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Chemical Structure| 34136-57-7

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Product Details of [ 34136-57-7 ]

CAS No. :34136-57-7
Formula : C9H9N
M.W : 131.17
SMILES Code : N#CC1=CC=CC(CC)=C1
MDL No. :MFCD00045601
InChI Key :WEDBHNMGFLTQNC-UHFFFAOYSA-N
Pubchem ID :96692

Safety of [ 34136-57-7 ]

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

Computational Chemistry of [ 34136-57-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 40.93
TPSA ?

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

23.79 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.06
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

2.47
Log Po/w (WLOGP)?

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

2.12
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.

2.1
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

2.61
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.27

Water Solubility

Log S (ESOL):?

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

-2.59
Solubility 0.339 mg/ml ; 0.00259 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.

-2.61
Solubility 0.319 mg/ml ; 0.00243 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

-3.24
Solubility 0.0757 mg/ml ; 0.000577 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.

-5.35 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

2.0
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)

1.18

Application In Synthesis of [ 34136-57-7 ]

* 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.

  • Upstream synthesis route of [ 34136-57-7 ]

[ 34136-57-7 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 74-85-1 ]
  • [ 69113-59-3 ]
  • [ 34136-57-7 ]
YieldReaction ConditionsOperation in experiment
61% With (1,2-dimethoxyethane)dichloronickel(II); N,N,N,N,-tetramethylethylenediamine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; water; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; for 24 h; Schlenk technique; Sealed tube; Irradiation General procedure: Aryl-halide (0.2 mmol, 1 equiv.), Ir(dtbbpy)(ppy)2PF6 (1.8 mg, 0.002 mmol, 1 mol percent), NiCl2.glyme (4.4mg, 0.02 mmol, 10 mol percent), DMSO (2.0 mL) was added to a 10 mL schlenk flask equipped with a magnetic stirrer bar. This resulting mixture was sealed and degassed via vacuum evacuation and subsequent backfill with ethylene for three times. Then, N,N,N’,N’-tetramethylethylenediamine, TMEDA(60 μL, 2 equiv.), N,N-diisopropylethylamine, DIPEA (70 μL, 2 equiv.) and H2O (7.2 μL, 2 equiv.) were subsequently added in this order. The mixture was then irradiated with blue LED (2 meter strip, 18 W)with ethylene balloon for 24 hours at 80oC (Figure S1). The reaction was added water (30 mL) and extracted with ethyl acetate (10 mL) three times. Combined organic layer was successively washed with brine three times and dried over Na2SO4 and concentrated under reduced pressure. The residue was then subjected to flash column chromatography (hexane or hexane/ethyl acetate) to yield theproduct
References: [1] Chem, 2019, p. 192 - 203.
  • 2
  • [ 74-85-1 ]
  • [ 6952-59-6 ]
  • [ 34136-57-7 ]
YieldReaction ConditionsOperation in experiment
55% With (1,2-dimethoxyethane)dichloronickel(II); N,N,N,N,-tetramethylethylenediamine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; water; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; for 24 h; Schlenk technique; Sealed tube; Irradiation General procedure: Aryl-halide (0.2 mmol, 1 equiv.), Ir(dtbbpy)(ppy)2PF6 (1.8 mg, 0.002 mmol, 1 mol percent), NiCl2.glyme (4.4mg, 0.02 mmol, 10 mol percent), DMSO (2.0 mL) was added to a 10 mL schlenk flask equipped with a magnetic stirrer bar. This resulting mixture was sealed and degassed via vacuum evacuation and subsequent backfill with ethylene for three times. Then, N,N,N’,N’-tetramethylethylenediamine, TMEDA(60 μL, 2 equiv.), N,N-diisopropylethylamine, DIPEA (70 μL, 2 equiv.) and H2O (7.2 μL, 2 equiv.) were subsequently added in this order. The mixture was then irradiated with blue LED (2 meter strip, 18 W)with ethylene balloon for 24 hours at 80oC (Figure S1). The reaction was added water (30 mL) and extracted with ethyl acetate (10 mL) three times. Combined organic layer was successively washed with brine three times and dried over Na2SO4 and concentrated under reduced pressure. The residue was then subjected to flash column chromatography (hexane or hexane/ethyl acetate) to yield theproduct
References: [1] Chem, 2019, p. 192 - 203.
  • 3
  • [ 2725-82-8 ]
  • [ 557-21-1 ]
  • [ 34136-57-7 ]
YieldReaction ConditionsOperation in experiment
62% at 80℃; for 12 h; Commercially available 1-brom-3-ethyl-benzene (1.1 g), zinc cyanide (508 mg), tetrakis-(triphenylphospine)palladium (333 mg) were dissolved in dry toluene (8 mL), degassed and stirred at 80° C. in a sealed pressure tube under argon. After 12 h the mixture was concentrated to dryness. The remaining residues was purified by column chromatography (silica, cyclohexane/EtOAc, 95:5) to afford the title compound (470 mg; 62percent). [MH]+=132.
References: [1] Patent: US2006/173183, 2006, A1, . Location in patent: Page/Page column 82.
[2] Patent: US2005/272779, 2005, A1, . Location in patent: Page/Page column 57.
[3] Patent: WO2004/14881, 2004, A2, . Location in patent: Page 99.
  • 4
  • [ 557-21-1 ]
  • [ 2725-82-8 ]
  • [ 34136-57-7 ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; for 4 h; Inert atmosphere (Step 1)
A suspension of 1-bromo-3-ethylbenzene (2.00 g, 10.8 mmol), zinc cyanide (698 mg, 5.94 mmol) and tetrakis(triphenylphosphine)palladium (624 mg, 0.540 mmol) in DMF (20 mL) was stirred at 80° C. for 4 hrs. under an argon atmosphere.
The reaction mixture was concentrated under reduced pressure and ethanol was added to the concentrated residue.
The insoluble material was filtered off and the filtrate was concentrated to give 3-ethylbenzonitrile as a brown oil (1.07 g, 76percent).
References: [1] Patent: US2015/329556, 2015, A1, . Location in patent: Paragraph 1881-1882.
  • 5
  • [ 100-41-4 ]
  • [ 25309-65-3 ]
  • [ 34136-57-7 ]
References: [1] ACS Catalysis, 2019, vol. 9, # 3, p. 1979 - 1984.
  • 6
  • [ 544-97-8 ]
  • [ 28188-41-2 ]
  • [ 34136-57-7 ]
  • [ 620-22-4 ]
References: [1] Journal of Organic Chemistry, 1993, vol. 58, # 24, p. 6908 - 6910.
  • 7
  • [ 60-29-7 ]
  • [ 100-47-0 ]
  • [ 34136-57-7 ]
References: [1] Journal of the Chemical Society, 1949, p. Spl. 229.
  • 8
  • [ 587-02-0 ]
  • [ 34136-57-7 ]
References: [1] Justus Liebigs Annalen der Chemie, 1918, vol. 417, p. 87.
  • 9
  • [ 7446-70-0 ]
  • [ 60-29-7 ]
  • [ 100-47-0 ]
  • [ 34136-57-7 ]
References: [1] Journal of the Chemical Society, 1949, p. Spl. 229.
 

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