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[ CAS No. 5344-27-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 5344-27-4
Chemical Structure| 5344-27-4
Chemical Structure| 5344-27-4
Structure of 5344-27-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5344-27-4 ]

CAS No. :5344-27-4 MDL No. :MFCD00129038
Formula : C7H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :DWPYQDGDWBKJQL-UHFFFAOYSA-N
M.W : 123.15 Pubchem ID :72921
Synonyms :

Calculated chemistry of [ 5344-27-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.17
TPSA : 33.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.37
Log Po/w (XLOGP3) : 0.1
Log Po/w (WLOGP) : 0.62
Log Po/w (MLOGP) : 0.22
Log Po/w (SILICOS-IT) : 1.52
Consensus Log Po/w : 0.76

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.03
Solubility : 11.5 mg/ml ; 0.0938 mol/l
Class : Very soluble
Log S (Ali) : -0.35
Solubility : 54.9 mg/ml ; 0.446 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.21
Solubility : 0.752 mg/ml ; 0.00611 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 5344-27-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H227-H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5344-27-4 ]

* 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 [ 5344-27-4 ]
  • Downstream synthetic route of [ 5344-27-4 ]

[ 5344-27-4 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 5344-27-4 ]
  • [ 622-26-4 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 2894
[2] Collection of Czechoslovak Chemical Communications, 1957, vol. 22, p. 1173,1177
[3] Journal of the American Chemical Society, 1947, vol. 69, p. 630,631
  • 2
  • [ 10445-91-7 ]
  • [ 50-00-0 ]
  • [ 5344-27-4 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: With chloro-trimethyl-silane; ethylene dibromide; zinc In tetrahydrofuran at 70℃; for 2 h; Schlenk technique; Inert atmosphere
Stage #2: at 70℃; for 6 h; Schlenk technique; Inert atmosphere
General procedure: Phenethyl alcohol (3a) A two neck Schlenk flask equipped with a magnetic stirring bar and septum was heated with heat gun (~400 °C) for 10 min under high vacuum. After cooling to room temperature, the flask was flushed with argon (3 times). Zn-dust (654 mg, 2.0 equiv, 10.0 mmol) was added followed by THF (20 mL). 1,2-Dibromoethane (5 molpercent) was added and the reaction mixture was heated until ebullition occurs. After cooling to rt, chlorotrimethylsilane (1 molpercent) was added and the mixture was heated again till ebullition occurs. The flask was again cooled to rt and benzyl chloride (633 mg, 5.0 mmol, 1 equiv) was added as a solution in THF (10 mL) and it was heated at 70 °C for 2 h and cooled to rt. Paraformaldehyde (450 mg, 3.0 equiv. 15.0 mmol) was slowly added at rt and the flask was again heated at 70 °C for 6 h. The solution was cooled to rt and saturated NH4Cl solution was added. The phases were separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layer was washed with water (20 mL), brine (10 mL) and then dried over Na2SO4. The solvents were evaporated under reduced pressure and the residue was purified by silica gel column chromatography using cyclohexane or cyclohexane/ethyl acetate as an eluent to obtain phenethyl alcohol (3a) (510 mg, 83percent) as a colourless liquid.
Reference: [1] Synthetic Communications, 2017, vol. 47, # 10, p. 968 - 974
  • 3
  • [ 54401-85-3 ]
  • [ 5344-27-4 ]
Reference: [1] Helvetica Chimica Acta, 1982, vol. 65, # 6, p. 1868 - 1884
[2] Monatshefte fuer Chemie, 1957, vol. 88, p. 830,836
[3] Patent: US4968678, 1990, A,
[4] Organometallics, 2013, vol. 32, # 19, p. 5581 - 5588
[5] Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2573 - 2590
  • 4
  • [ 108-89-4 ]
  • [ 50-00-0 ]
  • [ 5344-27-4 ]
Reference: [1] Chemische Berichte, 1909, vol. 42, p. 130
[2] Justus Liebigs Annalen der Chemie, 1920, vol. 420, p. 218
[3] CHEMTECH, 1956, vol. 8, p. 378,382
  • 5
  • [ 13121-99-8 ]
  • [ 5344-27-4 ]
Reference: [1] Helvetica Chimica Acta, 1982, vol. 65, # 6, p. 1868 - 1884
  • 6
  • [ 108-89-4 ]
  • [ 5344-27-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2573 - 2590
  • 7
  • [ 29800-89-3 ]
  • [ 5344-27-4 ]
Reference: [1] Chemische Berichte, 1956, vol. 89, p. 2896,2901
  • 8
  • [ 5344-27-4 ]
  • [ 502509-10-6 ]
Reference: [1] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 22, p. 3329 - 3332
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