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[ CAS No. 81810-66-4 ] {[proInfo.proName]}

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Chemical Structure| 81810-66-4
Chemical Structure| 81810-66-4
Structure of 81810-66-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 81810-66-4 ]

CAS No. :81810-66-4 MDL No. :MFCD09753267
Formula : C18H14N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :IOKWXGMNRWVQHX-VAWYXSNFSA-N
M.W : 306.32 Pubchem ID :5387181
Synonyms :
Chemical Name :2-Cinnamoyl-3-methylquinoxaline 1,4-dioxide

Calculated chemistry of [ 81810-66-4 ]

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.06
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 91.04
TPSA : 67.99 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) : -6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.3
Log Po/w (XLOGP3) : 1.72
Log Po/w (WLOGP) : 2.2
Log Po/w (MLOGP) : 2.8
Log Po/w (SILICOS-IT) : 1.79
Consensus Log Po/w : 1.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.14
Solubility : 0.222 mg/ml ; 0.000725 mol/l
Class : Soluble
Log S (Ali) : -2.76
Solubility : 0.528 mg/ml ; 0.00172 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.46
Solubility : 0.105 mg/ml ; 0.000344 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 3.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.12

Safety of [ 81810-66-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P321-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H341-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 81810-66-4 ]

* 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 [ 81810-66-4 ]
  • Downstream synthetic route of [ 81810-66-4 ]

[ 81810-66-4 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 100-52-7 ]
  • [ 13297-17-1 ]
  • [ 81810-66-4 ]
YieldReaction ConditionsOperation in experiment
95% With (2-hydroxyethyl)ammonium formate; calcium chloride In methanol at 50 - 65℃; for 3 h; in 250 mLIn a three-necked flask,After adding 64 mL of methanol and 5.05 g (0.0455 mol) of anhydrous CaCl2, the mixture was dissolved with stirring and then added dropwise3.70 g (0.0344 mol)HydroxyEthylamineFormateSub-liquid,Further, 20.25 g (0.1908 mol) of benzaldehyde was added, the temperature was raised to 50 ° C with stirring, 37.50 g (0.1718 mol)Acetylmethylquine,Slowly heated to 60-65 ° C,The reaction was incubated for 3 hours, TThe LC traces the reaction to the end point and stops the reaction. Cooling down to 25 ° C, suction filtration,Washed 3 times with methanol,Drained,Vacuum drying,To give 49.98 g of a bright yellow powdery solid,M.p. 189-191 ° C,Product purity 98.7percent,Yield 95.0percent.
95% With Acetate de N,N-dimethylamino-4 pyridinium In ethanol at 70℃; for 3 h; Green chemistry A mixture of 2-acetyl-3-methyl-quinoxaline 1,4-dioxide (2) (8.09 g, 0.040 mol) andbenzaldehyde (6.37 g, 0.060 mol) in 50 mL ethanol was heated at 70 °C for 30 min to obtain aclear solution, and then 4-(dimethylamino)pyridinium acetate (0.364 g, 2.0 mmol), readilyprepared according to literature,9 was added to the solution. The solution was then stirred at70 °C for 3 h. On cooling the solution to 0 °C, yellow crystals precipitated within 3 h. Theyellow crystals were collected by filtration, washed with ethanol, and air-dried. The motherliquor was evaporated to recycle the catalyst 4-(dimethylamino)pyridinium acetate. Recrystallizationof the yellow crystals afforded compound 3. Yield: 12.3 g (95 percent). Analytical andspectral data for 3 are presented in the Supplementary material to this paper.
94% With magnesium sulfate; acetic acid In methanol; 2,2'-iminobis[ethanol] at 55℃; for 4 h; Anhydrous magnesium sulfate (1.2 g, 0.01 mol) was added to 100 mL of methanol to stir and dissolve, and 1.05 g (0.01 mol) of diethanolamine was added.Anhydrous acetic acid 0.3g (0.005mol), stirring to dissolve after adding benzaldehyde 6.4g (0.06mol), dissolved directly after adding dissolved 2-acetyl-3-methylquinoxaline-1,4-dioxide 10g (0.046mol), heated to 55 ° C, the reaction began, the system first clarified and precipitated Solid, keep warm for 4 hours,The reaction is complete. Cool to room temperature and hold at room temperature for more than 2 hours. Crystallize and filter to obtain crude quinocetone,Wash the cake thoroughly with fresh methanol,Dry to obtain the product 13.1g, yield 94percent,98.5percent purity.
Reference: [1] Patent: CN105566234, 2016, A, . Location in patent: Paragraph 0016; 0017; 0018
[2] Journal of the Serbian Chemical Society, 2018, vol. 83, # 3, p. 265 - 270
[3] Patent: CN104672155, 2017, B, . Location in patent: Paragraph 0018; 0032-0041
[4] Heterocycles, 1987, vol. 26, # 1, p. 55 - 58
[5] European Journal of Medicinal Chemistry, 2010, vol. 45, # 10, p. 4682 - 4686
  • 2
  • [ 480-96-6 ]
  • [ 100-52-7 ]
  • [ 123-54-6 ]
  • [ 81810-66-4 ]
YieldReaction ConditionsOperation in experiment
80% With tributylbenzylammonium hydroxide In ethanol at 50℃; for 1 h; In 500 ml reactor was added 100 ml of ethanol, benzofurazan 13.6 g (0.1 mol), acetyl acetone 20 g (0.2 mol), benzaldehyde 22 g (0.2 mol), magnetic Mg-Al hydrotalcite solid base catalyst 6 grams, tributylbenzyl basic quaternary ammonium salt 11 grams, at 50 ° C for 1 hour, the reaction is completed, filter out the solid base catalyst, the filtrate with activated carbon treatment,Place precipitated pale yellow solid product was filtered and dried to give the cake quinocetone 24.5 g, 80percent yield.
Reference: [1] Patent: CN105294581, 2016, A, . Location in patent: Paragraph 0028; 0029
  • 3
  • [ 480-96-6 ]
  • [ 81810-66-4 ]
Reference: [1] Journal of the Serbian Chemical Society, 2018, vol. 83, # 3, p. 265 - 270
  • 4
  • [ 88-74-4 ]
  • [ 81810-66-4 ]
Reference: [1] Journal of the Serbian Chemical Society, 2018, vol. 83, # 3, p. 265 - 270
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