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[ CAS No. 171290-52-1 ] {[proInfo.proName]}

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Chemical Structure| 171290-52-1
Chemical Structure| 171290-52-1
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Product Details of [ 171290-52-1 ]

CAS No. :171290-52-1 MDL No. :MFCD03839985
Formula : C10H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HUSBBWQIJMRKLI-UHFFFAOYSA-N
M.W : 162.19 Pubchem ID :4661321
Synonyms :

Calculated chemistry of [ 171290-52-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.36
TPSA : 18.46 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) : -5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.58
Log Po/w (XLOGP3) : 2.11
Log Po/w (WLOGP) : 1.76
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 2.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.41
Solubility : 0.627 mg/ml ; 0.00387 mol/l
Class : Soluble
Log S (Ali) : -2.13
Solubility : 1.21 mg/ml ; 0.00744 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.73
Solubility : 0.306 mg/ml ; 0.00188 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 171290-52-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 171290-52-1 ]

* 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 [ 171290-52-1 ]
  • Downstream synthetic route of [ 171290-52-1 ]

[ 171290-52-1 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 171290-52-1 ]
  • [ 19179-31-8 ]
YieldReaction ConditionsOperation in experiment
52% With N-Bromosuccinimide; silver(I) nitrite In 1,2-dichloro-ethane at 20℃; for 8 h; Sealed tube 3,5-dimethoxyphenylacetylene 81 mg (0.50 mmol), silver nitrite 154 mg (1 mmol), N-bromosuccinimide 178 mg (1 mmol)10 mL of a pressure-tight sealed container was sequentially added, and 5 mL of 1,2-dichloroethane was further added.The mixture was stirred at room temperature, and the reaction was checked by TLC. The reaction was completed in 8 hours.The reaction solution was diluted with 10 mL of dichloromethane, and filtered to give a clear liquid.Separation by column chromatography (extraction of petroleum ether/ethyl acetate in a volume ratio of 100:1)The eluate containing the desired product were collected and the solvent was evaporated to give a white solid 3,5-dimethoxy-benzonitrile 42.4mg (52percent yield).
Reference: [1] Patent: CN107641088, 2018, A, . Location in patent: Paragraph 0064; 0065; 0066
  • 2
  • [ 205746-51-6 ]
  • [ 171290-52-1 ]
YieldReaction ConditionsOperation in experiment
81% With n-butyllithium In tetrahydrofuran; hexane at -50℃; Schlenk technique; Inert atmosphere Solid 1-(2,2-dibromovinyl)-3,5-dimethoxybenzene (2.99 g, 9.28 mmol,1 equiv) was dissolved in dry THF (50 mL) under argon with stirring at −50 °C (dry ice/acetonitrilebath). A solution of nBuLi (24.0 mL, 1.6 M in hexanes, 38.4 mmol, 4.1 equiv) was added dropwiseafter which TLC indicated completion of the reaction. The mixture was quenched with saturatedammonium chloride (40 mL), extracted with CH2Cl2 (3 × 20 mL), dried (NaSO4), filtered andevaporated, giving an orange brown oil (1.61 g). Purification by flash column chromatography(pure pentane, followed by 19:1 pentane:Et2O) gave a pure colourless crystalline solid (1.22 g,81percent), Rf = 0.24 (pentane), m.p. 46–47 °C with literature properties.3 1H NMR (400.1 MHz, CDCl3):δ 6.72 (d, J = 2.3 Hz, 2H, ArH), 6.50 (t, J = 2.3 Hz, 1H, ArH), 3.76 (s, 6H, OCH3), 3.15 (s, 1H,CCH). 13C NMR (100.6 MHz, CDCl3): δ 160.6 (C), 123.4 (C), 110.0 (CH), 102.3 (CH), 83.7 (C),76.9 (CH), 55.4 (CH3).
78.8%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 2 h;
Stage #2: With ammonium chloride In tetrahydrofuran; n-heptane; ethylbenzene
General procedure: Lithium diisopropylamide solution (2 M in heptane/THF/ethylbenzene, 5 equiv) was slowly added to appropriate 2,2-dibromo-vinyl derivatives 40a3-d3 (1 equiv), dissolved in dry THF at -78 oC. The temperature was kept at -78 oC, and the mixture was stirred for 2 h. The reaction was quenched with saturated NH4Cl solution and extracted with CH2Cl2. The combined organic solutions were dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography.
