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Chemical Structure| 20101-92-2

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Product Details of [ 20101-92-2 ]

CAS No. :20101-92-2
Formula : C8H8ClNO
M.W : 169.61
SMILES Code : O=C(N)CC1=CC=C(Cl)C=C1
MDL No. :MFCD02380705
Boiling Point : No data available
InChI Key :BFYGROHYLCZLGS-UHFFFAOYSA-N
Pubchem ID :643286

Safety of [ 20101-92-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317
Precautionary Statements:P280

Computational Chemistry of [ 20101-92-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 2
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 44.13
TPSA ?

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

43.09 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.43
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

1.47
Log Po/w (WLOGP)?

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

1.37
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.

1.84
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

1.94
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.61

Water Solubility

Log S (ESOL):?

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

-2.09
Solubility 1.38 mg/ml ; 0.00814 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.

-1.98
Solubility 1.77 mg/ml ; 0.0104 mol/l
Class?

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

Very 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

-3.0
Solubility 0.169 mg/ml ; 0.000998 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.

-6.29 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

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)

1.09

Application In Synthesis of [ 20101-92-2 ]

* 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 [ 20101-92-2 ]

[ 20101-92-2 ] Synthesis Path-Downstream   1~35

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  • 4-chloromethylene-morpholinium; perchlorate [ No CAS ]
  • 5-(4-chloro-phenyl)-2-(4-methoxy-phenyl)-6-morpholin-4-ylmethyleneamino-[1,3]thiazinylium; perchlorate [ No CAS ]
  • 5
  • [ 14294-10-1 ]
  • [ 20101-92-2 ]
  • 4-chloromethylene-morpholinium; perchlorate [ No CAS ]
  • 5-(4-chloro-phenyl)-2-morpholin-4-yl-6-morpholin-4-ylmethyleneamino-[1,3]thiazinylium; perchlorate [ No CAS ]
  • 6
  • [ 7204-46-8 ]
  • [ 20101-92-2 ]
  • 4-chloromethylene-morpholinium; perchlorate [ No CAS ]
  • 5-(4-chloro-phenyl)-2-diethylamino-6-morpholin-4-ylmethyleneamino-[1,3]thiazinylium; perchlorate [ No CAS ]
  • 7
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  • [ 684-16-2 ]
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  • 8
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  • 4-chloromethylene-morpholinium; perchlorate [ No CAS ]
  • [ 4714-69-6 ]
  • 5-(4-chloro-phenyl)-2-(4-dimethylamino-phenyl)-6-morpholin-4-ylmethyleneamino-[1,3]thiazinylium; perchlorate [ No CAS ]
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  • [ 50-00-0 ]
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  • 7-chloro-1,2,3,4-tetrahydroisoquinolin-3-one [ No CAS ]
  • 11
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  • N,N'-methylenebis(4-chlorophenylacetamide) [ No CAS ]
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  • 13
  • [ 20026-96-4 ]
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  • 3,4-Bis-(4-chloro-phenyl)-3H-pyridine-2,6-dione [ No CAS ]
  • 14
  • [ 3533-13-9 ]
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  • 15
  • [ 16616-42-5 ]
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  • 17
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  • 3-(4-Chloro-phenyl)-4-(2-chloro-phenyl)-3H-pyridine-2,6-dione [ No CAS ]
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  • 19
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  • [ 1022-37-3 ]
  • [ 4843-42-9 ]
  • 3-(4-Chloro-phenyl)-4-naphthalen-1-yl-3H-pyridine-2,6-dione [ No CAS ]
  • 20
  • [ 20101-92-2 ]
  • [ 58686-68-3 ]
  • 3-(4-Chloro-phenyl)-4-(3-chloro-phenyl)-3H-pyridine-2,6-dione [ No CAS ]
  • 21
  • [ 20101-92-2 ]
  • [ 55723-88-1 ]
  • 3-(4-Chloro-phenyl)-4-naphthalen-2-yl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one [ No CAS ]
  • 22
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  • 33
  • [ 26069-13-6 ]
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  • [ 20101-92-2 ]
  • 2-p-chlorobenzoyl-exo-11-p-chlorophenylacetamido-4,endo-11-dimethyl-3-azatricyclo<5.3.1.04,9>undec-2-ene [ No CAS ]
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  • [ 20101-92-2 ]
YieldReaction ConditionsOperation in experiment
100% With Acetaldehyde oxime; In methanol; at 65℃; for 4h; General procedure: A typical reaction was carried out in a 10 mL flask. Benzonitrile (2 mmol), CuII-4 A (0.2 g), acetaldoxime (6 mmol) and MeOH (4 mL) were stirred at 65 C for 4 h. The solid was filtered, washed with MeOH and the filtrate evaporated. The residue was subjected to GC-MS analysis and NMR spectroscopy. The filtered catalyst can be recycled after drying at about 150 C for 1 h.
96% With [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; water; 1-benzyl-1-azonia-3,5-diaza-7-phosphaadamantyl chloride; for 1h;Schlenk technique; Reflux; Green chemistry;Catalytic behavior; General procedure: In a Schlenk-tube of approximately 12 mL volume, 0.05 mmol Ru(II)-precursor (1, 2 or RuCl3×3H2O) and 0.15 mmol phosphine ligand were dissolved in 3 mL water. This was followed by addition of 1 mmol nitrile. The tube was equipped with a reflux condenser and then immersed to an oil bath of 108-110 C temperature. The reaction mixture was stirred magnetically under reflux on air. In case of aliphatic nitriles heavy-walled closed reaction tubes of 5 mL volume were used. At the end of the reaction (or at other appropriate reaction times) 50 muL samples were withdrawn from the hot reaction mixture and these were extracted with 3×2 mL dichloromethane. A 1.5 mL portion of the combined organic phases was passed through a plug of unhydrous MgSO4 and the resulting clear solution was analysed by gas chromatography.
90% With sodium azide; water; at 90℃; for 8h; General procedure: To an aqueous mixture of nitrile (1 mmol) in water (7 mL) was added NaN3 (0.1 mmol, 0.0065 g), then the reaction mixture was stirred vigorously in an oil bath preset at 90 C for the appropriate time as mentioned in Table 1. After completion of the reaction (monitoredby TLC), the reaction mixture was cooled and the precipitated-outsolid was filtered and washed with water (3 × 5 mL) to give the pure product. The products were identified by their 1H NMR spectra and their physical data (m.p.) were compared with those described in the literature. Spectral data for the selected compound are as follows.
80% With water; In ethanol; at 50 - 60℃; for 2.5h; General procedure: Amberlyst A26 OH (0.11 g) was added to a suspension ofthe nitrile (1 mmol) in EtOH-H2O (0.5 mL). The reactionmixture was stirred at 50-60 C, and the progress of thereaction was followed by TLC. After the completion ofreaction, the mixture was diluted with acetone or EtOAc andfiltered to remove the catalyst. The desired products wereisolated by evaporation of the EtOAc or addition of H2O and filtration of the precipitate.

 

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