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[ CAS No. 75717-53-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 75717-53-2
Chemical Structure| 75717-53-2
Chemical Structure| 75717-53-2
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Product Details of [ 75717-53-2 ]

CAS No. :75717-53-2 MDL No. :MFCD00032567
Formula : C9H9ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :XDJYHQZFRFJSSV-UHFFFAOYSA-N
M.W : 200.62 Pubchem ID :12397785
Synonyms :

Calculated chemistry of [ 75717-53-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.95
TPSA : 46.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 2.6
Log Po/w (WLOGP) : 1.82
Log Po/w (MLOGP) : 1.13
Log Po/w (SILICOS-IT) : 2.2
Consensus Log Po/w : 1.94

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.274 mg/ml ; 0.00136 mol/l
Class : Soluble
Log S (Ali) : -3.23
Solubility : 0.119 mg/ml ; 0.000594 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.92
Solubility : 0.238 mg/ml ; 0.00119 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 75717-53-2 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P201-P202-P261-P264-P270-P271-P280-P302+P352-P304+P340-P308+P313-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331-H341 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 75717-53-2 ]

* 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 [ 75717-53-2 ]
  • Downstream synthetic route of [ 75717-53-2 ]

[ 75717-53-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 75717-53-2 ]
  • [ 39581-55-0 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With potassium acetate In ethanol for 1 h; Heating / reflux
Stage #2: With hydrogenchloride In ethanol; water
To an ice-cooled solution of boron trichloride (1.2 equiv., 10 mmol, 10 ml of a solution of 1M BC13 in dichloromethane) under N2-atmosphere was added dropwise a solution of J (1 g, 8 mmol,) in dichloromethane (5 ml). Then, chloroacetonitrile (0.7 g, 10 mmol, 1.2 equiv. ) was added dropwise, followed by aluminum(III) chloride (0.5 g, 4 mmol, 0.5 equiv. ) in one portion. The reaction mixture was allowed to warm up to room temperature and was stirred for 6 h. The reaction mixture was diluted with dichloromethane and quenched with IN hydrochloric acid at 0°C. After stirring for 10 min, the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried (MgS04) and concentrated Purification by flash chromatography on silica gel (eluent: dichloromethane) afforded the desired product K [Hammond, Milton L.; Zambias, Robert A.; Chang, Michael N.; Jensen, Norman P.; McDonald, John; Thompson, Kathryn; Boulton, David A.; Kopka, Ihor E.; Hand, Karen M. Journal of Medicinal Chemistry 1990,33(3), 908-18] (1 g, yield = 60percent). Intermediate K (0.15 g, 0.75 mmol, I equiv. ) and potassium acetate (0.22 g, 2.2 mmol, 3 equiv. ) were refluxed in ethanol (10 ml) for 1 h. After cooling, the reaction mixture was filtered and concentrated. The residue was mixed with water, and acidified with IN hydrochloric acid to pH = 1. The aqueous solution was extracted with ethyl acetate, the combined extracts were dried (MgS04), filtered and concentrated to afford the desired product L [Hammond, Milton L.; Zambias, Robert A.; Chang, Michael N. ; Jensen, Norman P. ; McDonald, John; Thompson, Kathryn; Boulton, David A.; Kopka, Ihor E.; Hand, Karen M. Journal of Medicinal Chemistry 1990, 33(3), 908-18] (110 mg, yield = 90 percent) as a pink solid The experimental procedures for the condensation reaction of compound L with 4-nitroaniline in acetic acid to form compound M, followed by Vilsmeier-Haack formulation and subsequent Knoevenagel condensation of the benzofuran carbaldehyde N with ethyl cyanoacetate to form compound 0, and finally, intramolecular cyclisation to compound 37 were performed using analogous procedures as exemplified in example 1 for the synthesis of compound f starting from compound a. Compound 37 was obtained as a yellow powder (30 mg, purity (LC) = 80 percent).
86.8% With sodium acetate In ethanol for 2 h; Reflux Compound 3 (3.8 g, 18.9 mmol) was dissolved in ethanol (50.0 mL),Sodium acetate (3.3 g, 39.8 mmol) was added with stirring and refluxed for 2 h.After concentration, add water, extract with dichloromethane (80 mL×3), combine the organic layers, and wash.Saturated brine wash, dry anhydrous Na2SO4,Column chromatography after concentration (PE/EA 15:1, v/v) gave the target compound 4 (2.7 g, 86.8percent).
Reference: [1] European Journal of Medicinal Chemistry, 2010, vol. 45, # 12, p. 5950 - 5957
[2] Patent: WO2005/111035, 2005, A1, . Location in patent: Page/Page column 78-79
[3] Patent: CN107365322, 2017, A, . Location in patent: Paragraph 0098; 0102
[4] Organic Letters, 2008, vol. 10, # 4, p. 573 - 576
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 3, p. 909 - 918
[6] Patent: WO2015/95261, 2015, A1, . Location in patent: Page/Page column 96
[7] Patent: WO2015/89842, 2015, A1, . Location in patent: Page/Page column 95
[8] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 195 - 208
  • 2
  • [ 75717-53-2 ]
  • [ 13196-10-6 ]
Reference: [1] Patent: WO2015/95261, 2015, A1,
[2] Patent: WO2015/89842, 2015, A1,
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