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Chemical Structure| 6342-63-8 Chemical Structure| 6342-63-8

Structure of 6342-63-8

Chemical Structure| 6342-63-8

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Product Details of [ 6342-63-8 ]

CAS No. :6342-63-8
Formula : C9H9BrO2
M.W : 229.07
SMILES Code : COC1=CC(C(C)=O)=C(Br)C=C1
MDL No. :MFCD02683853
InChI Key :YOUSWNMOPSGTSG-UHFFFAOYSA-N
Pubchem ID :240433

Safety of [ 6342-63-8 ]

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

Computational Chemistry of [ 6342-63-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 50.83
TPSA ?

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

26.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.18
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

2.58
Log Po/w (WLOGP)?

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

2.66
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.

2.16
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

2.84
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.48

Water Solubility

Log S (ESOL):?

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

-3.12
Solubility 0.172 mg/ml ; 0.000752 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.

-2.78
Solubility 0.379 mg/ml ; 0.00166 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

-3.72
Solubility 0.0436 mg/ml ; 0.000191 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.

-5.87 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

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)

1.55

Application In Synthesis of [ 6342-63-8 ]

* 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 [ 6342-63-8 ]

[ 6342-63-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1025707-93-0 ]
  • [ 6342-63-8 ]
  • C14H16O3 [ No CAS ]
  • 2
  • [ 1025707-93-0 ]
  • [ 6342-63-8 ]
  • [ 1537903-29-9 ]
  • 3
  • [ 6342-63-8 ]
  • [ 5460-32-2 ]
  • [ 1616489-48-5 ]
YieldReaction ConditionsOperation in experiment
75% With potassium tert-butylate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 80℃; for 2h;Schlenk technique; Inert atmosphere; General procedure: In an oven dried Schlenk tube under nitrogen atmosphere, were added aryliodides 2a-2f (0.50 mmol), ortho-bromoacetophenone 1a-1c (0.55mmol), Pd(OAc)2 (2 mol%), xantphos (4 mol%) and tBuOK (0.65 mmol) followed by addition of dry toluene (4 mL). The resulted reaction mixture was stirred at 80 C for 45 min to 3 h. Progress of the reaction was monitored by TLC till the reaction is completed. The reaction mixture was then quenched with saturated aqueous NH4Cl and the aqueous layer was extracted with ethyl acetate (3 20 mL). The combined organic layers were dried (Na2SO4) and concentrated under in vacuo. The crude product 3ac-3cf was purified by column chromatography on silica gel using petroleum ether/ethyl acetate as eluent.
  • 4
  • [ 1036378-83-2 ]
  • [ 6342-63-8 ]
  • C27H22O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 60℃;Inert atmosphere; To a 2L reaction flask in a nitrogen atmosphere was added 1- (2-bromo-5-methoxyphenyl) ethanone, 68 g (190.86 mmol) of the compound [6-1] and 410 ml of 1,4-dioxane are introduced and the temperature is raised.4.24 g (3.64 mmol) of tetrakis (triphenylphosphine) palladium (0) and 75.4 g (545.33 mmol) of potassium carbonate dissolved in distilled water were added at 60 C and stirred overnight under reflux.When the reaction was completed, the reaction mixture was cooled to room temperature, and ethyl acetate,Extracted with distilled water, and the organic layer is treated with anhydrous magnesium sulfate and filtered.The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography,64.7 g (94%) of an intermediate compound [6-2] in a clear oil state was prepared.
64.3 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 60℃; for 15h;Reflux; 40 g (174.59 mmol) of 1- (2-bromo-5-methoxyphenyl) ethanone and 65.3 g (183.32 mmol) of the compound [41-1] were placed in a 2 L reaction flask, 400 ml of 1,4-dioxane is added and the temperature is raised. 4.03 g (3.4918 mmol) of tetrakis (triphenylphosphine) palladium (0) was added at 60 C, 72.39 g (523.77 mmol) of potassium carbonate dissolved in distilled water was added, and the mixture was refluxed and stirred for 15 hours.When the reaction is completed, the reaction mixture is cooled to room temperature, extracted with ethyl acetate / distilled water, and treated with anhydrous magnesium sulfate. The reaction mixture is distilled under reduced pressure. The crude product was separated and purified by silica gel chromatography to obtain 64.3 g (97 wt%) of an intermediate compound [41-2] in a clear oil state
 

Historical Records

Technical Information

• Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Nomenclature of Ethers • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Ethers • 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 Dihalides • Reactions of Ethers • 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 • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

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