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[ CAS No. 20876-37-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 20876-37-3
Chemical Structure| 20876-37-3
Chemical Structure| 20876-37-3
Structure of 20876-37-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 20876-37-3 ]

CAS No. :20876-37-3 MDL No. :MFCD00100652
Formula : C14H13NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :PBSZHNXXFIYDBU-UHFFFAOYSA-N
M.W : 243.26 Pubchem ID :292648
Synonyms :

Calculated chemistry of [ 20876-37-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.14
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 71.21
TPSA : 55.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.42
Log Po/w (XLOGP3) : 4.17
Log Po/w (WLOGP) : 3.33
Log Po/w (MLOGP) : 2.42
Log Po/w (SILICOS-IT) : 1.68
Consensus Log Po/w : 2.8

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.2
Solubility : 0.0152 mg/ml ; 0.0000624 mol/l
Class : Moderately soluble
Log S (Ali) : -5.03
Solubility : 0.00225 mg/ml ; 0.00000924 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.83
Solubility : 0.00357 mg/ml ; 0.0000147 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.33

Safety of [ 20876-37-3 ]

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 [ 20876-37-3 ]

* 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 [ 20876-37-3 ]
  • Downstream synthetic route of [ 20876-37-3 ]

[ 20876-37-3 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 5460-31-1 ]
  • [ 100-39-0 ]
  • [ 20876-37-3 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3 h; 41.5 g (300 mmol) of potassium carbonate and 200 ml of N,N-dimethylformamide were added to 30.6 g (200 mmol) of 2-methyl-3-nitrophenol.
Then, 23.8 ml (200 mmol) of benzyl bromide was added thereto in an argon stream with stirring and the mixture was stirred at room temperature for 3 hours.
After the reaction was completed, the reaction solution was poured into 1000 ml of water and the mixture was extracted with 800 ml of toluene and 500 ml of the same twice.
The organic layer was successively washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure, whereby 49.3 g of the title compound was obtained as yellow powder (yield: quantitative).
Rf value: 0.48 (n-hexane:ethyl acetate=4:1 (v/v))
Mass spectrum (CI, m/z): 244 (M++1)
1H-NMR spectrum (CDCl3, δppm): 2.42 (s, 3H), 5.13 (s, 2H), 7.08-7.11 (m, 1H), 7.21-7.27 (m, 1H), 7.32-7.44 (m, 6H)
87% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3 h; A mixture of 2-methyl-3-nitrophenol (672 mg, 4.4 mmol), cesium carbonate (2.1 g, 6.44 mmol), and benzyl bromide (751 mg, 4.4 mmol) in DMF (6 mL) was stirred at room temperature for 3 h. The reaction mixture was poured into ice water. The light yellow precipitation was filtered off, washed several times with water, and dried, to provide 1-nitro-2-methyl-3-[(phenylmethyl)oxy]benzene (930 mg, 87percent yield). (at)HNMR (400 MHz, d4-methanol): 8 7.47 (d, 1H), 7.45 (s, 1H), 7.40 (s, 1H), 7.39 (d, 1H), 7.37 (d, 1H), 7.34 (m, 1H), 7.32 (s, 1H), 7.29 (d, 1H), 4.90 (s, 2H), 2.35 (s, 3H).
8.6 g With potassium carbonate In acetonitrile at 90℃; for 2 h; To a 500-mL 3-necked round-bottom flask was placed a solution of 2-methyl-3-nitrophenol (10 g,65.30 mmol) and K2C03 (13 g,94.06 mmol) in CH3CN (100 mL) then BnBr (13 g,76.01 mmol) was added. The reaction was stirred at 90°C for 2 h,cooled to rt,filtered,and concentrated under reduced pressure. Thecrude product was purified by column chromatography eluting with EtOAc/petroleum ether (1:9) affording 8.6 g of the title compound as a yellow oil.
Reference: [1] Patent: US2009/12123, 2009, A1, . Location in patent: Page/Page column 9-10
[2] Patent: WO2005/117909, 2005, A2, . Location in patent: Page/Page column 119
[3] Journal of the Chemical Society, 1948, p. 1605,1608
[4] Heterocycles, 1981, vol. 16, # 7, p. 1119 - 1124
[5] Patent: EP1870099, 2007, A1, . Location in patent: Page/Page column 14
[6] Patent: WO2017/62581, 2017, A1, . Location in patent: Paragraph 0209
  • 2
  • [ 100-39-0 ]
  • [ 20876-37-3 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide
Stage #2: at 20℃; for 3 h;
(Referential Example 22)
Synthesis of 2-benzyloxy-6-nitrotoluene (referential compound 22-1)
Potassium carbonate (41.5 g, 300 mmol) and 200 ml of N,N-dimethylformamide were added to 30.6 g (200 mmol) of 2-methyl-3-nitrophenol.
After that, 23.8 ml (200 mmol) of benzyl bromide was added thereto with stirring in an argon stream and the mixture was stirred at room temperature for 3 hours.
After the reaction was finished, the reaction solution was poured into 1,000 ml of water and and the mixture was extracted with 800 ml of toluene and 500 ml of the same for two times.
The organic layer was successively washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 49.3 g of the title compound as yellow powder (yield: quantitative).
Rf value: 0.48 (n-hexane: ethyl acetate = 4:1 (v/v))
Mass spectrum (CI, m/z): 244 (M+ + 1)
1H-NMR spectrum (CDCl3, δ ppm): 2.42 (s, 3H), 5.13 (s, 2H), 7.08-7.11 (m, 1H), 7.21-7.27 (m, 1H), 7.32-7.44 (m, 6H)
Reference: [1] Patent: EP1679308, 2006, A1, . Location in patent: Page/Page column 42
  • 3
  • [ 5460-31-1 ]
  • [ 100-44-7 ]
  • [ 20876-37-3 ]
Reference: [1] Archiv der Pharmazie, 1988, vol. 321, # 8, p. 487 - 489
[2] Organic Syntheses, 1985, vol. 63, p. 214 - 214
[3] Tetrahedron, 1968, vol. 24, p. 6093 - 6109
  • 4
  • [ 603-83-8 ]
  • [ 20876-37-3 ]
Reference: [1] Tetrahedron, 1968, vol. 24, p. 6093 - 6109
  • 5
  • [ 20876-37-3 ]
  • [ 850364-08-8 ]
Reference: [1] Organic Process Research and Development, 2007, vol. 11, # 1, p. 30 - 38
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