[ CAS No. 6501-72-0 ] {[proInfo.proName]}

Name: 6501-72-0|2-(3-Phenyl-4,5-dihydroisoxazol-5-yl)acetic acid|98%
Brand: Ambeed
SKU: A590582
Price: 13.0 USD
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Quality Control of [ 6501-72-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6501-72-0 ]

SDS Specification

Alternatived Products of [ 6501-72-0 ]

Product Details of [ 6501-72-0 ]

CAS No. :	6501-72-0	MDL No. :	MFCD08696167
Formula :	C₁₁H₁₁NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MUFJHYRCIHHATF-UHFFFAOYSA-N
M.W :	205.21	Pubchem ID :	10798271
Synonyms :	GIT 27

Calculated chemistry of [ 6501-72-0 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.27
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	58.39
TPSA :	58.89 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) :	-6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.41
Log Po/w (XLOGP3) :	1.35
Log Po/w (WLOGP) :	1.27
Log Po/w (MLOGP) :	1.18
Log Po/w (SILICOS-IT) :	2.22
Consensus Log Po/w :	1.49

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.06
Solubility :	1.78 mg/ml ; 0.00869 mol/l
Class :	Soluble
Log S (Ali) :	-2.19
Solubility :	1.33 mg/ml ; 0.00647 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.56
Solubility :	0.572 mg/ml ; 0.00279 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.22

Safety of [ 6501-72-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6501-72-0 ]

* 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 [ 6501-72-0 ]
Downstream synthetic route of [ 6501-72-0 ]

[ 6501-72-0 ] Synthesis Path-Upstream 1~3

1
[ 1378834-78-6 ]
[ 625-38-7 ]
[ 6501-72-0 ]

Reference： [1] Patent: WO2006/97273, 2006, A1, . Location in patent: Page/Page column 13

2
[ 613-91-2 ]
[ 6501-72-0 ]

Reference： [1] Synthetic Communications, 1997, vol. 27, # 16, p. 2733 - 2742

3
[ 625-38-7 ]
[ 698-16-8 ]
[ 6501-72-0 ]

Reference： [1] Journal of Pharmacology and Experimental Therapeutics, 2007, vol. 320, # 3, p. 1038 - 1049

[ 6501-72-0 ] Synthesis Path-Downstream 1~14

1
2,2-Dimethyl-5-(3-phenyl-4,5-dihydro-isoxazol-5-yl)-[1,3]dioxane-4,6-dione [ No CAS ]
[ 6501-72-0 ]

Reference： [1]Synthetic Communications,1997,vol. 27,p. 2733 - 2742

2
[ 67-56-1 ]
[ 6501-72-0 ]
[ 6501-73-1 ]

Reference： [1]Synthetic Communications,1998,vol. 28,p. 2457 - 2466

4
[ 625-38-7 ]
[ 698-16-8 ]
[ 6501-72-0 ]

Reference： [1]Journal of Pharmacology and Experimental Therapeutics,2007,vol. 320,p. 1038 - 1049

5
[ 6501-72-0 ]
(+/-)-5-(2-phenyl-2-oxoethyl)-3-isoxazolidinone [ No CAS ]

Reference： [1]Synthetic Communications,1998,vol. 28,p. 2457 - 2466

6
[ 613-91-2 ]
[ 6501-72-0 ]

Reference： [1]Synthetic Communications,1997,vol. 27,p. 2733 - 2742

7
[ 1378834-78-6 ]
[ 625-38-7 ]
[ 6501-72-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In tetrahydrofuran; water; for 12.0h;	Benzaldehyde (I5 32.8 mmol) and hydroxylamine hydrochloride (33 mmol) were dissolved in methanol (100 ml) followed by addition of sodium carbonate (65 mmol). Overnight reaction gave the oxime derivative in 95% (2, 30.4 mmol). Chlorination of the oxime using N-chlorosuccinimide (31.6 mmol) in DMF (100 ml) quantitatively furnished chlorooxime (3). Compound 3 was then dissolved in THF/H2O (*0/20) and treated with 3- butenoate (24.5 mmol) and sodium carbonate (73.6 mmol). After completion, (12 h), the product was extracted with ethyl acetate and the organic extracts were washed with brine and dried over magnesium sulfate. GIT-27 was crystallized from ethyl acetate/heptane mixture. The structure was confirmed by IH-NMR, 13 C-NMR and mass spectroscopy. The daily dosage regimen will presumably vary within wide ranges, for instance from 0.1 to 10 mg/kg body weight.

Reference： [1]Patent: WO2006/97273,2006,A1 .Location in patent: Page/Page column 13

8
4-hydroxy-2-oxofurazan-3-carboxylic acid amide [ No CAS ]
[ 6501-72-0 ]
(3-phenyl-4,5-dihydro-isoxazol-5-yl)acetic acid 4-carbamoyl-2-oxofurazan-3-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20.0℃; for 24.0h;	A stirred solution of 4-hydroxy-2-oxyfurazan-3-carboxylic acid amide (170 mg, 1.07 mmole), (3-phenyl-4,5-dihydro-isoxazol-5-yl) acetic acid (262 mg, 1.28 mmole) and DMAP (65 mg, 0.53 mmole) in CH2CI2 (10 mL) was added with DCC (264 mg, 1.28 mmole). After stirring at room temperature for 24 h, diethyl ether (50 mL) was added and the mixture was filtered through Celite. Concentration of the filtrate followed by flash column chromatography (4:1 EtOAc:hexane) of the residue afforded the desired ester (356 mg, 96%). "eta NMR (300 MHz1 C3D6O) delta 2.78 (d, J= 5 Hz, 1 H)1 2.91 (d, J= 5 Hz, 1 H) 3.30 (d, J= 8 Hz, 1H), 3.62 (d, J= 8 Hz1 1 H), 5.14 (m, 1 H), 5.48 (S1 2H), 7.42 (m, 3H)1 7.68 (d, J=8Hz, 2H). C NMR (75 MHz1 C3D6O) delta 39.2, 39.4, 57.1 , 77.5, 110.7, 126.6, 128.7, 130.0, 154.9, 155.8,156.5, 169.3.

Reference： [1]Patent: WO2008/138516,2008,A1 .Location in patent: Page/Page column 6

9
[ 2680576-45-6 ]
[ 6501-72-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2.1: dimethylsulfide borane complex / dichloromethane / 3 h / 0 - 20 °C 2.2: 12 h / 5 °C