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[ CAS No. 428-97-7 ] {[proInfo.proName]}

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Chemical Structure| 428-97-7
Chemical Structure| 428-97-7
Structure of 428-97-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 428-97-7 ]

CAS No. :428-97-7 MDL No. :MFCD24386313
Formula : C9H14F2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :YVPKMLFMDHSTKJ-UHFFFAOYSA-N
M.W :224.20 Pubchem ID :20455495
Synonyms :

Calculated chemistry of [ 428-97-7 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.78
Num. rotatable bonds : 8
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.09
TPSA : 52.6 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) : -6.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.28
Log Po/w (XLOGP3) : 1.71
Log Po/w (WLOGP) : 2.37
Log Po/w (MLOGP) : 1.55
Log Po/w (SILICOS-IT) : 2.0
Consensus Log Po/w : 1.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.78
Solubility : 3.73 mg/ml ; 0.0166 mol/l
Class : Very soluble
Log S (Ali) : -2.43
Solubility : 0.832 mg/ml ; 0.00371 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.27
Solubility : 1.21 mg/ml ; 0.00541 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.12

Safety of [ 428-97-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 428-97-7 ]

* 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 [ 428-97-7 ]
  • Downstream synthetic route of [ 428-97-7 ]

[ 428-97-7 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 667-27-6 ]
  • [ 140-88-5 ]
  • [ 428-97-7 ]
YieldReaction ConditionsOperation in experiment
97.4% With N,N,N,N,-tetramethylethylenediamine; copper; acetic acid In tetrahydrofuran at 50℃; for 0.5 h; Copper powder (700 mg of) and tetrahydrofuran (5.8 mL of) added to the reaction vessel, and stirred at 50 , thereto was added ethyl acrylate (0.50 g of) and ethyl bromodifluoroacetate (2.53 g), followed by successively thereto solution of TMEDA (0.29g) and acetic acid (0.27g). The reaction for 0.5 hours and then ends. To the resulting mixture was added 10percent aqueous ammonium chloride solution, and the resulting mixture was filtered through a celite pad to remove the copper residue, and extracted with methyl t-butyl ether to obtain diethyl 2,2-difluoroglutarate ( 1.09g, yield 97.4percent).Furthermore, in addition to water (0.10g) acetic acid Alternatively, the same method as described above carried out to obtain diethyl 2,2-difluoro-glutarate (1.08 g of, yield 96.4percent).
55.0 g With N,N,N,N,-tetramethylethylenediamine; copper In tetrahydrofuran at 50℃; for 3 h; Preparation 1
Synthesis of diethyl 2,2-difluoropentanedioate
To a solution of ethyl bromodifluoroacetate (33.2 g) in tetrahydrofuran (94.0 g) was added ethyl acrylate (8.2 g) and copper powder (10.9 g).
After heating to 50° C., TMEDA (9.5 g) was added dropwise and the reaction mixture was then stirred for 3 hours at the same temperature.
Upon disappearance of ethyl acrylate as the starting material, to the reaction solution was added methyl t-butyl ether (MTBE, 73.7 g) followed by addition of 10percent aqueous ammonium chloride solution (49.8 g) dropwise, and the mixture was then stirred for 30 minutes.
The remaining copper residue was removed by filtration through a celite, and methyl t-butyl ether (MTBE, 66.3 g) was added to separate the layers.
The separated organic layer was washed successively with 10percent aqueous NH4Cl solution (66.3 g) and 3 N aqueous hydrochloric acid solution (99.6 g) in order and then distilled under reduced pressure to obtain 55.0 g of the desired title compound.
1H NMR (400 MHz, CDCl3) δ 1.26 (t, J=7.2 Hz, 3H), 1.37 (t, J=7.2 Hz, 3H), 2.37-2.49 (m, 2H), 2.55 (t, J=7.2 Hz, 2H), 4.16 (q, J=7.2 Hz, 2H), 4.29 (q, J=7.2 Hz, 2H).
Reference: [1] Patent: CN104159884, 2016, B, . Location in patent: Paragraph 0060; 0061; 0062; 0063; 0064
[2] Synthesis, 2012, vol. 44, # 20, p. 3165 - 3170,6
[3] Patent: WO2009/82134, 2009, A2, . Location in patent: Page/Page column 41-42
[4] Patent: WO2012/30106, 2012, A2, . Location in patent: Page/Page column 11
[5] Patent: US2013/165659, 2013, A1, . Location in patent: Paragraph 0098; 0099; 0100
  • 2
  • [ 141-52-6 ]
  • [ 80997-33-7 ]
  • [ 428-97-7 ]
YieldReaction ConditionsOperation in experiment
92.7% With ozone In dichloromethane at -20℃; for 0.833333 h; In this embodiment, diethyl 2,2-difluoroglutarate is prepared by simultaneous oxidation and esterification, as follows:The obtained in Example 13,3-difluorocyclopentene (66mmol)Dissolved in 132mL of dichloromethane,Add 2.5 mL of a 2.5 mol/L sodium ethoxide solution,Then cooled to -20 ° C,Slowly enter ozone gas,After 50 min, the reaction system turned light blue.After the reaction is over,Stop introducing ozone gas,Diluted with methyl tert-butyl ether and water to the reaction system,After stirring, the solution is allowed to stand for separation.The aqueous layer was extracted with methyl tert-butyl ether.Combine the organic phase,The organic layer was dried over anhydrous sodium sulfate and filtered.The filtrate was concentrated to give a bright yellow oil.Vacuum distillation,Collecting the main fraction,13.6 g of light yellow transparent liquid was obtainedDiethyl 2,2-difluoroglutarate,The yield was 92.0percent.
Reference: [1] Patent: CN108191647, 2018, A, . Location in patent: Paragraph 0040-0044
  • 3
  • [ 5965-53-7 ]
  • [ 428-97-7 ]
Reference: [1] Patent: US4324730, 1982, A,
  • 4
  • [ 64-17-5 ]
  • [ 380-86-9 ]
  • [ 428-97-7 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 3193
  • 5
  • [ 667-27-6 ]
  • [ 140-88-5 ]
  • [ 428-97-7 ]
  • [ 1412175-17-7 ]
Reference: [1] Synthesis, 2012, vol. 44, # 20, p. 3165 - 3170,6
  • 6
  • [ 667-27-6 ]
  • [ 140-88-5 ]
  • [ 454-31-9 ]
  • [ 428-97-7 ]
Reference: [1] Synthesis, 2012, vol. 44, # 20, p. 3165 - 3170,6
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