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[ CAS No. 452339-73-0 ] {[proInfo.proName]}

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Chemical Structure| 452339-73-0
Chemical Structure| 452339-73-0
Structure of 452339-73-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 452339-73-0 ]

CAS No. :452339-73-0 MDL No. :MFCD21362968
Formula : C13H15NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :JUEBDVANOFZMMX-NSHDSACASA-N
M.W : 249.26 Pubchem ID :10933894
Synonyms :

Calculated chemistry of [ 452339-73-0 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 67.38
TPSA : 56.79 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 1.36
Log Po/w (WLOGP) : 1.26
Log Po/w (MLOGP) : 1.26
Log Po/w (SILICOS-IT) : 2.19
Consensus Log Po/w : 1.65

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.42
Solubility : 0.941 mg/ml ; 0.00378 mol/l
Class : Soluble
Log S (Ali) : -2.16
Solubility : 1.74 mg/ml ; 0.007 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.48
Solubility : 0.0829 mg/ml ; 0.000333 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.17

Safety of [ 452339-73-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 452339-73-0 ]

* 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 [ 452339-73-0 ]
  • Downstream synthetic route of [ 452339-73-0 ]

[ 452339-73-0 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 452339-72-9 ]
  • [ 452339-73-0 ]
YieldReaction ConditionsOperation in experiment
90.2% With heteropoly acid In ethyl acetate at 10 - 15℃; Take (1) 5g of raw materials was added to 40ml of ethyl acetate was stirred, then add 0.05 heteropoly acid crystals 10-15 ° C reaction3-5h, HPLC detection of the reaction solution, when (1) the type of raw material no longer down to stop the reaction, cooled to room temperature; using a pore size of 0.2 micronsMicroporous membrane filter to remove heteropoly acid crystals, washed, concentrated to give the product.
70% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 10 - 20℃; for 1 h; Example 7
Preparation of (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (IX)
Compound VIII (1.0eqt) in DMF (10V) was cooled to 10-15° C., added potassium tert-butoxide (1.1 eqt) slowly in portions.
The reaction mass was allowed to stir over a period of one hour at room temperature.
The mixture was cooled to 10° C. and chilled water was added.
This was allowed to stir over a stipulated time period and filtered, suck dried.
The crude product thus obtained was dissolved in DMF (˜0.2V) and was cooled to 10-15° C. and slowly added drop wise ice cold water.
The precipitated mass was allowed to stir for 1 h at 10-15° C.
The reaction mass was filtered, suck dried and the product was dried under vacuum at 54-55° C. over a period of time 5-6 h, to obtain highly chiral pure titled compound.
Yield: 70percent; purity by HPLC: 99.99percent; Chiral purity: R-isomer: 99.97percent; S-isomer: 0.03percent
700 mg With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 0 - 20℃; for 3 h; Inert atmosphere 100mL three bottles, Nitrogen protection, 0 ° C, Compound 1 _15 (1 g, 3. Lmmo 1) was dissolved in N, N-dimethylformamide (10 mL) Potassium tert-butoxide (38111 ^, 3.41) 11] 101) was added. The reaction was carried out at room temperature for 3 hours. Ethyl acetate (50 mL) Washed sequentially with water (50 mL) and saturated brine (50 mL) Organic phase dry, filter, concentrate, Recrystallization from a mixed solution (20 mL) of ethyl acetate and petroleum ether (1/20 of the ratio) gave 700 mg of a white solid.
Reference: [1] Patent: CN106957313, 2017, A, . Location in patent: Paragraph 0014-0015
[2] Organic and biomolecular chemistry, 2003, vol. 1, # 7, p. 1106 - 1111
[3] Patent: US2015/239862, 2015, A1, . Location in patent: Paragraph 0133; 0134
[4] Patent: WO2004/22547, 2004, A1, . Location in patent: Page 43-44
[5] Patent: WO2004/37773, 2004, A1, . Location in patent: Page 46
[6] Patent: WO2003/72539, 2003, A1, . Location in patent: Page/Page column 46-47
[7] Patent: WO2003/91204, 2003, A1, . Location in patent: Page/Page column 38-39
[8] Patent: CN107188813, 2017, A, . Location in patent: Paragraph 0054; 0079-0080
  • 2
  • [ 208925-08-0 ]
  • [ 530-62-1 ]
  • [ 452339-73-0 ]
YieldReaction ConditionsOperation in experiment
51% With triethylamine In chloroform at 20℃; Intermediate 34. (/?)-5-(2,2-Dimethyl-4H-1 ,3-benzodioxin-6-yl)-1 ,3-oxazolidin-2-one; To a solution of (f?)-2-amino-1-(2,2-dimethyl-4H-1 ,3-benzodioxin-6-yl)ethanol (2.53 g, 11.3 mmol) in chloroform (12 ml.) was added carbonyldiimidazol (2.75 g, 17 mmol) and triethylamine (2.37 ml_, 17 mmol). The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue diluted with ethyl acetate (25 ml_). The organic layer was washed with water (2 x 10 ml_), brine (10 ml_), dried (Na2SO4), and the solvent reduced under reduced pressure. Purification by column chromatography with silica gel and n-hexane/ethyl acetate (1 :2) as eluent yielded the title compound (1.63 g, 51percent).1H NMR (300 MHz, CDCI3): 1.55 (s, 6 H); 3.54 (t, J=8.1 Hz, 1H); 3.94 (t, J=8.7 Hz, 1H); 4.86 (s, 2H); 5.10 (bs, 1H); 5.56 (t, J=8.1 Hz, 1H); 6.85 (d, J=8.5 Hz, 1H); 7.04-7.07 (m, 1H); 7.15-7.18 (m, 1H).
Reference: [1] Patent: WO2006/122788, 2006, A1, . Location in patent: Page/Page column 54
  • 3
  • [ 102293-80-1 ]
  • [ 452339-73-0 ]
Reference: [1] Organic and biomolecular chemistry, 2003, vol. 1, # 7, p. 1106 - 1111
[2] Patent: US2015/239862, 2015, A1,
[3] Patent: CN107188813, 2017, A,
  • 4
  • [ 452339-71-8 ]
  • [ 452339-73-0 ]
Reference: [1] Organic and biomolecular chemistry, 2003, vol. 1, # 7, p. 1106 - 1111
[2] Patent: US2015/239862, 2015, A1,
[3] Patent: CN107188813, 2017, A,
  • 5
  • [ 452339-70-7 ]
  • [ 452339-73-0 ]
Reference: [1] Organic and biomolecular chemistry, 2003, vol. 1, # 7, p. 1106 - 1111
[2] Patent: US2015/239862, 2015, A1,
[3] Patent: CN107188813, 2017, A,
  • 6
  • [ 54030-34-1 ]
  • [ 452339-73-0 ]
Reference: [1] Patent: US2015/239862, 2015, A1,
[2] Patent: CN107188813, 2017, A,
  • 7
  • [ 52113-69-6 ]
  • [ 452339-73-0 ]
Reference: [1] Patent: US2015/239862, 2015, A1,
[2] Patent: CN107188813, 2017, A,
  • 8
  • [ 2316-64-5 ]
  • [ 452339-73-0 ]
Reference: [1] Patent: US2015/239862, 2015, A1,
[2] Patent: CN107188813, 2017, A,
  • 9
  • [ 1761-61-1 ]
  • [ 452339-73-0 ]
Reference: [1] Patent: CN107188813, 2017, A,
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