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Chemical Structure| 64611-67-2 Chemical Structure| 64611-67-2

Structure of 64611-67-2

Chemical Structure| 64611-67-2

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Product Details of [ 64611-67-2 ]

CAS No. :64611-67-2
Formula : C8H7NO4
M.W : 181.15
SMILES Code : O=[N+](C1=CC=C(C(CO)=O)C=C1)[O-]
MDL No. :MFCD00599385
InChI Key :DRGHCHSDUDQWHJ-UHFFFAOYSA-N
Pubchem ID :317552

Safety of [ 64611-67-2 ]

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

Computational Chemistry of [ 64611-67-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 3
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 46.62
TPSA ?

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

83.12 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.9
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

0.88
Log Po/w (WLOGP)?

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

0.77
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.

0.57
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

-0.6
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.5

Water Solubility

Log S (ESOL):?

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

-1.66
Solubility 3.95 mg/ml ; 0.0218 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.21
Solubility 1.12 mg/ml ; 0.00617 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

-1.56
Solubility 5.04 mg/ml ; 0.0278 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

No
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

No
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.

-6.78 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

1.0
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

2.0 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)

1.47

Application In Synthesis of [ 64611-67-2 ]

* 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 [ 64611-67-2 ]

[ 64611-67-2 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 99-81-0 ]
  • [ 64611-67-2 ]
YieldReaction ConditionsOperation in experiment
54% With silver nitrate; In water; acetone; for 4h;Reflux; 6.15 mmol of alpha-brome-4-nitroacetophenone was dissolved in 7mL of chloroform and treated with a solution of 6.15 mmol of hexamethylenetetramine in 6 mL of chloroform. After 24 h at room temperature, the reaction was cooled with ice bath and the formed precipitated washed with 15 mL of chloroform and 10 mL of ethanol, rendering the hexamethylenetetramine salt. The desired amine was obtained treating the salt with a solution of 1:2 of concentrated hydrochloric acid and ethanol (Yield: 84%). The reaction was maintained for 72 h at room temperature; the precipitated was filtered out and washed with water and then ethanol, rendering hydrochloric salt of alpha-amine-p-nitroacetophenone (Yield: 80%).
50% With water; silver nitrate; In acetone; for 4h;Heating / reflux; A mixture of 2-bromo-1-(4-nitrophenyl)ethanone (5 g, 20.5 mmol) and silver nitrate (5 g, 29.4 mmol) in water (250 mL) and acetone (150 mL) was heated to reflux for 4 hours then cooled to room temperature. The suspension was filtered and the filtrate was extracted twice with dichloromethane. The combined extracts were dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 2:1 hexanes/ethyl acetate to provide 3.7 g (50%) of the desired product. Rf=0.4 (1:1 hexanes/ethyl acetate)
3.7 g (50%) With silver nitrate; In water; acetone; EXAMPLE 13A 2-Hydroxy-1 -(4-nitrophenyl)ethanone A mixture of 2-bromo-1-(4-nitrophenyl)ethanone (5 g, 20.5 mmol) and silver nitrate (5 g, 29.4 mmol) in water (250 mL) and acetone (150 mL) was heated to reflux for 4 hours then cooled to room temperature. The suspension was filtered and the filtrate was extracted twice with dichloromethane. The combined extracts were dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 2:1 hexanes/ethyl acetate to provide 3.7 g (50%) of the desired product. Rf=0.4 (1:1 hexanes/ethyl acetate).
  • 2
  • 2-Fluoro-2-(4-nitro-phenyl)-oxirane [ No CAS ]
  • [ 64611-67-2 ]
  • 5
  • Trifluoro-acetic acid 2-(4-nitro-phenyl)-2-oxo-ethyl ester [ No CAS ]
  • [ 64611-67-2 ]
  • 6
  • Ethyl-methyl-[1-(4-nitro-phenyl)-vinyloxy]-silane [ No CAS ]
  • [ 64611-67-2 ]
  • 8
  • [ 100-19-6 ]
  • [ 64611-67-2 ]
