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Chemical Structure| 1798-83-0 Chemical Structure| 1798-83-0

Structure of 1798-83-0

Chemical Structure| 1798-83-0

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Product Details of [ 1798-83-0 ]

CAS No. :1798-83-0
Formula : C11H15Cl2NO
M.W : 248.15
SMILES Code : O=C(C1=CC=C(Cl)C=C1)CCN(C)C.[H]Cl
MDL No. :MFCD00084951
Boiling Point : No data available
InChI Key :MQURAWQCJQTMJM-UHFFFAOYSA-N
Pubchem ID :200370

Safety of [ 1798-83-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 1798-83-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 6
Fraction Csp3 0.36
Num. rotatable bonds 4
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 65.93
TPSA ?

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

20.31 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

3.01
Log Po/w (WLOGP)?

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

3.28
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.

2.59
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

2.63
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.3

Water Solubility

Log S (ESOL):?

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

-3.31
Solubility 0.122 mg/ml ; 0.000493 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.

-3.1
Solubility 0.197 mg/ml ; 0.000792 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

-3.89
Solubility 0.032 mg/ml ; 0.000129 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

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.

-5.68 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

0.0
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)

1.35

Application In Synthesis of [ 1798-83-0 ]

* 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 [ 1798-83-0 ]

[ 1798-83-0 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 288-32-4 ]
  • [ 1798-83-0 ]
  • [ 113193-72-9 ]
YieldReaction ConditionsOperation in experiment
In water; for 5h;Reflux; General procedure: The appropriate acetophenone 1a-d (200 mmol), dimethylamine hydrochloride (270 mmol) andparaformaldehyde (90 mmol) were heated to reflux in absolute ethanol (35 mL) in the presence ofcatalytic amount of concentrated hydrochloric acid (0.5 mL). Reflux of the reaction mixture was continuedunder stirring for two hours, cooled and acetone (200 mL) was added. The formed Mannich basehydrochlorides 2a-d were precipitated, filtered off and dried. Subsequently, compounds 2a-d (100 mmol)were dissolved in water (100 mL) and imidazole (200 mmol) was added. The reaction mixture washeated to reflux for five hours, cooled and the precipitated solids were collected by filtration to giveketones 3a-d which were pure enough to be used in the next step.
  • 3
  • [ 288-88-0 ]
  • [ 1798-83-0 ]
  • [ 81234-31-3 ]
YieldReaction ConditionsOperation in experiment
11 g With sodium acetate; In ethanol; for 12h;Reflux; 15 g of N, N-dimethyl-3-oxo-3,4-chlorophenyl-propyl-1-ammonium chloride are addedInto 270 ml of ethanol,Then add 40g of anhydrous sodium acetate and 19g1,2,3-triazole,Heated to reflux for 12 hours,Concentrate, add water and ethyl acetate,Extract the liquid, collect the organic phase,Dry, concentrate,11 g of 1, 4-chlorophenyl-3- (1H-1,2,4-triazol-1-yl) propan-1-one was obtained.
  • 4
  • [ 142-08-5 ]
  • [ 1798-83-0 ]
  • [ 108664-77-3 ]
  • 5
  • [ 491-36-1 ]
  • [ 1798-83-0 ]
  • [ 108664-81-9 ]
  • 6
  • [ 55244-11-6 ]
  • [ 1798-83-0 ]
  • 2,7-Bis-(4-chlorphenyl)-1,4,4a,5-tetrahydro<1,8>naphthyridin-4a-carbonitril [ No CAS ]
  • 7
  • [ 55244-11-6 ]
  • [ 1798-83-0 ]
  • 2-Amino-6-(4-chlorphenyl)-3,4-dihydro-3-<3-oxo-3-(4-chlorphenyl)propyl>nicotinonitril [ No CAS ]
  • 8
  • [ 81471-31-0 ]
