Home Cart Sign in  
Chemical Structure| 3162-29-6 Chemical Structure| 3162-29-6
Chemical Structure| 3162-29-6

*Storage: Inert atmosphere,Room Temperature.

*Shipping: Normal

Acetopiperone

CAS No.: 3162-29-6

4.5 *For Research Use Only !

Cat. No.: A407964 Purity: 98%

Change View

Size Price

USA Stock *0-1 Day

Global Stock *5-7 Days

In Stock
5g łÇî¶ÊÊ In Stock In Stock Login
10g ł§Ê¶ÊÊ In Stock In Stock Login
25g łÍÿ¶ÊÊ In Stock In Stock Login
100g łÇ§î¶ÊÊ In Stock In Stock Login
500g łÿÊò¶ÊÊ In Stock In Stock Login
1kg łóòʶÊÊ Inquiry In Stock Login

Please Login or Create an Account to: See VIP prices and availability

  • 5g

    łÇî¶ÊÊ

  • 10g

    ł§Ê¶ÊÊ

  • 25g

    łÍÿ¶ÊÊ

  • 100g

    łÇ§î¶ÊÊ

  • 500g

    łÿÊò¶ÊÊ

  • 1kg

    łóòʶÊÊ

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

  • 1-2 Day Shipping
  • High Quality
  • Technical Support Online Technical Q&A
Product Citations

Product Details of [ 3162-29-6 ]

CAS No. :3162-29-6
Formula : C9H8O3
M.W : 164.16
SMILES Code : C1=C(C=CC2=C1OCO2)C(=O)C
MDL No. :MFCD00005831
InChI Key :BMHMKWXYXFBWMI-UHFFFAOYSA-N
Pubchem ID :76622

Safety of [ 3162-29-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Calculated chemistry of [ 3162-29-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 42.7
TPSA ?

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

35.53 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.93
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

0.64
Log Po/w (WLOGP)?

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

1.62
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.

0.84
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

2.21
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.45

Water Solubility

Log S (ESOL):?

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

-1.56
Solubility 4.47 mg/ml ; 0.0272 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.

-0.96
Solubility 17.9 mg/ml ; 0.109 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

-2.48
Solubility 0.547 mg/ml ; 0.00333 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

Yes
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.

-6.85 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)

1.91

Application In Synthesis [ 3162-29-6 ]

* 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 [ 3162-29-6 ]

