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[ CAS No. 5400-79-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 5400-79-3
Chemical Structure| 5400-79-3
Chemical Structure| 5400-79-3
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Product Details of [ 5400-79-3 ]

CAS No. :5400-79-3 MDL No. :MFCD01320352
Formula : C8H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :VGJWAMLZUUGEQY-UHFFFAOYSA-N
M.W : 156.18 Pubchem ID :223136
Synonyms :

Calculated chemistry of [ 5400-79-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.94
TPSA : 43.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 0.26
Log Po/w (WLOGP) : 0.92
Log Po/w (MLOGP) : 0.58
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 1.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.77
Solubility : 26.3 mg/ml ; 0.168 mol/l
Class : Very soluble
Log S (Ali) : -0.73
Solubility : 29.0 mg/ml ; 0.185 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.39
Solubility : 6.32 mg/ml ; 0.0405 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.38

Safety of [ 5400-79-3 ]

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

Application In Synthesis of [ 5400-79-3 ]

* 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 [ 5400-79-3 ]
  • Downstream synthetic route of [ 5400-79-3 ]

[ 5400-79-3 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 5400-79-3 ]
  • [ 98-78-2 ]
Reference: [1] Journal of the Chemical Society, 1921, vol. 119, p. 499
  • 2
  • [ 64-17-5 ]
  • [ 98-78-2 ]
  • [ 5400-79-3 ]
YieldReaction ConditionsOperation in experiment
96% at 15 - 20℃; General procedure: To a solution of 3-oxocyclohexane carboxylic acid (63.0g, 0.443mol) in ethanol (950mL), SOCl2 (38.8mL, 0.532mol) was added at 15°C. The reaction mixture was stirred at rt overnight, and then evaporated under reduced pressure. The residue was dissolved in CHCl3 (500mL) and stirred with saturated aq NaHCO3 (200mL) for 30min. The layers were separated, and the aqueous layer was extracted with CHCl3 (2×50mL). The combined organic phases were dried over Na2SO4 and evaporated in vacuo. The residue was distilled under reduced pressure to give 23.
Reference: [1] Journal of Fluorine Chemistry, 2017, vol. 199, p. 60 - 66
[2] Journal of the Chemical Society, 1908, vol. 93, p. 575
  • 3
  • [ 98-78-2 ]
  • [ 75-03-6 ]
  • [ 5400-79-3 ]
YieldReaction ConditionsOperation in experiment
71% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 18 h; A solution of cyclopentanone-3-carboxylic acid (5.00 g, 39 mmol), caesium carbonate (12.82 g, 39 mmol) and ethyl iodide (9.12 g, 4.75 ml, 58.5 mmol) in DMF (50 ml) was stirred at RT for 18 h. The mixture was then concentrated i. vac., the residue was taken up in toluene, the mixture was concentrated again and 2 N hydrochloric acid and EtOAc were then added. The aq. phase was extracted with EtOAc (3.x.30 ml) and the combined organic phases were washed with aq. sodium thiosulfate soln. The organic phase was dried with Na2SO4 and concentrated i. vac.Yield: 4.34 g (71percent)
Reference: [1] Patent: US2008/306084, 2008, A1, . Location in patent: Page/Page column 48
  • 4
  • [ 64-17-5 ]
  • [ 5400-79-3 ]
YieldReaction ConditionsOperation in experiment
47% With triethylamine In dichloromethane at 0 - 20℃; for 2 h; Triethylamine (3.8 g, 30 mmol, 2.0 eq.) and ethanol (754 mg, 16.37 mmol, 2.0 eq.) were subsequently added dropwise solution of 3-oxocyclopentanecarbonyl chloride (1.28 g, 8.2 mmol, 1.0 eq.) in dichloromethane (20 mL) at 0° C.
