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Structure of 529-23-7

Chemical Structure| 529-23-7

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Product Details of [ 529-23-7 ]

CAS No. :529-23-7
Formula : C7H7NO
M.W : 121.13
SMILES Code : NC1=C(C=O)C=CC=C1
MDL No. :MFCD00007709
InChI Key :FXWFZIRWWNPPOV-UHFFFAOYSA-N
Pubchem ID :68255

Safety of [ 529-23-7 ]

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

Computational Chemistry of [ 529-23-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 36.23
TPSA ?

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

43.09 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.98
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

1.57
Log Po/w (WLOGP)?

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

1.09
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.

0.79
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

1.28
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.14

Water Solubility

Log S (ESOL):?

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

-2.01
Solubility 1.19 mg/ml ; 0.00983 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.

-2.09
Solubility 0.995 mg/ml ; 0.00822 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

-1.94
Solubility 1.39 mg/ml ; 0.0115 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

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

Yes
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.

-5.92 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)

1.0

Application In Synthesis of [ 529-23-7 ]

* 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 [ 529-23-7 ]

[ 529-23-7 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 110-89-4 ]
  • [ 64-17-5 ]
  • [ 529-23-7 ]
  • [ 123-54-6 ]
  • [ 14208-35-6 ]
  • 2
  • [ 14208-35-6 ]
  • [ 529-23-7 ]
  • 3-(2-amino-phenyl)-1-(2-methyl-[3]quinolyl)-propenone [ No CAS ]
  • 3
  • [ 529-23-7 ]
  • [ 123-54-6 ]
  • [ 14208-35-6 ]
YieldReaction ConditionsOperation in experiment
95% With Nafion NR50; In ethanol; at 200℃; for 1.0h;Microwave irradiation; General procedure: A mixture of 2-aminobenzophenone 2 (1.0 mmol), ketone 3 or 4 (1.1 mmol), and Nafion NR50 (20 mol%) in ethanol (10 mL) was loaded into a dried 35 mL microwave vial at 25 C. The mixture was subjected to microwave irradiation and stirred at 200 C for 1 h. Consumption of the starting materials was confirmed by TLC. The mixture was cooled to 25 C and then transferred to a 100 mL round-bottom flask; the solvent was concentrated under reduced pressure to afford crude product. The solid crude product was recrystallized (hexane-EtOAc, 5:1 to 2:1). The oily or gummy crude product was purified by column chromatography (silica gel, hexanes-EtOAc, 4:1 to 1:1). This afforded products 1a-ac, 5a-k, and 6a-p.
64% With magnesium(II) chloride hexahydrate; In ethanol; at 80℃; for 12.0h;Schlenk technique; General procedure: A mixture of 2-aminoaryl ketones 1 (0.50 mmol), β-ketoesters/ketones 2 (1.0 mmol), and magnesium chloride (MgCl2 · 6H2O, 20.3 mg, 0.10 mmol) in EtOH (3 mL) was added into a Schlenk flask (25 mL) and the mixture was stirred at 80 C until the reaction was finished. Then the solvent was evaporated under reduced pressure and the residue was purified by column chromatography.
51% In water; for 5.0h;Reflux; To compound 6-1 (1.0 g, 8.25 mmol) dissolved in water (20 mL) was added acetylacetone (826 mg, 8.25 mmol) and reacted at reflux for 5 h. When the completion of the reaction was monitored by LC-MS, the reaction solution was poured into ice water, then extracted with ethyl acetate. The organic phases were combined, washed once with saturated aqueous salt solution, dried with sodium sulfate, filtered and concentrated, and purified by column chromatography to obtain the target product 6-2 (780 mg) with a yield of 51%.
  • 4
  • [ 696-59-3 ]
  • [ 529-23-7 ]
  • [ 26709-65-9 ]
  • [ 31739-56-7 ]
  • 5
  • [ 529-23-7 ]
  • [ 10234-66-9 ]
  • [ 89522-17-8 ]
  • 6
  • [ 7732-18-5 ]
  • [ 529-23-7 ]
  • furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
  • [ 123-54-6 ]
  • [ 14208-35-6 ]
  • 7
  • [ 815-68-9 ]
  • [ 529-23-7 ]
  • [ 14208-35-6 ]
  • 9
  • [ 529-23-7 ]
  • [ 150374-99-5 ]
