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[ CAS No. 614-16-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 614-16-4
Chemical Structure| 614-16-4
Chemical Structure| 614-16-4
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Product Details of [ 614-16-4 ]

CAS No. :614-16-4 MDL No. :MFCD00001942
Formula : C9H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :ZJRCIQAMTAINCB-UHFFFAOYSA-N
M.W : 145.16 Pubchem ID :64799
Synonyms :

Calculated chemistry of [ 614-16-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.19
TPSA : 40.86 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.29
Log Po/w (XLOGP3) : 0.97
Log Po/w (WLOGP) : 1.78
Log Po/w (MLOGP) : 1.08
Log Po/w (SILICOS-IT) : 2.0
Consensus Log Po/w : 1.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.62
Solubility : 3.46 mg/ml ; 0.0238 mol/l
Class : Very soluble
Log S (Ali) : -1.42
Solubility : 5.57 mg/ml ; 0.0384 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.81
Solubility : 0.223 mg/ml ; 0.00153 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 614-16-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 614-16-4 ]

* 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 [ 614-16-4 ]
  • Downstream synthetic route of [ 614-16-4 ]

[ 614-16-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 614-16-4 ]
  • [ 4369-55-5 ]
YieldReaction ConditionsOperation in experiment
75% With hydroxylamine; sodium hydroxide In water for 14 h; Inert atmosphere; Reflux General procedure: Ketonitrile 5 (100 mmol) was added to 15percent aqueous NaOH solution(100 mL) followed by hydroxylamine (200 mmol). The resulting mixture was heated at reflux for 14 h, cooled down to r.t., theresulting precipitate was isolated by filtration and crystallized from isopropyl alcohol.
19.8% With sodium hydroxide; hydroxyammonium sulfate In ethanol; water at 20 - 80℃; for 24 h; Example 145; N-(3-Phenylisoxazol-5-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide; (1) 3-Phenylisoxazole-5-amine; A mixture of 3-oxo-3-phenylpropanenitrile (5.00 g, 34.4 mmol), hydroxylamine sulfate (3.10 g, 18.9 mmol), ethanol (35 ml) and an aqueous solution (35 ml) of sodium hydroxide (1.66 g, 41.4 mmol) was stirred at 80°C for 24 hours. After cooling to room temperature, the reaction mixture was adjusted to pH=11 by addition of an aqueous 8N sodium hydroxide solution and then extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 1 : 1) to obtain the desired product (1.09 g, 19.8percent) as a solid. 1H-NMR (CDCl3) δ; 4.00 (2H, br s), 6.09 (1H, s), 7.41 - 7.46 (3H, m), 7.70 - 7.73 (2H, m).
Reference: [1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 6, p. 1914 - 1925
[2] Organic Letters, 2017, vol. 19, # 4, p. 934 - 937
[3] Organic Letters, 2018, vol. 20, # 9, p. 2774 - 2777
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 3, p. 1082 - 1105
[5] Patent: EP1813606, 2007, A1, . Location in patent: Page/Page column 81
[6] Justus Liebigs Annalen der Chemie, 1891, vol. 266, p. 329
[7] Heterocycles, 1991, vol. 32, # 6, p. 1153 - 1158
  • 2
  • [ 614-16-4 ]
  • [ 14208-52-7 ]
Reference: [1] Patent: US2013/131040, 2013, A1,
  • 3
  • [ 614-16-4 ]
  • [ 621-03-4 ]
Reference: [1] Gazzetta Chimica Italiana, 1951, vol. 81, p. 511,521
  • 4
  • [ 24424-99-5 ]
  • [ 614-16-4 ]
  • [ 257892-43-6 ]
YieldReaction ConditionsOperation in experiment
62.9%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 60℃; for 2.25 h; Cooling with ice
Stage #2: With water; sodium hydroxide In tetrahydrofuran at 20℃; for 0.333333 h; Cooling with ice
A solution of 3-oxo-3-phenylpropanenitrile (7.26 g, 50 mmol) in tetrahydrofuran (100 mL) was added, over 15 minutes, to an ice cooled solution of a 1.0 M solution of lithium aluminum hydride in tetrahydrofuran (100 mL).
The mixture was stirred for 15 minutes at room temperature, then at 60° C. for 2 hours.
The mixture was cooled in an ice bath and quenched by the dropwise addition of water (3.8 mL), followed by the dropwise addition of 4 M sodium hydroxide solution (3.8 mL), followed by the dropwise addition of water (11.4 mL).
The mixture was stirred at room temperature for an additional 20 minutes, and the solids were then removed by suction filtration, rinsing the solids with tetrahydrofuran.
The mixture was stirred overnight with BOC-anhydride (13 g, 59.6 mmol), concentrated under reduced pressure, and the residue purified by chromatography on silica gel, eluting with hexanes-ethyl acetate (70:30) to give racemic (3-hydroxy-3-phenyl-propyl)-carbamic acid tert-butyl ester. (Yield 7.9 g, 62.9percent).
Reference: [1] Patent: US2012/184548, 2012, A1, . Location in patent: Page/Page column 12; 13
  • 5
  • [ 614-16-4 ]
  • [ 257892-43-6 ]
Reference: [1] Patent: US2012/184508, 2012, A1,
[2] Patent: US2012/184542, 2012, A1,
[3] Patent: US2012/184548, 2012, A1,
[4] Patent: US2012/184562, 2012, A1,
[5] Patent: US2012/238564, 2012, A1,
[6] Patent: US2012/184508, 2012, A1,
[7] Patent: US2012/184548, 2012, A1,
[8] Patent: US2012/184562, 2012, A1,
[9] Patent: US2012/184542, 2012, A1,
[10] Patent: US2012/238564, 2012, A1,
[11] Patent: WO2006/113837, 2006, A2,
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