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[ CAS No. 7423-55-4 ] {[proInfo.proName]}

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Chemical Structure| 7423-55-4
Chemical Structure| 7423-55-4
Structure of 7423-55-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 7423-55-4 ]

CAS No. :7423-55-4 MDL No. :MFCD00043030
Formula : C7H7NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :IUTPJBLLJJNPAJ-UHFFFAOYSA-N
M.W : 169.13 Pubchem ID :573621
Synonyms :

Calculated chemistry of [ 7423-55-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.29
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.16
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) : -7.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.68
Log Po/w (XLOGP3) : 0.04
Log Po/w (WLOGP) : -0.99
Log Po/w (MLOGP) : -0.81
Log Po/w (SILICOS-IT) : -0.34
Consensus Log Po/w : -0.28

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -0.72
Solubility : 32.5 mg/ml ; 0.192 mol/l
Class : Very soluble
Log S (Ali) : -1.16
Solubility : 11.7 mg/ml ; 0.069 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.19
Solubility : 261.0 mg/ml ; 1.54 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.14

Safety of [ 7423-55-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7423-55-4 ]

* 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 [ 7423-55-4 ]
  • Downstream synthetic route of [ 7423-55-4 ]

[ 7423-55-4 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 6066-82-6 ]
  • [ 7423-55-4 ]
  • [ 55750-62-4 ]
Reference: [1] Analytical Chemistry, 2016, vol. 88, # 22, p. 10837 - 10841
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12243 - 12247[3] Angew. Chem., 2016, vol. 128, # 40, p. 12431 - 12435,5
[4] International Journal of Molecular Sciences, 2017, vol. 18, # 9,
[5] Tetrahedron Letters, 1998, vol. 39, # 11, p. 1321 - 1324
[6] Organic Letters, 2004, vol. 6, # 20, p. 3561 - 3564
[7] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6400 - 6407
[8] Chemical Communications, 2011, vol. 47, # 25, p. 7068 - 7070
[9] Chemistry - A European Journal, 2011, vol. 17, # 46, p. 13059 - 13067
[10] Patent: US2014/56810, 2014, A1, . Location in patent: Paragraph 0181
[11] Organic and Biomolecular Chemistry, 2014, vol. 12, # 34, p. 6624 - 6633
[12] Journal of Controlled Release, 2015, vol. 220, p. 660 - 670
[13] Patent: WO2015/196167, 2015, A1, . Location in patent: Paragraph 0269; 0277
  • 2
  • [ 7423-55-4 ]
  • [ 105832-38-0 ]
  • [ 55750-62-4 ]
Reference: [1] Patent: US9242011, 2016, B2, . Location in patent: Page/Page column 48
[2] Patent: US9480753, 2016, B2, . Location in patent: Page/Page column 120
  • 3
  • [ 7423-55-4 ]
  • [ 55750-62-4 ]
YieldReaction ConditionsOperation in experiment
1.2 g With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2.5 h; 10152] 3-Maleimidopropionic acid (1.0 g, 5.9 mmol) was dissolved in tetrahydroffiran (20 ml). 2-Succinimido- 1,1,3,3- tetramethyluronium tetrafluoroborate (TSTU, 2.14 g, 7.1 mmol) and ethyldiisopropylamine (1.24 ml, 7.1 mmol) were added subsequently. N,N-Dimethylformamide (5 ml) was added. The reaction mixture was stirred at room temperature, while it was turning sluggish. The mixture was stirred for 2 mi N,N-Dimethylformamide (5 ml) was added. The mixture was stirred for 2.5 h at room temperature. It was diluted with dichloromethane (150 ml) and was washed subsequently with a 10percent aqueous solution of sodium hydrogensulphate (150 ml), a saturated aqueous solution of sodium hydrogencarbonate (150 ml) and water (150 ml). It was dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was recrystallized from ethyl acetate to give 1.20 g of 3-(2,5-dioxo-2,5-dihydropyrrol-1-yl)propionic acid2,5-dioxopyrrolidiny-1 -yl ester. MS: mlz=289, required for [M+Na]: 28910154] ‘H-NMR (CDC13) ö 2.82 (m, 4H); 3.02 (t, 2H); 3.94 (t, 2H), 6.73 (s, 2H).
