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Structure of 4971-56-6

Chemical Structure| 4971-56-6

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Product Details of [ 4971-56-6 ]

CAS No. :4971-56-6
Formula : C4H4O3
M.W : 100.07
SMILES Code : O=C(C1)OCC1=O
MDL No. :MFCD00010086
Boiling Point : No data available
InChI Key :JCGNDDUYTRNOFT-UHFFFAOYSA-N
Pubchem ID :521261

Safety of [ 4971-56-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Computational Chemistry of [ 4971-56-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 7
Num. arom. heavy atoms 0
Fraction Csp3 0.5
Num. rotatable bonds 0
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 20.71
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

43.37 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.63
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.14
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.5
Log Po/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.

-0.89
Log Po/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

1.07
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.03

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.37
Solubility 42.5 mg/ml ; 0.424 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.

-0.32
Solubility 48.3 mg/ml ; 0.482 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very 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

-0.43
Solubility 37.4 mg/ml ; 0.373 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.

-7.01 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

2.0
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

1.0 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)

1.19

Application In Synthesis of [ 4971-56-6 ]

* 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 [ 4971-56-6 ]

[ 4971-56-6 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 4971-56-6 ]
  • [ 20291-40-1 ]
  • [ 375374-83-7 ]
  • 2
  • [ 4971-56-6 ]
  • [ 86-81-7 ]
  • [ 1124-16-9 ]
  • C21H25N3O5 [ No CAS ]
  • 3
  • [ 4971-56-6 ]
  • [ 3325-11-9 ]
  • [ 331-64-6 ]
  • 10-(2-fluoro-4-methoxyphenyl)-6,7,9,10-tetrahydro-1H-furo[3,4-b][1,2,3]triazolo[4,5-f]quinolin-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% In ethanol; for 1h;Reflux; General procedure: The compound tetronic acid (102 mg, 1.02 mmol) was dissolved in 4 mL of ethanol, followed by addition of 3,4,5-trimethoxybenzaldehyde (200 mg, 1.02 mmol) and 2,4-dimethoxypyrimidine-5-amine (158 mg, 1.02 mmol). The reaction mixture was reflux at ethanol temperature for 1 h. Then reaction mixture was allowed to cool to room temperature, and the precipitated product was collected by vacuum filtration and washed with ethanol (3 mL) then recrystallized from ethanol to afford pure compound 11a as a white solid in 390 mg, 92percent yield.
  • 4
  • [ 4971-56-6 ]
  • [ 3325-11-9 ]
  • [ 86-81-7 ]
  • 10-(3,4,5-trimethoxyphenyl)-6,7,9,10-tetrahydro-1H-furo[3,4-b][1,2,3]triazolo[4,5-f]quinolin-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In ethanol; for 1h;Reflux; General procedure: The compound tetronic acid (102 mg, 1.02 mmol) was dissolved in 4 mL of ethanol, followed by addition of 3,4,5-trimethoxybenzaldehyde (200 mg, 1.02 mmol) and 2,4-dimethoxypyrimidine-5-amine (158 mg, 1.02 mmol). The reaction mixture was reflux at ethanol temperature for 1 h. Then reaction mixture was allowed to cool to room temperature, and the precipitated product was collected by vacuum filtration and washed with ethanol (3 mL) then recrystallized from ethanol to afford pure compound 11a as a white solid in 390 mg, 92percent yield.
  • 5
  • [ 4971-56-6 ]
  • [ 1005-39-6 ]
  • [ 56990-02-4 ]
  • [ 1309571-71-8 ]
  • 6
  • [ 4971-56-6 ]
  • [ 1005-39-6 ]
  • [ 86-81-7 ]
  • [ 1309571-70-7 ]
  • 7
  • [ 4971-56-6 ]
  • [ 1878-91-7 ]
  • 3-(p-bromophenoxyacetyl)tetronic acid [ No CAS ]
  • 8
  • [ 4971-56-6 ]
  • [ 827-41-8 ]
  • [ 31680-08-7 ]
  • 4-(4-methoxy-3-nitrophenyl)-3-phenyl-4,5,7,8-tetrahydro-1H-furo[3,4-b]pyrazolo[4,3-e]pyridin-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In ethanol; for 1h;Reflux; General procedure: The compound tetronic acid (100 mg, 1 mmol) was dissolved in 4 mL of ethanol, followed by the addition of 3,4,5-trimethoxybenzaldehyde (5a) (196 mg, 1 mmol) and 3-phenyl-1H-pyrazol-5-amine (159 mg, 1 mmol). The reaction mixture was reflux at ethanol temperature for 1 h. The reaction mixture was allowed to cool to room temperature. Now, the precipitated product was collected by vacuum filtration, washed with ethanol (3 mL) and then recrystallized from acetone to afford pure compound 8a as in 390 mg, 93 % yield.
  • 9
  • [ 4971-56-6 ]
  • [ 28177-52-8 ]
  • 7-chloro-1H-2,8-dioxacyclopenta[a]inden-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With 1-butyl-3-methylimidazolium hydroxide; In water; at 20.0℃; for 7.0h;Green chemistry; General procedure: A mixture of 2-iodophenol 1 (2.0 mmol), tetronic acid 2 (2.0 mmol), water 3 ml and [bmIm]OH (10 mol%) was stirred at room temperature for 5 h. After completion of reaction as indicated by TLC, 20 mL of water was added to the reaction mixture and stirred well. The product was extracted with EtOAc (3 * 20 mL). The combined organic layer were dried over anhydrous Na2SO4 to afford the crude product and recrystallized from ethanol to obtain analytically pure compound 4 (75-90%). After isolation of the product, the remaining aqueous layer containing the ionic liquid was washed with ether (2x10 mL) to remove organic impurity and filtered. The filtrate was extracted with dichloro methane (2 * 10 mL), dried over MgSO4 and evaporated under reduced pressure to afford [bmIm]OH, which was reused thrice in subsequent runs without further purification.
 

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