52397-81-6|4,6-Dichloro-2,3-dihydro-1H-inden-1-one| Ambeed

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Quality Control of [ 52397-81-6 ] Purity: 97% SDS Specification

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Product Details of [ 52397-81-6 ]

CAS No. :	52397-81-6
Formula :	C₉H₆Cl₂O
M.W :	201.05
SMILES Code :	ClC1=CC(Cl)=C2CCC(=O)C2=C1
MDL No. :	MFCD08276785
InChI Key :	BIGNWTAXBIQGAZ-UHFFFAOYSA-N
Pubchem ID :	12206518

Safety of [ 52397-81-6 ]

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

Computational Chemistry of [ 52397-81-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	49.51
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.	2.11
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	2.92
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.12
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.	2.84
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	4.0
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.0

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.3
Solubility	0.102 mg/ml ; 0.000506 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.	-2.94
Solubility	0.231 mg/ml ; 0.00115 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	-4.35
Solubility	0.00892 mg/ml ; 0.0000444 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	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.	-5.45 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)	1.79

Application In Synthesis of [ 52397-81-6 ]

* 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 [ 52397-81-6 ]

[ 52397-81-6 ] Synthesis Path-Downstream 1~35

1
[ 52397-82-7 ]
[ 52397-81-6 ]

Yield	Reaction Conditions	Operation in experiment
55%	With aluminum (III) chloride; In dichloromethane; at 20℃; for 3.0h;Inert atmosphere; Reflux;	Oxalyl chloride (6.9 g, 55 mmol) was added dropwise at room temperature to a solution of 3-(2,4-dichlorophenyl)propanoic acid (7, 11 g, 50 mmol) in 20 ml of dichloromethane. The mixture was stirred for 2 h at room temperature, then the excess oxalyl chloride was removed in vacuo to give 3-(2,4-dichlorophenyl)propanoyl chloride, which was dissolved in 50 ml of dichloromethane. This solution was added dropwise at room temperature to amixture of aluminium chloride (7.3 g, 55 mmol) in 50 ml dichloromethane.Subsequently the reaction mixture was heated for 3 h to reflux, cooled to room temperature again and poured on ice-water. After separation of the phases, the organic layer was washed with saturated aqueous sodium bicarbonate solution and water, dried over sodium sulfate and concentrated under reduced pressure. The remainder was purified by chromatography on silica gel, using hexane /dichloromethane 1 : 1 as eluent system to deliver 4,6-dichloroindan-1-one (8, 5.4g, 27 mmol, 55 %). 1H-NMR (400 MHz, CDCl3): delta = 2.69 (t, 2H, J = 5.7 Hz),3.05 (t, 2H, J = 5.7 Hz), 7.63 (d, 1H, J = 2.0 Hz), 7.94 (d, 1H, J = 2.0 Hz). LC-MS:Rt = 1.02 min; MS: m/z = 201 [M+1]+.

References: [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 8812 - 8829.
[2]Synlett,2019,vol. 30,p. 59 - 62.
[3]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

2
[ 52397-81-6 ]
[ 141-78-6 ]
[ 166251-39-4 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

3
[ 52397-81-6 ]
[ 248607-96-7 ]
2-[3-(4,6-Dichloroindan-1-ylamino)prop-1-ylamino]-1H-quinolin-4-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 665 - 668.

4
[ 1201-99-6 ]
[ 52397-81-6 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

5
[ 55144-92-8 ]
[ 52397-81-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; thionyl chloride;aluminium chloride; In dichloromethane;	Example 15 4,6-Dichloroindan-1-one (Not According to the Invention) Thionyl chloride (36.9 g) was added dropwise at 40 C. to a solution of 3-(2,4-di-chlorophenyl)propionic acid (43.8 g) in methylene chloride (200 ml). After reaction was complete, excess thionyl chloride and the solvent were removed by distillation. The oily residue was added dropwise at 40 C. to a suspension of aluminium chloride (53.3 g) in methylene chloride (200 ml). The reaction mixture was added to dilute hydrochloric acid after 18 hours at 40 C. The aqueous phase was separated off and extracted once with methylene chloride (250 ml). The combined organic phases were freed from the solvent. The residue was recrystallized from cyclohexane. 30 g of a colorless solid (m.p.: 115-116 C.) were obtained.
	In PPA; hexane; water;	a 4,6-Dichloroindanone 3-(2,4-dichlorophenyl)propanoic acid (0.44 g, 2 mmol) in polyphosphoric acid (7 g) was heated to 100 C. under argon. After 90 min the mixture was cooled and treated with water (20 ml) and extracted with hexane (40 ml). The hexane layer was dried (MgSO4), and evaporated to dryness. The residue was purified by column chromatography on silica gel eluding with 0-30% dichloromethane in hexane to give the title product as a yellow solid, (0.018 g, 4.5%), deltaH (CDCl3) 2.8 (2H, m), 3.1 (2H, m), 7.6 (1H, d), 7.65 (1H, d).
12.2 g (55%)		3b) 4,6-dichloro-1-indanone was prepared in a similar manner to that described in Example 1c from 3-(2,4-dichlorophenyl) propanoic acid (24.3 g, 0.11 mol). Chromatography on silica gel with hexanes:dichloromethane (1:1) as eluent gave 12.2 g (55%) of 4,6-dichloro-1-indanone as a white solid.

