14472-80-1|4-(4-Chlorophenyl)cyclohexanone| Ambeed

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Quality Control of [ 14472-80-1 ] Purity: 97% SDS Specification

COA

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Product Details of [ 14472-80-1 ]

CAS No. :	14472-80-1
Formula :	C₁₂H₁₃ClO
M.W :	208.68
SMILES Code :	O=C1CCC(C2=CC=C(Cl)C=C2)CC1
MDL No. :	MFCD11850091
InChI Key :	JNBOVWFOTNYTES-UHFFFAOYSA-N
Pubchem ID :	14617880

Safety of [ 14472-80-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 14472-80-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.42
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	58.54
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.07 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.39
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.93
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.57
Log P_o/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.	3.12
Log P_o/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	3.95
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.19

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.23
Solubility	0.123 mg/ml ; 0.000588 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.	-2.95
Solubility	0.234 mg/ml ; 0.00112 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	-4.34
Solubility	0.00943 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

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	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	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.49 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	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 [ 14472-80-1 ]

* 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 [ 14472-80-1 ]

[ 14472-80-1 ] Synthesis Path-Downstream 1~35

1
[ 101598-25-8 ]
[ 14472-80-1 ]

References: [1]Journal of Organic Chemistry,1962,vol. 27,p. 4603 - 4606.

2
[ 36716-71-9 ]
[ 14472-80-1 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 7629 - 7632.
[2]Journal of Medicinal Chemistry,1972,vol. 15,p. 1239 - 1243.

3
[ 14472-80-1 ]
[ 98322-65-7 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 7629 - 7632.

4
[ 126991-59-1 ]
[ 25253-51-4 ]
[ 14472-80-1 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 7629 - 7632.

Yield	Reaction Conditions	Operation in experiment
		Step 4 A solution of the ketal P (5.81 g, 23.06 mmol) in acetone (200 mL) was treated with p-toluenesulfonic acid monohydrate (876 mg) and heated at 60° C. overnight. Solvent was removed and the residue was taken up in EtOAc, washed with aqueous Na2CO3 solution, brine, dried and concentrated to give the crude product as a yellow oil (5.38 g, >100percent yield). Purification through flash chromatography (heaxane/EtOAc, 80/20-->60/40) provided 4-(4-chlorophenyl)cyclohexanone as a light yellow oil (4.54 g, 95percent yield). MS (EI) m/e 208 (M+), Calcd for C12H13C102, 208.

6
[ 25253-51-4 ]
[ 14472-80-1 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In water; acetone; at 70℃; for 3h;	4-(4-Chlorophenyl)-cyclohex-3-enone monoethylene ketal (291.0 g, 1.15 mol) was dissolved in ethyl acetate (2.3 L) at RT and transferred to a Parr autoclave reactor. Palladium on carbon (9.0 g, 3 wt %) was added to the reaction mass and flushed twice with nitrogen and once with hydrogen. Subsequently, a hydrogen pressure of 5-7 kg/cm2 was maintained for 7h at RT. Reaction was monitored on TLC; after completion of reaction, palladium on carbon was filtered through a Celite bed. The mother liquor was evaporated under reduced pressure to give crude product as light yellow semi solid of 4-(4-Chlorophenyl)-cyclohexanone monoethylene ketal (v).Crude 4-(4-Chlorophenyl)-cyclohexanone monoethylene ketal (v) was suspended in 50:50 acetone: water (1000 mL) at 25 C and ^-TSA (11.5 g, 5 mol %) was added to it. The reaction mass was heated to 70 C and stirred for 3h after which it was cooled to RT. Acetone was evaporated under reduced pressure and resultant slurry was added to sodium bicarbonate solution and stirred for 30 min at 5 C and filtered off to afford pure product as off-white solid (198.0 g, 88 % yield). Generally yield of the product ranges from 80 to 90 %. FTIR (neat): 2939, 1712, 1490, 1 164, 1091, 1013, 833 cm-1.1H NMR (CDC13, 200 MHz): delta 1.85 -1.93 (m, 2H), 2.18-2.22 (m, 2H), 2.49-2.59 (m, 4H) 2.98- 3.05 (m, 1H), 7.14-7.19 (m, 2H), 7.25-7.30 (m, 2H); 13C NMR (CHC13, 100 MHz): S 33.8, 41.3, 42.1, 128.0, 128.4, 132.2, 143.2, 210.7; DSC (10 C/min): Peak at 63.39 C

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2013,vol. 52,p. 1299 - 1312.
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4910 - 4914.
[3]Journal of the American Chemical Society,2012,vol. 134,p. 17023 - 17026,4.
[4]Journal of the American Chemical Society,2012,vol. 134,p. 20208 - 20208.
[5]Patent: WO2012/153162,2012,A1 .Location in patent: Page/Page column 38.
[6]Angewandte Chemie - International Edition,2015,vol. 54,p. 14748 - 14752.
Angew. Chem.,2015,vol. 127,p. 14961 - 14965,5.
[7]Angewandte Chemie - International Edition,2017,vol. 56,p. 2454 - 2458.
Angew. Chem.,2017,vol. 129,p. 2494 - 2498,5.

7
[ 14472-80-1 ]
[ 151-50-8 ]
ammonium bicarbonate [ No CAS ]
[ 868142-04-5 ]