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[ CAS No. 41959-29-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 41959-29-9
Chemical Structure| 41959-29-9
Chemical Structure| 41959-29-9
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Product Details of [ 41959-29-9 ]

CAS No. :41959-29-9 MDL No. :MFCD00213766
Formula : C14H19NO Boiling Point : -
Linear Structure Formula :- InChI Key :LSQZRPLAUOVRPZ-UHFFFAOYSA-N
M.W : 217.31 Pubchem ID :3698650
Synonyms :

Calculated chemistry of [ 41959-29-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.57
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 68.8
TPSA : 23.47 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) : -6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.55
Log Po/w (XLOGP3) : 2.08
Log Po/w (WLOGP) : 1.5
Log Po/w (MLOGP) : 2.28
Log Po/w (SILICOS-IT) : 2.07
Consensus Log Po/w : 2.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.64
Solubility : 0.494 mg/ml ; 0.00227 mol/l
Class : Soluble
Log S (Ali) : -2.2
Solubility : 1.36 mg/ml ; 0.00627 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.82
Solubility : 0.33 mg/ml ; 0.00152 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.21

Safety of [ 41959-29-9 ]

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

Application In Synthesis of [ 41959-29-9 ]

* 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 [ 41959-29-9 ]

[ 41959-29-9 ] Synthesis Path-Downstream   1~7

  • 2
  • [ 41959-29-9 ]
  • [ 776-74-9 ]
  • 2-benzyl-6-exo-diphenylmethoxy-2-azabicyclo[2.2.2]octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% In dichloromethane; EXAMPLE 18 2-Benzyl-6-endo-diphenylmethoxy-2-azabicyclo[2.2.2]octane STR38 A mixture of <strong>[41959-29-9]2-benzyl-2-azabicyclo[2.2.2]octan-6-exo-ol</strong> and 2-benzyl-2-azabicyclo[2.2.2]octan-6-endo-ol (940 mg; ratio 1.6:1 by 1 H-NMR--see Preparation 3) and bromodiphenylmethane (1.05 g) was heated at 150 C. for 1.5 hours and dissolved in dichloromethane. The resulting solution was washed with 5% aqueous sodium carbonate solution; dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-4% saturated methanolic ammonia solution as eluant. Appropriate fractions were combined and evaporated to give the desired compound as a colourless oil (250 mg, 16%) which was characterised by its 1 H-NMR spectrum. 1 H-NMR (CDCl3) delta=7.20-7.55 (15H, m); 5.45 (1H, s); 3.60-4.04 (3H, m); 3.12 (1H, d, J=6 Hz); 2.93 (1H, broad s); 2.65 (1H, broad s); 1.18-2.14 (7H, m).
  • 3
  • [ 79-37-8 ]
  • [ 74403-57-9 ]
  • [ 67-68-5 ]
  • [ 41959-29-9 ]
  • [ 10028-34-9 ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine; In hexane; dichloromethane; ethyl acetate; Preparation 4 2-Benzyl-3,6-dioxo-2-azabicyclo[2.2.2]octane STR51 A solution of dimethyl sulphoxide (2.34 g) in dichloromethane (5 ml) was added to a cooled (-60 C.) solution of oxalyl chloride (1.78 g) in dichloromethane (5 ml) and after 2 minutes the mixture was treated with a solution of 2-benzyl-2-azabicyclo[2.2.2]octan-3-one (2.31 g--commercially available) in dichloromethane (10 ml), stirred at -60 C. for 30 minutes, treated with triethylamine (5.05 g), allowed to warm up to room temperature, quenched with water and extracted into dichloromethane. The dichloromethane extracts were dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica using hexane plus 50% ethyl acetate as eluant. Appropriate fractions were combined and evaporated to give the desired compound (2.10 g, 92%) as a colourless oil which was used directly in Preparation 3 without characterisation or further purification.
  • 4
  • [ 10028-34-9 ]
  • [ 41959-29-9 ]
