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[ CAS No. 14593-43-2 ] {[proInfo.proName]}

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Chemical Structure| 14593-43-2
Chemical Structure| 14593-43-2
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Product Details of [ 14593-43-2 ]

CAS No. :14593-43-2 MDL No. :MFCD00078288
Formula : C10H12O Boiling Point : -
Linear Structure Formula :CH2CHCH2OCH2C6H5 InChI Key :HUGHWHMUUQNACD-UHFFFAOYSA-N
M.W : 148.20 Pubchem ID :84542
Synonyms :

Calculated chemistry of [ 14593-43-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.44
TPSA : 9.23 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) : -5.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.37
Log Po/w (XLOGP3) : 2.56
Log Po/w (WLOGP) : 2.24
Log Po/w (MLOGP) : 2.4
Log Po/w (SILICOS-IT) : 2.83
Consensus Log Po/w : 2.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.51
Solubility : 0.457 mg/ml ; 0.00308 mol/l
Class : Soluble
Log S (Ali) : -2.4
Solubility : 0.588 mg/ml ; 0.00397 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.37
Solubility : 0.0628 mg/ml ; 0.000424 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 14593-43-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P210-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P370+P378-P403+P235-P501 UN#:N/A
Hazard Statements:H227-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14593-43-2 ]

* 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 [ 14593-43-2 ]
  • Downstream synthetic route of [ 14593-43-2 ]

