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[ CAS No. 52798-01-3 ] {[proInfo.proName]}

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Chemical Structure| 52798-01-3
Chemical Structure| 52798-01-3
Structure of 52798-01-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 52798-01-3 ]

CAS No. :52798-01-3 MDL No. :MFCD02181140
Formula : C10H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OHTZXQYRHDVXLJ-UHFFFAOYSA-N
M.W : 175.18 Pubchem ID :1512619
Synonyms :

Calculated chemistry of [ 52798-01-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.02
TPSA : 50.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.05
Log Po/w (XLOGP3) : 1.55
Log Po/w (WLOGP) : 1.27
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 2.03
Consensus Log Po/w : 1.65

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.05
Solubility : 1.58 mg/ml ; 0.00899 mol/l
Class : Soluble
Log S (Ali) : -2.21
Solubility : 1.08 mg/ml ; 0.00614 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.96
Solubility : 0.192 mg/ml ; 0.00109 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 52798-01-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52798-01-3 ]

* 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 [ 52798-01-3 ]
  • Downstream synthetic route of [ 52798-01-3 ]

[ 52798-01-3 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 67-56-1 ]
  • [ 5462-71-5 ]
  • [ 52798-01-3 ]
YieldReaction ConditionsOperation in experiment
98% at 75℃; for 4 h; Concentrated sulfuric acid (98percent, 4.5 g, 54.8 mmol) was added dropwise to a solution of 2- (4-cyanophenyl) acetic acid (3 g, 180 mmol)In 40 ml of methanol, and the reaction was stirred for 4 hours at 75 ° C.Cool to room temperature and adjust pH to 8 with saturated aqueous sodium bicarbonate.The mixture was extracted with ethyl acetate. The extract was dried and concentrated to give 3.2 g (98percent) of the title compound.
Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 6, p. 2598 - 2600
[2] Patent: CN107474024, 2017, A, . Location in patent: Paragraph 0602; 0603; 0604
[3] Patent: WO2013/8162, 2013, A1, . Location in patent: Page/Page column 58; 59
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 131 - 134
  • 2
  • [ 41841-16-1 ]
  • [ 52798-01-3 ]
YieldReaction ConditionsOperation in experiment
67.9% at 200℃; for 4 h; Inert atmosphere Step S1:Compound 1 (423.7 g) was charged to the reactor under nitrogen and NMP (2.1 L) and CuCN were added.(214g), heated to reflux at 200 ° C, stirred at this temperature for 4 hours (analysis of the product of this stage by IPC),After cooling to room temperature, ethyl acetate (2.1 L) and a saturated aqueous solution of NH4Cl (2.1 L) were added and filtered.The organic layer was separated and washed with saturated NH4Cl (2.1 L).Aqueous layers were combined and extracted with 1.2L of ethyl acetate,The organic layers were combined, washed with aq.Concentrated, add 200 ml of ethyl acetate and 2 L of PE, stir for 30 minutes, filter, dry,Compound 2 was obtained (220 g, yield 67.9percent,IPC retention time: 2.19 min), as a brown solid.
61% at 200℃; for 1 h; Microwave irradiation Example 38AMethyl 4-cyanophenylacetate; 5.1 g (56.7 mmol) of copper(I) cyanide were added to a solution of 10 g (43.7 mmol) of methyl 4-bromophenylacetate in 44 ml of NMP, and, in a microwave oven, the mixture was then heated to 200° C. for 60 min. The reaction mixture was then purified by flash chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 5:1). This gave 4.65 g (61percent of theory) of the title compound.GC-MS (Method 1): Rt=5.13 min; m/z=175 (M)+.1H-NMR (400 MHz, DMSO-d6): δ [ppm]=3.24-3.35 (m, 3H), 3.83 (s, 2H), 7.49 (d, 2H), 7.80 (d, 2H).
Reference: [1] Patent: CN108864114, 2018, A, . Location in patent: Paragraph 0123-0126
[2] Patent: US2012/172448, 2012, A1, . Location in patent: Page/Page column 28
  • 3
  • [ 623-00-7 ]
  • [ 96-34-4 ]
  • [ 52798-01-3 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1990, # l, p. 48 - 49
