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[ CAS No. 2411-83-8 ] {[proInfo.proName]}

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Chemical Structure| 2411-83-8
Chemical Structure| 2411-83-8
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Product Details of [ 2411-83-8 ]

CAS No. :2411-83-8 MDL No. :MFCD00039520
Formula : C8H8O4 Boiling Point : -
Linear Structure Formula :- InChI Key :DOAJWTSNTNAEIY-UHFFFAOYSA-N
M.W : 168.15 Pubchem ID :75484
Synonyms :

Calculated chemistry of [ 2411-83-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.77
TPSA : 66.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.69
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 0.88
Log Po/w (MLOGP) : 0.74
Log Po/w (SILICOS-IT) : 0.73
Consensus Log Po/w : 1.12

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.08
Solubility : 1.38 mg/ml ; 0.00823 mol/l
Class : Soluble
Log S (Ali) : -2.54
Solubility : 0.484 mg/ml ; 0.00288 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.32
Solubility : 8.1 mg/ml ; 0.0482 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 2411-83-8 ]

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

Application In Synthesis of [ 2411-83-8 ]

* 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 [ 2411-83-8 ]
  • Downstream synthetic route of [ 2411-83-8 ]

[ 2411-83-8 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 2411-83-8 ]
  • [ 1668-84-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 4, p. 871 - 887
  • 2
  • [ 2411-83-8 ]
  • [ 769-30-2 ]
Reference: [1] Patent: CN103804341, 2018, B,
  • 3
  • [ 2411-83-8 ]
  • [ 101417-40-7 ]
Reference: [1] Patent: CN103804341, 2018, B,
  • 4
  • [ 2411-83-8 ]
  • [ 66411-55-0 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 2, p. 635 - 644
  • 5
  • [ 2411-83-8 ]
  • [ 5768-39-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 4, p. 871 - 887
[2] Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 2, p. 635 - 644
[3] Patent: WO2016/131098, 2016, A1,
[4] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 604 - 614
[5] Patent: CN104016960, 2018, B,
  • 6
  • [ 2411-83-8 ]
  • [ 74-95-3 ]
  • [ 33842-16-9 ]
YieldReaction ConditionsOperation in experiment
81.2% With caesium carbonate In N,N-dimethyl-formamide at 110℃; for 3 h; 6.0 g (0.036 mol) of II and cesium carbonate (0.54 mol) are dissolved in 50 ml of DMF.Dibromomethane 11.5 ml (0.54 mol) was added dropwise at room temperature. After dripping, the temperature was raised to 110°C for 3 hours.The reaction was stopped after the reaction was cooled to room temperature and filtered. Add an equal volume of water and ethyl acetate to the filtrate to separate the solution.The aqueous phase is extracted twice with ethyl acetate, the organic phases are combined, washed with water, and washed with saturated brine.Anhydrous sodium sulfate was dried for 8 h. The desiccant was filtered off, the solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography.Elution with petroleum ether:ethyl acetate (6:1) to collect the desired components,Evaporation under reduced pressure gave a white solid of 5.2 g, yield 81.2percent.
Reference: [1] Patent: CN103804341, 2018, B, . Location in patent: Paragraph 0064; 0068; 0069
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 4, p. 871 - 887
[3] Patent: US2004/34046, 2004, A1,
[4] Patent: WO2004/4732, 2004, A1, . Location in patent: Page/Page column 65-66
[5] Patent: WO2005/34939, 2005, A1, . Location in patent: Page/Page column 76
[6] Patent: WO2004/5284, 2004, A1, . Location in patent: Page 68
  • 7
  • [ 2411-83-8 ]
  • [ 75-11-6 ]
  • [ 33842-16-9 ]
YieldReaction ConditionsOperation in experiment
52%
Stage #1: With potassium fluoride In N,N-dimethyl-formamide at 20℃; for 0.5 h;
Stage #2: at 100℃; for 5 h;
Methyl 2,3-dihydroxybenzoate (1.0 g, 5.95 mmol) in DMF (16 mL) was treated with KF (1 .79 g, 30.9 mmol) and stirred at ambient temperature for 30 minutes. Diiodomethane (1 .79 g, 6.7 mmol) was added and the reaction heated at 100 °C for 5 hours. The reaction mixture was cooled to rt, poured onto water (100 mL) and extracted using diethyl ether (2 x 50 mL). The combined organics were washed with water (50 mL), brine(50 mL), dried (MgS04) and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 10percent EtOAc-petroleum ether eluent to give methyl benzo[ ][1 ,3]dioxole-4- carboxylate as a white crystalline solid (0.56 g; 52percent);1H NMR (400 MHz, CDCI3): δ = 7.41 (dd, J= 8.0, 1.2 Hz, 1 H), 6.97 (dd, J= 8.0, 1 .2 Hz, 1 H), 6.86 (t, J = 8.0 Hz, 1 H), 6.1 (s, 2H), 3.93 (s, 3H).
37%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃;
Stage #2: at 60℃; for 6 h;
Weigh compound D-1 (1 g, 6.0 mmol) in 10 mL DMF. Add anhydrous potassium carbonate (2.5 g, 17.8 mmol), The reaction was stirred at room temperature overnight. Slowly add CH2I2 (1.9 g, 7.1 mmol) after overnight Solution with 5mL DMF, After heating, the reaction is heated to about 60°C. TLC monitors the end of the reaction, After about 6 hours, the reaction is over. Pour into ice water, Extract with ethyl acetate (50 mL × 2) The organic phase was washed three times and dried over anhydrous Na2SO4. Filtering, Concentrated as a pale yellow oil, Separation with 300-400 mesh silica gel column chromatography, The eluent was n-hexane:ethyl acetate=3:1 (v/v) to obtain 396 mg of white crystals. Yield 37percent.
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 604 - 614
[2] Patent: WO2016/131098, 2016, A1, . Location in patent: Page/Page column 167; 168
[3] Patent: CN104016960, 2018, B, . Location in patent: Paragraph 0084-0087; 0091-0093
[4] Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 2, p. 635 - 644
  • 8
  • [ 2411-83-8 ]
  • [ 75-09-2 ]
  • [ 33842-16-9 ]
Reference: [1] Steroids, 2010, vol. 75, # 12, p. 967 - 973
  • 9
  • [ 2411-83-8 ]
  • [ 4442-53-9 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 2, p. 635 - 644
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 11, p. 2947 - 2954
[3] Patent: CN106905335, 2017, A,
  • 10
  • [ 2411-83-8 ]
  • [ 20734-66-1 ]
Reference: [1] Archiv der Pharmazie, 2011, vol. 344, # 9, p. 557 - 563
  • 11
  • [ 2411-83-8 ]
  • [ 154447-36-6 ]
Reference: [1] Australian Journal of Chemistry, 2003, vol. 56, # 11, p. 1099 - 1106
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