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Chemical Structure| 17057-04-4
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Product Details of [ 17057-04-4 ]

CAS No. :17057-04-4 MDL No. :MFCD00458571
Formula : C11H7NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :LKUOJDGRNKVVFF-UHFFFAOYSA-N
M.W : 217.17 Pubchem ID :86925
Synonyms :

Calculated chemistry of [ 17057-04-4 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.97
TPSA : 74.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.3
Log Po/w (XLOGP3) : 0.62
Log Po/w (WLOGP) : 0.43
Log Po/w (MLOGP) : 0.72
Log Po/w (SILICOS-IT) : 0.63
Consensus Log Po/w : 0.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.72
Solubility : 4.11 mg/ml ; 0.0189 mol/l
Class : Very soluble
Log S (Ali) : -1.76
Solubility : 3.75 mg/ml ; 0.0173 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.53
Solubility : 6.37 mg/ml ; 0.0293 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 17057-04-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17057-04-4 ]

* 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.

  • Upstream synthesis route of [ 17057-04-4 ]
  • Downstream synthetic route of [ 17057-04-4 ]

[ 17057-04-4 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 108-31-6 ]
  • [ 150-13-0 ]
  • [ 17057-04-4 ]
YieldReaction ConditionsOperation in experiment
92% at 20℃; for 1 h; (1) equipped with a mechanical stirrer, thermometer,Constant pressure injector 500mL three-necked flask followed by 35g of maleic anhydride (0.357mol)And 100mL acetone, stirring at 20 until dissolved, at the same time,49 g (0.357 mol) p-aminobenzoic acid was dissolved in 250 mL acetone,Forming a transparent solution to be used; then,The preparation of p-aminobenzoic acid acetone solution was added dropwise to 500mL three-necked flask,After the dropwise addition, continue the reaction 1h, suction filtration (solvent recovery), washing,Recrystallization, dried to give yellow crystalsN- (4-carboxyphenyl) maleimide acid77.28g,Yield 92percent, purity 99.3percent (HPLC)
37%
Stage #1: at 20℃; for 4 h;
Stage #2: With sodium acetate In acetic anhydride at 80℃; for 6 h;
A solution of p-aminobenzoic acid (128 mg, 0.94 mmol) and excess maleic anhydride (137 mg, 1.40 mmol) was added to ethyl acetate (20 mL), the reaction was stirred at room temperature for 4 h. After the reaction was completed, the precipitate was filtered, washed with a small amount of ethyl acetate (8 mL), dried, finally, a white powder was obtained. The crude white powder (220 mg, 0.94 mmol) was added to acetic anhydride (10 mL). A catalytic amount of sodium acetate (25 mg, 0.30 mmol) was added, the reaction temperature was controlled at 80 ° C, reaction time was 6 h, after completion of the reaction, the reaction mixture was poured into 40 mL of ice water, stirring for 30min, precipitation of white solid, filtered, the precipitate was washed with deionized water until neutral, vacuum drying, column chromatography on silica gel yielded a light yellow solid (75 mg, 37percent). Compound 31H NMR and 13C NMR are shown in Fig. 1 and Fig. 2, respectively.
Reference: [1] Patent: CN107286072, 2017, A, . Location in patent: Paragraph 0017; 0018; 0019
[2] Revue Roumaine de Chimie, 2008, vol. 53, # 9, p. 743 - 752
[3] Acta Crystallographica Section C: Crystal Structure Communications, 2011, vol. 67, # 2, p. o67-o70
[4] Patent: CN106243118, 2016, A, . Location in patent: Paragraph 0029
[5] Revue Roumaine de Chimie, 2001, vol. 46, # 10, p. 1167 - 1173
[6] Revue Roumaine de Chimie, 2002, vol. 47, # 3-4, p. 257 - 262
[7] Patent: US5198551, 1993, A,
[8] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 22, p. 5926 - 5931
[9] Organic and Biomolecular Chemistry, 2009, vol. 7, # 17, p. 3400 - 3406
[10] Revue Roumaine de Chimie, 2012, vol. 57, # 11, p. 929 - 937
[11] Journal of Polymer Science, Part A: Polymer Chemistry, 2015, vol. 53, # 1, p. 123 - 132
[12] RSC Advances, 2016, vol. 6, # 104, p. 101900 - 101910
  • 2
  • [ 5432-04-2 ]
  • [ 17057-04-4 ]
YieldReaction ConditionsOperation in experiment
