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[ CAS No. 3759-28-2 ] {[proInfo.proName]}

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Chemical Structure| 3759-28-2
Chemical Structure| 3759-28-2
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Product Details of [ 3759-28-2 ]

CAS No. :3759-28-2 MDL No. :MFCD00001895
Formula : C9H6N2 Boiling Point : -
Linear Structure Formula :- InChI Key :GKHSEDFDYXZGCG-UHFFFAOYSA-N
M.W : 142.16 Pubchem ID :77368
Synonyms :

Calculated chemistry of [ 3759-28-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.68
TPSA : 47.58 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.42
Log Po/w (XLOGP3) : 1.5
Log Po/w (WLOGP) : 1.62
Log Po/w (MLOGP) : 1.08
Log Po/w (SILICOS-IT) : 2.11
Consensus Log Po/w : 1.55

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.0
Solubility : 1.41 mg/ml ; 0.00991 mol/l
Class : Soluble
Log S (Ali) : -2.11
Solubility : 1.11 mg/ml ; 0.00782 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.95
Solubility : 0.16 mg/ml ; 0.00112 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.28

Safety of [ 3759-28-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3759-28-2 ]

* 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 [ 3759-28-2 ]
  • Downstream synthetic route of [ 3759-28-2 ]

[ 3759-28-2 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 3759-28-2 ]
  • [ 13130-79-5 ]
Reference: [1] Dalton Transactions, 2015, vol. 44, # 36, p. 15905 - 15913
[2] Patent: US6340759, 2002, B1, . Location in patent: Example 421
  • 2
  • [ 3759-28-2 ]
  • [ 4456-77-3 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 7, p. 1740 - 1750
  • 3
  • [ 7647-01-0 ]
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  • [ 4456-77-3 ]
Reference: [1] Chemische Berichte, 1887, vol. 20, p. 2504
  • 4
  • [ 3759-28-2 ]
  • [ 7664-93-9 ]
  • [ 4456-77-3 ]
Reference: [1] Chemische Berichte, 1887, vol. 20, p. 2504
  • 5
  • [ 100-47-0 ]
  • [ 75-05-8 ]
  • [ 16532-78-8 ]
  • [ 876-31-3 ]
  • [ 3759-28-2 ]
Reference: [1] Chemical Communications, 2013, vol. 49, # 36, p. 3793 - 3795
  • 6
  • [ 22115-41-9 ]
  • [ 3759-28-2 ]
YieldReaction ConditionsOperation in experiment
33% for 1.5 h; Reflux The synthesis procedure of (E)-2-(2-(1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)vinyl)benzonitrile (PY-oCN) was performed by the following steps (Fig. 3). At first 2-(bromomethyl)benzonitrile was synthesized also as an intermediate for the next pyrazoline derivative (PY-oCNCN). First 2-methylbenzonitrile (25 g, 0.21 mol) was dissolved in 150 cm3 of CCl4. Equimolar amount of NBS and 0.3 g of AIBN were added. The reaction mixture was refluxed for 5 h and after cooling to 40 °C it was filtered and the solvent was evaporated. The residue was chromatographed on silica gel with DCM as eluent. Only the first fraction was collected. The yield of reaction was 25 g (57 percent). According to the following procedure final compound – (E)-2-(2-(1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)vinyl)benzonitrile was obtained. The 2-(bromomethyl)benzonitrile from the first step of synthesis described above (0.4 g, 2 mmol) and triphenylphosphine (0.524 g, 2 mmol) were dissolved and boiled in dry benzene overnight. The resulting salt was filtered, washed with hot benzene and used without further purification. To the suspension of phosphonium salt in dry THF (25 cm3), under inert atmosphere at room temperature, sodium ethanolate (0.108 g, 2 mmol) was added. The color of the mixture became deep red and after that the solution was stirred for another 30min. After that time the solution of 1-phenyl-4,5-dihydro-1H-pyrazole-3-carbaldehyde (0.348 g, 2 mmol) in dry THF (10 cm3) was added drop wise and was stirred overnight at 50 °C. Next the solvent was evaporated and DCM was added to the orange residue until it became homogenous. The product was purified on silica gel with DCM as eluent. It was crystallized from heptane with yield of reaction 0.325 g (59.5 percent). To obtain – (E)-2-(1-cyano-2-(1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)vinyl)benzonitrile, which is a derivative of PY-oCN, it was necessary to synthesize another intermediate. The 2-(bromomethyl)benzonitrile (5 g, 25.5 mmol), which was obtained before, was dissolved in a mixture of ethanol (50 cm3) and water (10 cm3). Potassium cyanide (2.6 g, 40 mmol) was added to this solution. Then it was refluxed for 1.5 h and subsequently poured onto