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Chemical Structure| 6290-17-1 Chemical Structure| 6290-17-1

Structure of 6290-17-1

Chemical Structure| 6290-17-1

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Product Details of [ 6290-17-1 ]

CAS No. :6290-17-1
Formula : C9H16O4
M.W : 188.22
SMILES Code : CC1(OCC(O1)C)CC(OCC)=O
MDL No. :MFCD00151819
InChI Key :GSIXJEIRJVOUFB-UHFFFAOYSA-N
Pubchem ID :95392

Safety of [ 6290-17-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
Class:3
UN#:1993
Packing Group:

Computational Chemistry of [ 6290-17-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 0
Fraction Csp3 0.89
Num. rotatable bonds 4
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 46.76
TPSA ?

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

44.76 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.48
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

0.68
Log Po/w (WLOGP)?

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

1.09
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.

0.56
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

1.55
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.27

Water Solubility

Log S (ESOL):?

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

-1.17
Solubility 12.7 mg/ml ; 0.0674 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.

-1.2
Solubility 12.0 mg/ml ; 0.0636 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

-1.61
Solubility 4.6 mg/ml ; 0.0244 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

Yes
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.

-6.97 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

0.0 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)

3.27

Application In Synthesis of [ 6290-17-1 ]

* 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 [ 6290-17-1 ]