The reaction was stirred at room temperature for 2 hours, quenched with water (20 mL).
The aqueous phase was extracted with methylene chloride (10 mL*2).
The combined organic phases were dried over anhydrous sodium sulfate, and concentrated to give the crude product, which was purified by silica gel column chromatography (eluent: petroleum ether:ethyl acetate=1:1) to give the title compound (0.6 g, yield: 47percent).
Reference: [1] Patent: US2016/200730, 2016, A1, . Location in patent: Paragraph 0443; 0444
  • 5
  • [ 64-17-5 ]
  • [ 5400-79-3 ]
YieldReaction ConditionsOperation in experiment
79% at 42℃; for 3 h; A solution of 14 (240mg, 1.39mmol) and K2CO3 (20mg, 0.14mmol) in ethanol (14mL) was stirred at 42°C for 3h, after which the solution was quenched with HCl (0.30M) and extracted with ethyl acetate several times; the organic layer was collected, washed with saturated NaCl, dried (MgSO4), concentrated under reduced pressure, and chromatographed in silica gel column (ethyl acetate/hexanes, 2:3) to afford a colorless oil 15 (173mg, 79percent). IR (KBr): 2974, 1737, 1462, 1405, 1375, 1199, 1158, 1031cm−1; 1H NMR (400MHz, CDCl3): δ 4.05 (q, J=7.2Hz, 2H), 3.03 (quintet, J=7.9Hz, 1H), 1.98∼2.42 (m, 6H), 1.16 (t, J=7.2Hz, 3H); 13C NMR (100MHz, CDCl3) δ: 216.4, 174.0, 60.7, 40.9, 40.7, 37.1, 26.3, 13.9; MS (EI, 75eV) m/z (rel intensity) 156 (M+, 13), 128 (66), 111 (27), 100 (58), 83 (67), 73 (9), 55 (100), 45 (5).
Reference: [1] Tetrahedron, 2013, vol. 69, # 46, p. 9591 - 9599
  • 6
  • [ 68196-91-8 ]
  • [ 5400-79-3 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 2, p. 511 - 518
[2] Green Chemistry, 2017, vol. 19, # 21, p. 5122 - 5130
  • 7
  • [ 83832-60-4 ]
  • [ 5400-79-3 ]
Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 19, p. 5917 - 5919
  • 8
  • [ 83844-81-9 ]
  • [ 5400-79-3 ]
Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 19, p. 5917 - 5919
  • 9
  • [ 10267-94-4 ]
  • [ 5400-79-3 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 2, p. 511 - 518
[2] Green Chemistry, 2017, vol. 19, # 21, p. 5122 - 5130
  • 10
  • [ 4683-24-3 ]
  • [ 5400-79-3 ]
Reference: [1] Tetrahedron, 2013, vol. 69, # 46, p. 9591 - 9599
[2] Tetrahedron, 2013, vol. 69, # 46, p. 9591 - 9599
  • 11
  • [ 98-78-2 ]
  • [ 5400-79-3 ]
Reference: [1] Patent: US2016/200730, 2016, A1,
  • 12
  • [ 25662-28-6 ]
  • [ 5400-79-3 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 21, p. 5122 - 5130
  • 13
  • [ 691-83-8 ]
  • [ 105-53-3 ]
  • [ 5400-79-3 ]
Reference: [1] Journal of the Chemical Society, 1926, p. 1484
[2] Journal of the Chemical Society, 1926, p. 1484
[3] Journal of the Chemical Society, 1926, p. 1484
  • 14
  • [ 2409-52-1 ]
  • [ 105-53-3 ]
  • [ 5400-79-3 ]
Reference: [1] Journal of the Chemical Society, 1926, p. 1484
[2] Journal of the Chemical Society, 1926, p. 1484
[3] Journal of the Chemical Society, 1926, p. 1484
  • 15
  • [ 691-83-8 ]
  • [ 5400-79-3 ]
Reference: [1] Journal of the Chemical Society, 1926, p. 1484
  • 16
  • [ 38230-84-1 ]
  • [ 5400-79-3 ]
Reference: [1] Journal of the Chemical Society, 1908, vol. 93, p. 575
  • 17
  • [ 5400-79-3 ]
  • [ 939398-48-8 ]
Reference: [1] Journal of Fluorine Chemistry, 2017, vol. 199, p. 60 - 66
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