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[ CAS No. 290-37-9 ] {[proInfo.proName]}

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Product Details of [ 290-37-9 ]

CAS No. :290-37-9 MDL No. :MFCD00006122
Formula : C4H4N2 Boiling Point : -
Linear Structure Formula :- InChI Key :KYQCOXFCLRTKLS-UHFFFAOYSA-N
M.W : 80.09 Pubchem ID :9261
Synonyms :

Calculated chemistry of [ 290-37-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 22.03
TPSA : 25.78 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) : -6.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.78
Log Po/w (XLOGP3) : -0.26
Log Po/w (WLOGP) : 0.48
Log Po/w (MLOGP) : -0.92
Log Po/w (SILICOS-IT) : 1.19
Consensus Log Po/w : 0.25

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.91
Solubility : 9.79 mg/ml ; 0.122 mol/l
Class : Very soluble
Log S (Ali) : 0.18
Solubility : 120.0 mg/ml ; 1.5 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.53
Solubility : 2.35 mg/ml ; 0.0293 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 290-37-9 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P240-P210-P264-P280-P370+P378-P337+P313 UN#:1325
Hazard Statements:H228-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 290-37-9 ]

* 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 [ 290-37-9 ]
  • Downstream synthetic route of [ 290-37-9 ]

[ 290-37-9 ] Synthesis Path-Upstream   1~60

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Reference: [1] Patent: US2540476, 1948, ,
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Reference: [1] Research on Chemical Intermediates, 2012, vol. 38, # 8, p. 1743 - 1750
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YieldReaction ConditionsOperation in experiment
88% With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 16 h; General Procedure 1:; Diazine Oxidation;The appropriate diazine (1 equiv.) and mCPBA (1 equiv.) were dissolved in DCM (0.2 M). The reaction was allowed to stir for 16 hours. PPh3 (0.5 equiv.) was then added to reduce any unreacted peracid and the mixture was stirred for an additional 4 h. The volatiles were evaporated under reduce pressure and the residue was purified via silica gel column chromatography.; Pyrazine N-oxide (80)
Synthesised according to general procedure 1.
Purification via silica gel column chromatography using 100percent EtOAc then a mixture of 20percent MeOH/EtOAc gave a white solid (88percent).
1H NMR (300 MHz, CDCl3, 293K, TMS): δ 8.50 (2H, d, J=3.9 Hz), 8.14 (2 H, d, J=4.8 Hz).13C NMR (75 MHz, CDCl3, 293K, TMS): 147.8, 134.0.HRMS calculated for C4H4N2O1 (M+) 96.0324; Found: 96.0295.Melting point ° C.: 103.2-104.5IR (vmax/cm-1): 3120, 3088, 1595, 861, 847, 838.Rf (20percent MeOH/EtOAc): 0.3
50% With dihydrogen peroxide; acetic acid In water at 70 - 80℃; for 5.5 h; A solution of pyrazine (2.5 g, 31 mmol) in AcOH (30 mL) was stirred at 70-80 °C while a mixture of 30percent H2O2 (3.55 g, 32 mmol) and AcOH (25 mL) was added dropwise over 30 min. After the addition, heating was continued for 5 h then the mixture was evaporated under reduced pressure and the residue was taken up in CH2Cl2 (125 mL). Drying over anhydrous Na2CO3 and evaporation gave a solid, which was recrystallised from hexane to give the title product (1.48 g, 50percent) as colourless crystals, mp 113-114 °C (lit.6 113-114 °C); δH 8.11 (2H, m) and 8.48 (2H, m).
Reference: [1] Organic Letters, 2017, vol. 19, # 18, p. 4707 - 4709
[2] Organic Letters, 2018, vol. 20, # 8, p. 2346 - 2350
[3] Angewandte Chemie - International Edition, 2006, vol. 45, # 46, p. 7781 - 7786
[4] Patent: US2008/132698, 2008, A1, . Location in patent: Page/Page column 17-18
[5] Chemical Communications, 2015, vol. 51, # 12, p. 2425 - 2428
[6] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1986, p. 1585 - 1588
[7] Chemistry - A European Journal, 2013, vol. 19, # 44, p. 14998 - 15003
[8] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 5, p. 1386 - 1394
[9] Heterocyclic Communications, 2001, vol. 7, # 4, p. 307 - 312
[10] Tetrahedron, 2012, vol. 68, # 29, p. 5845 - 5851
[11] Journal of Organic Chemistry, 1958, vol. 23, p. 1603,1605
[12] Journal of the American Chemical Society, 1959, vol. 81, p. 5160,5163
[13] Journal of Organic Chemistry, 2017, vol. 82, # 4, p. 2059 - 2066
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Reference: [1] Tetrahedron, 1995, vol. 51, # 43, p. 11855 - 11862
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Reference: [1] Tetrahedron, 1995, vol. 51, # 43, p. 11855 - 11862
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  • [ 5049-61-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1285 - 1287
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  • [ 109-08-0 ]
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Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990, vol. 39, # 7.1, p. 1340 - 1345[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990, # 7, p. 1483 - 1488
[5] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[6] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
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Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[4] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
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Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
