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Chemical Structure| 7152-15-0 Chemical Structure| 7152-15-0

Structure of 7152-15-0

Chemical Structure| 7152-15-0

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Product Details of [ 7152-15-0 ]

CAS No. :7152-15-0
Formula : C8H14O3
M.W : 158.20
SMILES Code : C(=O)(CC(=O)C(C)C)OCC
MDL No. :MFCD00009198
InChI Key :XCLDSQRVMMXWMS-UHFFFAOYSA-N
Pubchem ID :81583

Safety of [ 7152-15-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225
Precautionary Statements:P210-P403+P235
Class:3
UN#:3272
Packing Group:

Computational Chemistry of [ 7152-15-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 0
Fraction Csp3 0.75
Num. rotatable bonds 5
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 42.05
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.

1.92
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

1.29
Log Po/w (WLOGP)?

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

1.16
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.

0.97
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

1.38
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.35

Water Solubility

Log S (ESOL):?

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

-1.3
Solubility 7.86 mg/ml ; 0.0497 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.

-1.8
Solubility 2.5 mg/ml ; 0.0158 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

-1.52
Solubility 4.72 mg/ml ; 0.0299 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.

-6.35 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

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)

1.71

Application In Synthesis of [ 7152-15-0 ]

* 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.

  • Downstream synthetic route of [ 7152-15-0 ]