  • [ 1798-83-0 ]
  • [ 81471-39-8 ]
  • 9
  • [ 50-00-0 ]
  • [ 506-59-2 ]
  • [ 99-91-2 ]
  • [ 1798-83-0 ]
YieldReaction ConditionsOperation in experiment
93.2% General procedure: A reaction mixture of the aralkyl-ketone (IV) (0.1 mol), the hydrochloride of the corresponding amine (VIII) (0.11 mol) and the polyformaldehyde (0.13 mol) dissolved in 95% ethanol (20 mL) is added with wt % concentrated HCl (0.2 mL) and refluxed for 5 h. TLC (dichloromethane: methanol=20:1) indicates a complete consumption of the starting material (IV). The solvent is concentrated down till dry. To the residue, dichloromethane (100 mL) and saturated NaHCO3 solution (40 mL) are added, followed by a 20-min stirring. The organic phase is separated and washed with 5 wt % dilute HCl solution (30 mL). After dried over anhydrous MgSO4, the organic phase is filtered and then concentrated to give the crude product which is then dissolved in ethyl acetate (30 mL) and formed a hydrochloride by adding hydrochloric acid alcohol to the mixture. The intermediate (III) is thus obtained with a yield of 70-90% based on the intermediate (IV).
62% With hydrogenchloride; In ethanol; water; at 80 - 90℃; for 30h; To a solution of 4’-chloroacetophenone (10 g, 65 mmol) in absolute EtOH (50 ml_) at room temperature were added paraformaldehyde (1.94 g, 64 mol), N,N- dimethylamine hydrochloride (5.27 g, 64.68 mmol) and cone. HCI (2 ml_). The resulting reaction mixture was stirred at between 80-90 C for 30 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by column chromatography with silica gel (60-120 mesh) eluting with 2% EtOAc/hexane) and trituration with Et20 (100 ml_) to afford the title compound (10 g, 40 mmol, 62 %).
59.2% With sulfuric acid; In acetonitrile; for 9h;Reflux; Inert atmosphere; General procedure: To a solution of acetophenone (1 eq.), paraformaldehyde (1.3 eq.) and N,N-dimethylamine hydrochloride (1.3 eq) in acetonitrile (35 mL) was added sulfuric acid (1 mL) dropwise. The reaction mixture was stirred at reflux temperature for 9 h. After the solution was cooled to room temperature, the reaction mixture was poured into acetone (50 mL). The formed precipitate was filtered, washed with acetone, and dried over by vacuum.
With hydrogenchloride; In ethanol; water; for 5h;Heating / reflux; 1 -(4-Chloro-phenyl)-3-dimethylamino-propan-1 -one hydrochlorideTo EtOH (80 mL), p-chloroacetophenone (77.3 g, 0.50 mol), dimethylamine hydrochloride (52.7 g, 0.65 mol), paraformaldehyde (19.8 g, 0.66 mol) and concentrated aqueous HCI (1 mL) were added and the mixture was refluxed for 5 h. The mixture was cooled to 400C, acetone (400 mL) was added, and under stirring the mixture was cooled further to 20C. The precipitate was filtered, washed with acetone and PA, and air dried to obtain 69.5 g of product which was used without further purification in the subsequent step.
With hydrogenchloride; In ethanol; for 2h;Reflux; General procedure: The appropriate acetophenone 1a-d (200 mmol), dimethylamine hydrochloride (270 mmol) andparaformaldehyde (90 mmol) were heated to reflux in absolute ethanol (35 mL) in the presence ofcatalytic amount of concentrated hydrochloric acid (0.5 mL). Reflux of the reaction mixture was continuedunder stirring for two hours, cooled and acetone (200 mL) was added. The formed Mannich basehydrochlorides 2a-d were precipitated, filtered off and dried. Subsequently, compounds 2a-d (100 mmol)were dissolved in water (100 mL) and imidazole (200 mmol) was added. The reaction mixture washeated to reflux for five hours, cooled and the precipitated solids were collected by filtration to giveketones 3a-d which were pure enough to be used in the next step.

