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[ CAS No. 861841-90-9 ] {[proInfo.proName]}

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Chemical Structure| 861841-90-9
Chemical Structure| 861841-90-9
Structure of 861841-90-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 861841-90-9 ]

CAS No. :861841-90-9 MDL No. :MFCD22570434
Formula : C15H15NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :VHNDAASEYRABBJ-UHFFFAOYSA-N
M.W : 257.28 Pubchem ID :21072822
Synonyms :

Calculated chemistry of [ 861841-90-9 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.13
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 74.04
TPSA : 72.55 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.35
Log Po/w (XLOGP3) : 2.59
Log Po/w (WLOGP) : 2.61
Log Po/w (MLOGP) : 1.66
Log Po/w (SILICOS-IT) : 2.56
Consensus Log Po/w : 2.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.27
Solubility : 0.138 mg/ml ; 0.000537 mol/l
Class : Soluble
Log S (Ali) : -3.76
Solubility : 0.0445 mg/ml ; 0.000173 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.47
Solubility : 0.0088 mg/ml ; 0.0000342 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.17

Safety of [ 861841-90-9 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 861841-90-9 ]

* 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 [ 861841-90-9 ]
  • Downstream synthetic route of [ 861841-90-9 ]

[ 861841-90-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 861841-90-9 ]
  • [ 79-04-9 ]
  • [ 869478-09-1 ]
YieldReaction ConditionsOperation in experiment
50% at 0 - 20℃; Heating / reflux 21.0 mL (258 mmol) chloroacetyl chloride are added dropwise to 60.0 g (233 mmol) 1-(3-amino-5-benzyloxy-2-hydroxy-phenyl)-ethanone and 70.0 g (506 mmol) potassium carbonate while being cooled with the ice bath.
Then the mixture is stirred overnight at ambient temperature and then for 6 hours at reflux temperature.
The hot reaction mixture is filtered, then evaporated down to approx.
400 mL and combined with ice water.
The precipitate obtained is suction filtered, dried and purified by chromatography on a short silica gel column (dichloromethane:methanol=99:1).
The fractions containing the product are evaporated down, suspended in isopropanol/diisopropylether, suction filtered and washed with diisopropylether. Yield: 34.6 g (50percent); mass spectroscopy [M+H]+=298.
50% at 0 - 20℃; Heating / reflux c) 8-acetyl-6-benzyloxy-4H-benzo[1,4]oxazin-3-one: 21.0 mL (258 mmol) chloroacetyl chloride are added dropwise to 60.0 g (233 mmol) 1-(3-amino-5-benzyloxy-2-hydroxy-phenyl)-ethanone and 70.0 g (506 mmol) potassium carbonate while cooling with the ice bath. Then the mixture is stirred overnight at ambient temperature and then for 6 hours at reflux temperature. The hot reaction mixture is filtered, then evaporated down to about 400 mL and combined with ice water. The precipitate formed is suction filtered, dried and purified chromatography on a short silica gel column (dichloromethane:methanol=99:1). The fractions containing the product are evaporated down, suspended in isopropanol/diisopropylether, suction filtered and washed with diisopropylether. Yield: 34.6 g (50percent); mass spectroscopy [M+H]+=298.
17.53 g With potassium carbonate In acetonitrile for 20 h; Reflux 1000 ml three-neck bottle in, under the condition of ice, to compounds 1 - 7 (159 mmol), potassium carbonate (65.8 g, 477 mmol) of acetonitrile (700 ml) solution adds by drops the chlorine acetyl chloride (27 g, 238 mmol), room temperature reaction 4 h, continue to heating to reflux the reaction 16 h. The condiments filtering, the filtrate is concentrated to 200 ml, is added to the 1 L ice water, ice bath conditions for the continuation of stirring 1 h, filtered, washed with water, drying. The resulting solid silica gel column purification (dichloromethane: methanol=99:1), after concentration isopropyl alcohol/methyl cyclohexane recrystallized, filtering to obtain light brown color solid product 17.53 g.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1410 - 1414
[2] Patent: US2005/267106, 2005, A1, . Location in patent: Page/Page column 7
[3] Patent: WO2005/111005, 2005, A1, . Location in patent: Page/Page column 16
[4] Patent: US2007/249595, 2007, A1, . Location in patent: Page/Page column 11
[5] Patent: US2007/88160, 2007, A1, . Location in patent: Page/Page column 11
[6] Patent: US2005/255050, 2005, A1,
[7] Patent: US2010/22770, 2010, A1, . Location in patent: Page/Page column 6
[8] Patent: CN107188865, 2017, A, . Location in patent: Paragraph 0051; 0062; 0063
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