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[ CAS No. 203661-71-6 ] {[proInfo.proName]}

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Chemical Structure| 203661-71-6
Chemical Structure| 203661-71-6
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Product Details of [ 203661-71-6 ]

CAS No. :203661-71-6 MDL No. :MFCD17016202
Formula : C12H19NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :WQPZESPYNGQLQA-UHFFFAOYSA-N
M.W : 225.28 Pubchem ID :23565399
Synonyms :

Calculated chemistry of [ 203661-71-6 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 64.03
TPSA : 46.61 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) : -7.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.47
Log Po/w (XLOGP3) : 0.81
Log Po/w (WLOGP) : 1.6
Log Po/w (MLOGP) : 1.33
Log Po/w (SILICOS-IT) : 1.68
Consensus Log Po/w : 1.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.55
Solubility : 6.36 mg/ml ; 0.0282 mol/l
Class : Very soluble
Log S (Ali) : -1.37
Solubility : 9.6 mg/ml ; 0.0426 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.94
Solubility : 2.59 mg/ml ; 0.0115 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.63

Safety of [ 203661-71-6 ]

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

Application In Synthesis of [ 203661-71-6 ]

* 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 [ 203661-71-6 ]
  • Downstream synthetic route of [ 203661-71-6 ]

[ 203661-71-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1558037-99-2 ]
  • [ 203661-71-6 ]
YieldReaction ConditionsOperation in experiment
69% With ammonium chloride; zinc In methanol at 20℃; for 8 h; To a solution of R-4 (35.5 g, 121 mmol) in saturated NH4Cl (64.7 g, 1.21 mol) in MeOH (400 mL) is added Zn (79.1 g, 1.21 mol). The mixture is stirred at ambient temperature for 8 h. The mixture is treated with H2O and extracted with EtOAc. The organic layers are washed with brine, dried with Na2SO4, concentrated and purified by flash chromatography (SiO2, Hep to 25percent EtOAc in Hep) to afford R-5 (19 g, 69percent).
69% With ammonium chloride; zinc In methanol at 20℃; for 8 h; [0132] To a solution of 1-5 (35.5 g, 121 mmol) in saturatedNH4Cl (64.7 g, 1.21 mol) in MeOH (400 mL) is added Zn(79.1 g, 1.21 mol). The mixture is stirred at ambient temperaturefor 8 h. The mixture is treated with H20 and extractedwith EtOAc. The organic layers are washed with brine, driedwith Na2S04 , concentrated and purified by flash chromatography(Si02 , Hep to 25percent EtOAc in Hep) to afford 1-6 (19 g,69percent).
64% With ammonium chloride; zinc In methanol at 20℃; for 24 h; To a solution of R-4 (82.0 g, 279 mmol) and NH4C1 (151 g, 2790 mmol) in MeOH (1000 mL) is added Zn (90.6 g, 1390 mmol). The mixture is stirred at rt for 24 h. The mixture is treated with H20 and extracted with EtOAc. The organic layers are washed with brine, dried with Na2S04, concentrated and purified by flash chromatography (Si02, Hep to 25percentEtOAc in Hep) to afford R-5 (40 g, 64percent).
Reference: [1] Patent: US2014/45813, 2014, A1, . Location in patent: Paragraph 0113
[2] Patent: US2014/275014, 2014, A1, . Location in patent: Paragraph 0128; 0129; 0132
[3] Patent: WO2015/116485, 2015, A1, . Location in patent: Page/Page column 24; 25
  • 2
  • [ 114214-71-0 ]
  • [ 203661-71-6 ]
Reference: [1] Patent: US2014/45813, 2014, A1,
[2] Patent: US2014/275014, 2014, A1,
[3] Patent: WO2015/116485, 2015, A1,
  • 3
  • [ 203661-71-6 ]
  • [ 1239319-91-5 ]
YieldReaction ConditionsOperation in experiment
63% With sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 6 h; To the mixture of R-5 (19 g, 84.3 mmol) in THF (200 mL) is added NaBH4 (12.8 g, 337.2 mmol) at 0° C. and then stirred at ambient temperature for 6 h. The mixture is treated with MeOH and H2O, then extracted with EtOAc. The organic layers are washed with brine, dried with Na2SO4, concentrated and purified by flash chromatography (SiO2, Hep to 50percent EtOAc in Hep) to yield R-6 (12 g, 63percent).
63% With sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 6 h; [0133] Tothemixtureof1-6 (19 g, 84.3 mmol) in THF (200mL) is added NaBH4 (12.8 g, 337.2 mmol) at oo C. and thenstirred at ambient temperature for 6 h. The mixture is treatedwith MeOH and H20, then extracted with EtOAc. Theorganic layers are washed with brine, dried with Na2S04 ,concentrated and purified by flash chromatography (Si02 ,Hep to 50percent EtOAc in Hep) to yield 1-7 (12 g, 63percent).
63% With sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 6 h; To the mixture of R-5 (19 g, 84.3 mmol) in THF (200 mL) is added NaBH4 (12.8 g, 337.2 mmol) at 0°C and then stirred at ambient temperature for 6 h. The mixture is treated with MeOH and H20, then extracted with EtOAc. The organic layers are washed with brine, dried with Na2S04, concentrated and purified by flash chromatography (Si02, Hep to 50percentEtOAc in Hep) to yield R-6 (12 g, 63percent).
Reference: [1] Patent: US2014/45813, 2014, A1, . Location in patent: Paragraph 0114
[2] Patent: US2014/275014, 2014, A1, . Location in patent: Paragraph 0128; 0129; 0133
[3] Patent: WO2015/116485, 2015, A1, . Location in patent: Page/Page column 24; 25
[4] Patent: US2011/319381, 2011, A1, . Location in patent: Page/Page column 10
[5] Patent: US2012/129830, 2012, A1, . Location in patent: Page/Page column 10
[6] Patent: WO2014/45031, 2014, A1, . Location in patent: Page/Page column 43
[7] Tetrahedron, 2016, vol. 72, # 46, p. 7268 - 7275
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