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[ CAS No. 4383-25-9 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 4383-25-9
Chemical Structure| 4383-25-9
Chemical Structure| 4383-25-9
Structure of 4383-25-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4383-25-9 ]

CAS No. :4383-25-9 MDL No. :MFCD00465456
Formula : C13H19N Boiling Point : -
Linear Structure Formula :- InChI Key :IYWYMFZAZUYNLC-UHFFFAOYSA-N
M.W : 189.30 Pubchem ID :204463
Synonyms :

Calculated chemistry of [ 4383-25-9 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.54
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.94
TPSA : 12.03 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.76
Log Po/w (XLOGP3) : 3.1
Log Po/w (WLOGP) : 2.96
Log Po/w (MLOGP) : 2.94
Log Po/w (SILICOS-IT) : 3.21
Consensus Log Po/w : 3.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.09
Solubility : 0.155 mg/ml ; 0.000821 mol/l
Class : Soluble
Log S (Ali) : -3.02
Solubility : 0.18 mg/ml ; 0.000953 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.29
Solubility : 0.00966 mg/ml ; 0.0000511 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.14

Safety of [ 4383-25-9 ]

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 [ 4383-25-9 ]

* 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.

  • Upstream synthesis route of [ 4383-25-9 ]
  • Downstream synthetic route of [ 4383-25-9 ]

[ 4383-25-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 4383-25-9 ]
  • [ 122-01-0 ]
  • [ 945714-67-0 ]
YieldReaction ConditionsOperation in experiment
8 mg With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere General procedure: To generate Compound 1, cyclohexylamine (0.5M in MeOH) was combined with benzaldehyde (0.5M in MeOH) and stirred for 3h at 64°C. The mixture was cooled to rt, followed by two additions of sodium cyanoborohydride (0.5M in EtOH), each followed by stirring at rt for 30m. The mixture was then heated to 64°C for 6h. The reaction mixture was worked-up with water and extracted three times with CH2Cl2. The organic fractions were pooled, dried with magnesium sulfate, and reduced in vacuo. Thesecondary amine was then solubilized in dry CH2Cl2 and combined with 4-chloro-benzoylchloride. Equivalents were based upon the assumption that the secondary amine was formed in 100percent yield. Dimethylaminopyridine (0.1equiv) was solubilized in dry CH2Cl2 and added directly to the stirring solution of secondary amine, followed by addition of diisopropylethylamine (1.1equiv). The reaction was then capped, purged with nitrogen gas, and stirred at rt overnight. The reaction mixture was then reduced in vacuo to an oil, which was resolubilized and purified using reverse phase preparative HPLC (isocratic elution: 75percent acetonitrile, 25percent water). Following preparative HPLC, compound purity was determined using reverse phase analytical HPLC. Compounds were purified to an average purity of greater than 95percent (supplementary Table 1).For Compound 1: IR (thin film from CDCl3): 2935, 2858, 2246, 1624, 1495, 1418, 1091, 908, 838, 734 cm−1; 1H NMR (400MHz, CDCl3) δ 7.52 (4H), 7.36 (4H), 7.20 (2H), 4.55 (1H), 3.65 (1H), 1.80 (4H), 1.47 (4H), 1.06 (2H); 13C NMR (75MHz, CDCl3) δ 171.2, 142.5, 139.0, 135.2, 128.7, 128.4, 127.7, 126.8, 77.17, 59.4, 59.4, 44.6, 32.0, 30.8, 25.7, 25.1, 25.1, 9.29; HRMS m/z calculated for (M+H); 328.1390, found: 328.1477
Reference: [1] Tetrahedron, 2013, vol. 69, # 36, p. 7653 - 7658
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