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Structure of 2142-06-5

Chemical Structure| 2142-06-5

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Product Details of [ 2142-06-5 ]

CAS No. :2142-06-5
Formula : C11H11NO2
M.W : 189.21
SMILES Code : O=C(CC1)N(CC2=CC=CC=C2)C1=O
MDL No. :MFCD00516834
InChI Key :IONNJVQITCVNHK-UHFFFAOYSA-N
Pubchem ID :95241

Safety of [ 2142-06-5 ]

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

Computational Chemistry of [ 2142-06-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.27
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 55.73
TPSA ?

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

37.38 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.89
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

0.64
Log Po/w (WLOGP)?

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

0.8
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.

1.62
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

2.0
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.39

Water Solubility

Log S (ESOL):?

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

-1.6
Solubility 4.74 mg/ml ; 0.025 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.

-1.0
Solubility 18.9 mg/ml ; 0.0999 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

-3.03
Solubility 0.178 mg/ml ; 0.00094 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.

-7.0 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)

1.0

Application In Synthesis of [ 2142-06-5 ]

* 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 [ 2142-06-5 ]

[ 2142-06-5 ] Synthesis Path-Downstream   1~36

  • 1
  • [ 123-56-8 ]
  • [ 100-44-7 ]
  • [ 2142-06-5 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate; In neat (no solvent); at 60 - 65℃; for 0.0666667h;Microwave irradiation; Green chemistry; General procedure: A mixture of phthalimide (4.8 mmol, 0.70 g), alkyl halide(6.0 mmol), 4a or 4b (0.3 mmol, 3 mol%) and potassiumcarbonate (18.8 mmol, 2.6 g) was heated in a commercialmicrowave oven in an open Erlenmeyer flask at 60 8C-65 8Cfor the required time (as shown in Table 3) according to a50:10-s heating: cooling cycle, each at an 80% power level.The completion of the reaction was monitored using TLC.After cooling to r.t., the reaction mixture was extracted withmethylene chloride (2 25 mL). Then the extracts weredried over anhydrous Na2SO4, filtered, and the solvent wasevaporated to dryness to give the crude product. Solids werepurified through recrystallization in absolute EtOH, and liquids were purified over a silica gel column using hexane:EtOAc (96:4) as the eluent. The successful formation of theproducts was confirmed by 1H NMR, 13C NMR and FT-IRspectra.
  • 2
  • [ 54553-14-9 ]
  • [ 71-43-2 ]
  • [ 2142-06-5 ]
  • 3
  • [ 2142-06-5 ]
  • [ 64984-60-7 ]
  • 4
  • [ 2142-06-5 ]
  • [ 80301-56-0 ]
  • 5
  • [ 2142-06-5 ]
  • [ 875236-20-7 ]
  • 6
  • [ 2142-06-5 ]
  • [ 210106-84-6 ]
  • 7
  • [ 1466-67-7 ]
  • [ 543-20-4 ]
  • [ 2142-06-5 ]
  • 8
  • [ 110-15-6 ]
  • [ 100-46-9 ]
  • [ 2142-06-5 ]
YieldReaction ConditionsOperation in experiment
84% In water; at 100℃; for 2h;Green chemistry; General procedure: A solution of succinic acid (10 mmol) and primary amine (10 mmol) were dissolved in water (5.0 mL) in a flask, stirred, and maintained at boiling for the appropriate time. The reaction progress was monitored by TLC (1:1 n-hexane/acetone). After the reaction mixture was cooled to room temperature, the product was filtered and washed with water. It was recrystallized from methanol. The resulting product was identified using FT-IR, NMR spectroscopy, and GC-MS. Compounds of 1a, 1c, 1f, and 1j were reported in literature and fully characterized by spectral analysis.[23-26]
  • 9
  • [ 5291-77-0 ]
  • [ 2142-06-5 ]
  • [ 2399-66-8 ]
  • 12
  • [ 2142-06-5 ]
  • [ 27607-77-8 ]
  • [ 99885-52-6 ]
  • 13
  • [ 2142-06-5 ]
  • [ 36678-63-4 ]
  • [ 75648-87-2 ]
  • [ 127654-95-9 ]
  • 14
  • [ 2142-06-5 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 7510-08-9 ]
  • 15
  • [ 2142-06-5 ]
  • [ 41194-02-9 ]
YieldReaction ConditionsOperation in experiment
57% With sodium tetrahydroborate; In methanol; dichloromethane; at 0℃; for 2h; To a 0 C solution of <strong>[2142-06-5]N-benzylsuccinimide</strong> 3 (3 g, 16 mmol) in CH2Cl2-MeOH (80 mL, 1 : 3), NaBH4 (1.5 g, 40 mmol) was added portionwise over a period of 2 h with stirring. Then water (50 mL) was added and the volatiles were removed in vacuo. The precipitate formed was collected by filtration, washed with water and air-dried. The filtrate was extracted with dichloromethane, dried with MgSO4, and the solvent was removed in vacuo to give the addition crop of the target product. The products were combined and recrystallized from benzene. White powder, m.p.110-111 C (cf. Ref. 26: m.p. 105-106 C), yield 1.73 g (57%). 1H NMR (CDCl3), delta: 1.84-1.97 (m, 1 H, C(O)CH2CHaHb); 2.16-2.39 (m, 2 H, C(O)CH2); 2.50-2.70 (m, 1 H,C(O)CH2CHaHb); 4.27 (d, 1 H, OH, J = 7.8 Hz); 4.17 (d, 1 H, NCHaHbPh, J = 14.8 Hz); 4.85 (d, 1 H, NCHaHbPh, J = 14.8 Hz); 5.03-5.12 (m, 1 H, CH); 7.22-7.38 (m, 5 H, Ph). 13C NMR (CDCl3), delta: 28.10, 29.00, 43.42, 82.47, 127.67, 128.35, 128.76, 136.55, 174.98.
