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[ CAS No. 538-58-9 ] {[proInfo.proName]}

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Chemical Structure| 538-58-9
Chemical Structure| 538-58-9
Structure of 538-58-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 538-58-9 ]

CAS No. :538-58-9 MDL No. :MFCD00004790
Formula : C17H14O Boiling Point : -
Linear Structure Formula :- InChI Key :WMKGGPCROCCUDY-PHEQNACWSA-N
M.W : 234.29 Pubchem ID :640180
Synonyms :

Calculated chemistry of [ 538-58-9 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 75.96
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.87
Log Po/w (XLOGP3) : 4.12
Log Po/w (WLOGP) : 3.76
Log Po/w (MLOGP) : 3.86
Log Po/w (SILICOS-IT) : 4.51
Consensus Log Po/w : 3.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.12
Solubility : 0.0179 mg/ml ; 0.0000763 mol/l
Class : Moderately soluble
Log S (Ali) : -4.18
Solubility : 0.0153 mg/ml ; 0.0000653 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.05
Solubility : 0.00209 mg/ml ; 0.00000893 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.45

Safety of [ 538-58-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 538-58-9 ]

* 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 [ 538-58-9 ]
  • Downstream synthetic route of [ 538-58-9 ]

[ 538-58-9 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 538-58-9 ]
  • [ 32005-36-0 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With sodium chloride In methanol for 18 h; In sealed flask; Inert atmosphere
Stage #2: With sodium acetate In methanol at 60℃; Inert atmosphere
.) Synthesis According to Inorganic Synthesis, 28, 110 (1990)The synthesis is carried out under inert gas. 2.096 g (11.73 mmol) PdCl2 and 0.686 g (11.73 mmol) NaCl are provided under argon, and 59 ml of methanol are added.Next the reaction mixtures is stirred over night for 18 hours in the sealed flask. Then the dark red-brown solution is filtered through a G3 frit under argon. No residue is evident on the frit.The filtrate solution is transferred to a 500 ml three-necked flask using 293 ml of methanol, and heated to 60° C. At this temperature, 8.563 g (36.54 mmol) dibenzylidene acetone are added under argon. Then, the addition of 17.595 g (214.49 mmol) sodium acetate is made.A voluminous, reddish solid precipitates. Subsequently, the reaction mixture is cooled to room temperature. The product is removed by filtration and washed with 300 ml of methanol, 300 ml of water, and 300 ml of acetone. The product is dried in vacuo at room temperature.Appearance: dark-brown solidSolubility Test:1.00 g of the product are dissolved in 150 ml of chloroform and stirred at room temperature for 30 minutes. The solution is then aspirated through a membrane filter. The filter is washed with 30 ml of water and 30 ml of acetone and subsequently dried over night at 45° C. in vacuo. The residue accounts for 1.4percent.Result:m(product): 6.4 gYield with respect to Pd: 94CHCl3-insoluble ingredients: 1.4
94% at 40℃; for 4 h; Inert atmosphere Bis(dibenzylideneacetone)palladium(0) (Pd(dba)2)was synthesized by reducing PdCl2 with methanol in thepresence of sodium acetate and dba [30]. Dibenzylideneacetone(3.4500 g, 1.472 × 10–2 mol), sodium acetatetrihydrate (4.8525 g, 3.568 × 10–2 mol), and methanol(113 mL) were placed in a two-neck round-bottomflask. The reaction mixture was stirred at 50°C for 45–60 min to obtain a solution, and PdCl2 (0.7875 g,4.434 × 10–3 mol) was added. The resulting solutionwas stirred in an argon atmosphere at 40°C for 4 h.This yielded a dark violet precipitate of the Pd(dba)2complex, which was collected on a fritted glass filterunder argon, washed with water and acetone, andvacuum-dried (30°C/2–3 Torr) for 3 h. The productyield was 2.4 g. (94percent of the theoretical yield); m =152°C. According to the literature, m of thePd(dba)2 complex is 152°C [31]. UV spectra:Pd(dba)2, 525 nm (d → d* transition, ε525 =6400 L mol–1 cm–1); non-coordinated dba, 325 nm(n → π* transition, ε325 = 33540 L mol–1 cm–1).
Reference: [1] Patent: US7999126, 2011, B2, . Location in patent: Page/Page column 3; 4
[2] Kinetics and Catalysis, 2011, vol. 52, # 5, p. 702 - 710
[3] Kinetics and Catalysis, 2017, vol. 58, # 1, p. 34 - 45[4] Kinet. Katal., 2017, vol. 58, # 1, p. 36 - 48,13
[5] Russian Journal of General Chemistry, 2012, vol. 82, # 2, p. 206 - 211
[6] Organic Syntheses, 2005, vol. 81, p. 54 - 62
  • 2
  • [ 538-58-9 ]
  • [ 32005-36-0 ]
YieldReaction ConditionsOperation in experiment
95.4% With sodium acetate In methanol at 57℃; Inert atmosphere Experiment 1The synthesis was carried out under inert gas. 300 ml of methanol were provided in the reaction flask under argon and heated to 57° C. Then 8.245 g (35.2 mmol) dibenzylidene acetone and 3.495 g (1.248 g Pd, 11.7 mmol Pd) Na2[PdCl4] were added in the presence of an argon flow.Then, 7.80 g (95.1 mmol) anhydrous Na-acetate were added to the reaction mixture at 57° C. After cooling to room temperature, the stirrer was switched off and the mixture allowed to stand for 1.5 h upon which the product sedimented. The supernatant mother liquor was decanted and the product was washed with 300 ml of washing solution (methanol/fully demineralised water=1/1) to be free of NaCl. The product was washed with 70 ml of water (chloride test: negative) and subsequently with 300 ml of acetone and 200 ml of petroleum spirit. The product was dried over night in vacuo at 40° C.Appearance: reddish-brown solidSolubility Test:1.00 g of the product were dissolved in 150 ml of chloroform and stirred for 30 minutes at room temperature. The solution was aspirated through a membrane filter. The filter was washed with 30 ml of water and 30 ml of acetone, and the filter was subsequently dried over night at 45° C. in vacuo. The residue accounted for 0percent.Result:m(product): 6.4 gYield with respect to Pd: 95.4percentCHCl3-insoluble ingredients: 0percentAnalysis:
95%
Stage #1: at 60℃; for 0.5 h;
Stage #2: With sodium acetate In methanol for 0.25 h;
5.0 g of sodium palladium sodium chloride (Na2PdCl4, 17.0 mmol) was added with stirring,A mixture of 12 g (51 mmol) of dibenzylideneacetone and 50 ml of methanol was heated to about 60 ° C,After stirring, stirring was continued for 30 minutes, 1.6 g (20 mmol) of sodium acetate was added, stirred for 15 minutes, cooled to room temperature,A light brown solid was precipitated, filtered, washed with water and acetone, and dried to give 9.3 g of solid, 95percent yield,
Reference: [1] Patent: US7999126, 2011, B2, . Location in patent: Page/Page column 3; 4
[2] Patent: CN105175397, 2017, B, . Location in patent: Paragraph 0050-0052
[3] Australian Journal of Chemistry, 1987, vol. 40, # 6, p. 1083 - 1106
  • 3
  • [ 67-66-3 ]
  • [ 3375-31-3 ]
  • [ 538-58-9 ]
  • [ 52522-40-4 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 5, p. 1677 - 1683
  • 4
  • [ 7440-05-3 ]
  • [ 538-58-9 ]
  • [ 52522-40-4 ]
Reference: [1] Russian Chemical Bulletin, 2003, vol. 52, # 6, p. 1376 - 1379
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