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Chemical Structure| 5137-55-3 Chemical Structure| 5137-55-3

Structure of 5137-55-3

Chemical Structure| 5137-55-3

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Product Details of [ 5137-55-3 ]

CAS No. :5137-55-3
Formula : C25H54ClN
M.W : 404.16
SMILES Code : CCCCCCCC[N+](CCCCCCCC)(C)CCCCCCCC.[Cl-]
MDL No. :MFCD00011862
InChI Key :XKBGEWXEAPTVCK-UHFFFAOYSA-M
Pubchem ID :21218

Safety of [ 5137-55-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H314-H360-H373-H410
Precautionary Statements:P202-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Class:8(6.1)
UN#:2923
Packing Group:

Computational Chemistry of [ 5137-55-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 27
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 21
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 130.52
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.

-0.41
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

5.53
Log Po/w (WLOGP)?

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

5.52
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.

2.99
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

8.69
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.46

Water Solubility

Log S (ESOL):?

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

-4.44
Solubility 0.0146 mg/ml ; 0.000036 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-5.29
Solubility 0.00207 mg/ml ; 0.00000513 mol/l
Class?

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

Moderately 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

-9.93
Solubility 0.0000000474 mg/ml ; 0.0000000001 mol/l
Class?

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

Poorly 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

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.

-4.84 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

1.0
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

3.0
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<3.0
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)

3.24

Application In Synthesis of [ 5137-55-3 ]

* 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 [ 5137-55-3 ]

[ 5137-55-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 13338-63-1 ]
  • [ 5137-55-3 ]
  • [ 16588-34-4 ]
  • [ 162705-20-6 ]
YieldReaction ConditionsOperation in experiment
48.5% With sodium hydroxide; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; water; Step 1 Preparation of (Z)-3-(3-nitro-4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile 5.0 g of 3-nitro-4-chlorobenzaldehyde, 5.6 g of <strong>[13338-63-1]3,4,5-trimethoxyphenylacetonitrile</strong>, 1.3 g of sodium hydroxide and 500 mg of trioctylmethylammonium chloride were dissolved in 10 ml of water and 50 ml of dichloromethane. The mixture was stirred vigorously for 3 hours at room temperature. The ice water was added to the mixture and the mixture was extracted with dichloromethane three times and dried over anhydrous sodium sulfate. The organic layer was concentrated and the residue was crystallized from ethyl acetate to give 4.9 g of the intended compound. The yield was 48.5%. 1 H-NMR(CDCl3): 8.23 (1H, J=2.1), 8.15 (1H, dd, J=2.1, 8.4), 7.67 (1H, d, J=8.4), 7.41 (1H, s), 6.88 (2H, s), 3.94 (6H, s), 3.91 (3H, s), mass spectrum (m/z): 374 (M+); melting point 198-199 C.
  • 2
  • [ 31680-07-6 ]
  • [ 13338-63-1 ]
  • [ 5137-55-3 ]
  • [ 162705-18-2 ]
YieldReaction ConditionsOperation in experiment
14.1% With sodium hydroxide; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; water; Step 1 Preparation of (Z)-3-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile 5.0 g of 3-nitro-4-methylbenzaldehyde, 6.27 g of <strong>[13338-63-1]3,4,5-trimethoxyphenylacetonitrile</strong>, 1.44 g of sodium hydroxide and 500 mg of trioctylmethylammonium chloride were dissolved in 25 ml of water and 500 ml of dichloromethane. The mixture was stirred vigorously for 3 hours at room temperature. The ice water was added to the mixture and the mixture was extracted with dichloromethane three times and dried over anhydrous sodium sulfate. The organic layer was concentrated and the residue was purified by silica gel column chromatography (dichloromethane) to give 1.5 g of the intended compound. The yield was 14.1%. 1 H-NMR(CDCl3): 8.35 (1H, J=1.5), 8.18 (1H, dd, J=1.5, 8.1), 7.47 (1H, d, J=8.1), 7.44 (1H, s), 6.88 (2H, s), 3.95 (6H, s), 3.90 (3H, s), 2.67 (3H, s); mass spectrum (m/z): 354 (M+); melting point 162-163 C.
  • 3
  • [ 126-33-0 ]
  • [ 99-54-7 ]
  • [ 5137-55-3 ]
  • [ 350-30-1 ]
YieldReaction ConditionsOperation in experiment
85% With potassium fluoride;AlCl3; EXAMPLE 1 A mixture of 87 g (1.5 mol) of potassium fluoride and 250 g of tetramethylene sulphone in a glass reaction vessel was subjected to incipient distillation for the removal of water until 25 g of tetramethylene sulphone had passed over. 192 g of 3,4-dichloro-nitrobenzene, 10 g (0.025 mol) of methyl -trioctyl-ammonium chloride and 1.65 g (0.0125 mol) of AlCl3 were then added and the was 97% (determined by gas chromatography). The reaction mixture was then worked up by distillation. 149 g of 3-chloro-4-fluoro-nitrobenzene having a boiling point of 92-93 C. at 10 mbar were obtained. This corresponds to a yield of 85% of theory.
  • 4
  • Reactive Red 120 [ No CAS ]
  • [ 5397-31-9 ]
  • [ 5137-55-3 ]
  • C66H72N16O22S6(6-)*6C25H54N(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 1 Red Complex from Reactive Red 120, 3-(2-Ethylhexyloxyl)Propylamine and Aliquat 336 (0102) 14.7 gram of Reactive Red 120 (50% dye content), 2.81 gram of 3-(2-ethylhexyloxy)-propyl amine, 0.84 gram of sodium bicarbonate and 30 mL of water were charged into a reactor equipped with agitator, temperature control and condenser. The mixture was heated to 80 C. for several hours until the starting material Reactive Red 120 was gone as monitored by TLC. Then 12.1 gram of Aliquat 336 was added slowly and stirred at 80 C. for one hour. The reaction mixture was cooled to room temperature and dark red solid was precipitated. The solid was filtered and washed with water to remove salts. 24.1 gram of red solid with color value of 12.8 was obtained.
 

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