51% With 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium hydrogensulfate In 1-Propyl acetate for 3 h; Reflux General synthetic procedure: To a stirring solution of maleic anhydride (29.42 g, 30 mmol) in dry toluene (300 mL) was added dropwise a solution of aniline (27.4 mL, 30 mmol) in dry toluene (10 mL) at room temperature. The mixture was vigorously stirred for 3 h, and the formed precipitate was separated by filtration. The cake was washed with toluene and dried under reduced pressure to give N-phenylmaleamic acid, as a yellow solid, 95percent yield. N-phenylmaleamic acid (4.176 g, 21.8 mmol) thus obtained was added to a flask charged with ionic liquid I (2.302 g, 7.28 mmol) and propyl acetate (66 mL), and the mixture was heated to reflux, and the formed water during the reaction was removed by using a Dean-Stark trap. After maintaining the refluxing for 3 h under intensive stirring, the mixture was cooled to room temperature. The upper layer containing propyl acetate and product were separated by decanting, and the lower layer was extracted by propyl acetate (50 mL .x. 3). The organic layers were combined, followed by evaporation under vacuum to give N-phenylmaleimide as a pale-yellow crystal solid. Yield, 83percent. 1H NMR (300 MHz, CDCl3) δ 7.47 (t,2H), 7.33-7.39 (t, 3H), 6.85 (s, 2H).
Reference: [1] Journal of Medicinal Chemistry, 1983, vol. 26, # 1, p. 85 - 90
[2] Journal fuer Praktische Chemie (Leipzig), 1985, vol. 327, # 5, p. 789 - 798
[3] Molecules, 2012, vol. 17, # 7, p. 7927 - 7940
[4] Synthetic Communications, 2005, vol. 35, # 15, p. 2017 - 2023
[5] Tetrahedron Letters, 2012, vol. 53, # 32, p. 4245 - 4247
[6] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 7843 - 7854
[7] Chemical & Pharmaceutical Bulletin, 1981, vol. 29, # 4, p. 1130 - 1135
[8] Magnetic Resonance in Chemistry, 1999, vol. 37, # 9, p. 682 - 686
[9] Revue Roumaine de Chimie, 2003, vol. 48, # 11, p. 881 - 890
[10] Macromolecules, 2004, vol. 37, # 15, p. 5544 - 5549
[11] European Journal of Medicinal Chemistry, 2005, vol. 40, # 7, p. 732 - 735
[12] Patent: EP1156036, 2001, A2,
[13] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 3, p. 797 - 801
  • 3
  • [ 36847-93-5 ]
  • [ 17057-04-4 ]
YieldReaction ConditionsOperation in experiment
70% for 1.5 h; Reflux Equimolar quantities of p-aminobenzoic acid and maleic anhydride were stirred in tetrahydrofuran (THF) at room temperature for one and half hours to yield maleanilic acid (1) in the form of yellow solid with yield 80percent, mp 210 °C.3 Equimolar quantities of maleanilic acid (1) and sodium acetate were refluxed for one and half hours in the presence of acetic anhydride followed by cooling at room temperature. Thereafter, the contents were poured in crushed ice containing beaker and kept overnight to afford light yellow precipitate, which were filtered and washed with water to get light yellow solid N-arylmaleimide (2) (Fig. 1). Yield 70percent, mp 155-157 °C, 1H NMR (400 MHz, DMSO-d6).3
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 1, p. 521 - 530
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 74 - 77
[3] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 24, p. 4876 - 4881
[4] Patent: WO2017/177316, 2017, A1, . Location in patent: Sheet 0062; 00132; 00134
  • 4
  • [ 150-13-0 ]
  • [ 110-16-7 ]
  • [ 17057-04-4 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 22, p. 8036 - 8043
[2] Journal of the Chemical Society, 1957, p. 4133
  • 5
  • [ 36847-93-5 ]
  • [ 108-24-7 ]
  • [ 17057-04-4 ]
YieldReaction ConditionsOperation in experiment
1.65 g
Stage #1: at 50℃; for 2 h; Inert atmosphere
Stage #2: at 70℃; for 2 h; Inert atmosphere
The diacid 3 (2.01 g, 8.54 mmol) was treated with acetic anhydride (4.0 mL, 36.28 mmol) and anhydrous sodium acetate (350 mg, 4.27 mmol) and the mixture heated at 50 °C for 2 h. Afterwards, the solution was evaporated to dryness and stirred with water at 70 °C for a period of 2 h. The resulting precipitate was filtered and dried in a desiccator overnight to yield 1.65 g (89 percent) of maleimide 4. The spectral data of this derivative correspond to those reported in the literature [30]. IR (ν, cm−1): 3475–2600 (CO2H), 1715 (C=O), 1704 (C=O); 1H NMR (acetone-d6, δ ppm): 8.14 and 7.57 (2 × d, J=8.6Hz, 4H, aromatic), 7.08 (s, 2H, maleimide); 13C MNR (acetone-d6, δ ppm) 169.3 (2), 166.2, 136.2, 134.7 (2), 130.1 (2), 129.3, 125.8 (2); ESI+HRMS: (M+H)+ calculated for C11H8NO4 = 218.0448; found =218.0447.
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 96, p. 259 - 268
  • 6
  • [ 150-13-0 ]
  • [ 17057-04-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 1, p. 521 - 530
[2] Tetrahedron Letters, 2012, vol. 53, # 32, p. 4245 - 4247
[3] Molecules, 2012, vol. 17, # 7, p. 7927 - 7940
[4] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 3, p. 797 - 801
[5] European Journal of Medicinal Chemistry, 2015, vol. 96, p. 259 - 268
[6] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 24, p. 4876 - 4881
[7] Patent: WO2017/177316, 2017, A1,
  • 7
  • [ 108-31-6 ]
  • [ 62-23-7 ]
  • [ 17057-04-4 ]
Reference: [1] Organic Letters, 2001, vol. 3, # 22, p. 3491 - 3494
  • 8
  • [ 5432-04-2 ]
  • [ 17057-04-4 ]
Reference: [1] Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2987,2990; engl. Ausg. S. 3016, 3019
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