56503-39-0|(E)-Ethyl 2-cyano-2-(hydroxyimino)acetate| Ambeed

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Quality Control of [ 56503-39-0 ] Purity: 95% SDS Specification

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Product Details of [ 56503-39-0 ]

CAS No. :	56503-39-0
Formula :	C₅H₆N₂O₃
M.W :	142.11
SMILES Code :	O=C(OCC)/C(C#N)=N/O
MDL No. :	MFCD00002112

Safety of [ 56503-39-0 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H228-H301+H311+H331-H315-H319
Precautionary Statements:	P240-P210-P241-P280-P370+P378-P501-P261-P270-P271-P264-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405
Class:	4.1(6.1)
UN#:	2926
Packing Group:	Ⅲ

Computational Chemistry of [ 56503-39-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	0
Fraction Csp3	0.4
Num. rotatable bonds	3
Num. H-bond acceptors	5.0
Num. H-bond donors	1.0
Molar Refractivity	31.6
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	82.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.13
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	1.32
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.1
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.	-1.06
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	-0.19
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.22

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.35
Solubility	6.28 mg/ml ; 0.0442 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.66
Solubility	0.313 mg/ml ; 0.0022 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	0.06
Solubility	163.0 mg/ml ; 1.15 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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	No
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.	-6.23 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	3.0 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)	2.21

Application In Synthesis of [ 56503-39-0 ]

* 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 [ 56503-39-0 ]
Downstream synthetic route of [ 56503-39-0 ]

[ 56503-39-0 ] Synthesis Path-Upstream 1~1

1
[ 56503-39-0 ]
[ 7440-06-4 ]
[ 37842-58-3 ]

References: [1] Patent: US5003099, 1991, A, .

[ 56503-39-0 ] Synthesis Path-Downstream 1~35

1
[ 56503-39-0 ]
[ 98-88-4 ]
[ 20992-39-6 ]

References: [1]Bulletin de la Societe Chimique de France,1971,p. 2711 - 2716.

2
[ 56503-39-0 ]
[ 122-04-3 ]
[ 33001-46-6 ]

References: [1]Bulletin de la Societe Chimique de France,1971,p. 2711 - 2716.

3
[ 56503-39-0 ]
[ 124-63-0 ]
[ 20992-38-5 ]

References: [1]Bulletin de la Societe Chimique de France,1971,p. 2711 - 2716.

4
[ 56503-39-0 ]
[ 98-59-9 ]
[ 20992-37-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In cyclohexane; ethyl acetate;	EXAMPLE 63 In ethyl acetate (50 ml) are dissolved <strong>[56503-39-0]ethyl 2-hydroxyimino-2-cyanoacetate</strong> (7.1 g) and triethylamine (7.0 ml). To the solution is added p-toluenesulfonyl chloride (9.5 g) with stirring under ice-cooling, and the mixture is stirred for 2 hours and allowed to stand overnight. The reaction mixture is filtered and the filtrate is concentrated. To the residue is added cyclohexane and the resulting crystals are separated by filtration and dried to give ethyl 2-(p-toluenesulfonyloxyimino)-2-cyanoacetate (13.9 g), melting point: 84-87 C. Anal. Calcd. for C12 H12 O5 N2 S: C, 48.64; H, 4.08; N, 9.46. Found: C, 48.63; H, 3.91; N, 9.51.
49.18 g	With triethylamine; In ethyl acetate; at 20℃; for 2h;Cooling with ice;	A) Ethyl (2E)-cyano([(4-methylphenyl)sulfonyl]oxy}imino)acetate To a solution of <strong>[56503-39-0]ethyl (2E)-cyano(hydroxyimino)acetate</strong> (41.63 g) and triethylamine (45.53 g) in ethyl acetate (300 mL), p-toluenesulfonyl chloride (57.2 g) was gradually added under ice cooling. The reaction mixture was stirred at room temperature for 2 hours. The insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. Water (300 mL) was added to the residue, and the mixture was stirred for 15 minutes. The deposited precipitate was filtered and dried under reduced pressure to obtain the title compound (49.18 g). 1H NMR (400 MHz, CDCl3) delta 1.38 (3H, t, J = 7.2 Hz), 2.48 (3H, s), 4.41 (2H, q, J = 7.2 Hz), 7.41 (2H, d, J = 8.0 Hz), 7.92 (2H, d, J = 8.4 Hz).

References: [1]Bulletin des Societes Chimiques Belges,1993,vol. 102,p. 749 - 760.
[2]Bulletin de la Societe Chimique de France,1971,p. 2711 - 2716.
[3]Patent: US4242507,1980,A .
[4]Patent: EP3287441,2018,A1 .Location in patent: Paragraph 0344.

5
[ 56503-39-0 ]
[ 21286-54-4 ]
[ 128702-19-2 ]

References: [1]Bulletin des Societes Chimiques Belges,1989,vol. 98,p. 923 - 930.

6
[ 56503-39-0 ]
[ 90185-58-3 ]
[ 90185-59-4 ]

References: [1]Australian Journal of Chemistry,1984,vol. 37,p. 155 - 163.

7
[ 56503-39-0 ]
[ 90185-46-9 ]
[ 90185-49-2 ]

References: [1]Australian Journal of Chemistry,1984,vol. 37,p. 155 - 163.

8
[ 56503-39-0 ]
[ 152623-35-3 ]