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[ CAS No. 590-90-9 ] {[proInfo.proName]}

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Limited Quantity USD 15-60
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3d Animation Molecule Structure of 590-90-9
Chemical Structure| 590-90-9
Chemical Structure| 590-90-9
Structure of 590-90-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 590-90-9 ]

CAS No. :590-90-9 MDL No. :MFCD00059005
Formula : C4H8O2 Boiling Point : -
Linear Structure Formula :HO(CH2)2COCH3 InChI Key :LVSQXDHWDCMMRJ-UHFFFAOYSA-N
M.W : 88.11 Pubchem ID :111509
Synonyms :

Calculated chemistry of [ 590-90-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 22.7
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.71
Log Po/w (XLOGP3) : -0.8
Log Po/w (WLOGP) : -0.04
Log Po/w (MLOGP) : -0.33
Log Po/w (SILICOS-IT) : 0.13
Consensus Log Po/w : -0.06

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.25
Solubility : 157.0 mg/ml ; 1.78 mol/l
Class : Highly soluble
Log S (Ali) : 0.5
Solubility : 276.0 mg/ml ; 3.13 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.35
Solubility : 39.4 mg/ml ; 0.448 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 590-90-9 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P403+P235 UN#:1993
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 590-90-9 ]

* 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 [ 590-90-9 ]
  • Downstream synthetic route of [ 590-90-9 ]

[ 590-90-9 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 590-90-9 ]
  • [ 25055-82-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 3, p. 870 - 873[2] Angew. Chem., 2017, vol. 129, # 3, p. 888 - 891,4
[3] Journal of the American Chemical Society, 2017, vol. 139, # 17, p. 6078 - 6081
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5716 - 5726
[5] Angewandte Chemie - International Edition, 2008, vol. 47, # 1, p. 90 - 93
[6] Journal of the American Chemical Society, 2014, vol. 136, # 30, p. 10777 - 10782
[7] Synthesis, 2010, # 17, p. 2997 - 3003
[8] Angewandte Chemie - International Edition, 2017, vol. 56, # 10, p. 2744 - 2748[9] Angew. Chem., 2017, vol. 129, # 10, p. 2788 - 2792,5
  • 2
  • [ 590-90-9 ]
  • [ 108-95-2 ]
  • [ 5471-51-2 ]
YieldReaction ConditionsOperation in experiment
65% With D218 resin In toluene at 80 - 120℃; for 7 h; Large scale 4) 1 kg of dry D218 resin was charged into the fluidized bed reactor.6kg of phenol and 1.2kg of toluene were put into the reaction kettle. The reactor was heated and the column was opened. The bottom of the reaction liquid was flowed through the resin layer and the temperature of the column was stable at 80 . Start dropping 78percent of the butanone alcohol 1.6kg, 1h drops finished.After 15 min of incubation, the reactor was heated to 120 ° C and the reaction was continued for 7 h.The yield of raspberry ketone was 65percent.
Reference: [1] Patent: CN104355977, 2016, B, . Location in patent: Paragraph 0043
[2] Kogyo Kagaku Zasshi, 1954, vol. 57, p. 42[3] Chem.Abstr., 1955, p. 10907
  • 3
  • [ 590-90-9 ]
  • [ 108-95-2 ]
  • [ 22409-85-4 ]
  • [ 5471-51-2 ]
Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 20, p. 5901 - 5904
[2] Journal of Organic Chemistry, 1994, vol. 59, # 20, p. 5901 - 5904
[3] Patent: US2011/257439, 2011, A1, . Location in patent: Page/Page column 5
  • 4
  • [ 590-90-9 ]
  • [ 108-95-2 ]
  • [ 5471-51-2 ]
YieldReaction ConditionsOperation in experiment
82.5 %Chromat. With N,N,N-triethyl-N-(propanesulfonic acid)ammonium hydrogensulfate In neat (no solvent) at 50℃; for 1.5 h; In a typical reaction, Phenol(1, 0.5 mol), IL (0.03 mol) were added into a threeneckedround bottom flask equipped with magneticstirrer and butanolone (2, 0.1 mol) and dripped intothe above solution slowly. The resulting mixture washeated to 50°C and magnetically stirred for 30 minwhen the drop was completed. After the reaction wascompleted (TLC detected), the upper organic phasewas separated from IL by decantation and analyzed viagas chromatography (GC), IL was recovered from theaqueous solution by removing water at 70°C undervacuum for 6 h, and used directly for the next run (seeScheme 2).
Reference: [1] Petroleum Chemistry, 2018, vol. 58, # 1, p. 56 - 61[2] Neftekhimiya, 2018, vol. 58, # 1, p. 56 - 61,6
  • 5
  • [ 590-90-9 ]
  • [ 6322-49-2 ]
YieldReaction ConditionsOperation in experiment
1.06 g With thionyl chloride In dichloromethane at 20℃; 4-Hydroxy-2-butanone (0.881 g; 10 mmol), 2 ml of DCM, and thionyl chloride (1.46 ml; 20 mmol) were charged in a reaction flask and stirred at rt overnight. The mixture was evaporated and dried by nitrogen flow to yield 1.06 g of 2-chlorobutan-2-one. 1 H-NMR (400 MHz, rfe-DMSO): δ 2.12 (s, 3H), 2.94 (t, 2H), 3.74 (t, 2H).
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 27, p. 6713 - 6716
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1936, vol. 202, p. 1687
[3] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 909[4] Chem. Zentralbl., 1939, vol. 110, # I, p. 4953
[5] Patent: WO2015/169999, 2015, A1, . Location in patent: Page/Page column 63
  • 6
  • [ 590-90-9 ]
  • [ 2867-59-6 ]
Reference: [1] Barell-Festschr. <Basel 1946> S.90,
[2] Chem.Abstr., 1947, p. 6199
[3] ChemCatChem, 2015, vol. 7, # 23, p. 3838 - 3841
  • 7
  • [ 590-90-9 ]
  • [ 61477-40-5 ]
YieldReaction ConditionsOperation in experiment
0.45 g With SEC-BUTYLAMINE; magnesium chloride In aq. phosphate buffer; dimethyl sulfoxide at 15℃; for 24 h; Enzymatic reaction A mixture of 0.9 gm enzyme ECS-ATA-134 and 7.5 ml PLP solution was added to asol uti on of phosphate buffer (15 ml, of example 2), secondary butyl amine (20 ml) andmagnesium chloride (5 ml) followed Li addition of a substrate solution (0.6 gm 4-Hydroxy butanone in S ml Dimethyl sulfoxide). The reaction mixture was stirred at 1Sfor 24 hours. The reaction mixture was extracted with ethyl acetate and the solvent wasremav’ed by distillation to obtain (R)-3-aminobutan-1 -ol. Y ield: 0.45 gm, 100percent R-isomer.
Reference: [1] Patent: WO2018/20380, 2018, A1, . Location in patent: Page/Page column 6
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