ice. Deep green-blue solution was extracted with DCM. The extract was dried with MgSO4 and passed on alumina (neutral) in DCM to give yellowish solution. The eluent was evaporated and the residue crystallized from methanol. The yield of the intermediate was 1.2 g (33 percent). The last step of (E)-2-(1-cyano-2-(1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)vinyl)benzonitrilesynthesis was as follows (cf. Fig. 3). Anhydrous sodium acetate was added (0.05 g) to the solution of 2-(cyanomethyl)benzonitrile (0.4 g, 2.8 mmol) and 1-phenyl-4,5-dihydro-1H-pyrazole-3-carbaldehyde (0.490 g, 2.8 mmol), in dry ethanol. Then it was stirred and refluxed overnight. The solvent was evaporated and oily residue was chromatographed on silica gel with DCM as eluent. After evaporation of DCM the oil was dissolved in boiling heptane. After cooling below 0 °C the orange solid precipitated from the solution and then it was filtered. The yield of this synthesis was 0.216 g (efficiency: 26 percent).
Reference: [1] Dyes and Pigments, 2014, vol. 102, p. 63 - 70
  • 7
  • [ 88284-48-4 ]
  • [ 109-77-3 ]
  • [ 86-29-3 ]
  • [ 3759-28-2 ]
  • [ 92427-55-9 ]
  • [ 127667-03-2 ]
Reference: [1] Chemical Communications, 2007, # 15, p. 1505 - 1507
  • 8
  • [ 773837-37-9 ]
  • [ 40400-15-5 ]
  • [ 3759-28-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 14, p. 2345 - 2351
  • 9
  • [ 75266-12-5 ]
  • [ 16136-52-0 ]
  • [ 3759-28-2 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 19, p. 6159 - 6161
  • 10
  • [ 1258406-20-0 ]
  • [ 3759-28-2 ]
  • [ 1258406-25-5 ]
  • [ 1258406-26-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2010, vol. 8, # 22, p. 5166 - 5173
[2] Organic and Biomolecular Chemistry, 2010, vol. 8, # 22, p. 5166 - 5173
  • 11
  • [ 394-47-8 ]
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Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 14, p. 2703 - 2718
  • 12
  • [ 86369-35-9 ]
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Reference: [1] Synthesis, 2010, # 19, p. 3332 - 3338
  • 13
  • [ 87895-15-6 ]
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  • [ 28867-76-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 8, p. 1813 - 1818
  • 14
  • [ 529-19-1 ]
  • [ 3759-28-2 ]
Reference: [1] Israel Journal of Chemistry, 1971, vol. 9, p. 111 - 118
  • 15
  • [ 1443-60-3 ]
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Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 19, p. 6159 - 6161
  • 16
  • [ 75275-87-5 ]
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Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 19, p. 6159 - 6161
  • 17
  • [ 75275-88-6 ]
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Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 19, p. 6159 - 6161
  • 18
  • [ 235-25-6 ]
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Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 19, p. 6159 - 6161
  • 19
  • [ 23589-33-5 ]
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Reference: [1] Australian Journal of Chemistry, 1972, vol. 25, p. 607 - 624
  • 20
  • [ 143-33-9 ]
  • [ 22115-41-9 ]
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Reference: [1] Israel Journal of Chemistry, 1971, vol. 9, p. 111 - 118
  • 21
  • [ 151-50-8 ]
  • [ 612-13-5 ]
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Reference: [1] Chemische Berichte, 1887, vol. 20, p. 2224
  • 22
  • [ 100-47-0 ]
  • [ 75-05-8 ]
  • [ 16532-78-8 ]
  • [ 876-31-3 ]
  • [ 3759-28-2 ]
Reference: [1] Chemical Communications, 2013, vol. 49, # 36, p. 3793 - 3795
  • 23
  • [ 151-50-8 ]
  • [ 22115-41-9 ]
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Reference: [1] Journal of the Chemical Society, 1955, p. 2214,2216
  • 24
  • [ 67-56-1 ]
  • [ 163977-20-6 ]
  • [ 3759-28-2 ]
  • [ 124-41-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1991, # 11, p. 1715 - 1720
  • 25
  • [ 64-17-5 ]
  • [ 7732-18-5 ]
  • [ 151-50-8 ]
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Reference: [1] Chemische Berichte, 1887, vol. 20, p. 2222
  • 26
  • [ 3759-28-2 ]
  • [ 18698-99-2 ]
Reference: [1] Chemical Communications, 1997, # 11, p. 1041 - 1042
[2] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 21, p. 3197 - 3204
  • 27
  • [ 67-56-1 ]
  • [ 3759-28-2 ]
  • [ 80900-33-0 ]
  • [ 80900-34-1 ]
Reference: [1] Tetrahedron Letters, 1981, vol. 22, # 41, p. 4107 - 4110
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