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[ CAS No. 155020-44-3 ] {[proInfo.proName]}

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Chemical Structure| 155020-44-3
Chemical Structure| 155020-44-3
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Product Details of [ 155020-44-3 ]

CAS No. :155020-44-3 MDL No. :MFCD09027197
Formula : C8H8FNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :GUGQUCUSGQOTGG-UHFFFAOYSA-N
M.W : 201.15 Pubchem ID :10465417
Synonyms :

Calculated chemistry of [ 155020-44-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.21
TPSA : 64.28 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 1.79
Log Po/w (WLOGP) : 2.17
Log Po/w (MLOGP) : 1.62
Log Po/w (SILICOS-IT) : 0.12
Consensus Log Po/w : 1.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.33
Solubility : 0.932 mg/ml ; 0.00463 mol/l
Class : Soluble
Log S (Ali) : -2.76
Solubility : 0.351 mg/ml ; 0.00174 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.32
Solubility : 0.967 mg/ml ; 0.00481 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.13

Safety of [ 155020-44-3 ]

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 [ 155020-44-3 ]

* 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 [ 155020-44-3 ]
  • Downstream synthetic route of [ 155020-44-3 ]

[ 155020-44-3 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 771-69-7 ]
  • [ 124-41-4 ]
  • [ 66684-59-1 ]
  • [ 66684-60-4 ]
  • [ 155020-44-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 9, p. 1362 - 1370
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 9, p. 1362 - 1370
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 9, p. 1362 - 1370
  • 2
  • [ 771-69-7 ]
  • [ 124-41-4 ]
  • [ 66684-59-1 ]
  • [ 66684-60-4 ]
  • [ 155020-44-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 9, p. 1362 - 1370
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 9, p. 1362 - 1370
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 9, p. 1362 - 1370
  • 3
  • [ 771-69-7 ]
  • [ 124-41-4 ]
  • [ 155020-44-3 ]
YieldReaction ConditionsOperation in experiment
99% at 4 - 20℃; for 0.5 h; A freshly prepared solution of sodium methoxide [0.58 g (25 mmol) of sodium dissolved in 3 niL of anhydrous methanol] was added dropwise to a solution of 2 g (11.2 mmol) of l52,3-trifluoro-4-nitrobenzene in 30 mL of anhydrous methanol under nitrogen at +40C. The resulting mixture was stirred overnight at room temperature and quenched with 1 M aqueous citric acid (0.1 eq) and methanol was evaporated under reduced pressure. The residue was taken up with ether, washed with 1 M citric acid, brine and dried over anhydrous magnesium sulfate and filtered off. The filtrate was evaporated under reduced pressure to give 2.2 g (99percent yield) of the crude product, which was purified by crystallisation from hexane. H1 NMR (CDCl3) 3.95 (s, 3H, OMe); 4.06 (d, 3H5 J= 1.6 Hz); 6.72 (dd, IH, CH5 J = 9.4 Hz5 J = 7.5 Hz) 7.72 (dd, IH, CH, J = 9.4 Hz, J = 2.23 Hz).
80% at 0 - 20℃; Example 25 N-(2-cvano- 1 -(7-fluoro- 1 -hydroxy- 1.3 -dihydrobenzo [c] [ 1.2"|oxaborol-6-yloxy)propan-2-v l)-4-(trifluoromethoxy)benzamide To a stirring solution of l,2,3-trifluoro-4-nitrobenzene (80 g, 0.45 mmol) in MeOH (800 mL) is slowly added MeONa (54 g, 0.99 mmol) in portions at 0°C. The resulting mixture is stirred at rt overnight. TLC showed the reaction is completed. The solvent is evaporated and the residue is washed with water, acidified with diluted HC1 solution to pH=7.0 and extracted with EtOAc. The separated organics is dried and concentrated to give a residue, which is purified by silica gel chromatography (PE:EtOAc=100:l to 30:1) to give the desired product (72 g, 80percent yield).
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 19, p. 6469 - 6475
[2] Patent: WO2006/84338, 2006, A1, . Location in patent: Page/Page column 90
[3] Journal of the American Chemical Society, 2011, vol. 133, # 9, p. 2989 - 2997
[4] Patent: WO2014/149793, 2014, A1, . Location in patent: Page/Page column 85
  • 4
  • [ 67-56-1 ]
  • [ 771-69-7 ]
  • [ 155020-44-3 ]
YieldReaction ConditionsOperation in experiment
89% for 48 h; Reflux Step 1:To a solution of 1,2,3-trifluoro-4-nitrobenzene(5.00 g, 28.2 mmol) in anhydrous MeOH (100 mL) was added NaOMe (6.86 g, 12.7 mmol). The reaction mixture was heated at reflux for 48 h, adjusted to pH 6 with 2 M citric acid, and extracted with EtOAc (2 × 400 mL). The organic layers were combined, washed with brine (50 mL), dried over MgSO4, and concentrated under reduced pressure to give 2-fluoro-1,3-dimethoxy-4-nitrobenzene as a yellow powder (5.10 g, 89percent).1H-NMR (CDCl3):δ3.97 (s, 3H, CH3), 4.07 (d, 3H,J= 1.1 Hz, CH3), 6.74 (dd, 1H,J= 9.3 & 7.6 Hz, Ph-H), 7.74 (dd, 1H,J= 9.4 & 2.1 Hz, Ph-H).
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 139, p. 762 - 772
  • 5
  • [ 771-69-7 ]
  • [ 155020-44-3 ]
Reference: [1] Patent: US6162931, 2000, A,
  • 6
  • [ 771-69-7 ]
  • [ 124-41-4 ]
  • [ 66684-59-1 ]
  • [ 66684-60-4 ]
  • [ 155020-44-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 9, p. 1362 - 1370
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 9, p. 1362 - 1370
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 9, p. 1362 - 1370
  • 7
  • [ 155020-44-3 ]
  • [ 103068-40-2 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 19, p. 6469 - 6475
[2] Journal of the American Chemical Society, 2011, vol. 133, # 9, p. 2989 - 2997
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