  • 4-(N-(2-formylphenyl)sulfamoyl)phenyl pivalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 20℃; for 4h; General procedure: Initially, phenol (10 mmol) was dissolved in acetonitrile. Themixture solution was slowly added 3,3-dimethylbutyryl chloride(1.5 equiv) at 0 C, and then stirred at room temperature for 12 h.The solvent was evaporated at reduced pressure. The residue waspurified by silica gel column chromatography using a mixture ofn-hexane and acetone to afford the phenyl pivalate. Subsequently,phenyl pivalate was dissolved in acetonitrile. The mixture solutionwas slowly added chlorosulfonic acid (1.5 equiv) at 0 C andreacted at 0 C for 15 min, and then refluxed at 75 C for 2 h. Thesolutions were quenched by ice; the resulting mixtures were filtrated;and the residues was purified by silica gel column chromatographyusing a mixture of n-hexane/ethyl acetate to afford<strong>[150374-99-5]4-(chlorosulfonyl)phenyl pivalate</strong> (Scheme 1). To a mixture solutionof 2-aminoacetophenone, 1-(2-aminophenyl)propan-1-one,1-(2-aminophenyl)butan-1-one, 1-(2-aminophenyl)pentan-1-one,or 2-aminobenzaldehyde (each 1.0 equiv) in pyridine, respectively,was added <strong>[150374-99-5]4-(chlorosulfonyl)phenyl pivalate</strong>, and then stirred atroom temperature for 4 h. The reaction mixture was concentratedand purified by silica gel column chromatography using a mixtureof n-hexane/acetone solutions, to afford the products (Scheme 2,1-5).
  • 10
  • [ 326-62-5 ]
  • [ 529-23-7 ]
  • 3-(2-fluorophenyl)quinolin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% General procedure: General Procedure for the Synthesis of ArylquinsTo a solution of 2.38 mmol (1.3 equiv) of the appropriate benzyl cyanide in 3 mL of anhydrous DMF at 0C was added 2.38 mmol (1.3 equiv) of potassium tert-butoxide. The mixture was stirred for 15 min, and 1.83 mmol of appropriate 2-aminobenzaldehyde dissolved in 1 mL of anhydrous DMF was added dropwise at 0C. The mixture was warmed to 25C and stirred for 3-4 h at 90C. After cooling the mixture was quenched by pouring into water to afford a precipitate that was collected and purified by recrystallization and/or chromatography as noted for individual compounds described below.3-(2-Fluorophenyl)quinolin-2-amine (Arylquin 8). Purified by chromatography on silica gel using 1:10 methanol-dichloromethane (Rf=0.55): Yield 79%, mp 152-153C.1H NMR (DMSO-d6 [M+H+] -7.44 (m, 4H), 7.37-7.32 (m, 2H), 7.22-7.18 (m, 1H), 6.03 (s, 2H, NH2). 13C NMR (DMSO-d6 G - +] 155.85, 147.59, 137.86, 131.77 (d, J=3.3Hz), 130.36 (d, J=8.0Hz), 129.52, 127.65, 124.95, 124.90, 124.77 (d, J=16.1Hz), 122.80, 121.59, 118.76, 116.11 (d, J=22.2Hz). HRMS (ESI) calcd for C15H12FN2 [MH+]: 239.09790. Found: 239.09831. Anal. Calcd for C15H11FN2: C, 75.62; H, 4.65. Found: C, 72.39; H, 4.71.
  • 11
  • [ 529-23-7 ]
  • [ 922-67-8 ]
  • [ 53951-84-1 ]
  • 13
  • [ 1006-67-3 ]
  • [ 529-23-7 ]
  • [ 73013-67-9 ]
YieldReaction ConditionsOperation in experiment
33% With [RuCl2pentamethylcyclopentadiene]n; silver trifluoroacetate; trifluoroacetic acid; In 2,2,2-trifluoroethanol; at 80℃; for 8h; The preparation method of compound I-25,Including the following process: 0.2mmol of 2-aminobenzaldehyde,<strong>[1006-67-3]5-phenylisoxazole</strong> 0.3mmol,Dichloro (pentamethylcyclopentadienyl) ruthenium () 0.005mmol,Silver trifluoroacetate 0.02mmol,Add 0.2mmol trifluoroacetic acid to the reaction tube,Dissolved in an appropriate amount of trifluoroethanol solvent,React at 80 for 8 hours,The reaction solution was filtered through diatomaceous earth, and the filtrate was concentrated,Purification by column chromatography gave 15.0 mg of the target product with a yield of 33%.
33% With bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)]; silver trifluoroacetate; trifluoroacetic acid; In 2,2,2-trifluoroethanol; at 80℃; for 10h; General procedure: A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with 2-aminobenzaldehyde 1a (0.1 mmol), isoxazole 2a (0.12 mmol), [Cp*RuCl2]2 (2.5 mol %), CF3COOAg (10 mol %), CF3COOH (1 equiv.) in anhydrous CF3CH2OH (1.5 mL). The reaction mixture was stirred at 80 for 10 h under air atmosphere. When the reaction was completed, the mixture was cooled to room temperature and then purified by column chromatography on silica gel with ethyl acetate/petroleum ether (1:5) to give the desired product 3a.
 

Historical Records

Technical Information

• Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Vilsmeier Reagent • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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