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[ CAS No. 51725-82-7 ] {[proInfo.proName]}

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Chemical Structure| 51725-82-7
Chemical Structure| 51725-82-7
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Product Details of [ 51725-82-7 ]

CAS No. :51725-82-7 MDL No. :MFCD03424817
Formula : C12H14O3 Boiling Point : -
Linear Structure Formula :- InChI Key :UNULPFKXRJPSCO-UHFFFAOYSA-N
M.W : 206.24 Pubchem ID :2760276
Synonyms :

Calculated chemistry of [ 51725-82-7 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.31
TPSA : 43.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.28
Log Po/w (XLOGP3) : 2.36
Log Po/w (WLOGP) : 2.13
Log Po/w (MLOGP) : 1.89
Log Po/w (SILICOS-IT) : 2.81
Consensus Log Po/w : 2.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.57
Solubility : 0.553 mg/ml ; 0.00268 mol/l
Class : Soluble
Log S (Ali) : -2.91
Solubility : 0.253 mg/ml ; 0.00123 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.62
Solubility : 0.0489 mg/ml ; 0.000237 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 51725-82-7 ]

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 [ 51725-82-7 ]

* 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 [ 51725-82-7 ]
  • Downstream synthetic route of [ 51725-82-7 ]

[ 51725-82-7 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 577-16-2 ]
  • [ 105-58-8 ]
  • [ 51725-82-7 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: With sodium hydride In toluene; mineral oil at 20℃; for 0.25 h; Inert atmosphere
Stage #2: for 18 h; Reflux; Inert atmosphere
To a stirred suspension of sodium hydride (60percent dispersion in mineral oil, 7.20 g, 180 mmol, 3.6 equiv) in toluene (300 mL) was slowly added diethyl carbonate (23.6 g, 200 mmol, 4.0 equiv) at ambient temperature. After stirring for 15 minutes, 2-methyl acetophenone (6.70 g, 50.0 mmol, 1.0 equiv) was added, and the resultant mixture heated to reflux for 18 hours. Glacial acetic acid (15 mL) was then added drop-wise over 10 minutes, followed by the cautious addition of ice cold water (150 mL). The resultant mixture was extracted with ethyl acetate and the combined organic extracts dried over magnesium sulfate and concentrated under vacuum. The resultant residue was purified by flash column chromatography on silica gel (gradient: 0 to 5percent ethyl acetate in pentane) to afford 7.94 g (77percent) of 3-oxo-3-o-tolyl-propionic acid ethyl ester as an oil (4:1 mixture of keto/enol tautomers). 1H NMR (Keto tautomer) (400 MHz, CDCl3) δ: 7.66 (s, 1H), 7.41 (s, 1H), 7.30-7.25 (m, 2H), 4.22-4.15 (m, 2H), 3.96-3.94 (m, 2H), 2.55 (s, 3H), 1.28-1.22 (m, 3 H).
54% With sodium hydride In toluene; mineral oil for 16 h; Reflux To a solution of 1-(2-methylphenyl)ethan-1-one (5 g, 37.26 mmol) in toluene (130 mL) was added diethyl carbonate (13.21 g, 111.79 mmol) andNaH (60percent, 2.98 g, 74.53 mmol). The reaction mixture was refluxed for 16 hours. After cooling, the reaction mixture was poured into ice water (200 mL) and extracted in to ethyl acetate (3 x 200 mL). The combined organic layers were dried overmagnesium sulfate, filtered and evaporated under reduced pressure to provide 9.5 g of a yellow oil. The oil was chromatographed by silica gel column chromatography (ethyl acetate in heptanes) to provide the title compound as an orange oil (6.23 g, 54percent yield). LC-MS: tRl.99 mi [M+H]207.
Reference: [1] Patent: US2012/22043, 2012, A1, . Location in patent: Page/Page column 89
[2] Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7582 - 7591
[3] Patent: WO2015/183839, 2015, A1, . Location in patent: Page/Page column 254; 255
[4] Chemistry - A European Journal, 2008, vol. 14, # 27, p. 8082 - 8085
[5] European Journal of Organic Chemistry, 2015, vol. 2015, # 17, p. 3656 - 3660
[6] Organic Letters, 2017, vol. 19, # 23, p. 6344 - 6347
[7] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2107 - 2112
[8] Organic and Biomolecular Chemistry, 2018, vol. 16, # 25, p. 4683 - 4687
  • 2
  • [ 623-73-4 ]
  • [ 529-20-4 ]
  • [ 51725-82-7 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7599 - 7608
[2] Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7599 - 7608
  • 3
  • [ 211318-51-3 ]
  • [ 51725-82-7 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 50, p. 8859 - 8861
[2] Tetrahedron Letters, 2007, vol. 48, # 7, p. 1147 - 1149
  • 4
  • [ 141-97-9 ]
  • [ 933-88-0 ]
  • [ 51725-82-7 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2005, vol. 53, # 24, p. 9566 - 9570
[2] Chemische Berichte, 1935, vol. 68, p. 227,230
[3] Diss. <T. H. Berlin 1932> S. 60,
  • 5
  • [ 95-46-5 ]
  • [ 6148-64-7 ]
  • [ 82102-37-2 ]
  • [ 51725-82-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 37, p. 9763 - 9766[2] Angew. Chem., 2013, vol. 125, # 37, p. 9945 - 9948
  • 6
  • [ 100884-03-5 ]
  • [ 51725-82-7 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 4, p. 839 - 850
  • 7
  • [ 529-20-4 ]
  • [ 51725-82-7 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 7, p. 1147 - 1149
  • 8
  • [ 141-78-6 ]
  • [ 933-88-0 ]
  • [ 51725-82-7 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 24, p. 5597 - 5601
  • 9
  • [ 89-71-4 ]
  • [ 141-78-6 ]
  • [ 51725-82-7 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 4, p. 906 - 916
  • 10
  • [ 1071-46-1 ]
  • [ 933-88-0 ]
  • [ 51725-82-7 ]
Reference: [1] Tetrahedron, 1992, vol. 48, # 36, p. 7763 - 7774
  • 11
  • [ 933-88-0 ]
  • [ 51725-82-7 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 4, p. 839 - 850
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