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[ CAS No. 805245-41-4 ] {[proInfo.proName]}

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Chemical Structure| 805245-41-4
Chemical Structure| 805245-41-4
Structure of 805245-41-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 805245-41-4 ]

CAS No. :805245-41-4 MDL No. :MFCD25977137
Formula : C44H45FO4Si Boiling Point : -
Linear Structure Formula :- InChI Key :FGVFROJJJDOTDT-RJBDQUNGSA-N
M.W : 684.91 Pubchem ID :86268842
Synonyms :

Calculated chemistry of [ 805245-41-4 ]

Physicochemical Properties

Num. heavy atoms : 50
Num. arom. heavy atoms : 30
Fraction Csp3 : 0.27
Num. rotatable bonds : 11
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 200.39
TPSA : 36.92 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 6.04
Log Po/w (XLOGP3) : 9.7
Log Po/w (WLOGP) : 9.01
Log Po/w (MLOGP) : 6.04
Log Po/w (SILICOS-IT) : 8.18
Consensus Log Po/w : 7.79

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -9.92
Solubility : 0.0000000832 mg/ml ; 0.0000000001 mol/l
Class : Poorly soluble
Log S (Ali) : -10.39
Solubility : 0.0000000278 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -14.75
Solubility : 0.0 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 7.63

Safety of [ 805245-41-4 ]

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 [ 805245-41-4 ]

* 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 [ 805245-41-4 ]
  • Downstream synthetic route of [ 805245-41-4 ]

[ 805245-41-4 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 805245-40-3 ]
  • [ 805245-41-4 ]
YieldReaction ConditionsOperation in experiment
73% With n-butyllithium; N-fluorobis(benzenesulfon)imide In tetrahydrofuran; hexane at -78℃; for 1 h; (3R,4R,6aR)-tert-Butyl-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yloxy)-diphenyl-silane (11)
To a stirred solution of 10 (11.66 g, 14.71 mmol) and N-fluorobenzenesulfonimide (5.566 g, 17.65 mmol) in dry tetrahydrofuran (100 ml) was slowly added n-butyllithum (27.6 ml, 44.13 mmol, 1.6 M solution in hexanes) at -78° C. under nitrogen atmosphere and the reaction mixture was stirred at the same temperature for 1 hour.
The mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate.
The organic layer was dried over anhydrous magnesium sulfate, and evaporated.
The residue was purified by flash silica gel column chromatography (hexane:ethyl acetate=6:1) to afford 11 (7.35 g, 73percent) as a white solid; 1H NMR (400 MHz, CDCl3) δ 7.81-7.17 (m, 25H), 4.94 (t, J=7.2 Hz, 1H), 4.35 (m, 1H), 4.25 (m, 1H), 3.89 (t, J=12.0 Hz, 1H), 3.77 (t, J=12.0 Hz, 1H), 1.42 (s, 3H), 1.38 (s, 3H), 1.08 (s, 9H).
Reference: [1] Patent: US2005/222185, 2005, A1, . Location in patent: Page/Page column 7
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5641 - 5644
[3] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 5-7, p. 707 - 708
[4] Patent: WO2014/145807, 2014, A1, . Location in patent: Page/Page column 9; 26; 27
[5] Patent: WO2014/145807, 2014, A1,
  • 2
  • [ 805245-40-3 ]
  • [ 805245-41-4 ]
YieldReaction ConditionsOperation in experiment
45% With n-butyllithium; N-fluorobis(benzenesulfon)imide In tetrahydrofuran; hexane; n-heptane; tert-butyl methyl ether at -78℃; for 1.5 h; Inert atmosphere n-Butyllithium (11 mL, 17.6 mmol, 1.6M solution in hexanes)was added dropwise to a cooled (78 °C) solution of 7 [9] (5.58 g,7.04 mmol) and N-fluorobenzenesulfonimide (3.33 g, 10.56 mmol)in anhydrous THF/tert-butyl methyl ether/n-heptane (3:1:1.5,90 mL total, 0.08 M) over a period of 1 h under N2. After stirring atthe same temperature for 30 min, the reaction mixture wasquenched with saturated aqueous NH4Cl (100 mL) and was dilutedwith EtOAc (100 mL). Then the layers were separated and theaqueous layer was extracted with EtOAc (2 x 50 mL). The combinedorganic layers were washed successively with H2O and brine, driedover anhydrous MgSO4, filtered, and evaporated. Finally, the residuewas purified by medium pressure liquid chromatography(silica gel, hexanes/EtOAc = 25/1) to give vinyl fluoride 8a (2.17 g,45percent), 8b (1.03 g, 22percent) and 8c (0.84 g, 18percent).8a: [α]D25-8.42 (c 0.19, MeOH); 1H NMR (400 MHz, CDCl3)δ 7.80 (d, J 6.6 Hz, 2 H), 7.72 (d, J 6.6 Hz, 2 H), 7.35-7.44 (m,13 H), 7.16-7.27 (m, 8 H), 4.93 (t, J = 6.6 Hz, 1 H), 4.34 (s, 1 H),3.22-3.25 (m, 1 H), 3.89 (d, J = 11.8 Hz, 1 H), 3.77 (d, J = 12.3 Hz,1 H), 1.44 (s, 3 H), 1.38 (s, 3 H), 1.07 (s, 9 H); 13C NMR (100 MHz,CDCl3) δ 157.3 (d, J = 288.0 Hz), 143.8, 136.0 (d, J = 23.1 Hz), 133.5 (d,J = 21.2 Hz), 129.7 (d, J = 4.9 Hz), 127.7, 127.5 (d, J = 9.2 Hz), 127.0,115.6 (d, J = 4.2 Hz), 111.8, 87.0, 78.6 (d, J = 8.8 Hz), 75.3 (d,J = 7.2 Hz), 71.0 (d, J = 18.9 Hz), 56.3, 29.5 (d, J = 29.8), 27.9, 27.2,26.7, 19.4; 19F NMR (376 MHz, CDCl3) δ -128.2; MS (ESI+) found707.2968 [calcd for C44H45FNaO4Si (M + Na)+ 707.2969].
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 406 - 417
  • 3
  • [ 805245-38-9 ]
  • [ 805245-41-4 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 5-7, p. 707 - 708
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5641 - 5644
[3] Patent: WO2014/145807, 2014, A1,
[4] Patent: WO2014/145807, 2014, A1,
[5] Patent: US2005/222185, 2005, A1,
  • 4
  • [ 805245-39-0 ]
  • [ 805245-41-4 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 5-7, p. 707 - 708
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5641 - 5644
[3] Patent: WO2014/145807, 2014, A1,
[4] Patent: WO2014/145807, 2014, A1,
[5] Patent: US2005/222185, 2005, A1,
  • 5
  • [ 88559-56-2 ]
  • [ 805245-41-4 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 5-7, p. 707 - 708
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5641 - 5644
[3] Patent: US2005/222185, 2005, A1,
  • 6
  • [ 67814-68-0 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: US2005/222185, 2005, A1,
  • 7
  • [ 54503-64-9 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: US2005/222185, 2005, A1,
  • 8
  • [ 95666-80-1 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: US2005/222185, 2005, A1,
  • 9
  • [ 681853-96-3 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: US2005/222185, 2005, A1,
  • 10
  • [ 865838-13-7 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: US2005/222185, 2005, A1,
  • 11
  • [ 865838-12-6 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: US2005/222185, 2005, A1,
  • 12
  • [ 77-76-9 ]
  • [ 805245-41-4 ]
Reference: [1] Patent: WO2014/145807, 2014, A1,
[2] Patent: WO2014/145807, 2014, A1,
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