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Chemical Structure| 6628-86-0 Chemical Structure| 6628-86-0

Structure of 6628-86-0

Chemical Structure| 6628-86-0

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Product Details of [ 6628-86-0 ]

CAS No. :6628-86-0
Formula : C7H4ClNO3
M.W : 185.57
SMILES Code : C1=C(Cl)C=CC(=C1C=O)[N+](=O)[O-]
MDL No. :MFCD00007289
InChI Key :SWGPIDCNYAYXMJ-UHFFFAOYSA-N
Pubchem ID :81123

Safety of [ 6628-86-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 6628-86-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 45.66
TPSA ?

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

62.89 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.02
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

1.9
Log Po/w (WLOGP)?

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

2.06
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.

0.86
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

0.48
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.26

Water Solubility

Log S (ESOL):?

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

-2.43
Solubility 0.697 mg/ml ; 0.00375 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.

-2.84
Solubility 0.266 mg/ml ; 0.00143 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

-2.34
Solubility 0.84 mg/ml ; 0.00453 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.

-6.08 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

3.0 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)

1.62

Application In Synthesis of [ 6628-86-0 ]

* 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 [ 6628-86-0 ]

[ 6628-86-0 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 288-16-4 ]
  • [ 6628-86-0 ]
  • [ 39254-70-1 ]
  • 2
  • [ 6628-86-0 ]
  • [ 4596-92-3 ]
YieldReaction ConditionsOperation in experiment
70% With vasicine; In ethylene glycol; at 80℃; for 48.0h; General procedure: The mixture of nitrocompound (0.5 mmol) and vasicine (0.5 mmol) in ethylene glycol (2 mL) was stirred at 80C for 24-48 h. Time was not optimized separately for all substrates. After completion of reaction as monitored by TLC, the reaction mixture was cooled to ambient temperature and extracted with ethyl acetate. The ethyl acetate layer was dried under reduced pressure using rotatory evaporator. The crude was chromatographed over silica gel to afford the desired product.
  • 3
  • [ 6628-86-0 ]
  • [ 14205-39-1 ]
  • [ 50607-30-2 ]
  • 3-carbomethoxy-2-methyl-5-oxo-4-(2-nitro-5-chlorophenyl)-1,4,5,6,7,8-hexahydro-pyrido<4,3-b>pyridine [ No CAS ]
  • 4
  • [ 6628-86-0 ]
  • [ 2605-68-7 ]
  • [ 307335-62-2 ]
  • 5
  • [ 5781-53-3 ]
  • [ 6628-86-0 ]
  • [ 53308-95-5 ]
  • 2-(7-chloro-2,3-dioxo-1,2,3,5-tetrahydro-benzo[<i>e</i>][1,4]diazepin-4-yl)-pentanoic acid amide [ No CAS ]
  • 6
  • [ 6628-86-0 ]
  • [ 19063-55-9 ]
  • 7
  • [ 6628-86-0 ]
  • [ 27328-68-3 ]
  • 8
  • [ 1001-26-9 ]
  • [ 6628-86-0 ]
  • [ 375854-57-2 ]
  • 9
  • [ 6628-86-0 ]
  • [ 129799-08-2 ]
  • [ 1262131-40-7 ]
YieldReaction ConditionsOperation in experiment
Preparation of 1-tert-butyl 3-methyl 4-(5-chloro-2-nitrobenzyl)piperazine-1,3-dicarboxylate (52)1.5 g (8.2 mmol) of the aldehyde 51 and 2.0 g (8.2 mmol) of the amine 5 are initially introduced in a mixture of 50 ml of dichloroethane and 50 ml of THF. 0.940 ml of glacial acetic acid are then added, and the mixture is stirred at RT for about 3 h. 5.5 g (24.6 mmol) of NaB(OAc)3 and a further 0.940 ml of acetic acid are subsequently added, and the mixture is stirred overnight at room temperature. The batch is stirred with saturated NaHCO3 solution, diluted with dichloromethane and extracted by shaking. The organic phase is again washed by shaking with water, the aqueous phase is again extracted by shaking with DCM. The combined organic phases are dried over Na2SO4, filtered off with suction and evaporated to dryness in vacuo. The 3.5 g of crude product obtained are dissolved in THF, adsorbed onto Isolute and separated on silica gel 60 (Flashmaster). The relevant fractions are combined and evaporated to dryness in a rotary evaporator, thus giving the desired product 52 (1.6 g, 21% yield) in a purity of 45% (mass: [M+]=414; HPLC method D, RT=3.86 min) as yellow oil, which is reacted further without further purification.
  • 10
  • [ 6628-86-0 ]
  • [ 56904-86-0 ]
  • [ 1075-35-0 ]
YieldReaction ConditionsOperation in experiment
47% With triphenylphosphine; In diphenylether; at 260℃; for 1h; General procedure: In a 50 ml round bottom flask containing magnetic stir bar was charged with o-nitro benzaldehydes (2 mmol), phosphorane (2.2 mmol), triphenyl phosphine (4.6 mmol) and diphenyl ether (10 mL) and heated at 260 oC for 1 h. The reaction mass was then cooled to room temperature and poured on silica column. Products were isolated by eluting with petrolium ether to 3:1 pet ether: ethyl acetate.
 

Historical Records

Technical Information

• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • 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 • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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