76% With caesium carbonate In dimethyl sulfoxide at 115℃; Sealed tube; Inert atmosphere General procedure: Following a modified literature procedure[10] dibromoalkenes S2 (1.0 equiv.), Cs2CO3 (2.5 equiv.) and DMSO (0.1M) are mixed in a sealed tube and heated to 115 °C overnight. The reaction is quenched by pouring the reaction mixture into brine (20 mL/mmol). The resulting mixture is extracted with tert-butyl methyl ether (3x10 mL/mmol) and the combined organic layers are washed with brine (15 mL/mmol) and dried over Na2SO4. Removal of all volatiles gives the crude product which is purified by flash column chromatography to afford the terminal alkynes S3.
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 17, p. 1969 - 1972
[2] Chemistry Letters, 2008, vol. 37, # 2, p. 174 - 175
[3] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 273 - 279
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 6, p. 2386 - 2396
[5] Tetrahedron, 2017, vol. 73, # 33, p. 5023 - 5028
[6] Organic Letters, 2017, vol. 19, # 19, p. 5118 - 5121
  • 3
  • [ 400608-30-2 ]
  • [ 171290-52-1 ]
YieldReaction ConditionsOperation in experiment
91% at 20℃; for 2 h; To a solution of arylethynyltrimethylsilanes (30 mmol) in methanol (30 ml) was added potassium fluoride (3.5 g, 60 mmol). The reaction mixture was stirred at room temperature for 2 hours. After removal of methanol, the product was extracted with ether (100 ml x 3) and purified by chromatography on silica gel using petroleum ether as eluent to afford pure products.
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 12, p. 3856 - 3867
[2] Patent: WO2008/157745, 2008, A1, . Location in patent: Page/Page column 18
[3] Advanced Synthesis and Catalysis, 2010, vol. 352, # 14-15, p. 2405 - 2410
[4] Chinese Journal of Chemistry, 2011, vol. 29, # 5, p. 1059 - 1062
  • 4
  • [ 558-13-4 ]
  • [ 7311-34-4 ]
  • [ 171290-52-1 ]
YieldReaction ConditionsOperation in experiment
72 mg
Stage #1: With triphenylphosphine In dichloromethane at 0 - 20℃; for 0.5 h;
Stage #2: With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 2 h;
Stage #3: With ammonium chloride In tetrahydrofuran; n-heptane; ethylbenzene
General procedure: PPh3 (4 equiv) was added at 0 oC to a solution of CBr4 (2 equiv) in dry CH2Cl2. At the same temperature, the appropriate aldehyde 40a2-d2 (1 equiv) dissolved in dry CH2Cl2 was dropped slowly into the reaction mixture. The cooling bath was removed and the reaction mixture was stirred at room temperature. After 30 min, water was added and the contents of the aqueous phase were extracted with CH2Cl2. The combined organic phases were dried over Na2SO4 and concentrated. The residue was purified by silica gel flash column chromatography.; General procedure: Lithium diisopropylamide solution (2 M in heptane/THF/ethylbenzene, 5 equiv) was slowly added to appropriate 2,2-dibromo-vinyl derivatives 40a3-d3 (1 equiv), dissolved in dry THF at -78 oC. The temperature was kept at -78 oC, and the mixture was stirred for 2 h. The reaction was quenched with saturated NH4Cl solution and extracted with CH2Cl2. The combined organic solutions were dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography.
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 6, p. 2386 - 2396
  • 5
  • [ 25245-27-6 ]
  • [ 171290-52-1 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 12, p. 3856 - 3867
[2] Liebigs Annalen, 1995, # 9, p. 1663 - 1672
[3] Patent: WO2008/157745, 2008, A1,
  • 6
  • [ 10272-07-8 ]
  • [ 171290-52-1 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 12, p. 3856 - 3867
[2] Patent: WO2008/157745, 2008, A1,
  • 7
  • [ 7311-34-4 ]
  • [ 171290-52-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 6, p. 2386 - 2396
[2] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 273 - 279
[3] Tetrahedron, 2017, vol. 73, # 33, p. 5023 - 5028
[4] Organic Letters, 2017, vol. 19, # 19, p. 5118 - 5121
  • 8
  • [ 86988-56-9 ]
  • [ 171290-52-1 ]
Reference: [1] Patent: WO2008/157745, 2008, A1,
  • 9
  • [ 39151-19-4 ]
  • [ 171290-52-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 19, p. 3790 - 3796
  • 10
  • [ 1132-21-4 ]
  • [ 171290-52-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 19, p. 3790 - 3796
  • 11
  • [ 171290-51-0 ]
  • [ 171290-52-1 ]
Reference: [1] Liebigs Annalen, 1995, # 9, p. 1663 - 1672
  • 12
  • [ 20469-65-2 ]
  • [ 171290-52-1 ]
Reference: [1] Chinese Journal of Chemistry, 2011, vol. 29, # 5, p. 1059 - 1062
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