50% With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 0℃; for 3h; N-benzylsuccinamidal: Powered sodium borohydride (0.5 g, 10.75 mmol) was added portionwise to a stirred solution of <strong>[2142-06-5]N-benzylsuccinimide</strong> (1.0 g, 5 mmol) in 1:1 tetrahydrofuran-ethanol (15 mL) at 0 C. After 3 h, the reaction was quenched by the addition of 10% aqueous hydrochloric acid (2.5 mL) and the mixture was diluted with water, extracted with ethyl acetate, and dried with Na2SO4 and concentrated. A solid was obtained which had m.p. 104-106 C after crystallization from ethyl acetate (0.65 g, 50%). 1H NMR (300 MHz, CDCl3) ppm 1.74-2.72 (m, 4 H), 4.15 (d, J = 15.1 Hz, 1 H), 4.84 (d, J = 15.1 Hz, 1 H), 5.07 (dd, J = 2.1 Hz, 4.2 Hz, 1 H), 7.30 (s, 5 H). Anal. Calcd for C11H13NO2: C 69.09 H 6.85 N 7.32; found: C 69.12, H 6.78, N 7.17. IR (KBr, cm-1) 3355, 1685 (C=O).
  • 16
  • [ 64984-60-7 ]
  • [ 2142-06-5 ]
YieldReaction ConditionsOperation in experiment
95% With ammonium peroxodisulfate; In 1,4-dioxane; dimethyl sulfoxide; at 100℃; for 7h; General procedure: A solution of amine (1 equiv) and anhydride (1.1 equiv) in 1,4-dioxane was stirred at room temperature (or 100 C if necessary) in a two neck round bottom flask equipped with a water condenser. As soon as all the amine converts to the corresponding amic acid (monitored by TLC), ammonium persulfate [(NH4)2S2O8] (2 equiv) and DMSO (2 equiv) were added and the reaction mixture was heated to 100 C. Heating was continued at the same temperature until completion (3-10 h) of the reaction. After completion, the reaction mixture was filtered through a cotton plug and dioxane was removed under vacuo. The residue was dissolved in ethyl acetate and washed with dilute HCl, saturated aqueous NaHCO3 and brine. The organic layer was dried over anhydrous Na2SO4 and evaporated under vacuo to furnish the corresponding imides in good to excellent yields with more than 98% purity (GC, NMR).
92% With sodium acetate; acetic anhydride; for 2h;Reflux; To N-benzylsuccinic acid monoamide, calcined sodium acetate (1.02 g, 12.15 mmol) and acetic anhydride (50 mL) were added and the mixture was refluxed for 2 h. Removal of the solvent in vacuo and recrystallization of the residue from diethyl ether afforded N-benzylsuccinimide (3), white crystals, m.p. 96-98 C (cf. Ref. 26: m.p. 102-103 C), yield 8.7 g (92%). 1H NMR (CDCl3), delta: 2.68 (s, 4 H, 2 CH2); 4.65 (s, 2 H, PhCH2); 7.28-7.39 (m, 5 H, Ph).
With sodium acetate; acetic anhydride; for 2h;Reflux; General procedure: The synthesis of maleimides 1-47 was performed by mixing an equimolar amount of the appropriate maleic anhydrides 68-72 in 5 mL of CHCl3 and anilines 73, 78-90, amines 91-94 or phenylalkylamines 74-77 (5 mmol) dissolved in 1 mL of CHCl3 and stirred during 1 h. The solid (maleamic acid) which precipitated out of the reaction mixture was filtered off. The whole amount of maleamic acid was dissolved in 5 mL of acetic anhydride and 100 mg of sodium acetate was added. The mixture was heated for 2 h under reflux. The reaction was cooled and quenched with water; then, the aqueous solution was extracted with Et2O, dried with Na2SO4, filtered, and the solvent was evaporated. The product was purified by silica gel column chromatography using a mixture of hexane and ethyl acetate (9:1) as eluent. Compounds 1-10, 16-26, 31-34, 36, 38-42 and 43-47 were previously reported.[3], [8], [21], [22], [23], [24], [25], [26], [27] and [28]
With sodium acetate; acetic anhydride; for 0.5h; General procedure: In a 100 mL three-necked flask provided with a stirrer, a reflux condenser, and adropping funnel were placed 2.0 g (20 mmol) of succinic anhydride and 25 mL of diethylether. The succinic anhydride dissolved upon stirring, at which point a solution of 1equiv. (20 mmol) of the corresponding amine in 5 mL of diethyl ether was run throughthe dropping funnel. The resulting thick suspension was stirred at room temperature for 1h and was then cooled in an ice bath. The N-substituted succinamic acid was recoveredby filtration and dried. The residue was then added to a flask containing a solution ofanhydrous sodium acetate (0.65 g, 8 mmol) in acetic anhydride (6.7 mL) and stirred overa steam bath for 30 min. The reaction mixture was then cooled to room temperature in acold water bath and was then poured into 100 mL of an ice-water mixture. Theprecipitated product was recovered by filtration, washed three times with 30 mL portionsof ice-cold water, and dried. The crude N-substituted succinimide was recrystallized fromethanol/water to afford the desired product.