[ 6290-17-1 ] Synthesis Path-Downstream   1~11

  • 3
  • [ 6290-17-1 ]
  • [ 2243-58-5 ]
  • [ 1192140-15-0 ]
  • [ 1357362-21-0 ]
YieldReaction ConditionsOperation in experiment
Example 26 (Comparative): Adaptation of the process by Ueda et al. 1982 for the preparation of the compound of formula (VII)/(VIIa) 5-methyl-l-(naphthalen-2-yl)-lH- pyrazol-3-olNaphthalen-2-ylhydrazine hydrochloride (30 g) and NaOMe (20,85 g) were slurried in toluene (300 ml) and heated to 80/85 °C. Ethyl 2-(2,4-dimethyl-l,3-dioxolan-2- yl)acetate (30,6 ml) was added and maintained for 90 min. Ethyl 2-(2,4-dimethyl-l,3- dioxolan-2-yl)acetate (8,2 ml) and NaOMe (2,5 g) were added and maintained for 2 h. NaOMe (1,7 g) was added and maintained for 1 h. The mixture was cooled to room temperature, water (450 ml) was added and pH adjusted to 6-8 with aqueous HC1. The organic layer was concentrated to dryness under vacuum and methanol (450 ml), HC1 35percent (18 ml) and water (54 ml) were added. The mixture was heated to reflux for 90 min and concentrated under vacuum to 165 ml of final volume. Water (120 ml) and CH2C12 (120 ml) were added and pH adjusted to 12,2-12,7 (basified with NaOH 25percent). Upper organic layer was discarded, and pH of lower aqueous layer was adjusted to 5,0- 7,0 with acetic acid 80percent. The solid was filtered, washed with water (45 ml) and slurried in ethyl acetate (102 ml) 2 h at 20/25 °C. The solid was filtered, washed with ethyl acetate (15 ml) and dried to yield 20,24 g (46percent) of a mixture [5-methyl-l- (naphthalen-2-yl)-lH-pyrazol-3-ol]: [3-methyl-l-(naphthalen-2-yl)-lH-pyrazol-5-ol] (80:20).
Example 26Adaptation of the process by Ueda et al.1982 for the preparation of 5-methyl-1-(naphthalen-2-yl)-1H -pyrazol-3-olNaphthalen-2-ylhydrazine hydrochloride (30 g) and NaOMe (20,85 g) were slurried in toluene (300 ml) and heated to 80/85 °C. Ethyl 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetate (30,6 ml) was added and maintained for 90 min.Ethyl 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetate (8,2 ml) and NaOMe (2,5 g) were added and maintained for 2 h. NaOMe (1,7 g) was added and maintained for 1 h.The mixture was cooled to room temperature, water (450 ml) was added and pH adjusted to 6-8 with aqueous HCl.The organic layer was concentrated to dryness under vacuum and methanol (450 ml), HCl 35percent (18 ml) and water (54 ml) were added.The mixture was heated to reflux for 90 min and concentrated under vacuum to 165 ml of final volume.Water (120 ml) and CH2Cl2 (120 ml) were added and pH adjusted to 12,2-12,7 (basified with NaOH 25percent).Upper organic layer was discarded, and pH of lower aqueous layer was adjusted to 5,0-7,0 with acetic acid 80percent.The solid was filtered, washed with water (45 ml) and slurried in ethyl acetate (102 ml) 2 h at 20/25 °C.The solid was filtered, washed with ethyl acetate (15 ml) and dried to yield 20,24 g (46percent) of a mixture [5-methyl-1-(naphthalen-2-yl)-1H-pyrazol-3-ol]: [3-methyl-1-(naphthalen-2-yl)-1H-pyrazol-5-ol] (80:20).
  • 4
  • [ 6290-17-1 ]
  • [ 1356907-02-2 ]
YieldReaction ConditionsOperation in experiment
82% Example 1 : Preparation of 2-(2,4-dimethyl-L3-dioxolan-2-yl)acetic acid [compoundThe acid 2-(2,4-dimethyl-l,3-dioxolan-2-yl)acetic acid was obtained as a derivative from saponification of the ester ethyl 2-(2,4-dimethyl-l,3-dioxolan-2-yl)acetate. The hydrolysis of ethyl 2-(2,4-dimethyl-l,3-dioxolan-2-yl)acetate in alkaline medium is described in different publications: a) Miranda et al, Tetrahedron, 1987, 143; b) Lelandais et al, Can. J. Chem., 1983, 584; c) Oku et al., J. Org. Chem., 1997, 2123. The acid was obtained with variable yields 50-82percent.3.6 g of ethyl 2-(2,4-dimethyl-l,3-dioxolan-2-yl)acetate in a solution of 1.18 g (1.1 equiv.) of KOH in 8 mL of water were mixed at room temperature under magnetic stirring. After 4 h, the basic aqueous layer was removed with 5 mL of tert-butyl methyl ether, recovering 257 mg (7percent) from the starting material. The aqueous layer was brought to dryness. The residue was stirred in a mixture with 2 ml NaCl-saturated water and 8 mL of CH2CI2 under vigorous stirring. H2SO4 were added until achieving an acidic pH. The organic layers were dried with sodium sulphate, filtered off and evaporated obtaining 2.344 g of the title compound (82percent considering the previously recovered 7percent).
82% Example 1Preparation of 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetic acidThe acid 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetic acid was obtained as a derivative from saponification of the ester <strong>[6290-17-1]ethyl 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetate</strong>.The hydrolysis of <strong>[6290-17-1]ethyl 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetate</strong> in alkaline medium is described in different publications: a) ; b) ; c) .The acid was obtained with variable yields 50-82percent.3.6 g of <strong>[6290-17-1]ethyl 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetate</strong> in a solution of 1.18 g (1.1 equiv.) of KOH in 8 mL of water were mixed at room temperature under magnetic stirring.After 4 h, the basic aqueous layer was removed with 5 mL of tert-butyl methyl ether, recovering 257 mg (7percent) from the starting material.The aqueous layer was brought to dryness.The residue was stirred in a mixture with 2 ml NaCl-saturated water and 8 mL of CH2Cl2 under vigorous stirring.H2SO4 were added until achieving an acidic pH.The organic layers were dried with sodium sulphate, filtered off and evaporated obtaining 2.344 g of the title compound (82percent considering the previously recovered 7percent).
  • 6
  • [ 6290-17-1 ]
  • [ 1356907-05-5 ]
  • 7
  • [ 6290-17-1 ]
  • [ 1356907-06-6 ]
  • 8
  • [ 6290-17-1 ]
  • C7H14O3 [ No CAS ]
  • 10
  • [ 6290-17-1 ]
  • C9H14N2O2 [ No CAS ]
  • 11
  • [ 6290-17-1 ]
  • C11H18N2O2 [ No CAS ]
 

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