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Chemical Structure| 4086-73-1 Chemical Structure| 4086-73-1

Structure of 4086-73-1

Chemical Structure| 4086-73-1

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Product Details of [ 4086-73-1 ]

CAS No. :4086-73-1
Formula : C13H22ClN
M.W : 227.77
SMILES Code : CCCCCCCC[N+]1=CC=CC=C1.[Cl-]
MDL No. :MFCD08458952
InChI Key :OVIYAWWBKPWUOH-UHFFFAOYSA-M
Pubchem ID :77708

Safety of [ 4086-73-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Computational Chemistry of [ 4086-73-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 6
Fraction Csp3 0.62
Num. rotatable bonds 7
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 69.54
TPSA ?

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

3.88 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

-2.77
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

-1.12
Log Po/w (WLOGP)?

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

0.34
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.

3.21
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

3.43
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.62

Water Solubility

Log S (ESOL):?

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

-0.38
Solubility 94.8 mg/ml ; 0.416 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.

1.53
Solubility 7710.0 mg/ml ; 33.8 mol/l
Class?

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

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

-4.43
Solubility 0.00854 mg/ml ; 0.0000375 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

Low
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

Yes
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.

-8.48 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

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<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)

1.46

Application In Synthesis of [ 4086-73-1 ]

* 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 [ 4086-73-1 ]

[ 4086-73-1 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 110-86-1 ]
  • [ 111-85-3 ]
  • [ 4086-73-1 ]
YieldReaction ConditionsOperation in experiment
52% at 85℃; for 24.0h; Pyridine (0.4 mol) and 1-chlorobutane (or 1-chlorohexane or 1-chlorooctane) (0.4 mol) were placed into a 250 cm3 round bottom flask equipped with an electric heat-jacket and vigorously stirred using a magnetic stirrer for 24 h; at 75 C ([C4-py]Cl) or 85 C ([C6-py]Cl and [C8-py]Cl). [C4-py]Cl and [C6-py]Cl, obtained in the form of the white solids directly after synthesis, were washed in Schlenk apparatus with diethyl ether (4 × 50 cm3) and hexane (4 × 50 cm3) and dried by nitrogen stream. [C8-py]Cl obtained in the form of a transparent yellow, dense, and viscous liquid was cooled to room temperature and extracted by turns with diethyl ether (4 × 50 cm3) and hexane (4 × 50 cm3) and dried by nitrogen stream. Yields: 77% for [C4-py]Cl, 39% for [C6-py]Cl, and 52% for [C8-py]Cl.
  • 2
  • [ 110-86-1 ]
  • [ 111-64-8 ]
  • [ 40089-91-6 ]
  • [ 4086-73-1 ]
  • 5
  • [ 865-47-4 ]
  • [ 4086-73-1 ]
  • [ 124-63-0 ]
  • [ 24424-99-5 ]
YieldReaction ConditionsOperation in experiment
90% With pyridine; sulfuric acid; sodium hydrogencarbonate; In hexane; water; EXAMPLE 8 In a one liter four-necked flask equipped with a stirrer, a thermometer, a gas-inlet tube and a dropping funnel which had been replaced with nitrogen, potassium tert.-butoxide (112.1 g, 1 mole) and hexane (600 ml) were charged. Through a mixture in the flask, carbon dioxide gas (26.9 liters, 1.2 moles) was bubbled at -10 to 0 C. over one hour while stirring. Then, to the resulting slurry form mixture, N-n-octylpyridinium chloride (11.4 g, 0.05 moles) and pyridine (11.4 g) were charged at 10 to -5 C. and then methanesulfonyl chloride (57.3 g, 0.5 mole) was dropwise added at the same temperature, followed by stirring at the same temperature for one hour. After the reaction, 5% sulfuric acid (250 ml) was added to the reaction mixture, and the mixture was stirred for 30 minutes, kept standing and separated. The resulting organic layer was washed with a 5% aqueous solution of sodium bicarbonate and water successively and concentrated under reduced pressure at 35 to 40 C. to obtain colorless liquid di-tert.-butyl dicarbonate (98.2 g). Yield, 90%. This product was analyzed by gas chromatography to find that a purity was 99.3%.
  • 6
  • [ 4086-73-1 ]
  • [ 124-63-0 ]
  • [ 865-48-5 ]
  • [ 24424-99-5 ]
YieldReaction ConditionsOperation in experiment
83% With sulfuric acid; sodium hydrogencarbonate; In hexane; water; EXAMPLE 20 In a one liter four-necked flask equipped with a stirrer, a thermometer, a gas-inlet tube and a dropping funnel which had been replaced with nitrogen, sodium tert.-butoxide (96.1 g, 1 mole) and hexane (600 ml) were charged. Through a mixture in the flask, carbon dioxide gas (26.9 liters, 1.2 moles) was bubbled at -10 to 0 C. over one hour while stirring. Then, to the resulting slurry form mixture, N-n-octylpyridinium chloride (11.4 g, 0.05 mole) was charged at -10 to -5 C. and then methanesulfonyl chloride (57.3 g, 0.5 mole) was dropwise added at the same temperature, followed by stirring at the same temperature for 3 hours. After the reaction, 5% sulfuric acid (250 ml) was added to the reaction mixture, and the mixture was stirred for 30 minutes, kept standing and separated. The resulting organic layer was washed with a 5% aqueous solution of sodium bicarbonate and water successively and concentrated under reduced pressure at 35 to 40 C. to obtain colorless liquid di-tert.-butyl dicarbonate (90.6 g). Yield, 83%. This product was analyzed by gas chromatography to find that a purity was 99.4%.
  • 7
  • [ 68494-08-6 ]
  • [ 4086-73-1 ]
  • copper dichloride [ No CAS ]
  • bis(N-n-octyl pyridinium) bis(2-thione-1,3-dithiole-4,5-dithiolato)copper(II) [ No CAS ]
  • 8
  • aluminum (III) chloride [ No CAS ]
  • [ 4086-73-1 ]
  • [ 945632-00-8 ]
YieldReaction ConditionsOperation in experiment
at 20℃;Inert atmosphere; To the obtained 1-alkylpyridinium chlorides, the equimolar amount of aluminium chloride was added stepwise carefully under a nitrogen atmosphere at room temperature. The mixtures were magnetically stirred and the transparent, slightly brownish chloroaluminate ionic liquids were obtained.
  • 9
  • [ 4086-73-1 ]
  • [ 1197813-87-8 ]
YieldReaction ConditionsOperation in experiment
Step 2: In a glass reactor equipped with a magnetic stirring mechanism 1.14 g (5 mmol) <strong>[4086-73-1]N-octylpyridinium chloride</strong>, obtained from step 1, was introduced and 1.22 g (7.5 mmol) of iron chloride (III) anhydrous was added. The mixture was stirred for 20 minutes at room temperature under an inert atmosphere. A dark red liquid was obtained. The spectroscopic characterizations (1H and 13C NMR) confirm the following chemical structure:
  • 10
  • [ 151-21-3 ]
  • [ 4086-73-1 ]
  • N-octyl pyridinium dodecyl sulphate [ No CAS ]
  • 11
  • [ 4086-73-1 ]
  • [ 90076-65-6 ]
  • 1-(n-octyl)pyridinium bis(trifluoromethylsulfonyl)imide [ No CAS ]
  • 12
  • [ 4086-73-1 ]
  • C13H22N(1+)*F(1-) [ No CAS ]
  • 13
  • aluminum (III) chloride [ No CAS ]
  • [ 4086-73-1 ]
  • C13H22N(1+)*Al2Cl7(1-) [ No CAS ]
 

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