Reference: [1] Patent: US2015/376262, 2015, A1, . Location in patent: Paragraph 0150 - 0154
  • 4
  • [ 7423-55-4 ]
  • [ 538-75-0 ]
  • [ 55750-62-4 ]
  • [ 57-13-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2009, vol. 7, # 17, p. 3400 - 3406
  • 5
  • [ 108-31-6 ]
  • [ 107-95-9 ]
  • [ 7423-55-4 ]
YieldReaction ConditionsOperation in experiment
67% at 170 - 180℃; for 1.5 h; First, 3-maleimidopropionic acid was synthesized according todescribed literature methods with modification [26,27]. A suspensionof maleic anhydride (3.21 g, 32.78 mmol) and β-alanine (3 g,33.67 mmol) in glacial AcOH (30 mL) was heated to reflux (bath temperature:170–180 °C) for 90min. The solutionwas cooled to roomtemperatureand the solvent was evaporated in vacuo. Residual AcOH wasremoved by coevaporation with toluene under vacuum (2 × 50 mL).The residue was treated with water (100 mL) and EtOAc (200 mL).The organic layer was separated while the aqueous layer was extractedwith EtOAc (2 × 100 mL). The combined organic extracts were dried(Na2SO4) and evaporated in vacuo. The crude product was purified bysilica gel column chromatography, eluting with 50percent ethyl acetate inhexanes, to afford 3-maleimidopropionic acid (3.7 g, 21.88 mmol, 67percentyield), the spectroscopic data of which was consistent with reporteddata.(27) 1H NMR (CDCl3) δ 8.93 (br s, 1H), 6.71 (s, 2H), 3.80 (t, J =7.2 Hz, 2H), 3.62–3.66 (m, 24H), 2.67 (t, J = 7.2 Hz, 2H).
Reference: [1] International Journal of Molecular Sciences, 2017, vol. 18, # 9,
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 9955 - 9968
[3] Journal of Controlled Release, 2015, vol. 220, p. 660 - 670
[4] Chemistry - A European Journal, 2015, vol. 21, # 38, p. 13186 - 13190
[5] Journal of the American Chemical Society, 2013, vol. 135, # 11, p. 4333 - 4363
[6] Synthesis, 2008, # 8, p. 1316 - 1318
[7] Chemical Communications, 2017, vol. 53, # 5, p. 959 - 962
[8] RSC Advances, 2018, vol. 8, # 5, p. 2818 - 2823
[9] Organic and Biomolecular Chemistry, 2009, vol. 7, # 16, p. 3308 - 3318
[10] Tetrahedron Letters, 1998, vol. 39, # 38, p. 6987 - 6990
[11] Organic Letters, 2010, vol. 12, # 9, p. 1920 - 1923
[12] Journal of the American Chemical Society, 2005, vol. 127, # 9, p. 2966 - 2973
[13] Tetrahedron Letters, 2001, vol. 42, # 12, p. 2377 - 2380
[14] Organic Letters, 2004, vol. 6, # 20, p. 3561 - 3564
[15] Organic and Biomolecular Chemistry, 2009, vol. 7, # 17, p. 3400 - 3406
[16] Chemical Communications, 2011, vol. 47, # 25, p. 7068 - 7070
[17] Chemistry - A European Journal, 2011, vol. 17, # 46, p. 13059 - 13067
[18] Patent: US2014/56810, 2014, A1, . Location in patent: Paragraph 0181
[19] Organic and Biomolecular Chemistry, 2014, vol. 12, # 34, p. 6624 - 6633
[20] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 2, p. 162 - 167
[21] Patent: WO2015/196167, 2015, A1, . Location in patent: Paragraph 0269; 0277
[22] Patent: CN104147619, 2018, B, . Location in patent: Paragraph 0045; 0046
[23] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 9, p. 2599 - 2609
  • 6
  • [ 57079-11-5 ]
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Reference: [1] Organic and Biomolecular Chemistry, 2009, vol. 7, # 17, p. 3400 - 3406
[2] Carbohydrate Polymers, 2016, vol. 149, p. 94 - 101
  • 7
  • [ 57079-11-5 ]
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Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6400 - 6407
[2] Organic and Biomolecular Chemistry, 2004, vol. 2, # 23, p. 3434 - 3441
[3] Chemistry - A European Journal, 2006, vol. 12, # 34, p. 8798 - 8812
  • 8
  • [ 108-31-6 ]
  • [ 64-19-7 ]
  • [ 107-95-9 ]
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Reference: [1] European Journal of Inorganic Chemistry, 2013, # 8, p. 1381 - 1389
  • 9
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Reference: [1] Synthesis (Germany), 2014, vol. 46, # 10, p. 1399 - 1406
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