  • 10
  • [ 1798-83-0 ]
  • [ 81471-33-2 ]
  • [ 81471-47-8 ]
  • 11
  • [ 1798-83-0 ]
  • [ 96335-37-4 ]
  • 2-(4-Chlorphenyl)-7,7-dimethyl-7,8-dihydro-1,6-naphthyridin-5(6H)-on [ No CAS ]
  • 12
  • [ 1798-83-0 ]
  • [ 96335-43-2 ]
  • 2-Methyl-6-(4-chlorphenyl)-pyrazolo<1,5-a>pyrido<2,3-d>pyrimidin-9(4H)-on [ No CAS ]
  • 13
  • [ 1798-83-0 ]
  • [ 266338-29-8 ]
  • 2-amino-6-(4-chlorophenyl)-3-cyanopyridine [ No CAS ]
  • 14
  • [ 1798-83-0 ]
  • [ 16254-21-0 ]
  • 15
  • [ 1798-83-0 ]
  • [ 2813-22-1 ]
  • [ 100749-28-8 ]
  • 16
  • [ 30354-18-8 ]
  • [ 99-91-2 ]
  • [ 1798-83-0 ]
  • 17
  • [ 1798-83-0 ]
  • [ 87142-62-9 ]
  • 18
  • [ 149-44-0 ]
  • [ 1798-83-0 ]
  • [ 63261-19-8 ]
  • 19
  • [ 16511-38-9 ]
  • [ 1798-83-0 ]
  • C28H23Cl2NO4 [ No CAS ]
  • C28H23Cl2NO4 [ No CAS ]
  • 20
  • [ 1131-18-6 ]
  • [ 1798-83-0 ]
  • 6-(4-Chloro-phenyl)-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine [ No CAS ]
  • 21
  • [ 16459-47-5 ]
  • [ 1798-83-0 ]
  • 6-(4-Chloro-phenyl)-3-methyl-1-(4-nitro-phenyl)-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine [ No CAS ]
  • 22
  • [ 1798-83-0 ]
  • 5-Ethylsulfanyl-[1,3,4]thiadiazol-2-ylamine; hydrochloride [ No CAS ]
  • [6-(4-Chloro-benzoyl)-2-ethylsulfanyl-6,7-dihydro-5H-[1,3,4]thiadiazolo[3,2-a]pyridin-8-yl]-(4-chloro-phenyl)-methanone [ No CAS ]
  • 23
  • [ 1798-83-0 ]
  • [ 40401-39-6 ]
  • 1,6-Bis-(4-chloro-phenyl)-3-methyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine [ No CAS ]
  • 24
  • [ 54030-57-8 ]
  • [ 1798-83-0 ]
  • 4-(4-chlorophenyl)-8-methylthio-2,3,6,7-tetrahydro-1H-pyrimido<4,5-b><1,4>diazepin-6-one [ No CAS ]
  • 25
  • [ 52943-88-1 ]
  • [ 1798-83-0 ]
  • 4-(p-chlorophenyl)-6-methyl-8-phenyl-2,3-dihydropyrazolo<3,4-b>diazepine [ No CAS ]
  • 4-(p-chlorophenyl)-8-methyl-6-phenyl-2,3-dihydropyrazolo<3,4-b>diazepine [ No CAS ]
  • 26
  • [ 85357-27-3 ]
  • [ 1798-83-0 ]
  • 4-(4-chlorophenyl)-8-methoxy-7-methyl-2,3,6,7-tetrahydro-1H-pyrimido<4,5-b><1,4>diazepin-6-one [ No CAS ]
  • 27
  • [ 39008-28-1 ]
  • [ 1798-83-0 ]
  • 4-(4-chlorophenyl)-8-methylthio-7-methyl-2,3,6,7-tetrahydro-1H-pyrimido<4,5-b><1,4>diazepin-6-one [ No CAS ]
  • 28
  • [ 1798-83-0 ]
  • [ 231302-65-1 ]
  • 6-(4-chlorobenzoyl)pyrido<2,3-d>pyrimidin-2,4(1H,3H)-dione [ No CAS ]
  • 29
  • [ 1798-83-0 ]
  • [ 231302-64-0 ]
  • 6-(4-chlorobenzoyl)-3-methyl-2-methylthiopyrido<2,3-d>pyrimidin-4(3H)-one [ No CAS ]
  • 30
  • [ 1004-74-6 ]
  • [ 1798-83-0 ]
  • 6,8-diamino-4-(4-chlorophenyl)-2,3-dihydropyrimido[4,5-b][1,4]diazepine [ No CAS ]
  • 31
  • [ 1798-83-0 ]
  • [ 118-70-7 ]
  • 6-amino-4-(4-chlorophenyl)-2,3-dihydropyrimido[4,5-b][1,4]diazepine [ No CAS ]
  • 32
  • [ 1798-83-0 ]
  • [ 95-54-5 ]
  • 4-(4-chlorophenyl)-2,3-dihydro-1H-1,5-benzodiazepine [ No CAS ]
  • 33
  • [ 1798-83-0 ]
  • [ 95-54-5 ]
  • 1-[2-(4-chlorobenzoyl)ethyl]-2,3-dihydro-4-(4-chlorophenyl)-1H-1,5-benzodiazepine [ No CAS ]
  • 34
  • [ 1798-83-0 ]
  • [ 95-54-5 ]
  • (+/-)-2-(4-chlorobenzoyl)-5-[2-(4-chlorobenzoyl)ethyl]-2a-(4-chlorophenyl)-1,2,2a,3,4,5-hexahydroazeto[1,2-a][1,5]benzodiazepine [ No CAS ]
  • 35
  • 1-(2-oxo-2-[2-oxo-2H-chromen-3-yl]ethyl)pyridin-1-ium bromide [ No CAS ]
  • [ 1798-83-0 ]
  • 3-[6-(4-chloro-phenyl)-pyridin-2-yl]-chromen-2-one [ No CAS ]
 

Historical Records

Technical Information

• Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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