[ 3162-29-6 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 50-00-0 ]
  • [ 3162-29-6 ]
  • [ 51304-61-1 ]
  • N-<1-(3,4-(methylenedioxy)phenyl)propionyl>-4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride [ No CAS ]
  • 2
  • [ 3162-29-6 ]
  • [ 17823-69-7 ]
  • [ 114361-59-0 ]
  • 4
  • [ 3162-29-6 ]
  • safrole oxide [ No CAS ]
  • [ 6880-91-7 ]
  • 5
  • [ 3162-29-6 ]
  • [ 618-89-3 ]
  • 1-(1,3-benzodioxol-5-yl)-3-(3-bromophenyl)-propan-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydride; In dimethyl sulfoxide; at 15 - 23℃; for 16h;Inert atmosphere; A dry, 500-mL, three-necked flask is fitted with a Teflon-coated magnetic stirring bar, a rubber septum, a thermometer, and a reflux condenser to which is attached a T-tube connected to a source of pure nitrogen. The remaining joint of the T-tube is connected to a bubbling device so that the rate of nitrogen flow can be observed throughout of the reaction. The apparatus is arranged so that the flask may be cooled intermittently with a water bath. After the reaction vessel has been flushed with nitrogen a static nitrogen atmosphere is maintained in the reaction vessel for the remainder of the reaction. The flask is charged with ca. 60% dispersion of sodium hydride (5 g, 0.125 mole) in mineral oil (Note 1). The mineral oil is washed from the hydride with petroleum benzine 40/60 (3 x 40 ml.) (Note 2). The supernatant petroleum benzine layer is removed using a Luer-lock hypodermic syringe with a stainless-steel needle inserted through the rubber septum. The residual sodium hydride is mixed with 80 ml_ of dimethyl sulfoxide (Note 3), and the rubber septum is replaced with a pressure-equalizing dropping funnel. A solution of 16.4 g (0.1 mole) of 1-(1 ,3-benzodioxol-5- yl)ethanone (Note 4) and 26.9 g (0.125 mole) of <strong>[618-89-3]methyl 3-bromobenzoate</strong> (Note 5) in 60 mL of dimethyl sulfoxide is placed in the dropping funnel. The funnel is stoppered, stirring is begun and the contents of the flask are cooled in a water bath to 15 0C. The solution of 1- (1 ,3-benzodioxol-5-yl)ethanone and <strong>[618-89-3]methyl 3-bromobenzoate</strong> is added slowly so that hydrogen evolution is maintained at the controllable rate and the temperature did not rise above 20 0C over a period of 60 minutes (Note 6). After the addition is completed, the bath is removed, and the reaction mixture is stirred at room temperature (23 0C) for 15 hours. The resulting red-brown homogeneous reaction mixture is poured slowly into 500 mL of an ice and water containing 5 mL of 85% orthophosphoric acid (Note 7) with stirring. After 1 hour stirring the product is removed by filtration (Note 8), washed by suction filtration with water (2 x 100 mL), and vacuum dried to constant weight at 40 0C for 6 hours to give 34.4 g of the crude (Note 9) product. Recrystallization from 200 mL of 99.9% ethanol and 200 mL ethyl acetate (Note 10) and drying in vacuum to constant weight at 40 C for 6 hours gives 28.5 g (82% yield) of pure (Note 11) 1-(1 ,3-benzodioxol-5-yl)-3-(3-bromophenyl)propane-1 ,3-dione, m.p. 136-137 0C. The filtrate is concentrated under reduced pressure to a volume ca. 30 mL, the crystalline solid that separates is collected on a filter, washed by suction filtration with ethanol (2 x 10 mL) and vacuum dried to constant weight at 40 0C for 6 hours, yielding an additional crop (3.15 g) of the crude product. The crude product is recrystallized twice from 20 mL of 99.9% ethanol and 20 mL ethyl acetate and vacuum dried to constant weight at 40 CC for 6 hours to afford additional 1.8 g (5% yield) of pure 1-(1 ,3-benzodioxol-5-yl)-3-(3- bromophenyl)propane-1 ,3-dione (Note 12). The total yield of the product is 30.3 g (87%).2. Notes1. Sodium hydride, 57-63% oil dispersion, order number 13431 available from Alfa Aesar GmbH & Co KG, Karlsruhe was used. 2. Petroleum benzine GR for analysis boiling range 40-60 0C, order number 101775 from Merck KGaA, Darmstadt was used.3. The dimethyl sulfoxide GR for analysis, order number 102952 from Merck KGaA, Darmstadt was used without further purification. 4. 1-(1 ,3-Benzodioxol-5-yl)ethanone, 98%, order number A13597 available from Alfa Aesar GmbH & Co KG, Karlsruhe was used.5. Methyl 3-bromobenzoate, 98%+, order number A16174 available from Alfa Aesar GmbH & Co KG, Karlsruhe was used.6. A foaming is observed during the addition of the solution. The usage of mechanical stirrer and an antifoaming agent like polyethylene glycol dimethyl ether may be necessary at the upscaling.7. The orthophosphoric acid, 85% w/w aq. solution, GR for analysis, order number 100573 from Merck KGaA, Darmstadt was used.8. The pH-value of the reaction mixture is pH = 7. By acidification with additionally 15 ml_ ortophosphoric acid to pH = 2, 1.3 g of 3-bromobenzoic acid may be obtained.9. Purity of the product determined by HPLC is 96.3%.10. The ethanol 99.9% absolute GR for analysis, order number 100983, and ethyl acetate GR for analysis, order number 109623 available from Merck KGaA, Darmstadt was used. 1 1. Purity of the product determined by HPLC is 99.3%. Analytical HPLC is performed by using a Waters HPLC system with a Waters 996 Photodiode Array Detector. All separations involved a mobile phase of 0.1% v/v trifluoroacetic acid (TFA) in water (solvent A) and 0.1% v/v TFA in acetonitrile (solvent B) by using a reversed phase (RP) column Eurospher RP 18, 100 A, 5 μm, 250 x 4.6 mm at flow rates of 1 mL/min. The compound is dissolved in acetonitrile GR for HPLC at a concentration 1 mg/mL. Peaks with retention times (RT) 20.9 and 10.3 min are enol and keto forms respectively ...
  • 7
  • [ 3162-29-6 ]
  • [ 210488-54-3 ]
 

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 3162-29-6 ]

Ketones

Chemical Structure| 1835-14-9

A356046 [1835-14-9]

1-(4-Hydroxy-3-methoxyphenyl)propan-1-one

Similarity: 0.86

Chemical Structure| 4038-14-6

A716345 [4038-14-6]

(3,4-Dimethoxyphenyl)(phenyl)methanone

Similarity: 0.84

Chemical Structure| 63740-97-6

A184479 [63740-97-6]

1-(Benzo[d][1,3]dioxol-5-yl)butan-1-one

Similarity: 0.83

Chemical Structure| 2107-69-9

A120912 [2107-69-9]

5,6-Dimethoxy-2,3-dihydro-1H-inden-1-one

Similarity: 0.83

Chemical Structure| 6412-87-9

A116135 [6412-87-9]

6,7-Dihydro-5H-indeno[5,6-d][1,3]dioxol-5-one

Similarity: 0.82

Related Parent Nucleus of
[ 3162-29-6 ]

Other Aromatic Heterocycles

Chemical Structure| 63740-97-6

A184479 [63740-97-6]

1-(Benzo[d][1,3]dioxol-5-yl)butan-1-one

Similarity: 0.83

Chemical Structure| 6412-87-9

A116135 [6412-87-9]

6,7-Dihydro-5H-indeno[5,6-d][1,3]dioxol-5-one

Similarity: 0.82

Chemical Structure| 6500-65-8

A363298 [6500-65-8]

2-Methoxy-6,7,8,9-tetrahydrobenzocyclohepten-5-one

Similarity: 0.78

Chemical Structure| 7797-83-3

A233781 [7797-83-3]

Benzo[d][1,3]dioxole-4-carbaldehyde

Similarity: 0.77

Chemical Structure| 20351-79-5

A154905 [20351-79-5]

8-Methoxychroman-4-one

Similarity: 0.73