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Chemical Structure| 40307-11-7 Chemical Structure| 40307-11-7

Structure of 1-Ethyl-4-ethynylbenzene
CAS No.: 40307-11-7

Chemical Structure| 40307-11-7

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Synonyms: 4-Ethylphenylacetylene

4.5 *For Research Use Only !

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Product Citations

Product Citations

Krzysztof Kuciński ; Grzegorz Hreczycho ;

Abstract: Commercially available and inexpensive potassium bis(trimethylsilyl)amide (KHMDS) serves as an efficient transition metal-free catalyst for the catalytic sp C−H silylation of several terminal alkynes including two pharmaceuticals. Overall, the presented system allows the synthesis of various attractive silylacetylenes under mild conditions, making this approach an environmentally benign and sustainable alternative to existing synthetic solutions.

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Product Details of [ 40307-11-7 ]

CAS No. :40307-11-7
Formula : C10H10
M.W : 130.19
SMILES Code : C#CC1=CC=C(CC)C=C1
Synonyms :
4-Ethylphenylacetylene
MDL No. :MFCD00173887
InChI Key :ZNTJVJSUNSUMPP-UHFFFAOYSA-N
Pubchem ID :142425

Safety of [ 40307-11-7 ]

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

Computational Chemistry of [ 40307-11-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.2
Num. rotatable bonds 1
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 44.15
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.5
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

3.51
Log Po/w (WLOGP)?

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

2.31
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.

4.38
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

3.29
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.2

Water Solubility

Log S (ESOL):?

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

-3.24
Solubility 0.0755 mg/ml ; 0.00058 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.

-3.19
Solubility 0.0834 mg/ml ; 0.00064 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

-3.23
Solubility 0.076 mg/ml ; 0.000583 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

Low
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.

-4.6 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

1.0
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

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<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)

1.51

Application In Synthesis of [ 40307-11-7 ]

* 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.

  • Downstream synthetic route of [ 40307-11-7 ]

[ 40307-11-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 40307-11-7 ]
  • [ 175278-00-9 ]
  • C17H13F3O [ No CAS ]
  • 2
  • [ 40307-11-7 ]
  • [ 2632-14-6 ]
  • 3
  • [ 40307-11-7 ]
  • [ 163622-50-2 ]
  • C16H14N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 120℃; for 0.5h;Microwave irradiation; Inert atmosphere; General procedure: Compound 6 (3.85 mmol), Pd(PPh3)4 (0.077 mmol), CuI (0.77 mmol), AmberliteIR-67, ethynylbenzene or 4-ethylphenylacetylene (4.6 mmol) in 30 mL of THF was heated for 30 min at 120 C in the microwave. After cooling to ambient temperature, the reaction mixture was filtered through a pad of Celite. The solvent was removed in vacuo, and the crude product was purified by flash column chromatography on silica gel (DCM/MeOH= 30/1) to give compound 7i or 7ii as a yellow solid.19 To a solution of 7i or 7ii (7.16 mmol) in DMF (20 mL) was added potassium carbonate (8.6 mmol) followed by 4-bromo-1-butene (8.6 mmol). After stirring at 30 C for 6 h, EtOAc (300 mL) was then added and the solution was washed three times with water. The combined organic phase was dried over Na2SO4 and concentrated. The residue was subjected to column chromatography on silica gel (DCM/MeOH= 30:1) to give compound 8i (83%) or 8ii (~56% yield over two steps). For 8i: Yellow solid; 1H NMR (300 MHz, CDCl3) delta 8.31 (s, 1H), 7.51 - 7.49 (m, 2H), 7.43 - 7.33 (m, 3H), 7.22 (s, 1H), 5.90 (s, 2H), 5.79 - 5.72 (m, 1H), 5.08 (t, J = 16.2, 10.8 Hz, 2H), 4.26 (t, J = 7.2 Hz, 2H), 2.60 (q, J = 6.9 Hz, 2H); For 8ii: Yellow solid; 1H NMR (300 MHz, CDCl3) delta 8.31 (s, 1H), 7.43 (d, J = 7.8 Hz, 2H), 7.20 - 7.18 (m, 3H), 5.92 (s, 2H), 5.82 - 5.73 (m, 1H), 5.17 (t, J =17.1, 9.9 Hz, 2H), 4.24 (t, J = 6.9 Hz, 2H), 2.75 - 2.52 (m, 4H), 1.24 (t, J = 7.5 Hz, 3H).
  • 4
  • [ 40263-57-8 ]
  • [ 40307-11-7 ]
  • 2-(4-ethylphenyl)furo[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With potassium phosphate; C43H36N4O4Pd; In dimethylsulfoxide-d6; at 120℃; for 10h; General procedure: In a typical run, performed in air, a 25 mL of round bottom askwas charged with a mixture of 2-iodophenol (0.50 mmol), terminalalkyne (0.60 mmol), and K3PO4 (1.00 mmol). A palladium complex(2a or 2b, 0.0005 mmol) was added to the mixture, followed byDMSO (ca. 2 mL) as a solvent, and then the reaction mixture washeated (either at 90C or at 120C) for 10 h. The reaction mixturewas cooled to room temperature, and water (ca. 20 mL) was added.The resulting mixture was extracted with EtOAc (ca. 50 mL). Theorganic layer was further extracted with EtOAc (ca. 2 20 mL). Theorganic layers were combined and vacuum dried to obtain a crudeproduct that was subsequently puried by column chromatog-raphy. The obtained benzofuran derivatives (3aa3ap) were char-acterized by NMR and Mass spectroscopy (See SupportingInformation Figures S4-S23).
 

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