[ CAS No. 2051-95-8 ]

Name: 2051-95-8|3-Benzoylpropionicacid|95%
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CAS No. :	2051-95-8	MDL No. :	MFCD00002792
Formula :	C₁₀H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KMQLIDDEQAJAGJ-UHFFFAOYSA-N
M.W :	178.19 g/mol	Pubchem ID :	72871
Synonyms :

Calculated chemistry of [ 2051-95-8 ]

Physicochemical Properties

Num. heavy atoms :	13
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 :	48.02
TPSA :	54.37 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.32
Log Po/w (XLOGP3) :	1.3
Log Po/w (WLOGP) :	1.73
Log Po/w (MLOGP) :	1.32
Log Po/w (SILICOS-IT) :	1.78
Consensus Log Po/w :	1.49

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.84
Solubility :	2.57 mg/ml ; 0.0144 mol/l
Class :	Very soluble
Log S (Ali) :	-2.04
Solubility :	1.62 mg/ml ; 0.00908 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.53
Solubility :	0.53 mg/ml ; 0.00297 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.14

Safety of [ 2051-95-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2051-95-8 ]

* 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.

Upstream synthesis route of [ 2051-95-8 ]
Downstream synthetic route of [ 2051-95-8 ]

[ 2051-95-8 ] Synthesis Path-Upstream 1~8

1
[ 2051-95-8 ]
[ 20375-65-9 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1986, vol. 22, # 7, p. 763 - 770[2] Khimiya Geterotsiklicheskikh Soedinenii, 1986, vol. 22, # 7, p. 951 - 958
[3] Journal of Heterocyclic Chemistry, 1983, vol. 20, # 6, p. 1473 - 1476
[4] Acta Poloniae Pharmaceutica - Drug Research, 2010, vol. 67, # 5, p. 555 - 562

2
[ 2051-95-8 ]
[ 2166-31-6 ]

Reference： [1] Synthetic Communications, 2001, vol. 31, # 5, p. 645 - 651
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1986, vol. 22, # 7, p. 763 - 770[3] Khimiya Geterotsiklicheskikh Soedinenii, 1986, vol. 22, # 7, p. 951 - 958
[4] Journal of Heterocyclic Chemistry, 1983, vol. 20, # 6, p. 1473 - 1476
[5] Chinese Chemical Letters, 2011, vol. 22, # 12, p. 1435 - 1438

3
[ 75-07-0 ]
[ 2051-95-8 ]
[ 101563-78-4 ]

Reference： [1] Journal of Organic Chemistry, 1959, vol. 24, p. 586,588
[2] Journal fuer Praktische Chemie (Leipzig), 1985, vol. 327, # 4, p. 536 - 542

4
[ 2051-95-8 ]
[ 4662-03-7 ]

Reference： [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2908 - 2920

5
[ 1066-33-7 ]
[ 2051-95-8 ]
[ 30741-72-1 ]

Reference： [1] Patent: WO2004/11448, 2004, A1, . Location in patent: Page 75

6
[ 2051-95-8 ]
[ 88611-67-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 18, p. 5539 - 5552

7
[ 2051-95-8 ]
[ 583-53-9 ]

Reference： [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 15, p. 5431 - 5435

8
[ 108-30-5 ]
[ 108-86-1 ]
[ 6340-79-0 ]
[ 2051-95-8 ]

Reference： [1] Journal of Organic Chemistry, 1992, vol. 57, # 1, p. 366 - 370

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Yield	Reaction Conditions	Operation in experiment
99.6%	With aluminum (III) chloride; at 35 - 80℃; for 3h;	Step 1, in a 250m1 round bottom flask, sequentially add 10g of succinic anhydride, 62g of benzene, 5g of aluminum trichloride and 15g of CsPW/CNT catalyst, and mix well by mechanical stirring, at this time the system temperature is 35 C;Step 2, heating to 80 C, the system gradually changed from orange to crimson, the lye absorbed a large amount of hydrogen chloride gas released, and the temperature was refluxed for 3 h;Step 3, after the end of the reaction, first cooled to room temperature, and then slowly add about 100m13M hydrochloric acid solution to the system, and then a solid is produced;Step 4. The solid was dissolved in about 60 ml of dichloromethane, and the phases were distinct, and the organic layer was milky white. The organic layer was washed twice with brine, and then dichloromethane was evaporated to afford white crystals.
84%	With aluminum (III) chloride; In benzene; for 0.75h;Reflux;	AlCl3 (66 g, 0.5 mol) and succinic anhydride (20 g, 0.2 mol) were added to anhydrous benzene (100 mL). The mixture was heated to reflux for 45 min. When cooled to room temperature, 100 mL ice water was slowly added dropwise under ice bath. The excess benzene was evaporated under atmospheric pressure, and then the residue was added activated carbon and filtered. The filtrate was acidified and the resulting precipitate was filtered to give the crude product, which was recrystallized with 30% ethanol to get product 25 (30 g, 84%) as colorless acicular crystal. Mp: 117-119 C (lit.
75%	With aluminum (III) chloride; for 4h;Reflux;	To a solution of succinic anhydride (0.1 mole) in benzene (50 mL), anhydrous aluminium chloride(0.125 mole) was added in small portions with stirring over a period of 2 hours. The reaction mixture was refluxed for 2 hours. After completion of the reaction, excess of benzene was removed by steam distillation. The reaction mixture was dissolved in sodium hydroxide solution, filtered, and hydrochloric acid was added to it. The solid mass obtained was filtered, washed with cold water, dried and recrystallized from methanol to give a colorless productwhich gave effervescence with sodium bicarbonate solution23-25.

