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[ CAS No. 109466-84-4 ] {[proInfo.proName]}

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Chemical Structure| 109466-84-4
Chemical Structure| 109466-84-4
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Product Details of [ 109466-84-4 ]

CAS No. :109466-84-4 MDL No. :MFCD09264065
Formula : C7H6N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :DKVANZONLCMNBC-UHFFFAOYSA-N
M.W : 166.13 Pubchem ID :13891180
Synonyms :

Calculated chemistry of [ 109466-84-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.06
TPSA : 88.91 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) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.55
Log Po/w (XLOGP3) : 1.57
Log Po/w (WLOGP) : 1.0
Log Po/w (MLOGP) : -0.31
Log Po/w (SILICOS-IT) : -0.88
Consensus Log Po/w : 0.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.33 mg/ml ; 0.008 mol/l
Class : Soluble
Log S (Ali) : -3.05
Solubility : 0.149 mg/ml ; 0.000896 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.36
Solubility : 7.25 mg/ml ; 0.0437 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 4.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.77

Safety of [ 109466-84-4 ]

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

Application In Synthesis of [ 109466-84-4 ]

* 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 [ 109466-84-4 ]
  • Downstream synthetic route of [ 109466-84-4 ]

[ 109466-84-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 109466-84-4 ]
  • [ 98276-57-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1774 - 1779
  • 2
  • [ 78468-34-5 ]
  • [ 109466-84-4 ]
YieldReaction ConditionsOperation in experiment
100% With manganese(IV) oxide In dichloromethane at 20℃; for 23 h; Inert atmosphere 5.1.133
6,7-Didehydro-17-methyl-7'-nitroquinolino[2',3':6,7]morphinan-3,14β-diol hydrochloride (SYK-71)
SYK-71 was prepared from compound 29c according to the procedure used to prepare SYK-27.
Yield, 98percent; a yellow amorphous solid.
Mp 247-249 °C (dec). Anal. Calcd for C24H23N3O4·1.0HCl·1.2H2O: C, 60.62; H, 5.60; N, 8.84. Found: C, 60.69; H, 5.61; N, 8.85.
86% With manganese(IV) oxide In tetrahydrofuran; dichloromethane at 20℃; for 2 h; A mixture of(2-amino-4-nitrophenyl)methanol (650 mg, 3.87 mmol) and manganese dioxide (1680 mg, 19.33 mmol) in THF (5 mL) and dichloromethane (25 mL) was stirred at room temperature for 2 h. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (40percent —* 50percent ethyl acetate in hexanes; 25g column) to afford 2-amino-4-nitrobenzaldehyde (550 mg, 86percent yield) as an orange solid: ‘H NMR (400MHz, DMSO-d6) ö 9.99 (s, 1H), 7.85 (d, J=8.6 Hz, 1H), 7.63 (d, J=2.3 Hz, 1H), 7.55 (br. s., 2H), 7.35 (dd, J=8.6, 2.3 Hz, 1H).
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[2] Patent: WO2015/6100, 2015, A1, . Location in patent: Page/Page column 113
[3] Patent: EP2128157, 2009, A1, . Location in patent: Page/Page column 103
[4] Patent: WO2015/95795, 2015, A1, . Location in patent: Paragraph 0586
  • 3
  • [ 528-75-6 ]
  • [ 109466-84-4 ]
YieldReaction ConditionsOperation in experiment
98 %Chromat. With hydrogen In methanol at 100℃; for 6 h; Autoclave General procedure: The hydrogenation of nitroarenes was carried out in a Teflon-lined stainless steel autoclave equipped with a pressure gauge anda magnetic stirrer. Typically, a mixture of 0.5 mmol nitroarene, 15molpercent Co/C–N–X catalyst, 100 L n-hexadecane and 2 mL solventwas introduced into the reactor at room temperature. Air in theautoclave was purged several times with H2. Then, the reactionbegan by starting the agitation (600 r/min) when hydrogen was reg-ulated to 1 MPa after the reaction temperature was reached. Afterreaction, the solid was isolated from the solution by centrifuga-tion. The products in the solution were quantified and identifiedby GC–MS analysis (Shimadzu GCMS-QP5050A equipped with a0.25 mm × 30 m DB-WAX capillary column).1H NMR and13C NMRdata were obtained on Bruker Avance III 400 spectrometer usingCDCl3or DMSO-d6 as solvent and tetrmethylsilane (TMS) as aninternal standard. The pure product in the scale-up experimentwas obtained by flash column chromatography (petroleum ether and ethyl acetate).
Reference: [1] Chemische Berichte, 1904, vol. 37, p. 1873
[2] Recueil des Travaux Chimiques des Pays-Bas, 1920, vol. 39, p. 581
[3] Journal of Molecular Catalysis A: Chemical, 2016, vol. 420, p. 56 - 65
  • 4
  • [ 619-17-0 ]
  • [ 109466-84-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[2] Patent: WO2015/6100, 2015, A1,
[3] Patent: WO2015/95795, 2015, A1,
  • 5
  • [ 52785-71-4 ]
  • [ 109466-84-4 ]
Reference: [1] Journal of Photochemistry and Photobiology A: Chemistry, 2010, vol. 214, # 2-3, p. 188 - 193
  • 6
  • [ 121-14-2 ]
  • [ 71-43-2 ]
  • [ 92-52-4 ]
  • [ 109466-84-4 ]
  • [ 99-09-2 ]
  • [ 619-17-0 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 10, p. 3306 - 3314
  • 7
  • [ 61599-67-5 ]
  • [ 71-43-2 ]
  • [ 121-14-2 ]
  • [ 109466-84-4 ]
Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 1086,1094
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