[2] Journal of Organic Chemistry, 1996, vol. 61, # 5, p. 1748 - 1755
[3] Tetrahedron, 2007, vol. 63, # 5, p. 1146 - 1153
  • 4
  • [ 557-21-1 ]
  • [ 14062-25-0 ]
  • [ 52798-01-3 ]
YieldReaction ConditionsOperation in experiment
38% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamideInert atmosphere; Reflux Step 2: To a solution of ethyl 2-(4-bromophenyl)acetate ( 3.24 g, 13.32 mmol) in anhydrous dimethylformamide was added zinc cyanide (939 mg, 7.99 mmol) , tetrakis(triphenylphosphine)palladium(0) (770 mg, 0.67 mmol). The reaction mixture was refluxed for overnight under N2. TLC showed complete consumption of starting material. The mixture was filtered through celite bed and the filterate was concentrated under reduced pressure. The mixture was extracted with ethyl acetateand washed with water and brine. The extract was dried over magnesium sulfate and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford ethyl 2-(4- (iminomethyl)phenyl)acetate. (962 mg, 38 percent)
Reference: [1] Patent: WO2013/45451, 2013, A1, . Location in patent: Page/Page column 51
  • 5
  • [ 67-56-1 ]
  • [ 131356-52-0 ]
  • [ 52798-01-3 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 19, p. 8673 - 8695
  • 6
  • [ 17201-43-3 ]
  • [ 52798-01-3 ]
Reference: [1] Patent: US6200976, 2001, B1,
  • 7
  • [ 104-85-8 ]
  • [ 79-22-1 ]
  • [ 52798-01-3 ]
Reference: [1] Organic Preparations and Procedures International, 1999, vol. 31, # 4, p. 407 - 412
  • 8
  • [ 67-56-1 ]
  • [ 2252-32-6 ]
  • [ 107-13-1 ]
  • [ 52798-01-3 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 26, p. 5775 - 5780
  • 9
  • [ 557-21-1 ]
  • [ 147283-85-0 ]
  • [ 52798-01-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 21, p. 5488 - 5492
  • 10
  • [ 1878-68-8 ]
  • [ 52798-01-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 10, p. 2647 - 2652
[2] Patent: WO2013/45451, 2013, A1,
  • 11
  • [ 156-38-7 ]
  • [ 52798-01-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 21, p. 5488 - 5492
  • 12
  • [ 14199-15-6 ]
  • [ 52798-01-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 21, p. 5488 - 5492
  • 13
  • [ 5462-71-5 ]
  • [ 52798-01-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 548 - 551
  • 14
  • [ 105-07-7 ]
  • [ 52798-01-3 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 19, p. 8673 - 8695
  • 15
  • [ 557-21-1 ]
  • [ 41841-16-1 ]
  • [ 52798-01-3 ]
Reference: [1] Patent: EP1229034, 2002, A1, . Location in patent: Page 120
  • 16
  • [ 41841-16-1 ]
  • [ 544-92-3 ]
  • [ 52798-01-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 10, p. 2647 - 2652
  • 17
  • [ 67-56-1 ]
  • [ 1360788-99-3 ]
  • [ 52798-01-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 548 - 551
  • 18
  • [ 52798-01-3 ]
  • [ 69395-13-7 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 42, p. 14737 - 14741
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 131 - 134
  • 19
  • [ 52798-01-3 ]
  • [ 96524-70-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 21, p. 5488 - 5492
  • 20
  • [ 52798-01-3 ]
  • [ 74-88-4 ]
  • [ 444807-47-0 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydride In N,N-dimethyl-formamide at 0 - 35℃; for 2 h; To a solution of methyl 4-cyanobenzeneacetate (2.646 g, 15.1 mmol) and iodomethane (2.4 ml) in N,N-dimethylformamide (50 ml) was slowly added 60percent oily sodium hydride (1.55 g, 38.8 mmol) under ice-cooling.
The reaction mixture was stirred for 2 hours at room temperature.
The reaction solution was slowly added to ice water, and extracted with ethyl acetate.
The extracts were washed with a saturated aqueous solution of sodium chloride, dried, and concentrated under reduced pressure.
The residue was subjected to a silica gel column chromatography (ethyl acetate/hexane 3:1) to give the title compound (2.996 g, yield 98percent).
1H NMR (CDCl3) δ 1.59 (6H, s), 3.67 (3H, s), 7.42-7.47 (2H, m), 7.61-7.65 (2H, m).
Reference: [1] Patent: EP1541576, 2005, A1, . Location in patent: Page/Page column 41
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