		General procedure: To liquid aromatic hydrocarbon (30 ml), anhydrous aluminum chloride (16.6 g, 0.125 mol) was added. Nitrobenzene (30 ml) was used as solvent in case of solid aromatic hydrocarbons. The mixture was stirred using a magnetic stirrer at room temperature for 30 min. To this, succinic anhydride (5 g, 0.05 mol) was added in five portions with continuous stirring. Vigorous reaction started with the evolution of HCl gas. Stirring was continued for another 6 h at room temperature. The mixture was left at room temperature for 48 h and then decomposed by adding ice-cold hydrochloric acid (50%, 100 ml). The excess solvent was removed by steam distillation. The solid precipitated out was treated with aqueous saturated sodium bicarbonate solution and filtered. Filtrate was acidified with dilute HCl (4% v/v) to give a precipitate. It was filtered and residue was washed with cold water, dried and crystallized from the appropriate solvent to give 1a-p.
	With aluminum (III) chloride; for 6h;	General procedure: Succinic anhydride (10 g, 10 mmol) was treated with differentaryl derivatives (17 g, 10 mmol) in the presence of anhydrous aluminum chloride (15 g, 11.25 mmol). The reaction mixture was stirred for 6 h. The desired product was purified by dissolving in 5 % sodium hydroxide solution and filtered. Dilute hydrochloric acid was added to mother liquor to precipitate the product. The solid mass so obtained was filtered, washed with cold water, dried and crystallized from acetone to give 8.6 g of the desired compound as a colorless solid.
		General procedure: After suspending anhydrous aluminum chloride (0.15 mol) in dry benzene (50 mL) under anhydrous conditions, the mixture was refluxed on a water bath. Succinic anhydride (0.10 mol) was then added to the reaction mixture in small portions with continuous stirring. Stirring and heating were continued for 6 h. The reaction mixture was left overnight at room temperature and then made acidic by addition of an ice cold solution of concentrated hydrochloric acid (2.5% v/v). The mixture was concentrated to a small volume by heating on a water bath. The separated precipitate was filtered. It was purified by dissolving in 5% w/v sodium bicarbonate solution, followed by extraction with ether. The aqueous layer on acidification with dilute hydrochloric acid gave benzoyl propionic acid. It was crystallized from aqueous ethanol to give a colorless compound [34, 34].
	With aluminum (III) chloride; In dichloromethane;Inert atmosphere;	General procedure: To an oven dried 250 mL round bottom flask containing succinic anhydride (3.00 g, 30.0 mmol) and the aromatic compound (1.1 equiv) in DCM (100 mL) was added aluminum chloride (2.2 equiv) portion-wise at room temperature in an atmosphere of argon over 5 minutes and allowed to stir until completion of reaction. The reaction was cooled at 0 C and quenched by carefully addition of aqueous solution of 1N HCl, extracted with THF and ethyl acetate (1:1) (2 x 200 mL), the organic layer dried under Na2SO4 and concentrated to give the product as a solid that was subsequently washed with hexanes and vacuum filtered to afford the crude product S1 used in the next step without further purification.
	With aluminum (III) chloride; In dichloromethane; at 20℃; for 6.5h;Cooling with ice;	25 mmol of benzene was dissolved in 30 mL of dichloromethane,25 mmol succinic anhydride was added,Ice water bath stirring conditions,In batches within 30min37.5 mmol of anhydrous AlCl3 was added,Followed by reaction at room temperature for 6 hours.After the reaction,Add ice hydrochloric acid quenching,Stir for ten minutes,Filter,Recrystallization from an appropriate 70% ethanol solution,Dried to give 4-phenyl-4-oxobutyric acid.
	With aluminum (III) chloride;	General procedure: The synthesis of compound PDP-6 was performed in a two steps. In the first step, anhydrous aluminium chloride (0.125 M) was reacted with a solution of succinic anhydride (0.1 M) prepared in benzene(50 mL) to produce 3-benzoylpropionic acid which was purified by recrystallization with methanol. In the second step, 3-benzoylpropionicacid (0.01 M) was reacted with a solution of hydrazine hydrate(0.015M) in ethanol to produce PDP-6 which was purified by recrystallization with ethanol. The detail procedure about synthesis of various pyridazinone derivatives including PDP-6 is presented in our previously published article [1]. The scheme for the synthesis of PDP-6 in two different steps is given in Supplementary Fig. 1 (Fig. S1).
	With aluminum (III) chloride;	The 4-oxo-4-phenyl butanoic acid is synthesized by the Friedel-Craft?s reaction between succinic anhydride and benzene in the presence of anhydrous aluminium chloride [12].
		Preparation of 4- oxo-4-(substituted phenyl) butanoic acids (2). These Compounds were synthesizedaccording to reports [26,27]. Succinic anhydride (1 equiv, 25 mmol) in 30 mL CH2Cl2 reactedwith substituted benzenes (1, 25 mmol) under stirring for 0.5 h in ice-water bath, then anhydrousaluminum chloride (37.5 mmol) was added to the CH2Cl2 solution (Scheme 1). The reaction was thenkept on room temperature for 6 h. After the reaction was stopped, icy aqueous hydrochloric acidsolution (0.1 mol/L, 10 mL) was drop to resultant solution under stirring for 10 min. Organic phasesolution was evaporated to give crude product. The crude product was further purified by crystallizationrepeatedly with 70% ethanol solution to afford 4-oxo-4-phenylbutanoic acid (2A) and4-oxo-4-(p-tolyl)butanoic acid (2B) [26], 4-(4-Methoxyphenyl)-4-oxobutanoic acid (2C) and 4-(4-Chlorophenyl)-4-oxobutanoic acid (2D).
	With aluminum (III) chloride; for 4h;Reflux;	To a solution of succinic anhydride (0.1 moles) in benzene (50 mL), anhydrous aluminium chloride (0.125 moles) was added in small portions with stirring over a period of 2 hours. The reaction mixture was refluxed for 2 hours. After completion of the reaction, the excess of benzene was removed by steam distillation. The reaction mixture was dissolved in sodium hydroxide solution, filtered, and hydrochloric acid was added to it. The solid mass obtained was filtered, washed with cold water, dried and recrystallized from methanol to obtain the title compound having a melting point of 1 l3C to 1 l6C.

