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Chemical Structure| 106263-50-7 Chemical Structure| 106263-50-7

Structure of 106263-50-7

Chemical Structure| 106263-50-7

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Product Details of [ 106263-50-7 ]

CAS No. :106263-50-7
Formula : C10H9ClO3
M.W : 212.63
SMILES Code : OC(=O)CCC(=O)C1=C(Cl)C=CC=C1
MDL No. :MFCD03844205
Boiling Point : No data available
InChI Key :JIFTXSSZTRPMNW-UHFFFAOYSA-N
Pubchem ID :20274428

Safety of [ 106263-50-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 106263-50-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.2
Num. rotatable bonds 4
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 53.03
TPSA ?

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

54.37 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.53
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

1.52
Log Po/w (WLOGP)?

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

2.39
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.

1.88
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

2.44
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.

-2.17
Solubility 1.44 mg/ml ; 0.00678 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.

-2.27
Solubility 1.14 mg/ml ; 0.00537 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

-3.15
Solubility 0.15 mg/ml ; 0.000705 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.

-6.52 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.

0.56

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

0.0 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)

1.51

Application In Synthesis of [ 106263-50-7 ]

* 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 [ 106263-50-7 ]

[ 106263-50-7 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 108-30-5 ]
  • [ 106-46-7 ]
  • [ 106263-50-7 ]
  • 2
  • [ 108-30-5 ]
  • [ 108-90-7 ]
  • [ 106263-50-7 ]
  • 3
  • [ 106263-50-7 ]
  • [ 3034-19-3 ]
  • γ-(2-nitrophenylhydrazono)-2-chlorophenylbutanoic acid [ No CAS ]
  • 4
  • 4-<2-chloro-phenyl>-4-oxo-butyric acid methyl ester(?) [ No CAS ]
  • [ 106263-50-7 ]
  • 5
  • [ 106263-50-7 ]
  • [ 106263-49-4 ]
  • 6
  • [ 106263-50-7 ]
  • [ 106263-38-1 ]
  • 7
  • [ 106263-50-7 ]
  • [ 106263-52-9 ]
  • 8
  • [ 106263-50-7 ]
  • [ 67-63-0 ]
  • isopropyl 4-chlorophenyl-4-oxobutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With sulfuric acid; for 144.0h;Reflux; 50 g (235 mmol) of <strong>[106263-50-7]4-chlorophenyl-4-oxobutanoic acid</strong> were solubilized in 300 ml of isopropanol, 0.63 ml (11.76 mmol) of sulfuric acid were added to this solution. The mixture was refluxed with heating for 6 d with magnetic stirring. After returning to r.t., the mixture was concentrated in vacuo, the crude residue was directly purified by flash chromatography on a silica gel cartridge (eluent: 100% dichloromethane). 59.83 g (yield=>99%) of isopropyl 4-chlorophenyl-4-oxobutanoate were obtained as a colorless oil. LC-MS: m/z=255 (MH+) UV purity at 254 nm=95%. 1H NMR (300 MHz, DMSO) δ 8.13-7.85 (m, 2H), 7.70-7.47 (m, 2H), 4.86 (dt, J=12.5, 6.3 Hz, 1H), 3.29-3.22 (m, 2H), 2.65-2.54 (m, 2H), 1.16 (d, J=6.3 Hz, 6H).
  • 9
  • [ 106263-50-7 ]
  • (+)-5-(2-chlorophenyl)dihydrofuran-2(3H)-one [ No CAS ]
  • 10
  • [ 106263-50-7 ]
  • C10H11ClO3 [ No CAS ]
  • 11
  • [ 108-30-5 ]
  • [ 694-80-4 ]
  • [ 106263-50-7 ]
YieldReaction ConditionsOperation in experiment
56% With bromobenzene; magnesium; In tetrahydrofuran; at -40 - 0℃; for 1.5h; General procedure: At -40 C, glutaric anhydride (B) (60mmol) / anhydrous THF (125mL)Slowly add 2chlorophenylmagnesium bromide (A ') / THF (50mL) to the solutionMagnesium filings (55 mmol) and bromobenzene (45 mmol) were generated in situ in the solution. after finishing,At the same temperature, the reaction mixture was continuously stirred for 1.5 hours,It was then cooled with 1N hydrochloric acid (250 mL). The mixture was extracted with ethyl acetate (250 mL3), and the extract was dried over anhydrous MgSO4,Concentrated in vacuo to give crude 5- (2-chlorophenyl) -5-oxovaleric acid (1'a),It was recrystallized from petroleum ether and ethyl acetate with a yield of 32%.
 

Historical Records

Technical Information

• Alkyl Halide Occurrence • Arndt-Eistert Homologation • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hunsdiecker-Borodin Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Preparation of Carboxylic Acids • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

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