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[ CAS No. 68043-53-8 ] {[proInfo.proName]}

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Chemical Structure| 68043-53-8
Chemical Structure| 68043-53-8
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Product Details of [ 68043-53-8 ]

CAS No. :68043-53-8 MDL No. :MFCD04038185
Formula : C9H7NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :KUAWMWVXZMQZLD-UHFFFAOYSA-N
M.W : 193.16 Pubchem ID :5228831
Synonyms :

Calculated chemistry of [ 68043-53-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.84
TPSA : 72.12 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) : -6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.22
Log Po/w (XLOGP3) : 1.2
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : -0.05
Log Po/w (SILICOS-IT) : 0.19
Consensus Log Po/w : 0.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.04
Solubility : 1.74 mg/ml ; 0.00902 mol/l
Class : Soluble
Log S (Ali) : -2.31
Solubility : 0.944 mg/ml ; 0.00489 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.24
Solubility : 1.11 mg/ml ; 0.00574 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.11

Safety of [ 68043-53-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 68043-53-8 ]

* 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 [ 68043-53-8 ]
  • Downstream synthetic route of [ 68043-53-8 ]

[ 68043-53-8 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 10572-16-4 ]
  • [ 68043-53-8 ]
YieldReaction ConditionsOperation in experiment
94% at 60℃; for 3 h; A mixture of 3-(4-nitrophenoxy)propanoic acid (6.5 g, 30 mmol), concentrated sulfuric acid (30 mL) and phosphorus pentoxide (5.2 g, 37 mmol) is stirred at 60 °C for 3 hours, poured onto ice, stirred for 15 minutes and extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a beige solid, 5.5 g (94percent yield) mp 171-173 °C, identified by NMR and mass spectral analyses.
85% With sulfuric acid In ethyl acetate at 50℃; for 5 h; A solution of 3-(4-nitrophenoxy)propionic acid (4 g) in concentrated sulphuric acid (40 mL) was heated at 50°C for 5 h. The reaction mixture was poured on ice (400 g) and, after complete melting of the ice, extracted with ethyl acetate (3 x 100 mL). The organic layers were collected, dried over anhydrous magnesium sulphate, filtered, and the filtrate was concentrated to dryness. The residue was dissolved in ethyl acetate (25 mL) and the solution was supplemented with hexane (75 mL) under stirring. The resulting precipitate was collected by filtration, washed with hexane and dried (yield: 85percent; melting point: 176-178°C.
77.8% at 65℃; for 3 h; Mix 3 -(4-nitrophenoxy propanoic acid (6.5 g, 30 mmol) and concentrated H2SO4 (30 mL). Once dissolved, add P205, stir at 65°C for 3 hrs. Cool to room temperature, pour slowly the reaction mixture to ice water (50 mL), stir for 15 min, and extract with EtOAc (100 mLx3). Combine the organic layers, wash with brine (100 mLx2), dry over anhydrous Na2S04, concentrate to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=l:l) affords the title compound (4.6 g, 77.8percent). MS: (M-l): 192.2.
77.8% at 65℃; for 3 h; Mix 3-(4-nitrophenoxy)propanoic acid (6.5 g, 30 mmol) and concentrated H2SO4 (30 mL).
Once dissolved, add P2O5, stir at 65° C. for 3 hrs.
Cool to room temperature, pour slowly the reaction mixture to ice water (50 mL), stir for 15 min, and extract with EtOAc (100 mL*3).
Combine the organic layers, wash with brine (100 mL*2), dry over anhydrous Na2SO4, concentrate to give the crude product.
Purification by chromatography (silica gel, EtOAc:PE=1:1) affords the title compound (4.6 g, 77.8percent). MS: (M-1): 192.2.
70% at 65℃; for 3 h; 3-(4-nitrophenoxy)propionic acid (8.8 g, 41.7 mmol) was added to a 100 mL reaction flask, and concentrated sulfuric acid (30 mL) was added to stir and dissolve. P2O5 (5.9 g, 41.7 mmol) was added, and the mixture was reacted at 65 ° C for 3 hours. After the reaction was completed, the reaction mixture was poured into ice water (50 mL), and stirred for 15 minutes, and then extracted with ethyl acetate (100 mL×3). The combined organic phase was washed with saturated aqueous sodium chloride (100mL × 2), dried over anhydrous sodium sulfate, the obtained crude product was separated and purified by column chromatography and concentrated (silica gel, eluent: ethyl acetate: petroleum ether = 1: 1) to give the title compound (5.6g, 70percent yield).

