[ CAS No. 24623-25-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 24623-25-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 24623-25-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 24623-25-4 ]

SDS Specification

Alternatived Products of [ 24623-25-4 ]

Product Details of [ 24623-25-4 ]

CAS No. :	24623-25-4	MDL No. :	MFCD06656901
Formula :	C₉H₇NO₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	QIIWEVWPOBNGLP-UHFFFAOYSA-N
M.W :	177.16	Pubchem ID :	90563
Synonyms :

Calculated chemistry of [ 24623-25-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.31
TPSA :	62.89 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.28
Log Po/w (XLOGP3) :	1.49
Log Po/w (WLOGP) :	1.72
Log Po/w (MLOGP) :	0.52
Log Po/w (SILICOS-IT) :	0.54
Consensus Log Po/w :	1.11

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.15
Solubility :	1.25 mg/ml ; 0.00704 mol/l
Class :	Soluble
Log S (Ali) :	-2.42
Solubility :	0.677 mg/ml ; 0.00382 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.5
Solubility :	0.567 mg/ml ; 0.0032 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.04

Safety of [ 24623-25-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 24623-25-4 ]

* 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.

Upstream synthesis route of [ 24623-25-4 ]
Downstream synthetic route of [ 24623-25-4 ]

[ 24623-25-4 ] Synthesis Path-Upstream 1~2

1
[ 24623-25-4 ]
[ 24623-24-3 ]
[ 51135-91-2 ]
[ 69975-65-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With ammonium chloride In ethanol at 90℃; for 1 h;	EXAMPLE 129B 6-amino-1-indanone [0367] A solution of Example 129A (19.68 g, 111 mmol) in ethanol (111 mL) was treated sequentially with iron powder (43.0 g, 770 mmol) and solid ammonium chloride (3.70 g, 69.2 mmol). The resulting suspension was stirred at 90° C. for 1 hour, cooled to room temperature, diluted with brine, and extracted with diethyl ether (4.x.100 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to provide the desired product as a 6:1 mixture of 6-amino- and 4-amino-1-indanone (14.20 g, 87percent). 1H NMR (300 MHz, DMSO-d6, 6-amino-1-indanone) δ 7.21 (d, 1H), 6.92 (dd, 1H), 6.75 (d, 1H), 5.27 (br s, 2H), 2.90 (t, 2H), 2.54 (m, 2H); 1H NMR (300 MHz, DMSO-d6), 4-amino-1-indanone) δ 7.10 (t, 1H), 6.81 (m, 2H), 2.80 (m, 2H), 2.59 (m, 2H).

Reference： [1] Patent: US2004/167128, 2004, A1, . Location in patent: Page 39

2
[ 24623-25-4 ]
[ 51135-91-2 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1958, vol. 23, p. 1902,1907
[2] Collection of Czechoslovak Chemical Communications, 1958, vol. 23, p. 1902,1907
[3] Journal fuer Praktische Chemie (Leipzig), 1934, vol. <2> 139, p. 94
[4] Patent: US3988460, 1976, A,
[5] Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 9, p. 1090 - 1093

[ 24623-25-4 ] Synthesis Path-Downstream 1~4

1
[ 24623-25-4 ]
[ 51135-91-2 ]

Yield	Reaction Conditions	Operation in experiment
	aluminum nickel; In 1,4-dioxane; methanol;	27.5 g 4-nitroindan-1-one were dissolved in 410 ml dioxan and 252 ml methanol and hydrogenated with hydrogen in the presence of Raney nickel at 50 C to give 4-amino-indan-1-one.
	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 6h;	To a solution of compound 2 (4-nitro-2,3-dihydro-1H-inden-1-one, 0.50g, 1 equiv) and Pd/C (10%wt, 100 mg, 20%) in methanol (10ml) was degased with H2, and the solution was stirred for 6 hours at rt. Then, Pd/C was filtrated off and the solution was concentrated in vacuo to get target product (3).

Reference： [1]Collection of Czechoslovak Chemical Communications,1958,vol. 23,p. 1902,1907
[2]Collection of Czechoslovak Chemical Communications,1958,vol. 23,p. 1902,1907
[3]Journal fur praktische Chemie (Leipzig 1954),1934,vol. <2> 139,p. 94
[4]Patent: US3988460,1976,A
[5]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 1090 - 1093
[6]Cell Chemical Biology,2019,vol. 26,p. 1027 - 22,1035

2
[ 2001-32-3 ]
[ 24623-25-4 ]

Reference： [1]Helvetica Chimica Acta,1961,vol. 44,p. 1736 - 1747
[2]Patent: WO2005/40100,2005,A1