  • 17
  • [ 66310-10-9 ]
  • [ 37912-62-2 ]
  • [ 2142-06-5 ]
  • 18
  • [ 115364-00-6 ]
  • [ 2142-06-5 ]
  • 9b-Hydroxy-1,2,5,9b-tetrahydro-pyrrolo[2,1-a]isoindol-3-one [ No CAS ]
  • 19
  • [ 3277-89-2 ]
  • [ 2142-06-5 ]
  • [ 159757-34-3 ]
  • 20
  • [ 2142-06-5 ]
  • [ 1462-75-5 ]
  • [ 159757-35-4 ]
  • 21
  • [ 108-30-5 ]
  • [ 100-46-9 ]
  • [ 2142-06-5 ]
  • [ 64984-60-7 ]
  • 22
  • [ 2142-06-5 ]
  • C11H7(2)H4NO2 [ No CAS ]
  • 23
  • [ 100-46-9 ]
  • [ 106-65-0 ]
  • [ 2142-06-5 ]
  • [ 149142-51-8 ]
  • 24
  • [ 115061-63-7 ]
  • [ 2142-06-5 ]
  • [ 136137-85-4 ]
  • [ 156150-59-3 ]
  • 25
  • (3R,4SR)-3-acetoxy-4-bromo-2,5-pyrrolidinedione [ No CAS ]
  • [ 2142-06-5 ]
  • [ 136137-85-4 ]
  • [ 156150-59-3 ]
  • 26
  • [ 108-30-5 ]
  • [ 100-46-9 ]
  • [ 2142-06-5 ]
YieldReaction ConditionsOperation in experiment
90% In toluene; at 20℃; for 40h;Dean-Stark; Reflux; To a solution of succinic anhydride (100 g, 1000 mmol) in toluene (3000 mL) was added benzylamine (107 g, 1000 mmol). The solution was stirred at room temperature for 24 h, then heated at reflux with a Dean-Stark apparatus for 16 hours. The mixture was then concentrated under reduced pressure to give l-benzylpyrrolidine-2,5-dione (170 g, 900 mmol, 90% yield).
  • 27
  • [ 2142-06-5 ]
  • [ 80522-42-5 ]
  • 1-Benzyl-2,5-bis-triisopropylsilanyloxy-1H-pyrrole [ No CAS ]
  • 28
  • N-Benzyl-succinamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester [ No CAS ]
  • [ 2142-06-5 ]
  • [ 40615-39-2 ]
  • 29
  • [ 2142-06-5 ]
  • [ 29897-82-3 ]
YieldReaction ConditionsOperation in experiment
82% With 1,1,3,3-Tetramethyldisiloxane; tris(pentafluorophenyl)borate; In 1,4-dioxane; at 110℃; for 16h;Inert atmosphere; Schlenk technique; General procedure: To the mixture of B(C6F5)3 (5.0mol%) and cyclic imides (1.0mmol) in dioxane, was added PhSiH3 (3.0mmol) slowly under an atmosphere of nitrogen. The reaction mixture was stirred and refluxed at 110C under an atmosphere of nitrogen. After the imide was consumed completely (detected by TLC) the mixture was added with aqueous ammonia (15mL) and extracted with CH2Cl2 (10mL×3). The combined organic phase was dried over Na2SO4, after removing the solvent under vacuum, the residue was purified by column chromatography to give the product.
  • 30
  • [ 145178-53-6 ]
  • [ 100-46-9 ]
  • [ 2142-06-5 ]
  • 31
  • [ 233269-19-7 ]
  • [ 2142-06-5 ]
  • 35
  • acidic succinate benzylamine [ No CAS ]
  • [ 2142-06-5 ]
  • 36
  • neutral succinate benzylamine [ No CAS ]
  • [ 2142-06-5 ]
 

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