YieldReaction ConditionsOperation in experiment
59% With sodium hydroxide; lithium borohydride; In tetrahydrofuran; 1,4-dioxane; ice-water; dichloromethane; water; Preparation 3 2-Benzyl-2-azabicyclo[2.2.2]octan-6-exo-ol and 2-benzyl-2-azabicyclo[2.2.2]octan-6-endo-ol (ratio 1.6:1) STR50 Lithium borohydride (1.65 g) was added portionwise over 30 minutes to a solution of 2-benzyl-3,6-dioxo-2-azabicyclo[2.2.2]octane (1.70 g--see Preparation 4) in dioxane (125 ml) and the mixture was stirred at room temperature for 17 hours and evaporated. The residue was partitioned between dichloromethane and 5% aqueous sodium carbonate solution and the organic layer was washed with water, dried over sodium sulphate and evaporated. The residue was dissolved in tetrahydrofuran (25 ml) and the solution was added dropwise over 30 minutes to a stirred, ice-cooled suspension of lithium aluminium hydride in tetrahydrofuran (75 ml). The mixture was stirred at room temperature for 72 hours, cooled in ice-water, quenched by the cautious dropwise sequential addition of water (1.14 g) in tetrahydrofuran (10 ml), 15% aqueous sodium hydroxide solution (1.14 g) and water (3.42 g) and filtered. The filtrate was evaporated and the residue was dissolved in dichloromethane, washed with 5% aqueous sodium carbonate solution, dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica using hexane:ethyl acetate:diethylamine (90:10:5) as the eluant. Appropriate fractions were combined and evaporated to give the desired compound as a colourless oil (940 mg, 59%) which was shown by 1 H-NMR to consist of a mixture of the exo- and endo-isomers in the ratio 1.6:1. This material was used directly in the preparation of Example 18.
  • 5
  • [ 41959-29-9 ]
  • 2-benzyl-6-exo-diphenylmethoxy-2-azabicyclo[2.2.2]octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% EXAMPLE 17 2-Benzyl-6-exo-diphenylmethoxy-2-azabicyclo[2.2.2]octane STR37 The title compound was prepared as described in Example 16 but using <strong>[41959-29-9]2-benzyl-2-azabicyclo[2.2.2]octan-6-exo-ol</strong> (see U.S. Pat. No. 4,013,668) instead of 2-benzyl-2-azabicyclo[2.2.1]heptane-7-anti-methanol. The title compound was obtained as a colourless oil (3.39 g, 86%). Analysis %: Found: C,84.4; H,7.5; N,3.6; C27 H29 NO requires: C,84.5; H,7.6; N,3.6.
  • 6
  • [ 38025-71-7 ]
  • [ 41959-29-9 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In tetrahydrofuran; hexane; water; EXAMPLE 10 To a suspension of 26.0 parts lithium aluminum hydride in 670 parts tetrahydrofuran under nitrogen at reflux is added with stirring a suspension of 43.0 parts endo-2-benzyl-6-hydroxy-2-azabicyclo[2.2.2]octan-3-one in 130 parts tetrahydrofuran over a 20 minute period. After refluxing the reaction mixture for about 64 hours, the mixture is decomposed by the successive addition of 27.4 parts water, 20.6 parts by volume of a 20% sodium hydroxide solution and 96 parts water. The solid is removed by filtration and washed with tetrahydrofuran. The filtrate is stripped in vacuo and the residue dissolved in ether. The ethereal solution is extracted with dilute hydrochloric acid and the hydrochloric acid extract basified with sodium hydroxide. The liberated oil is extracted into ethyl ether, dried over anhydrous sodium sulfate and stripped in vacuo. The residual solid is recrystallized from a mixture of ether and n-hexane to afford endo-2-benzyl-2-azabicyclo[2.2.2]octan-6-ol, melting at about 77-78.5 C. This compound is represented by the following structural formula. STR12
  • 7
  • [ 41088-52-2 ]
  • [ 100-46-9 ]
  • [ 41959-29-9 ]
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