Home Cart Sign in  
Chemical Structure| 1068-90-2 Chemical Structure| 1068-90-2

Structure of Diethyl acetamidomalonate
CAS No.: 1068-90-2

Chemical Structure| 1068-90-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

Synonyms: Diethyl 2-acetamidomalonate

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

  • {[ item.pr_size ]}

In Stock

- +

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

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 1068-90-2 ]

CAS No. :1068-90-2
Formula : C9H15NO5
M.W : 217.22
SMILES Code : O=C(OCC)C(NC(C)=O)C(OCC)=O
Synonyms :
Diethyl 2-acetamidomalonate
MDL No. :MFCD00009146
InChI Key :ISOLMABRZPQKOV-UHFFFAOYSA-N
Pubchem ID :14041

Safety of [ 1068-90-2 ]

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

Computational Chemistry of [ 1068-90-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 0
Fraction Csp3 0.67
Num. rotatable bonds 8
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 50.95
TPSA ?

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

81.7 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.37
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

0.32
Log Po/w (WLOGP)?

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

-0.38
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.

-0.08
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

0.34
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.51

Water Solubility

Log S (ESOL):?

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

-0.86
Solubility 30.0 mg/ml ; 0.138 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.

-1.6
Solubility 5.47 mg/ml ; 0.0252 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

-1.29
Solubility 11.2 mg/ml ; 0.0518 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.

-7.4 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

0.0
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

2.0 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<2.0
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)

1.93

Application In Synthesis of [ 1068-90-2 ]

* 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 [ 1068-90-2 ]

[ 1068-90-2 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 6414-69-3 ]
  • [ 1068-90-2 ]
  • [ 6969-27-3 ]
  • 2
  • [ 192702-01-5 ]
  • [ 1068-90-2 ]
  • [ 14937-92-9 ]
  • 3
  • [ 3290-06-0 ]
  • [ 1068-90-2 ]
  • [ 128833-97-6 ]
  • 4
  • [ 85482-13-9 ]
  • [ 1068-90-2 ]
  • [ 128833-95-4 ]
  • 5
  • [ 107-02-8 ]
  • [ 16732-66-4 ]
  • [ 1068-90-2 ]
  • [ 75816-17-0 ]
  • 8
  • [ 71831-21-5 ]
  • [ 1068-90-2 ]
  • [ 114791-23-0 ]
  • 9
  • [ 143-15-7 ]
  • [ 1068-90-2 ]
  • [ 35237-37-7 ]
  • 10
  • [ 104-21-2 ]
  • [ 1068-90-2 ]
  • [ 53612-87-6 ]
  • 11
  • [ 188187-03-3 ]
  • [ 1068-90-2 ]
  • [ 845552-89-8 ]
YieldReaction ConditionsOperation in experiment
Example 28 1 - [ (5-CHLORO-1, 2,3, 4-tetrahydroisoquinolin-3-yl) METHYL]-1-METHYL-1, 2- dihydrospiro [indole-3, 4'-piperidine] (A) 5-CHLORO-L-OXO-1, 2,3, 4-tetrahydroisoquinoline-3-carboxylic acid To a stirred suspension of 3-chloro-2-methylbenzoic acid (10.00 g, 58.6 mmol) in methanol (100 mL) was added dropwise thionyl chloride (8.5 mL, 117.2 mmol) at 0 C. The reaction mixture was refluxed for 2 h. After cooling down to room temperature, the reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (300 ML), washed with 1N NaOH solution (100 mL), water (100 mL) and brine (100 ML), dried (NA2S04), filtered, and concentrated to give 10.86 g of methyl ester as colorless oil. A mixture of this ester (10.80 g, 58.5 mmol), N-bromosuccinimide (10.45 g, 64.4 mmol), and benzoyl peroxide (0.71 g, 2.9 mmol) in carbon tetrachloride (70 mL) was refluxed for 3 h. After cooling down to room temperature, the reaction mixture was filtered and the filtrate wad concentrated to give 16.30 g of <strong>[188187-03-3]methyl 3-chloro-2-bromomethylbenzoate</strong> as a colorless oil. To a stirred suspension of NaH (2.45 g, 61.3 mmol) in DMF (50 mL) was added dropwise a solution of diethyl acetamidomalonate (12.10 g, 55.7 mmol) in DMF (50 mL) at room temperature. After 15 min stirreing, a solution of methyl 3-chloro-2- bromomethylbenzoate (16.3 g, 58. 5 mmol) in DMF (50 mL) at room temperature. After 18 h stirring, the reaction mixture was concentrated. The residue was dissolved in ethyl acetate (800 ML), washed with water (200 mL x 2) and brine (200 mL), dried (NA2S04), filtered, and concentrated to give 21.5 g of yellow solid, which was purified by silica gel column chromatography (hexane/ethyl acetate: 2/1 to 111) to afford 14.33 g (64.3 %) of coupling product as a white solid. A mixture of this solid (13.90 g, 34.7 mmol) and 47 % HBr (160 mL) was refluxed for 24 h. After cooling down to room temperature, the solid formed was collected by filtration and dried togive 6.16 g (78.6 %) of title compound as a cream color solid. LHNMR (300MHZ, DMSO-D6) O8. 26 (1H, d, J = 4. 0 HZ), 7.85 (1H, dd, J = 1.1, 7.7 Hz), 7.64 (1H, dd, J = 1. 3, 8. 1 HZ), 7.39 (1H, dd, J = 7. 9,7. 9 HZ), 4.34-4. 28 (1H, m), 3.42-3. 36 (1H, overlapped with water peak at 3.36 ppm), 3.26 (1H, dd, J = 6.8, 16.9 Hz).
  • 12
  • [ 3970-21-6 ]
  • [ 1068-90-2 ]
  • [ 35364-79-5 ]
  • [ 1337915-77-1 ]
  • [ 1337915-78-2 ]
  • 13
  • [ 57310-39-1 ]
  • [ 1068-90-2 ]
  • diethyl 2-acetamido-2-(3-bromo-4-chlorobenzyl)malonate [ No CAS ]
 

Historical Records

Categories

Pharmaceutical Intermediates of
[ 1068-90-2 ]

4-Chlorokynurenine Intermediates

Chemical Structure| 703-82-2

[703-82-2]

6-Chloro-1H-indole-3-carbaldehyde

Telcagepant Related Intermediates

Chemical Structure| 127474-54-8

[127474-54-8]

(R)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid

Chemical Structure| 6298-19-7

[6298-19-7]

2-Chloropyridin-3-amine

Chemical Structure| 452-58-4

[452-58-4]

2,3-Diaminopyridine

Chemical Structure| 97-51-8

[97-51-8]

2-Hydroxy-5-nitrobenzaldehyde

Ticagrelor Intermediates

Chemical Structure| 274693-55-9

[274693-55-9]

2-(((3aR,4S,6R,6aS)-6-Amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol

Chemical Structure| 51779-32-9

[51779-32-9]

Di-tert-butyl iminodicarboxylate

Chemical Structure| 34036-07-2

[34036-07-2]

3,4-Difluorobenzaldehyde

Chemical Structure| 145783-15-9

[145783-15-9]

4,6-Dichloro-2-(propylthio)pyrimidin-5-amine

Similar Product of
[ 1068-90-2 ]

Chemical Structure| 92877-34-4

A987324 [92877-34-4]

Diethyl acetamidomalonate-15N

Reason: Stable Isotope