-68-2

A118028 [380430-68-2]

(3-((tert-Butoxycarbonyl)amino)phenyl)boronic acid

Similarity: 0.81