Yield	Reaction Conditions	Operation in experiment
88%	With potassium hydroxide; In ethanol; at 20℃; for 48h;Heating / reflux;	A stirred suspension of isatin (5.Og, 22mmole) in EtOH (150ml) was treated portionwise with KOH (4.93g, deltadeltammole) and maintained at room temperature until solution was complete, then 3-benzoylpropionic acid (3.94g, 22mmole) was added and the mixture heated at reflux for 48hrs. The cooled mixture was concentrated under vacuum and the residue acidified to pH 3-4 with 5M HCI acid and the precipitate filtered off, washed with water and DCM, then dried to afford the title compound as a light brown solid (6.Og, 88%);1HNMR (400MHz, d6DMSO): 63.76 (2H, s), 7.46 - 7.56 (5H, m), 7.71 (1H, t), 7.84 (1H, t), 7.95 (1 H, d), 8.07 (1 H, d); m/z (APCI): 308.1 [M+H]+.
81%	With sodium hydroxide; at 90℃; for 18h;	Adding a 0.5% sodium hydroxide solution having a mass concentration of 33% to the reaction flask,Add 0.1mol to the stirring isatin and 0.1mol3-(benzoyl)propionic acid,Then the temperature was raised to 90 C and refluxed for 18 h.The end point of the reaction was monitored by thin layer chromatography.The reaction was cooled to room temperature.Pour the reactants into water 10 times the volume of the reactants.Adjust the pH to 1.3 with concentrated hydrochloric acid.There is a lot of solid precipitation,Filtered and dried,A yellow solid powder of 2-phenyl-3-carboxymethyl-quinoline-4-carboxylic acid having the molecular formula: C18H13NO4, molecular weight 307, yield 75-81%.

Yield	Reaction Conditions	Operation in experiment
98%	With sulfuric acid at 50℃; for 5h;	Methyl 4-oxopentanoate (2a) General procedure: Sulfuric acid (0.1 ml) was added to a solution of levulinic acid (0.782 g, 7.0 mmol) in methanol (10 ml) and the mixture was heated at 50° C for 5 hours. The solution was evaporated under reduced pressure, and the residue was partitioned between saturated aqueous solution of NaHCO3 and ethyl acetate. The organic layer was separated, extracted with brine solution and dried over anhydrous MgSO4. Evaporation under reduced pressure afforded compound 2a (0.901 g, 99%).
96%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;
95%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 24h;

[ CAS No. 2051-95-8 ]

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