[ 14593-43-2 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 14593-43-2 ]
  • [ 13807-91-5 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 6, p. 1428 - 1431
[2] Carbohydrate Research, 1983, vol. 121, p. 79 - 88
[3] Tetrahedron, 2005, vol. 61, # 50, p. 11986 - 11990
  • 2
  • [ 67-56-1 ]
  • [ 14593-43-2 ]
  • [ 31600-43-8 ]
  • [ 60656-87-3 ]
YieldReaction ConditionsOperation in experiment
60% With oxygen; ozone; sodium hydroxide In dichloromethane at -65℃; General procedure: (1) An ozone–oxygen mixture was bubbled through a solution of 10.00 mmol of ethers Ia or Ib in a mixture of 20 mL of 2.5 M NaOH in MeOH and 80 mL of CH2Cl2 at –65°C until blue color appeared. The reaction mixture was purged with argon, MTBE (70 mL) and water (30 mL) were added, stirred for 1 hat ambient temperature. The organic layer was separated, the aqueous layer was extracted with MTBE. The combined organic extracts were dried with Na2SO4. After evaporation, ether I produced 1.66 g of mixture of compounds II and III in 72 : 28 ratio (according to GLC and NMR data), column chromatography (Si2, PE, PE : MTBE = 5 : 1, 4 : 1) gave 1.07 g (60percent) of ester IIa and 0.47 g (32percent) of aldehyde III. After evaporation, ether Ib produced 1.61 g of a mixture of compound IIb and IIIb in 88 : 12 ratio (according to GLC and NMR), column chromatography (Si2, PE, PE : MTBE = 5 : 1, 4 : 1) resulted in 1.34 g (80percent) of ester IIb and 0.16 g (12percent) of aldehyde IIIb.
Reference: [1] Doklady Chemistry, 2015, vol. 462, # 1, p. 127 - 129[2] Dokl. Akad. Nauk, 2015, vol. 462, # 3, p. 307 - 309,3
  • 3
  • [ 67-56-1 ]
  • [ 14593-43-2 ]
  • [ 31600-43-8 ]
  • [ 127657-97-0 ]
YieldReaction ConditionsOperation in experiment
56%
Stage #1: at -78℃;
Stage #2: at -50 - 20℃; for 24 h;
General procedure: (2) An ozone–oxygen mixture was bubbled through a solution of 10.00 mmol of ethers Ia or Ib in50 mL of MeOH at –78°C until blue color appeared.The reaction mixture was purged with argon, 3.88 g(35.00 mmol) of NH2C(O)NHNH2 HCl. HCl was added at –50°C. The mixture was stirred at ambient temperature for 24 h. The reaction mixture was evaporated, the residue was dissolved in 100 mL of CHCl3, washed with 2 (to pH ≈ 7), and dried with Na2SO4. After evaporation, ether I produced 1.86 g of a mixture of compounds II and IV in 40 : 60 ratio(according to GLC and NMR), column chromatography (Si2, PE, PE : MTBE = 5 : 1, 4 : 1) afforded0.74 g (42percent) of ester IIa and 1.09 g (56percent) of acetal IV.After evaporation, ether Ib produced 1.64 g of a mixture of compounds IIb and IVb in 25 : 75 ratio (according to GLC and NMR data), column chromatography (Si2, PE, PE : MTBE = 5 : 1, 4 : 1) gave 0.40 g (24percent)of ester IIb and 1.15 g (63percent) of acetal IVb.
Reference: [1] Doklady Chemistry, 2015, vol. 462, # 1, p. 127 - 129[2] Dokl. Akad. Nauk, 2015, vol. 462, # 3, p. 307 - 309,3
  • 4
  • [ 14593-43-2 ]
  • [ 22539-93-1 ]
YieldReaction ConditionsOperation in experiment
96% With chromium(VI) oxide; palladium dichloride In water; acetonitrile at 20 - 60℃; for 12 h; General procedure: To a stirred solution of olefin (0.4mmol) in CH3CN (3.5mL) and H2O (0.5mL) were added PdCl2 (3.6mg, 0.02mmol, 5molpercent) and CrO3 (20mg, 0.6mmol, 0.5equiv) at room temperature. The reaction mixture was warmed to 60°C and stirred for specified time (see Tables 5–7) in a closed flask. The reaction mixture was then filtered through a small pad of silica gel and washed with EtOAc and the filtrate concentrated. The residue in some cases contained virtually pure compound and no further purification was necessary. In other cases the residue was purified by silica gel column chromatography using petroleum ether/EtOAc as an eluent to afford the methyl ketones.
77% With potassium bromate; palladium 10% on activated carbon In tetrahydrofuran; water at 65℃; General procedure: To the solution of olefine (1 mmol), in THF/water (4:1, 15 mL), 10percent Pd/C (0.05 mmol) and KBrO3 (3 mmol) were added. This mixture was heated at reflux temperature. After completion of reaction (checked by TLC), the mixture was diluted with water and filtered through Whatman 40 filter paper. The filtrate was extracted with ethyl acetate. The combined organic layer washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by column chromatography to get the product.
Reference: [1] Tetrahedron, 2014, vol. 70, # 32, p. 4760 - 4767
[2] Journal of Organic Chemistry, 2016, vol. 81, # 5, p. 2113 - 2121
[3] Journal of Organic Chemistry, 2014, vol. 79, # 12, p. 5787 - 5793
[4] Tetrahedron Letters, 2013, vol. 54, # 19, p. 2293 - 2295
[5] Tetrahedron Letters, 2009, vol. 50, # 24, p. 2893 - 2894
[6] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 11, p. 3155 - 3157
  • 5
  • [ 14593-43-2 ]
  • [ 22539-93-1 ]
  • [ 19790-60-4 ]
Reference: [1] ChemCatChem, 2015, vol. 7, # 15, p. 2318 - 2322
  • 6
  • [ 14593-43-2 ]
  • [ 54314-84-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 7-8, p. 1163 - 1167
  • 7
  • [ 14593-43-2 ]
  • [ 14618-80-5 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 27, p. 4751 - 4754
  • 8
  • [ 14593-43-2 ]
  • [ 2930-05-4 ]
  • [ 14618-80-5 ]
Reference: [1] Journal of the American Chemical Society, 1991, vol. 113, # 15, p. 5878 - 5880
[2] Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 5, p. 167 - 170
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