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[ CAS No. 216309-28-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 216309-28-3
Chemical Structure| 216309-28-3
Structure of 216309-28-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 216309-28-3 ]

CAS No. :216309-28-3 MDL No. :MFCD09258881
Formula : C9H12N2Si Boiling Point : -
Linear Structure Formula :- InChI Key :BESYUGWNHQDZIK-UHFFFAOYSA-N
M.W : 176.29 Pubchem ID :15349669
Synonyms :

Calculated chemistry of [ 216309-28-3 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.26
TPSA : 25.78 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) : -5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.43
Log Po/w (XLOGP3) : 2.4
Log Po/w (WLOGP) : 1.79
Log Po/w (MLOGP) : 1.18
Log Po/w (SILICOS-IT) : 0.8
Consensus Log Po/w : 1.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.82
Solubility : 0.27 mg/ml ; 0.00153 mol/l
Class : Soluble
Log S (Ali) : -2.58
Solubility : 0.46 mg/ml ; 0.00261 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.177 mg/ml ; 0.001 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.5

Safety of [ 216309-28-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 216309-28-3 ]

* 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 [ 216309-28-3 ]
  • Downstream synthetic route of [ 216309-28-3 ]

[ 216309-28-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 216309-28-3 ]
  • [ 153286-94-3 ]
Reference: [1] Monatshefte fur Chemie, 1998, vol. 129, # 10, p. 1035 - 1048
[2] Organic and biomolecular chemistry, 2003, vol. 1, # 3, p. 498 - 506
[3] Journal of Organic Chemistry, 2007, vol. 72, # 13, p. 4750 - 4755
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3743 - 3748
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 3033 - 3047
[6] Organic Letters, 2014, vol. 16, # 17, p. 4524 - 4527
  • 2
  • [ 584-08-7 ]
  • [ 216309-28-3 ]
  • [ 153286-94-3 ]
Reference: [1] Patent: US2008/70931, 2008, A1, . Location in patent: Page/Page column 12
  • 3
  • [ 4595-59-9 ]
  • [ 1066-54-2 ]
  • [ 216309-28-3 ]
YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide; diisopropylamine In toluene at 60℃; for 3 h; Example 3 N-((1R,2R)-2-Hydroxy-cyclohexyl)-6-(2-pyrimidin-5-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinamidea) 5-Trimethylsilanylethynyl-pyrimidine; Tetrakis(triphenylphosphine)palladium(O) (727 mg, 0.6 mmol) was added to a stirred, degassed suspension of 5-bromopyrimidine (5.0 g, 31.4 mmol) and copper(I)iodide (120 mg, 0.6 mmol) in toluene and diisopropylamine (1:1, 200 ml) under nitrogen. The reaction mixture was heated to 60° C., trimethylsilylacetylene (4.89 ml, 34.6 mmol) was added and the reaction mixture was stirred for 3 hours at 60° C.. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate (200 ml) and washed with saturated aqueous ammonium chloride solution (3.x.100 ml). The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (5percent ethyl acetate/heptane) to give 5-trimethylsilanylethynyl-pyrimidine as a pale brown solid, 4.71 g (85percent yield). LC at 215 nm; Rt 2.07: 88percent, m/z (ES+): 177 (M+H).
Reference: [1] Monatshefte fur Chemie, 1998, vol. 129, # 10, p. 1035 - 1048
[2] Patent: US2008/70931, 2008, A1, . Location in patent: Page/Page column 12
[3] Organic and biomolecular chemistry, 2003, vol. 1, # 3, p. 498 - 506
[4] Journal of Organic Chemistry, 2007, vol. 72, # 13, p. 4750 - 4755
[5] Patent: WO2003/91226, 2003, A1, . Location in patent: Page/Page column 47
[6] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3743 - 3748
[7] Organic Letters, 2014, vol. 16, # 17, p. 4524 - 4527
  • 4
  • [ 4595-59-9 ]
  • [ 216309-28-3 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 18, p. 6287 - 6290
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