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[ CAS No. 2875-79-8 ] {[proInfo.proName]}

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Chemical Structure| 2875-79-8
Chemical Structure| 2875-79-8
Structure of 2875-79-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2875-79-8 ]

CAS No. :2875-79-8 MDL No. :MFCD02585208
Formula : C16H13N3O Boiling Point : -
Linear Structure Formula :- InChI Key :FYSIBSOBMCDYHZ-UHFFFAOYSA-N
M.W : 263.29 Pubchem ID :661299
Synonyms :

Calculated chemistry of [ 2875-79-8 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 17
Fraction Csp3 : 0.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 78.04
TPSA : 38.13 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.53
Log Po/w (XLOGP3) : 3.02
Log Po/w (WLOGP) : 3.69
Log Po/w (MLOGP) : 2.55
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 2.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.74
Solubility : 0.0479 mg/ml ; 0.000182 mol/l
Class : Soluble
Log S (Ali) : -3.49
Solubility : 0.086 mg/ml ; 0.000327 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.73
Solubility : 0.00489 mg/ml ; 0.0000186 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.43

Safety of [ 2875-79-8 ]

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

Application In Synthesis of [ 2875-79-8 ]

* 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 [ 2875-79-8 ]
  • Downstream synthetic route of [ 2875-79-8 ]

[ 2875-79-8 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 122-39-4 ]
  • [ 530-62-1 ]
  • [ 2875-79-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 31, p. 6420 - 6431
  • 2
  • [ 416844-85-4 ]
  • [ 2875-79-8 ]
  • [ 899809-61-1 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #2: With sulfuric acid In tetrahydrofuran; hexane; water; toluene at 5 - 25℃; for 1 h;
Example 1 - Preparation of Amide-Method A(R) The following procedures can be operated on either the racemic or the enantiopure starting butyn-2-ol. To a stirred solution of sulfuric acid (cone, 40//L) in THF (24OmL) were sequentially added (R)-3 butyn-2-ol (40g, 0.57 mol) and then hexamethyldisilazane (49.6g, 0.31 mol) at room temperature. The solution was refluxed for 3-4 hours and then slowly cooled to -4O0C. The resulting mixture was slowly charged in hexyllithium (2.5M in hexane, 249 mL, 0.62 mol) while maintaining the temperature at -40 0C. This solution and a solution of diphenylcarbamylimidazole (180 g, 0,68 mol) in a mixed solvent of THF (1088mL) and toluene (435 mL) were mixed using pumps through a chilled static mixer and directly quenched into 5N sulfuric acid (56OmL, -50C). The quenched solution was warmed to 250C and stirred for 1 hour. The organic layer was separated, washed with 5N sulfuric acid (80 mL) and then twice with 10percent brine (20OmL each EPO <DP n="29"/>time). The pH of the final brine wash was adjusted to 5-7 with a 5percent NaHCO3 solution. The organic layer was then distilled and replaced with toluene (440 ml_). The toluene solution was added to heptane (40OmL) at 850C, cooled slowly to 2O0C and filtered. The filtered cake was washed with a mixed solution of toluene (8OmL) and heptane (SOmL). Ths cake was then dried in a vacuum oven at 50GC to afford the title compound in 84percent molar yield (120.6g, purity 99percent). Mp 1050C.1H NMR (400MHz, DMSO-d6) δ 1.04 (d, J=6.4Hz, 3H), δ 4.27 (dq, J=5.6 Hz, 6.4Hz, 1H), δ 5.49 (d, J = 5.6 Hz, 1H), δ 7.2-7.5 (m, 10H); 13C NMR (DMSO-d6) δ 23.7, 56.3, 76.9, 96.4, 126.8, 127.0, 128.5, 129.2, 129.4, 129.6, 141.5, 142.2, 152.9.
Reference: [1] Patent: WO2006/76452, 2006, A2, . Location in patent: Page/Page column 27; 28
[2] Patent: WO2006/76415, 2006, A2, . Location in patent: Page/Page column 37-38
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