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Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990, vol. 39, # 7.1, p. 1340 - 1345[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990, # 7, p. 1483 - 1488
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Reference: [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
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Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
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Reference: [1] Journal of Agricultural and Food Chemistry, 1999, vol. 47, # 10, p. 4332 - 4335
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Reference: [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
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Reference: [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
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Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2866 - 2869
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Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 17, p. 3288 - 3296
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Reference: [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 497 - 500
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Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
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Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
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Reference: [1] Chemical Communications, 2011, vol. 47, # 29, p. 8394 - 8396
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Reference: [1] Kinetics and Catalysis, 2016, vol. 57, # 5, p. 602 - 609[2] Kinet. Katal., 2016, vol. 57, # 5, p. 607 - 614,8
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Reference: [1] Applied Catalysis A: General, 2014, vol. 469, p. 398 - 409
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Reference: [1] Patent: US2540476, 1948, ,
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[2] Chemische Berichte, 1907, vol. 40, p. 4852
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YieldReaction ConditionsOperation in experiment
86% at 70℃; for 12 h; General procedure: In an oven dried glass tube containing a mixture of pyridine 1a (100 mg, 1.26 mmol), and potassium persulphate (683 mg, 2.53 mmol), formamide 2a (2 ml) was added and the reaction mixture was heated at 70 °C. Upon the completion of the reaction (monitored by TLC), saturated sodium bicarbonate solution (5 mL) was added and the crude product was extracted in ethyl acetate (3 X 5 mL). The crude product was purified by column chromatography to furnish compound 3aa as a white crystalline solid (122 mg, 79percent yield)
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 50, p. 4709 - 4712
[2] Tetrahedron, 1985, vol. 41, # 19, p. 4157 - 4170
[3] Chemical Communications, 2002, # 21, p. 2496 - 2497
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Reference: [1] Pharmaceutical Chemistry Journal, 1999, vol. 33, # 7, p. 381 - 383
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[2] Pharmaceutical Chemistry Journal, 1999, vol. 33, # 7, p. 381 - 383
[3] Pharmaceutical Chemistry Journal, 1999, vol. 33, # 7, p. 381 - 383
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Reference: [1] Chemical Communications, 2011, vol. 47, # 29, p. 8394 - 8396
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Reference: [1] Patent: US2540476, 1948, ,
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YieldReaction ConditionsOperation in experiment
50 mg With ammonium peroxodisulfate; zinc trifluoromethanesulfonate; silver nitrate In dichloromethane; water at 20℃; for 4 h; General procedure: Ammonium persulfate (3 equiv, 342 mg), phenylboronic acid (1.5 equiv, 91 mg), silver nitrate (0.2 equiv, 17 mg), and zinc trifluoromethanesulfonate (0.2 equiv, 36 mg) were combined ina 10 mL round bottom flask. A heterocycle (1 equiv, 0.5 mmol) was then added to the same flask and solvated with water (0.4 mL) and CH2Cl2 (1.6 mL). The resulting mixture was sonicated for 10 sec and placed on a stir plate to stir vigorously at room temperature for 4 h. The reaction was quenched with 28percent ammonium hydroxide (2 mL), diluted with water (10 mL), and extracted with CH2Cl2 (3 x 10 mL). The organic layer was dried over sodium sulfate, filtered through cotton, and evaporated en vacuo. The products were purified by column chromatography (SiO2, 5-20percent EtOAc/hexanes). Products 3b, 3c, and 3d required further purification by crystallization as the trifluoromethanesulfonic acid salts and recrystallization from THF/hexanes.
Reference: [1] Heterocycles, 2016, vol. 92, # 9, p. 1687 - 1697
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[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 42, p. 13147 - 13150[6] Angew. Chem., 2016, vol. 128, # 42, p. 13341 - 13344,4
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Reference: [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
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Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
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Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
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