  • [ 62-23-7 ]
  • 9
  • [ 110944-98-4 ]
  • [ 2712-78-9 ]
  • [ 64611-67-2 ]
  • Trifluoro-acetic acid 2-(4-nitro-phenyl)-2-oxo-ethyl ester [ No CAS ]
  • 16
  • [ 64611-67-2 ]
  • [ 27126-76-7 ]
  • [ 56177-37-8 ]
  • 17
  • [ 64611-67-2 ]
  • [ 1005-02-3 ]
  • [ 16280-67-4 ]
  • 18
  • [ 64611-67-2 ]
  • [ 357952-87-5 ]
  • 19
  • [ 64611-67-2 ]
  • [ 502934-29-4 ]
  • 20
  • [ 64611-67-2 ]
  • [ 287944-34-7 ]
  • 21
  • [ 64611-67-2 ]
  • [ 287944-27-8 ]
  • 22
  • [ 64611-67-2 ]
  • (S)-(+)-N-(4-(2,2-dimethyl-1,3-dioxolan-4-yl)phenyl)methanesulfonamide [ No CAS ]
  • 24
  • [ 110944-98-4 ]
  • [ 64611-67-2 ]
  • 25
  • [ 64611-67-2 ]
  • [ 109-77-3 ]
  • [ 606099-85-8 ]
YieldReaction ConditionsOperation in experiment
80% With diethylamine; In methanol; at 20℃; for 1h; A mixture of Example 13A (5 g, 27.6 mmol) and malononitrile (2.74 g, 41.4 mmol) in methanol (8.6 mL) at room temperature was treated with diethylamine (1.43 mL, 13.8 mmol), stirred for 1 hour, and poured into water. The resulting suspension was filtered and the filter cake was washed with water then purified by flash column chromatography on silica gel with 1:1 ethyl acetate/hexanes to provide 5 g (80%) of the desired product. MS (DCI) m/e 247 (M+NH4)+
  • 26
  • [ 64611-67-2 ]
  • [ 109-89-7 ]
  • [ 109-77-3 ]
  • [ 606099-85-8 ]
YieldReaction ConditionsOperation in experiment
5 g (80%) In methanol; ethyl acetate; EXAMPLE 13B 2-Amino-4-(4-nitrophenyl)-3-furonitrile A mixture of Example 13A (5 g, 27.6 mmol) and malononitrile (2.74 g, 41.4 mmol) in methanol (8.6 mL) at room temperature was treated with diethylamine (1.43 mL, 13.8 mmol), stirred for 1 hour, and poured into water. The resulting suspension was filtered and the filter cake was washed with water then purified by flash column chromatography on silica gel with 1:1 ethyl acetate/hexanes to provide 5 g (80%) of the desired product. MS (DCI) m/e 247 (M+NH4)+.
  • 27
  • [ 64611-67-2 ]
  • [ 62-55-5 ]
  • [ 33102-81-7 ]
  • 28
  • [ 64611-67-2 ]
  • [ 2227-79-4 ]
  • [ 2521-25-7 ]
  • 29
  • PEG 4000-sulfonyl chloride [ No CAS ]
  • [ 64611-67-2 ]
  • C8H6NO6PolS [ No CAS ]
  • 30
  • [ 64611-67-2 ]
  • [ 56506-90-2 ]
  • [ 1226790-03-9 ]
  • 31
  • [ 64611-67-2 ]
  • [ 1244056-14-1 ]
  • 32
  • [ 64611-67-2 ]
  • [ 18162-48-6 ]
  • [ 1229704-08-8 ]
  • 33
  • [ 64611-67-2 ]
  • [ 18162-48-6 ]
  • 2-(tert-butyldimethylsilyloxy)-1-(4-nitrophenyl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 3h; To a solution of <strong>[64611-67-2]2-hydroxy-1-(4-nitrophenyl)ethanone</strong> (1 g, 5.52 mmol) in DMF (25 ml) was added imidazole (564 mg, 8.28 mmol), followed by the addition of tert-butylchlorodimethylsilane (915 mg, 6.07 mmol). The reaction mixture was stirred at room temperature for 3 h. The mixture was poured into H2O (25 mL) and extracted with ethyl acetate (3*25 mL). The organic layers were combined, washed with H2O (5*25 mL), brine (1*25 mL), dried over MgSO4 and concentrated in vacuo to give 2-(tert-butyldimethylsilyloxy)-1-(4-nitrophenyl)ethanone as a yellow solid (1.6 g, 98%).
  • 34
  • [ 64611-67-2 ]
  • [ 95-54-5 ]
  • [ 5541-64-0 ]
YieldReaction ConditionsOperation in experiment
71% With gallium(III) perchlorate; In ethanol; at 25℃; General procedure: Representative experimental procedure for the synthesis of 2-phenylquinoxaline (3a) (Table 2, entry 1): A mixture of o-phenylenediamine (1a, 0.0541 g, 0.5 mmol), 2-hydroxyaceto-phenone (2a, 0.0681 g, 0.5 mmol) and Ga(ClO4)3 (0.018g, 0.05 mmol) in EtOH (3 mL) was stirred at room temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was directly purified by silica gel column chromatography (petroleum ether/ethyl acetate, 10:1) to afford the product 3a. The structures of all products were confirmed by IR, 1H NMR spectroscopy and melting points, which were consistent with literature data.
 

Historical Records

Technical Information

• Appel Reaction • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Fischer Indole Synthesis • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Jones Oxidation • Lawesson's Reagent • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

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[ 64611-67-2 ]

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