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[ CAS No. 23082-51-1 ] {[proInfo.proName]}

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Chemical Structure| 23082-51-1
Chemical Structure| 23082-51-1
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Product Details of [ 23082-51-1 ]

CAS No. :23082-51-1 MDL No. :MFCD09031331
Formula : C8H6ClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :PUUYGMZERWRIDS-UHFFFAOYSA-N
M.W : 199.59 Pubchem ID :12643796
Synonyms :

Calculated chemistry of [ 23082-51-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.47
TPSA : 62.89 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) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : 2.15
Log Po/w (WLOGP) : 2.45
Log Po/w (MLOGP) : 1.18
Log Po/w (SILICOS-IT) : 0.65
Consensus Log Po/w : 1.55

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.64
Solubility : 0.456 mg/ml ; 0.00228 mol/l
Class : Soluble
Log S (Ali) : -3.1
Solubility : 0.157 mg/ml ; 0.000789 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.73
Solubility : 0.367 mg/ml ; 0.00184 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.83

Safety of [ 23082-51-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 23082-51-1 ]

* 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 [ 23082-51-1 ]
  • Downstream synthetic route of [ 23082-51-1 ]

[ 23082-51-1 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 41995-04-4 ]
  • [ 105-53-3 ]
  • [ 23082-51-1 ]
YieldReaction ConditionsOperation in experiment
33%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.333333 h;
Stage #2: at 0 - 80℃; for 2.5 h;
Stage #3: at 80℃; for 6 h;
To a solution of diethyl malonate (12.0 g, 75 mmol) in THF (250 mL), NaH (3.6 g, 90 mmol) was added in portions and the resulting mixture was stirred at RT for 20 min. A solution of 4-chloro-2-nitrobenzoyl chloride in THF (100 mL) was added dropwise to the reaction mixture at 0 oC. The resulting mixture was stirred at RT for 30 min and then stirred at 80 oC for 2 h. The mixture was quenched with water and partitioned between water and ethyl acetate. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was dissolved in AcOH (25 mL) and 20percent H2SO4 (25 mL) and the resulting mixture was stirred at 80oC for 6 h. The mixture was extracted with ethyl acetate, washed with brine, water and NaHCO3 solution. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether = 1:5) to afford the desired product (5.0 g, 33percent yield) as a light yellow solid.
Reference: [1] Patent: WO2015/54572, 2015, A1, . Location in patent: Page/Page column 274
[2] Chemical and Pharmaceutical Bulletin, 1969, vol. 17, p. 596 - 604
[3] Patent: US2008/287458, 2008, A1, . Location in patent: Page/Page column 39
  • 2
  • [ 1262802-06-1 ]
  • [ 23082-51-1 ]
Reference: [1] Chemistry - A European Journal, 2010, vol. 16, # 46, p. 13590 - 13593
[2] Journal of Organic Chemistry, 2013, vol. 78, # 12, p. 5932 - 5948
  • 3
  • [ 99-91-2 ]
  • [ 23082-51-1 ]
Reference: [1] Patent: US4379929, 1983, A,
[2] Chemistry - A European Journal, 2010, vol. 16, # 46, p. 13590 - 13593
  • 4
  • [ 6280-88-2 ]
  • [ 105-53-3 ]
  • [ 23082-51-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7381 - 7387
  • 5
  • [ 6280-88-2 ]
  • [ 23082-51-1 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 232,236
[2] Patent: WO2015/54572, 2015, A1,
  • 6
  • [ 857560-75-9 ]
  • [ 23082-51-1 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 227,232
  • 7
  • [ 79406-57-8 ]
  • [ 23082-51-1 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 227,232
[2] Journal of the Chemical Society, 1947, p. 227,232
  • 8
  • [ 196408-40-9 ]
  • [ 23082-51-1 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 227,232
[2] Journal of the Chemical Society, 1947, p. 227,232
  • 9
  • [ 34662-32-3 ]
  • [ 23082-51-1 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 232,236
  • 10
  • [ 89-59-8 ]
  • [ 23082-51-1 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 232,236
  • 11
  • [ 861060-91-5 ]
  • [ 23082-51-1 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 227,232
  • 12
  • [ 41995-04-4 ]
  • [ 141-97-9 ]
  • [ 23082-51-1 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 232,236
  • 13
  • [ 2001-16-3 ]
  • [ 23082-51-1 ]
Reference: [1] Chemische Berichte, 1964, vol. 97, p. 1902 - 1909
  • 14
  • [ 20895-89-0 ]
  • [ 23082-51-1 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1968, p. 2747 - 2751
  • 15
  • [ 23082-51-1 ]
  • [ 39061-72-8 ]
YieldReaction ConditionsOperation in experiment
89% With iron; acetic acid In water for 16 h; Reflux 1-(2-Amino-4-chlorophenyl)ethanone A mixture of methyl 1-(4-chloro-2-nitrophenyl)ethanone (5.0 g, 25 mmol) and Fe (5.6 g, 100 mmol) in CH3COOH (50 mL) and H2O (50 mL) was stirred at reflux for 16 h. The mixture was allowed to cool to RT and quenched with saturated NaHCO3 aqueous solution. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3 aqueous solution and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether= 1:4) to afford the desired product (3.8 g, 89percent yield) as a yellow solid.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7381 - 7387
[2] Patent: WO2015/54572, 2015, A1, . Location in patent: Page/Page column 274
[3] Journal of the Chemical Society [Section] C: Organic, 1968, p. 2747 - 2751
[4] Patent: US4379929, 1983, A,
[5] Patent: US2008/287458, 2008, A1, . Location in patent: Page/Page column 39
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