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[ CAS No. 27876-24-0 ] {[proInfo.proName]}

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Chemical Structure| 27876-24-0
Chemical Structure| 27876-24-0
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Product Details of [ 27876-24-0 ]

CAS No. :27876-24-0 MDL No. :MFCD00068555
Formula : C11H17N Boiling Point : -
Linear Structure Formula :- InChI Key :YWSGFNIDQLIDGL-UHFFFAOYSA-N
M.W : 163.26 Pubchem ID :119735
Synonyms :

Calculated chemistry of [ 27876-24-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.55
Num. rotatable bonds : 5
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.24
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.64
Log Po/w (XLOGP3) : 4.35
Log Po/w (WLOGP) : 3.2
Log Po/w (MLOGP) : 2.39
Log Po/w (SILICOS-IT) : 3.49
Consensus Log Po/w : 3.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.63
Solubility : 0.038 mg/ml ; 0.000233 mol/l
Class : Soluble
Log S (Ali) : -4.34
Solubility : 0.00753 mg/ml ; 0.0000461 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.43
Solubility : 0.00612 mg/ml ; 0.0000375 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.5

Safety of [ 27876-24-0 ]

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

Application In Synthesis of [ 27876-24-0 ]

* 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 [ 27876-24-0 ]
  • Downstream synthetic route of [ 27876-24-0 ]

[ 27876-24-0 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 110-53-2 ]
  • [ 27876-24-0 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With n-butyllithium In tetrahydrofuran at -78 - 45℃; for 2 h;
Stage #2: at -78 - 20℃;
Stage #3: With water In tetrahydrofuran
4-Picoline (2.5 g, 26.84 mmol) was dissolved in (12 ml) of dry THF and the solution was cooled to -78 0C with an acetone - dry ice bath. n-Butyllithium (12.35 ml, 30.87 mmol) was added slowly while keeping the internal 0T below -50 0C. The reaction was allowed to warm up to room 0T and then stirred at 40 to 45 0C for 2 h. THF (12 ml) was added to dissolve the 4-picolyllithium slurry to give a deep orange solution. The 5 solution was cooled down to 0 0C and carefully added into the solution of 1- bromopentane (3.66 ml, 29.52 mmol) in THF (5.0 ml) at -78 0C. During the addition, the 0T was kept below -65 0C. The reaction was allowed to gradually warm up to room 0T and stirred overnight. The reaction was worked up by adding (1 - 1.5 ml) Of H2O. The crude was passed through RSF (Rapid Silica Filtration), eluting with EtOAc (volume = 6 x size <n="25"/>of column) and the solvent was evaporated by water aspirator. The residue was further purified by flash chromatography (Hex/EtOAc 1.5/1) and the combined fractions were concentrated by water aspirator to give 5 as a light yellow liquid (2.85 g, 65 percent). 1H NMR (200 MHz, CDCl3): δ 8.46 (2H, d, J = 6.5 Hz, CH (2,6)), 7.09 (2H, d, J = 6.5 Hz, 5 CH(3,5)), 2.59 (2H, t, J = 7.6 Hz, CH2(I')), 1-62 (2H, m, CH2(2')), 1.24 (6H, m, CH2(3',4',5')), 0.89 (3H, m, CH3(6')).
Reference: [1] Patent: WO2007/128059, 2007, A1, . Location in patent: Page/Page column 23-24
  • 2
  • [ 108-89-4 ]
  • [ 110-53-2 ]
  • [ 27876-24-0 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 27, p. 5284 - 5292
  • 3
  • [ 82126-17-8 ]
  • [ 27876-24-0 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 4, p. 429 - 432
[2] Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 7, p. 1994 - 1999
  • 4
  • [ 21369-64-2 ]
  • [ 181219-01-2 ]
  • [ 27876-24-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 6, p. 2205 - 2209[2] Angew. Chem., 2016, vol. 128, # 6, p. 2245 - 2249,5
  • 5
  • [ 110-86-1 ]
  • [ 592-41-6 ]
  • [ 27876-24-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 11, p. 3213 - 3216[2] Angew. Chem., 2013, vol. 125, # 11, p. 3295 - 3298,4
  • 6
  • [ 135351-43-8 ]
  • [ 27876-24-0 ]
Reference: [1] Gazzetta Chimica Italiana, 1991, vol. 121, # 2, p. 107 - 108
  • 7
  • [ 100-43-6 ]
  • [ 542-69-8 ]
  • [ 27876-24-0 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 36, p. 7706 - 7711
  • 8
  • [ 84355-16-8 ]
  • [ 27876-24-0 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 38, p. 3935 - 3936
  • 9
  • [ 110-86-1 ]
  • [ 27876-24-0 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 4, p. 429 - 432
[2] Tetrahedron Letters, 1982, vol. 23, # 38, p. 3935 - 3936
  • 10
  • [ 63755-30-6 ]
  • [ 27876-24-0 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 4, p. 429 - 432
  • 11
  • [ 84355-14-6 ]
  • [ 27876-24-0 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 38, p. 3935 - 3936
  • 12
  • [ 135351-35-8 ]
  • [ 27876-24-0 ]
Reference: [1] Gazzetta Chimica Italiana, 1991, vol. 121, # 2, p. 107 - 108
  • 13
  • [ 135351-39-2 ]
  • [ 27876-24-0 ]
Reference: [1] Gazzetta Chimica Italiana, 1991, vol. 121, # 2, p. 107 - 108
  • 14
  • [ 110-86-1 ]
  • [ 17774-09-3 ]
  • [ 1129-69-7 ]
  • [ 27876-24-0 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 18, p. 3423 - 3425
  • 15
  • [ 108-89-4 ]
  • [ 27876-24-0 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1953, vol. 72, p. 513,518, 520
  • 16
  • [ 3761-92-0 ]
  • [ 1129-69-7 ]
  • [ 27876-24-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 7, p. 1994 - 1999
  • 17
  • [ 1120-87-2 ]
  • [ 1188-92-7 ]
  • [ 27876-24-0 ]
Reference: [1] Heterocycles, 1986, vol. 24, # 10, p. 2793 - 2796
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