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Chemical Structure| 17945-54-9 Chemical Structure| 17945-54-9

Structure of 17945-54-9

Chemical Structure| 17945-54-9

Ethyl 3-(benzylamino)-3-methylbutanoate

CAS No.: 17945-54-9

4.5 *For Research Use Only !

Cat. No.: A176964 Purity: 95%

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Product Details of [ 17945-54-9 ]

CAS No. :17945-54-9
Formula : C14H21NO2
M.W : 235.32
SMILES Code : CC(C)(NCC1=CC=CC=C1)CC(OCC)=O
MDL No. :MFCD18206360
InChI Key :AYVCXYHRYDQWIC-UHFFFAOYSA-N
Pubchem ID :288946

Safety of [ 17945-54-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 17945-54-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 17
Num. arom. heavy atoms 6
Fraction Csp3 0.5
Num. rotatable bonds 7
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 69.18
TPSA ?

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

38.33 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.92
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

2.1
Log Po/w (WLOGP)?

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

2.36
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.

2.51
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

2.82
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.54

Water Solubility

Log S (ESOL):?

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

-2.42
Solubility 0.892 mg/ml ; 0.00379 mol/l
Class?

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

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.54
Solubility 0.686 mg/ml ; 0.00292 mol/l
Class?

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

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

-4.57
Solubility 0.00633 mg/ml ; 0.0000269 mol/l
Class?

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

Moderately 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

Yes
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.

-6.24 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

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)

1.73

Application In Synthesis of [ 17945-54-9 ]

* 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 [ 17945-54-9 ]

[ 17945-54-9 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 17945-54-9 ]
  • [ 17945-55-0 ]
YieldReaction ConditionsOperation in experiment
65% Step 2 3-Benzylamino-3-methyl-1-butanol To a solution of <strong>[17945-54-9]ethyl 3-benzylamino-3-methylbutyrate</strong> (7.35 g, 31.2 mmol) in THF (150 mL) was added LiAlH4 (2.40 g, 63.2 mmol) portionwise at 0 C. for 0.5 h, and the mixture was stirred at room temperature for 5 h. The mixture was cooled on iced-water bath, then dropped a little water. The mixture was diluted with ethyl acetate, then dried over anhydrous Na2SO4, filtered, and then concentrated in vacuo. Flash chromatography (EtOAc:MeOH=5:1) of the residue gave 3-benzylamino-3-methyl-1-butanol as a pale yellow oil (3.91 g, 65%). 1H-NMR (400 MHz, CDCl3) delta 1.26 (6H, s), 1.66 (2H, t, J=5.5 Hz), 3.76 (2H, s), 3.88 (2H, t, J=5.5 Hz), 7.22-7.35 (5H, m).
  • 2
  • [ 17945-54-9 ]
  • [ 100-39-0 ]
  • [ 17945-64-1 ]
  • 3
  • [ 638-10-8 ]
  • [ 100-46-9 ]
  • [ 17945-54-9 ]
YieldReaction ConditionsOperation in experiment
21% In ethanol; for 24.0h;Heating / reflux; Step 1 Ethyl 3-benzylamino-3-methylbutyrate A solution of ethyl 3,3-dimethylacrylate (19.3 g, 0.151 mol) in EtOH (150 mL) was added benzylamine (16.2 g, 0.151 mol) and refluxed for 24 h. The reaction mixture was concentrated in vacuo. The distillation of the residue gave ethyl 3-benzylamino-3-methylbutyrate as a colorless oil (7.48 g, 21%). 1H-NMR (400 MHz, CDCl3) delta 1.24 (6H, s), 1.26 (3H, t, J=7.3 Hz), 2.51 (2H, s), 3.72 (2H, s), 4.14 (2H, q, J=7.3 Hz), 7.20-7.38 (5H, m).
  • 5
  • [ 17945-54-9 ]
  • [ 17945-65-2 ]
  • 6
  • [ 17945-54-9 ]
  • [ 721385-55-3 ]
  • 7
  • [ 17945-54-9 ]
  • [ 17945-67-4 ]
  • 8
  • 4-chloroacetyl-7-hydroxyindole-2-carboxylic acid ethyl ester [ No CAS ]
  • [ 17945-54-9 ]
  • 4-[N-benzyl-N-(2-ethoxycarbonyl-1,1-dimethylethyl)aminoacetyl]-7-hydroxyindole-2-carboxylic acid ethyl ester hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
A. Under the conditions of Example 28, 2.57 g of 4-chloroacetyl-7-hydroxyindole-2-carboxylic acid ethyl ester is reacted with 2.35 g of <strong>[17945-54-9]3-benzylamino-3-methylbutyric acid ethyl ester</strong> and worked up, yielding 0.75 g of 4-[N-benzyl-N-(2-ethoxycarbonyl-1,1-dimethylethyl)aminoacetyl]-7-hydroxyindole-2-carboxylic acid ethyl ester hydrochloride, decomposition point 210-212 C.
 

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