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[ CAS No. 914299-79-9 ] {[proInfo.proName]}

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Chemical Structure| 914299-79-9
Chemical Structure| 914299-79-9
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Product Details of [ 914299-79-9 ]

CAS No. :914299-79-9 MDL No. :MFCD11016232
Formula : C10H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :MHZXKVPCJBPNKI-SNVBAGLBSA-N
M.W : 163.22 Pubchem ID :22860773
Synonyms :

Calculated chemistry of [ 914299-79-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.52
TPSA : 21.26 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.0
Log Po/w (XLOGP3) : 0.95
Log Po/w (WLOGP) : 0.64
Log Po/w (MLOGP) : 1.17
Log Po/w (SILICOS-IT) : 2.19
Consensus Log Po/w : 1.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.75
Solubility : 2.87 mg/ml ; 0.0176 mol/l
Class : Very soluble
Log S (Ali) : -0.98
Solubility : 17.0 mg/ml ; 0.104 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.06
Solubility : 0.143 mg/ml ; 0.000875 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 914299-79-9 ]

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 [ 914299-79-9 ]

* 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.

  • Upstream synthesis route of [ 914299-79-9 ]
  • Downstream synthetic route of [ 914299-79-9 ]

[ 914299-79-9 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
100% With hydrogen bromide In acetic acid at 0 - 20℃; for 16 h; Phenol (360mg, 3.82mmol) and 45percent HBr/ AcOH (1.6mL) were added to a solution of (3S)-3-phenyl-4-(para-toluenesulfonyl)morpholine (35mg, 0.11mmol) (prepared according to the procedures of Aggarwal21) at 0°C, before being warmed to room temperature and stirred for 16h. The reaction was cooled to 0°C and 20percent aqueous NaOH was cautiously added. The mixture was then diluted with Et2O, the organic layer was separated and extracted, dried (MgSO4), filtered and concentrated in vacuo. Purification by flash column chromatography (15percent MeOH/CH2Cl2) afforded the deprotected morpholine, (3S)-3-phenylmorpholine (19.4mg, quant.) as a colourless oil; Rf: (15percent MeOH/CH2Cl2) 0.35; [α]24D=+36.8[α]D24=+36.8 (c 0.87, CHCl3); νmax (ATR)/cm−1 3429, 2962, 2848, 2789, 1493, 1449, 1350, 1289, 1232, 1116, 1037, 984, 904, 880, 794, 756, 700, 650, 590; δH (400MHz, CDCl3) 7.42–7.26 (5H, m, 5×PhH), 3.94 (1H, dd, J 10.1 and 3.2), 3.88 (1H, dd, J 11.3 and 2.9), 3.84 (1H, dd, J 11.3 and 3.3), 3.69 (1H, td, J 11.3 and 2.7), 3.45 (1H, t, J 10.5), 3.12 (1H, td, J 11.6 and 3.3), 3.00 (1H, br dt, J 11.6); δC (100MHz, CDCl3) 139.8, 128.5, 127.9, 127.2, 73.2, 66.9, 60.4, 46.3; HRMS (ES+) M+ calculated for C10H14NO 164.1075, observed 164.1064.
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 1, p. 74 - 86
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YieldReaction ConditionsOperation in experiment
424 mg With lithium aluminium tetrahydride In tetrahydrofuran at 20 - 72℃; Step 3.
(S)-3-phenylmorpholine
To a LiAlH4/THF slurry (0.47 g/2 mL) was added dropwise (S)-5-phenylmorpholin-3-one in THF solution (481 mg in 6 mL) at room temperature over 5 min.
The resulting mixture was stirred at room temperature thereafter for 1 hour, then was heated with 72° C. oil bath overnight, then was cooled down to 0° C., quenched by sequential addition of H2O (0.47 mL), 3M aqueous solutionueous NaOH (0.47 mL) and H2O (1.4 mL), and the quenched residue was diluted with Et2O (30 mL), stirred for 10 min and the ethereal solution was separated by filtration.
The filtrate was concentrated, further dried under vacuum and (S)-3-phenylmorpholine (424 mg, 96percent yield) was obtained as colorless solid. LCMS (m/z): 164.2 (MH+), 0.33 min.
1.3 g With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 45℃; for 5 h; Inert atmosphere To a stirred solution of (5)-5-phenylmorpholin-3-one (Step 2 intermediate) (3.0 g, 19.9 mmol) in anhydrous THF (40 mL) was added lithium aluminum hydride (2.57 g, 67.8 mmol) in small portions at 0 °C under nitrogen atmosphere. The mixture was warmed to 45 °C and stirred for 5 h at the same temperature. The mixture was quenched with saturated aqueous sodium sulfate solution. Ethyl acetate was added to the aqueous mixture and stirred for 10 min. The suspension was filtered through celite and the filtrate was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was dried well to obtain 1.3 g of the desired product. NMR (300 MHz, CDCb) δ 3.00 (d, / = 1 1.7 Hz, 1H), 3.13 (t, = 8.7 Hz, 1H), 3.40 (t, = 10.8 Hz, 1H), 3.66 (t, = 10.5 Hz, 1H), 3.80-3.94 (m, 3H), 7.25-7.41 (m, 5H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 15, p. 4316 - 4320
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 20, p. 5319 - 5322[3] Angew. Chem., 2013, vol. 125, # 20, p. 5427 - 5430,4
[4] Patent: US9242996, 2016, B2, . Location in patent: Page/Page column 265; 266
[5] Patent: WO2018/116285, 2018, A1, . Location in patent: Page/Page column 24
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Reference: [1] ChemCatChem, 2016, vol. 8, # 1, p. 117 - 120
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Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 20, p. 5319 - 5322[2] Angew. Chem., 2013, vol. 125, # 20, p. 5427 - 5430,4
[3] Patent: US9242996, 2016, B2,
[4] Patent: WO2018/116285, 2018, A1,
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  • [ 291545-74-9 ]
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Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 20, p. 5319 - 5322[2] Angew. Chem., 2013, vol. 125, # 20, p. 5427 - 5430,4
[3] Patent: US9242996, 2016, B2,
[4] Patent: WO2018/116285, 2018, A1,
  • 6
  • [ 529-20-4 ]
  • [ 914299-79-9 ]
  • [ 138713-44-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 37, p. 10884 - 10888[2] Angew. Chem., 2015, vol. 54, p. 10884 - 10888,5
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