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[ CAS No. 5409-58-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 5409-58-5
Chemical Structure| 5409-58-5
Structure of 5409-58-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5409-58-5 ]

CAS No. :5409-58-5 MDL No. :MFCD00554996
Formula : C15H18ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :GUTDWEKYWTXJGD-UHFFFAOYSA-N
M.W : 263.76 Pubchem ID :24181903
Synonyms :

Calculated chemistry of [ 5409-58-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.27
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 78.42
TPSA : 20.31 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) : -5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.63
Log Po/w (WLOGP) : 3.78
Log Po/w (MLOGP) : 2.88
Log Po/w (SILICOS-IT) : 3.17
Consensus Log Po/w : 2.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.91
Solubility : 0.0325 mg/ml ; 0.000123 mol/l
Class : Soluble
Log S (Ali) : -3.74
Solubility : 0.0475 mg/ml ; 0.00018 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.95
Solubility : 0.00297 mg/ml ; 0.0000112 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.38

Safety of [ 5409-58-5 ]

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 [ 5409-58-5 ]

* 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 [ 5409-58-5 ]
  • Downstream synthetic route of [ 5409-58-5 ]

[ 5409-58-5 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 5409-58-5 ]
  • [ 25033-19-6 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydroxide; hydrazine; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol In water for 5 h; Heating General procedure: 3-dimethylamino-1-(naphthalen-1-yl)propan-1-one hydrochloride (50g, El equivalents) andtriethylene glycol (100 ml) were charged to the reactor at room temperature. 50percent NaOH (E2equivalents) was added while keeping the internal temperature at room temperature. 64percent hydrazine solution in water (E3 equivalents) was added dropwise followed by heating the reaction mixture to a temperature of 80±5°C for a period of 5 hours. Thereafter, water was distilled off in a vacuum of 30-40mbar at a temperature of 80±5°C. The precipitated salt was separated from the reaction mixture by filtration at a temperature of approximately 80°C andsubsequently washed with triethylene glycol brought to a temperature of approximately 80°C (20 Volpercent of the total amount of triethylene glycol).Bringing the reaction mixture to a temperature of 200±10°C for a period of about 5 hours gave crude 1-cyclopropyl-napthalene which was isolated by azeotropic distillation at a temperature of 190±10°C in a vacuum of 30-40mbar. For further purification and isolation ofthe obtained product water was added to the distillate and the product extracted with methyl tert.-butyl ether. The organic phase was washed with water and distilled in a vacuum of 50- lOOmbar at a temperature of 80°C.The isolated pure 1-cyclopropyl-naphtalene was obtained as clear, colorless or pale yellow liquid with a boiling point of 152°C at 13 Torr.
Reference: [1] Patent: WO2017/1516, 2017, A1, . Location in patent: Page/Page column 9; 10
  • 2
  • [ 5409-58-5 ]
  • [ 10320-49-7 ]
YieldReaction ConditionsOperation in experiment
98.2% With sodium hydroxide In water; toluene at 20℃; for 0.416667 - 0.666667 h; A. Preparation of a mixture of stereoisomeric forms of 6-bromo-α-r2- rdimethylamino>)ethyll-2-methoxy-α-l-naphthalenyl-β-phenyl-3-quinolineethanol.; (3-dimethylamino)-l'-propionaphthone-HCl (48.47 g; 183.8 mmol) was dissolved in water (157.5 g) and stirred for 5 to 10 minutes at room temperature. Sodium hydroxide (51.46 g; 386 mmol) was added as a 30 percent solution in water and the reaction mixture was stirred for 10 to 15 minutes. Toluene (105 g) was added and the mixture was stirred for 10 to 15 minutes followed by separation of the layers. To the organic layer, water (100 g) was added and stirring was continued for 10 to 15 minutes, followed by separation of the layers. The organic layer was concentrated in vacuo at 50 to 60 0C, yielding 98,2 percent of (3-dimethylammo)-l '-propionaphthone.
Reference: [1] Patent: WO2006/125769, 2006, A1, . Location in patent: Page/Page column 20
  • 3
  • [ 941-98-0 ]
  • [ 50-00-0 ]
  • [ 506-59-2 ]
  • [ 5409-58-5 ]
Reference: [1] Patent: WO2006/85118, 2006, A2, . Location in patent: Page/Page column 38
[2] Archiv der Pharmazie, 2013, vol. 346, # 2, p. 110 - 118
  • 4
  • [ 941-98-0 ]
  • [ 30354-18-8 ]
  • [ 5409-58-5 ]
Reference: [1] MedChemComm, 2015, vol. 6, # 8, p. 1554 - 1563
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