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[ CAS No. 522-66-7 ] {[proInfo.proName]}

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Chemical Structure| 522-66-7
Chemical Structure| 522-66-7
Structure of 522-66-7 * Storage: {[proInfo.prStorage]}

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Product Details of [ 522-66-7 ]

CAS No. :522-66-7 MDL No. :MFCD00151107
Formula : C20H26N2O2 Boiling Point : -
Linear Structure Formula :CH2OC19H22N2OH2 InChI Key :-
M.W : 326.43 Pubchem ID :-
Synonyms :
Chemical Name :(R)-((1S,2S,4S,5R)-5-Ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methanol

Calculated chemistry of [ 522-66-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.55
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 100.21
TPSA : 45.59 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.04
Log Po/w (XLOGP3) : 3.13
Log Po/w (WLOGP) : 2.69
Log Po/w (MLOGP) : 2.31
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.86

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.88
Solubility : 0.043 mg/ml ; 0.000132 mol/l
Class : Soluble
Log S (Ali) : -3.76
Solubility : 0.0572 mg/ml ; 0.000175 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.65
Solubility : 0.00726 mg/ml ; 0.0000222 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.3

Safety of [ 522-66-7 ]

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

Application In Synthesis of [ 522-66-7 ]

* 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 [ 522-66-7 ]

[ 522-66-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 17024-12-3 ]
  • [ 522-66-7 ]
  • dihydroquinine 9-O-(9'-phenanthryl) ether [ No CAS ]
  • 2
  • [ 42881-66-3 ]
  • [ 7285-11-2 ]
  • [ 522-66-7 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; In tetrahydrofuran; hexane; water; EXAMPLE 28 Preparation of Dihydroquinine and Dihydroquinidine To 20 ml. of anhydrous ether was added 1.98 ml. of a 1.62M solution of butyllithium in hexane. The resulting solution was cooled to -70 and with stirring under a nitrogen atmosphere a solution of 760 mg. of <strong>[42881-66-3]4-bromo-6-methoxyquinoline</strong> in 20 ml. of anhydrous tetrahydrofuran was added. After stirring the mixture containing 6-methoxy-4-quinolyllithium for 30 minutes at -70, a solution of 538 mg. of freshly distilled 5(R)-ethyl-4(S)-quinuclidine-2ε-carboxaldehyde in 10 ml. of anhydrous ether was added during 15 minutes. After completion of the addition, stirring was continued for two hours at -70. The reaction mixture then was hydrolyzed by the addition of water, allowed to warm up to room temperature and diluted with an equal volume of ether. The aqueous layer was separated and extracted three times with 15 ml. of ether each. The combined organic extract was dried over sodium sulfate and evaporated to dryness. The residue was chromatographed on silica gel plates (Merck F-254) with chloroform-triethylamine-methanol (85:10:5) as the solvent mixture. Elution of the lowest of the major bands with chloroform-methanol (1:1) gave 138 mg. of dihydroquinine, mp 169-170 after recrystallization from chloroform-ether, [α]25 D -144.5 (c 0.935, 95 percent ethanol).
  • 3
  • [ 42881-66-3 ]
  • [ 51743-68-1 ]
  • [ 1435-55-8 ]
  • [ 522-66-7 ]
  • [ 14645-32-0 ]
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