Reference: [1] Patent: WO2005/37830, 2005, A1, . Location in patent: Page/Page column 18
[2] Patent: EP2487171, 2012, A1, . Location in patent: Page/Page column 9
[3] Patent: WO2014/418, 2014, A1, . Location in patent: Page/Page column 97
[4] Patent: US2015/197511, 2015, A1, . Location in patent: Paragraph 0450; 0451
[5] Patent: CN108440404, 2018, A, . Location in patent: Paragraph 0075; 0079; 0080; 0081
[6] Journal of the Indian Chemical Society, 1939, vol. 16, p. 639,644
[7] Journal of the American Chemical Society, 1954, vol. 76, p. 5065,5067
[8] Journal of the American Chemical Society, 1954, vol. 76, p. 5065,5067
[9] Yaoxue Xuebao, 1959, vol. 7, p. 189,190[10] Chem.Abstr., 1960, p. 5637
[11] Patent: WO2012/107262, 2012, A1, . Location in patent: Page/Page column 19
[12] Tetrahedron, 2017, vol. 73, # 27-28, p. 3913 - 3922
  • 2
  • [ 491-37-2 ]
  • [ 68043-53-8 ]
Reference: [1] Patent: US2002/25965, 2002, A1,
[2] Patent: US5629321, 1997, A,
[3] Patent: US5719145, 1998, A,
[4] Patent: EP760364, 1997, A2,
[5] Patent: WO2015/38446, 2015, A1, . Location in patent: Page/Page column 48
  • 3
  • [ 491-37-2 ]
  • [ 68043-53-8 ]
  • [ 90322-49-9 ]
YieldReaction ConditionsOperation in experiment
9% at 0℃; for 2 h; /V-(3,4-Dihydro-2W-chromen-6-yl)acetamide (228). A solution of KNO3 (2.25 g, 22.3 mmol) in CH2SO4 (10 mL) was added dropwise to a stirred solution of 4-chromanone (225) (3.0 g, 20.2 mmol) in CH2SO4 (50 mL) at 0 0C and the mixture stirred at 0 0C for 2 h. The mixture was poured into ice/water (500 mL), stirred 30 min and the precipitate filtered. The solid was washed with water (3 x 10 mL) and dried. The solid was purified by chromatography, eluting with 20percent EtOAc/pet. ether, to give (i) 8-nitro-2,3-dihydro-4/-/- chromen-4-one (226) (369 mg, 9percent) as a white solid: mp (EtOAc/pet. ether) 120-121 0C; 1H NMR δ 8.17 (dd, J = 7.8, 1.8 Hz, 1 H, H-7), 8.10 (dd, J = 8.0, 1.8 Hz, 1 H, H-5), 7.12 (dd, J = 8.0, 7.8 Hz, 1 H, H-6), 4.73 (dd, J = 6.5, 6.4 Hz, 2 H, H-2), 2.95 (br t, J = 6.5 Hz, 2 H, H-3). Anal, calcd for C9H7NO4: C, 56.0; H, 3.7; N, 7.3. Found: C, 56.1; H, 3.7; N, 7.3percent; and (ii) 6-nitro-2,3-dihydro-4/-/-chromen-4-one (227) (3.17 g, 81percent) as a white solid: mp (EtOAc/pet. ether) 169-171 0C; 1H NMR δ 8.78 (d, J = 2.8 Hz, 1 H, H-5), 8.32 (dd, J = 9.1, 2.8 Hz, 1 H, H-7), 7.11 (d, J = 9.1 Hz, 1 H, H-8), 4.67 (dd, J = 6.6, 6.4 Hz, 2 H, H-2), 2.91 (dd, J = 6.6, 6.4 Hz, 2 H, H-3); 13C NMR δ 189.4, 165.7, 142.1, 130.3, 123.7, 120.8, 119.3, 67.6, 37.1. Anal, calcd for C9H7NO4: C, 56.0; H, 3.7; N, 7.3. Found: C, 56.1; H, 3.7; N, 7.4percent.A mixture of nitrochromanone 227 (2.0 g, 13.4 mmol) and Pd/C (5percent, 100 mg) in EtOH/EtOAc (4:1, 150 mL), water (10 mL), and cHCI (1 mL) was stirred under H2 (60 psi) for 16 h. The mixture was filtered through celite, washed with EtOH (3 x 25 mL) and the solvent evaporated. The residue was partitioned between dilute aqueous NH3 solution and DCM, the organic fraction dried, and the solvent evaporated. The residue was dissolved in dry dioxane (100 mL) and Ac2O (2.8 mL, 29.4 mmol) added dropwise. The solution was stirred at 20 0C for 16 h, diluted with water and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (50-100percent) of EtOAc/pet. ether, to give acetamide 228 (2.09 g, 70percent) as a white solid: mp 111-113 0C [lit. (Hach, V. Coll. Czech. Chem. Commun. 1959, 24, 3136-3140) mp (EtOH) 118 0C]; 1H NMR δ 7.28 (d, J = 2.2 Hz, 1 H, H-5), 7.02 (dd, J = 8.6, 2.2 Hz, 1 H, H-7), 6.72 (d, J = 8.6 Hz, 1 H, H-8), 4.15 (br dd, J = 5.2, 5.0 Hz, 2 H, H-2), 2.77 (br t, J = 6.5 Hz, 2 H, H-4), 2.13 (s, 3 H, CH3), 1.95- 2.02 (m, 2 H, H-3).
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 21, p. 6853 - 6865
[2] Patent: WO2006/104406, 2006, A1, . Location in patent: Page/Page column 148
[3] Patent: WO2015/145371, 2015, A1, . Location in patent: Page/Page column 48
  • 4
  • [ 100-02-7 ]
  • [ 68043-53-8 ]
Reference: [1] Journal of the Indian Chemical Society, 1939, vol. 16, p. 639,644
[2] Patent: EP2487171, 2012, A1,
[3] Patent: WO2012/107262, 2012, A1,
[4] Patent: WO2014/418, 2014, A1,
[5] Patent: US2015/197511, 2015, A1,
[6] Tetrahedron, 2017, vol. 73, # 27-28, p. 3913 - 3922
[7] Patent: CN108440404, 2018, A,
  • 5
  • [ 491-37-2 ]
  • [ 68043-53-8 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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