[ 7152-15-0 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 5754-35-8 ]
  • [ 7152-15-0 ]
  • [ 135833-73-7 ]
  • 2
  • [ 456-14-4 ]
  • [ 459-57-4 ]
  • [ 7152-15-0 ]
  • [ 123837-56-9 ]
  • 3
  • [ 7152-15-0 ]
  • [ 122-72-5 ]
  • [ 109704-48-5 ]
  • 4
  • [ 456-00-8 ]
  • [ 7152-15-0 ]
  • [ 139993-81-0 ]
YieldReaction ConditionsOperation in experiment
51.3% With sodium acetate; acetic acid; In water; (1) Ethyl 4-(4-fluorophenyl)-2-isopropylpyrrole-3-carboxylate 1 STR6 A mixture of 6.85 g (43.3 mmol) of ethyl isobutyrylacetate, 10.69 g (56.3 mmol) of 2-amino-4'-fluoracetophenone hydrochloride, 16.3 ml of acetic acid, 6.04 g of sodium acetate, and 10.8 ml of water is refluxed for 4 hours. After cooling, the reaction mixture is adjusted to pH 8 with saturated NaHCO3 and extracted with ether. The extract, 8.36 g, is subjected to column chromatography with silica gel, eluding with methylene chloride to give 6.12 g (Yield:51.3%) of the compound 1. NMR (CDCl3) delta: 1.14 (t, 3H, J=7 Hz); 1.31 (d, 6H, J=7 Hz); 3.81 (septet, 1H, J=7 Hz); 4.15 (q, 2H, J=7 Hz); 6.58 (d, 1H, J=2,4 Hz); 6.96-7.05 (m, 2H); 7.29-7.37 (m, 2H); 8.36 (brs, 1H).
  • 5
  • [ 7152-15-0 ]
  • [ 147118-40-9 ]
  • 6
  • [ 7152-15-0 ]
  • [ 10599-59-4 ]
  • 7
  • [ 6100-60-3 ]
  • [ 7152-15-0 ]
  • C13H14O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With sulfuric acid; at 0 - 20℃; To the mixture of compound 1 (3.0 g, 21.0 mmol) and compound 2 (4.0 g, 25.0 mmol), H2SO4(9 mL) was added slowly at 0 C. The mixture was stirred at RT overnight. The reaction mixture was poured into H2O (10 mL) and stirred for 30 mins, the formed precipitate was filtered and washed with water, dried to give compound 3 (2.0 g, 41% yield) as light yellow solid.
  • 8
  • [ 6100-60-3 ]
  • [ 7152-15-0 ]
  • 7-hydroxy-4-isopropyl-6-methoxy-2-oxo-2H-chromene-8-carbaldehyde [ No CAS ]
  • 9
  • [ 7152-15-0 ]
  • [ 658-27-5 ]
  • C15H17FN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With triethylamine; In ethanol; N,N-dimethyl acetamide; at 20 - 100℃; for 2h; Taking 25 ml round-bottom flask, the intermediate isobutyryl ethyl acetate (1.33g, 8 . 39mmol) dissolved in 11mLN, dipropylene N-dimethyl formamide methanol 100 C stirring overnight. After the reaction is distilled under reduced pressure to obtain crude products. The intermediate is dissolved in 11 ml of ethanol, add 1.1 ml triethylamine, <strong>[658-27-5]3-fluorophenylhydrazine</strong> hydrochloride compound (1.36g, 8 . 39mmol), the reaction room temperature for 2 hours. After the reaction, by adding 150 ml water, ethyl acetate extraction three times (50mLx3), combined with the phase, saturated salt water washing three times (50mLx3), anhydrous sodium sulfate for drying; concentrated, dry sample, rapid preparation of chromatographic silica gel column (ethyl acetate: petroleum ether = 30:1) separated to obtain oily liquid 832 mg, yield 36%.
  • 10
  • [ 7152-15-0 ]
  • [ 85482-13-9 ]
  • ethyl 2-(2,5-dichlorobenzyl)-4-methyl-3-oxopentanoate [ No CAS ]
  • 11
  • [ 7152-15-0 ]
  • [ 85482-13-9 ]
  • 2-amino-6-(2,5-dichlorobenzyl)-5-isopropyl[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one [ No CAS ]
  • 12
  • [ 76593-36-7 ]
  • [ 7152-15-0 ]
  • 7-(4-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)oxy)piperidin-1-yl)-2-isopropyl-8,9-dimethyl-4H-pyrimido[1,2-b]pyridazin-4-one [ No CAS ]
  • 13
  • [ 76593-36-7 ]
  • [ 7152-15-0 ]
  • 7-chloro-2-isopropyl-8,9-dimethyl-4H-pyrimido[1,2-b]pyridazin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% With polyphosphoric acid; at 120℃; for 2.0h; To a solution of 6-chioro-3-amino-4,5-dimethylpyridazine (550 mg) in polyphosphoric acid (5 mL) was added ethyl 4-methyl-3-oxo-pentanoate (1.13 mL}. The mixture was heated to 85 C for 1 hour, then 120 C for 1 hour. While still hot, the mixture was slowly added to a stirred solution of saturated aqueous NaHCOg (150 mL) and chloroform/IPA (4:1) (50 mL). Upon complete addition, the mixture was stirred for 10 minutes and the organic layer was isolated. The aqueous layer was further extracted with chloroform/IPA (4:1) (3 x 50 L) and the organic layers were pooled, dried over MgSC , filtered, and concentrated. The crude product was purified using a Teledyne I5CO Combi-Flash system (liquid loading with DCM, 80G column, 0 - 65% EtOAc/Hex, 20 min run). The column was then flushed with hexanes followed by 0 - 2% MeOH/DCM, 10 min to give the title compound (204 mg; 23% yield) as a solid. : NMR (400 MHz, CDCI3) d 6.47 (s, 1H), 3.63 (hept, J = 6.8 Hz, 1H), 2.56 (d, 1 = 1.0 Hz, 3H), 2.44 (d, J = 1.0 Hz, 3H), 1.32 (s, 3H), 1.30 (s, 3H). ES-MS [M+l]+: 252.
23% With polyphosphoric acid; at 120℃; for 2.0h; To a solution of 6-chioro-3-amino-4,5-dimethylpyridazine (550 mg) in polyphosphoric acid (5 mL) was added ethyl 4-methyl-3-oxo-pentanoate (1.13 mL}. The mixture was heated to 85 C for 1 hour, then 120 C for 1 hour. While still hot, the mixture was slowly added to a stirred solution of saturated aqueous NaHCOg (150 mL) and chloroform/IPA (4:1) (50 mL). Upon complete addition, the mixture was stirred for 10 minutes and the organic layer was isolated. The aqueous layer was further extracted with chloroform/IPA (4:1) (3 x 50 L) and the organic layers were pooled, dried over MgSC , filtered, and concentrated. The crude product was purified using a Teledyne I5CO Combi-Flash system (liquid loading with DCM, 80G column, 0 - 65% EtOAc/Hex, 20 min run). The column was then flushed with hexanes followed by 0 - 2% MeOH/DCM, 10 min to give the title compound (204 mg; 23% yield) as a solid. : NMR (400 MHz, CDCI3) d 6.47 (s, 1H), 3.63 (hept, J = 6.8 Hz, 1H), 2.56 (d, 1 = 1.0 Hz, 3H), 2.44 (d, J = 1.0 Hz, 3H), 1.32 (s, 3H), 1.30 (s, 3H). ES-MS [M+l]+: 252.
23% With polyphosphoric acid; at 120℃; for 2.0h; To a solution of 6-chioro-3-amino-4,5-dimethylpyridazine (550 mg) in polyphosphoric acid (5 mL) was added ethyl 4-methyl-3-oxo-pentanoate (1.13 mL}. The mixture was heated to 85 C for 1 hour, then 120 C for 1 hour. While still hot, the mixture was slowly added to a stirred solution of saturated aqueous NaHCOg (150 mL) and chloroform/IPA (4:1) (50 mL). Upon complete addition, the mixture was stirred for 10 minutes and the organic layer was isolated. The aqueous layer was further extracted with chloroform/IPA (4:1) (3 x 50 L) and the organic layers were pooled, dried over MgSC , filtered, and concentrated. The crude product was purified using a Teledyne I5CO Combi-Flash system (liquid loading with DCM, 80G column, 0 - 65% EtOAc/Hex, 20 min run). The column was then flushed with hexanes followed by 0 - 2% MeOH/DCM, 10 min to give the title compound (204 mg; 23% yield) as a solid. : NMR (400 MHz, CDCI3) d 6.47 (s, 1H), 3.63 (hept, J = 6.8 Hz, 1H), 2.56 (d, 1 = 1.0 Hz, 3H), 2.44 (d, J = 1.0 Hz, 3H), 1.32 (s, 3H), 1.30 (s, 3H). ES-MS [M+l]+: 252.
 

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