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.
[2]Patent: US2002/115885,2002,A1 .
[3]Patent: US6320051,2001,B1 .
[4]Patent: US5708033,1998,A .
[5]Journal of Medicinal Chemistry,2016,vol. 59,p. 8812 - 8829.
[6]Synlett,2019,vol. 30,p. 59 - 62.

6
[ 52397-81-6 ]
[ 174603-39-5 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

7
[ 52397-81-6 ]
2-(4,6-dichloro-indan-1-ylidene)-<i>N</i>-methyl-acetamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

8
[ 52397-81-6 ]
(E)-2-(4,6-dichloro-1-indanylidene)acetamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

9
[ 52397-81-6 ]
[ 166251-41-8 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

10
[ 52397-81-6 ]
[ 166251-40-7 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

Yield	Reaction Conditions	Operation in experiment
		Recrystallization of 1.0 g from hexanes gave 0.7 g of 4,6-dichloro-1-indanone as a white solid: mp 118-120 C.

12
[ 52397-81-6 ]
[ 166251-39-4 ]

Yield	Reaction Conditions	Operation in experiment
10.6 g (65%)		3c) Ethyl 2-(4,6-Dichloro-1-hydroxy-1-indanyl)acetate was prepared in a similar manner to that described in Example 1d from <strong>[52397-81-6]4,6-dichloro-1-indanone</strong>. Chromatography on silica gel with hexanes:ethyl acetate (8:2) as eluent gave 10.6 g (65%) of a yellow oil; NMR (CDCl)3): delta7.22-7.27 (m, 2H), 4.28 (br, 1H), 4.21 (m, 2H), 3.03 (m, 1H), 2.75 (m,3H), 2.30 (m, 2H), 1.28 (t, 3H).

References: [1]Patent: US5708033,1998,A .

13
[ 52397-81-6 ]
[ 55144-55-3 ]

Yield	Reaction Conditions	Operation in experiment
79%	With bromine; In methanol; dichloromethane; at 0 - 20℃; for 16.0h;Inert atmosphere;	A solution of <strong>[52397-81-6]4,6-dichloroindan-1-one</strong> (8, 2.5 g, 12.5 mmol) in 20 ml of dichloromethane and 10 ml of methanol was cooled to 0 C. A solution of bromine(2.0 g, 12.5 mmol) in 5 ml of methanol was then added dropwise. The reaction mixture is slowly warmed to room temperature and stirred for 16 h. The colourless solution was evaporated under reduced pressure to deliver 2-bromo-<strong>[52397-81-6]4,6-dichloroindan-1-one</strong> (9, 2.7 g, 9.8 mmol, 79 %) which was pure enough to be used in the next step without any further purification. 1H-NMR (400 MHz,CDCl3): delta = 3.38 (dd, 1H, J = 3.4, 18.4 Hz), 3.80 (dd, 1H, J = 7.4, 18.4 Hz), 4.66(dd, 1H, J = 3.1, 7.4 Hz), 7.59 (s, 1H), 7.92 (s, 1H). LC-MS: Rt = 1.34 min; MS: m/z = 278 [M+1]+.

References: [1]Synlett,2019,vol. 30,p. 59 - 62.
[2]European Journal of Medicinal Chemistry,2009,vol. 44,p. 3771 - 3776.

14
[ 52397-81-6 ]
[ 1188143-94-3 ]

References: [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 8812 - 8829.
[2]Journal of the American Chemical Society,2009,vol. 131,p. 12886 - 12887.

15
[ 2033-24-1 ]
[ 52397-81-6 ]
[ 1194065-60-5 ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 8583 - 8594.

16
[ 52397-81-6 ]
[ 4637-24-5 ]
[ 320419-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 83℃; for 3.0h;	202 mg (1 mmol) of <strong>[52397-81-6]4,6-dichloroindan-1-one</strong> are dissolved in 2 ml of tetrahydrofuran, and 263 mg of dimethylformamide dimethyl acetal (2.2 mmol) are added. The solution is stirred at 83 C. for 3 hours and concentrated in vacuo. The residue is triturated with diethyl ether and filtered off with suction. 216 mg of yellow crystals of 4,6-dichloro-2-[1-dimethylaminomethylidene]indan-1-one are obtained.

References: [1]Patent: US2011/201590,2011,A1 .Location in patent: Page/Page column 262; 263.

17
[ 52397-81-6 ]
1-[rac-cis-(1,2)-4,6-dichloro-1-(4-methanesulfonylphenoxy)indan-2-ylmethyl]pyrrolidine [ No CAS ]
1-[rac-trans-(1,2)-4,6-dichloro-1-(4-methanesulfonylphenoxy)indan-2-ylmethyl]pyrrolidine [ No CAS ]

References: [1]Patent: US2011/201590,2011,A1 .

18
[ 52397-81-6 ]
[ 1215279-73-4 ]

References: [1]Patent: US2011/201590,2011,A1 .

19
[ 52397-81-6 ]
C₁₄H₁₅Cl₂NO [ No CAS ]

References: [1]Patent: US2011/201590,2011,A1 .

20
[ 52397-81-6 ]
[ 1215272-30-2 ]