3
[ 24623-25-4 ]
[ 24623-24-3 ]
[ 51135-91-2 ]
[ 69975-65-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With ammonium chloride;iron; In ethanol; at 90℃; for 1h;	EXAMPLE 129B 6-amino-1-indanone [0367] A solution of Example 129A (19.68 g, 111 mmol) in ethanol (111 mL) was treated sequentially with iron powder (43.0 g, 770 mmol) and solid ammonium chloride (3.70 g, 69.2 mmol). The resulting suspension was stirred at 90 C. for 1 hour, cooled to room temperature, diluted with brine, and extracted with diethyl ether (4×100 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to provide the desired product as a 6:1 mixture of 6-amino- and 4-amino-1-indanone (14.20 g, 87%). 1H NMR (300 MHz, DMSO-d6, 6-amino-1-indanone) delta 7.21 (d, 1H), 6.92 (dd, 1H), 6.75 (d, 1H), 5.27 (br s, 2H), 2.90 (t, 2H), 2.54 (m, 2H); 1H NMR (300 MHz, DMSO-d6), 4-amino-1-indanone) delta 7.10 (t, 1H), 6.81 (m, 2H), 2.80 (m, 2H), 2.59 (m, 2H).

Reference： [1]Patent: US2004/167128,2004,A1 .Location in patent: Page 39

4
[ 2001-32-3 ]
[ 7440-44-0 ]
[ 24623-25-4 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;aluminium trichloride; In carbon disulfide; ice-water; dichloromethane;	C. Preparation of 4-nitro-1-indanone (Compound C, Schema 1) A stirred solution of 74.2 g (0.38 mole) of <strong>[2001-32-3]3-(2-nitrophenyl)propionic acid</strong> and 53.6 g (0.45 mole) of thionyl chloride in 250 mL of methylene chloride was heated under reflux for 16 hours. The reaction mixture was concentrated under reduced pressure to give a residue, which was dissolved in 100 mL of methylene chloride. The solution was concentrated under reduced pressure, and the residue was subjected to high vacuum to give 3-(2-nitrophenyl)propionyl chloride as an oil. A stirred mixture of 64.1 g (0.48 mole) of aluminum chloride and 300 mL of carbon disulfide was cooled to 5 C., and a solution of the nitrophenylpropionyl chloride from above in 100 mL of carbon disulfide was added dropwise. During the addition the temperature of the reaction mixture was maintained at 5-10 C. Upon complete addition, the reaction mixture was stirred at 5 C. for 0.25 hours, at ambient temperature for 0.5 hour, then under reflux for 3.5 hours, and finally at ambient temperature for 16 hours. The reaction mixture was poured into 100 mL of ice-water, and the mixture was stirred for one hour and extracted with four portions of 400 mL each of diethyl ether. The combined ether extracts were dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a solid residue. The residue was crystallized from ethanol after treatment with decolorizing carbon to give, in two fractions, 39.8 g of 4-nitro-1-indanone, m.p. 94-97 C.
	With thionyl chloride;aluminium trichloride; In carbon disulfide; ice-water; dichloromethane;	C. Preparation of 4-nitro-1-indanone (Compound C, Schema 1) A stirred solution of 74.2 g (0.38 mole) of <strong>[2001-32-3]3-(2-nitrophenyl)propionic acid</strong> and 53.6 g (0.45 mole) of thionyl chloride in 250 mL of methylene chloride was heated under reflux for 16 hours. The reaction mixture was concentrated under reduced pressure to give a residue, which was dissolved in 100 mL of methylene chloride. The solution was concentrated under reduced pressure, and the residue was subjected to high vacuum to give 3-(2-nitrophenyl)propionyl chloride as an oil. A stirred mixture of 64.1 g (0.48 mole) of aluminum chloride and 300 mL of carbon disulfide was cooled to 5 C., and a solution of the nitrophenylpropionyl chloride from above in 100 mL of carbon disulfide was added dropwise. During the addition the temperature of the reaction mixture was maintained at 5-10 C. Upon complete addition, the reaction mixture was stirred at 5 C. for 0.25 hours, at ambient temperature for 0.5 hour, then under reflux for 3.5 hours, and finally at ambient temperature for 16 hours. The reaction mixture was poured into 100 mL of ice-water, and the mixture was stirred for one hour and extracted with four portions of 400 mL each of diethyl ether. The combined ether extracts were dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a solid residue. The residue was crystallized from ethanol after treatment with decolorizing carbon to give, in two fractions, 39.8 g of 4-nitro-1-indanone, m.p. 94-97 C.

Reference： [1]Patent: US4368205,1983,A
[2]Patent: US4442296,1984,A

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Technical Information

? 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 ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? 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 Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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[ CAS No. 24623-25-4 ] {[proInfo.proName]}

Quality Control of [ 24623-25-4 ]

Related Doc. of [ 24623-25-4 ]

Product Details of [ 24623-25-4 ]

Calculated chemistry of [ 24623-25-4 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 24623-25-4 ]

Application In Synthesis of [ 24623-25-4 ]

[ 24623-25-4 ] Synthesis Path-Upstream 1~2

[ 24623-25-4 ] Synthesis Path-Downstream 1~4

Technical Information

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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