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[ CAS No. 2920-38-9 ] {[proInfo.proName]}

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Chemical Structure| 2920-38-9
Chemical Structure| 2920-38-9
Structure of 2920-38-9 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Guo, Sheng ; Wu, Yifan ; Luo, Shao-Xiong Lennon , et al. DOI:

Abstract: Heterogenous catalysts with confined nanoporous catalytic sites are shown to have high activity and size selectivity. A solution-processable nanoporous organic polymer (1-BPy-Pd) catalyst displays high catalytic performance (TON > 200K) in the heterogeneous Suzuki–Miyaura coupling (SMC) reaction and can be used for the preparation of the intermediates in the synthesis of pharmaceutical agents. In comparison to the homogeneous catalyst analogue (2,2′-BPy)PdCl2, the heterogenous system offers size-dependent catalytic activity when bulkier substrates are used. Furthermore, the catalyst can be used to create catalytic impellers that simplify its use and recovery. We found that this system also works for applications in heterogenous Heck and nitroarenes reduction reactions. The metal-binding nanoporous polymer reported here represents a versatile platform for size-selective heterogeneous and recyclable catalysts.

Keywords: nanoporous organic polymer ; heterogeneous catalyst ; Suzuki?Miyaura coupling reaction ; size-selective reaction ; catalyst processing

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; 128796-39-4 ; ; ; ;

Product Details of [ 2920-38-9 ]

CAS No. :2920-38-9 MDL No. :MFCD00001821
Formula : C13H9N Boiling Point : No data available
Linear Structure Formula :- InChI Key :BPMBNLJJRKCCRT-UHFFFAOYSA-N
M.W : 179.22 Pubchem ID :18021
Synonyms :

Calculated chemistry of [ 2920-38-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.59
TPSA : 23.79 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.22
Log Po/w (XLOGP3) : 3.26
Log Po/w (WLOGP) : 3.23
Log Po/w (MLOGP) : 3.0
Log Po/w (SILICOS-IT) : 3.54
Consensus Log Po/w : 3.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.57
Solubility : 0.0479 mg/ml ; 0.000267 mol/l
Class : Soluble
Log S (Ali) : -3.43
Solubility : 0.066 mg/ml ; 0.000368 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.0
Solubility : 0.0018 mg/ml ; 0.00001 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 2920-38-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P302+P352 UN#:3439
Hazard Statements:H302+H312-H331 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2920-38-9 ]

* 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.

  • Downstream synthetic route of [ 2920-38-9 ]

[ 2920-38-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 623-03-0 ]
  • argon [ No CAS ]
  • [ 224311-51-7 ]
  • [ 98-80-6 ]
  • [ 2920-38-9 ]
YieldReaction ConditionsOperation in experiment
159 mg (89%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; EXAMPLE 32 Synthesis of 4-cyanobiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-chlorobenzonitrile (136 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 ml), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 159 mg (89percent) of the title compound.
159 mg (89%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; Example 32 Synthesis of 4-cyanobiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-chlorobenzonitrile (136 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 159 mg (89percent) of the title compound.
  • 2
  • [ 109-69-3 ]
  • [ 2920-38-9 ]
  • [ 74-88-4 ]
  • [ 37909-95-8 ]
  • 4-butyl-4-phenylcyclohexa-2,5-dienone [ No CAS ]
  • trans-4-butyl-1-methyl-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]
  • cis-4-butyl-1-methyl-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
5%Spectr.; 9%Spectr. General procedure: To a suspension of the DA 12- sodium salt, butyl chloride or cyclohexyl bromide (1 equiv.) was added dropwise at -40 C and the reaction mixture was kept at the same conditions for 40÷60 min. Afterwards required alkyl bromide (1.1÷1.4 equiv.) was added (Table 1, entries 2÷5) and reaction mixture was treated as described above for dienone 2.
  • 3
  • [ 109-69-3 ]
  • [ 25542-62-5 ]
  • [ 2920-38-9 ]
  • [ 37909-95-8 ]
  • trans-4-butyl-1-(6-ethoxy-6-oxohexyl)-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]
  • cis-4-butyl-1-(6-ethoxy-6-oxohexyl)-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
14%Spectr. General procedure: To a suspension of the DA 12- sodium salt, butyl chloride or cyclohexyl bromide (1 equiv.) was added dropwise at -40 C and the reaction mixture was kept at the same conditions for 40÷60 min. Afterwards required alkyl bromide (1.1÷1.4 equiv.) was added (Table 1, entries 2÷5) and reaction mixture was treated as described above for dienone 2.
  • 4
  • [ 109-69-3 ]
  • [ 6621-59-6 ]
  • [ 2920-38-9 ]
  • [ 37909-95-8 ]
  • trans-4-butyl-1-(5-cyanopentyl)-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]
  • cis-4-butyl-1-(5-cyanopentyl)-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
10%Spectr. General procedure: To a suspension of the DA 12- sodium salt, butyl chloride or cyclohexyl bromide (1 equiv.) was added dropwise at -40 C and the reaction mixture was kept at the same conditions for 40÷60 min. Afterwards required alkyl bromide (1.1÷1.4 equiv.) was added (Table 1, entries 2÷5) and reaction mixture was treated as described above for dienone 2.
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