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[ CAS No. 123320-44-5 ] {[proInfo.proName]}

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Chemical Structure| 123320-44-5
Chemical Structure| 123320-44-5
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Product Details of [ 123320-44-5 ]

CAS No. :123320-44-5 MDL No. :MFCD23135734
Formula : C11H11NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :HHYMUVTUFJYDSQ-UHFFFAOYSA-N
M.W : 205.21 Pubchem ID :5324208
Synonyms :

Calculated chemistry of [ 123320-44-5 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.18
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.61
TPSA : 55.49 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) : -6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.41
Log Po/w (XLOGP3) : 1.32
Log Po/w (WLOGP) : 1.44
Log Po/w (MLOGP) : 1.0
Log Po/w (SILICOS-IT) : 2.11
Consensus Log Po/w : 1.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.22
Solubility : 1.23 mg/ml ; 0.00599 mol/l
Class : Soluble
Log S (Ali) : -2.09
Solubility : 1.68 mg/ml ; 0.0082 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.74
Solubility : 0.0376 mg/ml ; 0.000183 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.83

Safety of [ 123320-44-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 123320-44-5 ]

* 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 [ 123320-44-5 ]
  • Downstream synthetic route of [ 123320-44-5 ]

[ 123320-44-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 123320-44-5 ]
  • [ 2552-54-7 ]
Reference: [1] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1784 - 1795
  • 2
  • [ 123320-44-5 ]
  • [ 2552-53-6 ]
YieldReaction ConditionsOperation in experiment
67% With dipyridinium dichromate In dichloromethane at 20℃; for 16 h; Example 7B (0.45 g, 2.19 mmol) was dissolved in dichloromethane and treated with solid pyridinium dichromate (PDC, 1.24 g, 3.3 mmol). The resulting slurry was stirred at room temperature for 16 hours and then filtered through diatomaceous earth eluting with dichloromethane (3χ75 mL). The organic layer was washed with 1 /V aqueous HC1 (2x50 mL) and 10percent aqueous NaCl (100 mL), dried over anhydrous Na2S04(s), filtered, and concentrated in vacuo leaving a brown oil. The oil was purified by silica gel chromatography eluting with a gradient of hexane/ethyl acetate (95/5 to 70/30) to give the title compound as a tan solid (0.3 g, 67percent).
Reference: [1] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1784 - 1795
[2] Patent: WO2012/87833, 2012, A1, . Location in patent: Page/Page column 133
  • 3
  • [ 67-68-5 ]
  • [ 123320-44-5 ]
  • [ 2552-53-6 ]
Reference: [1] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1784 - 1795
  • 4
  • [ 205115-22-6 ]
  • [ 123320-44-5 ]
YieldReaction ConditionsOperation in experiment
90% at 15℃; for 3 h; To a solution of methyl 3-benzyloxyisoxazole-5-carboxylate (2.33 g, 9.99 mmol, 1.00 eq) in methanol (50 mL) was added sodium borohydride (756 mg, 19.98 mmol, 2.00 eq) in portions. The resulting mixture was stirred at 15 °C for 3 hr. TLC (petroleum ether : ethyl acetate = 5 : 1) showed the reaction was completed. The mixture was poured into hydrochloric acid (0.2 M, 200 niL), and extracted with ethyl acetate (150 niL x 2). The combined organic layers were washed with saturated brine (200 mL x 2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to afford (3-benzyloxyisoxazol-5-yl)methanol (1.85 g, 9.02 mmol, 90percent yield) as colorless oil. LC-MS (ESI) m/z: 206.1 [M+H+].
87%
Stage #1: at 20℃; for 20 h;
Stage #2: With hydrogenchloride In water at 20℃; for 2 h;
Example 7A (0.52g, 2.23 mmol) was dissolved in methanol (25 mL) and treated with solid sodium borohydride (0.1 lOg, 2.90 mmol). The solution began foaming which subsidedapproximately 10 minutes later. The reaction mixture was stirred at room temperature for 20 hours. Methanol (50 mL) and 1 N aqueous HC1 (100 mL) were then added to the mixture which was subsequently stirred for 2 hours at room temperature. The reaction mixture was concentrated in vacuo. The aqueous layer was extracted with dichloromethane (3x 100 mL). The combined organic washes were dried over anhydrous Na2S04(s), filtered and concentrated in vacuo leaving the title compound as a clear oil (0.4 g, 87percent).
Reference: [1] Patent: WO2018/140809, 2018, A1, . Location in patent: Paragraph 00443; 00551; 00554; 00555
[2] European Journal of Organic Chemistry, 1998, # 3, p. 473 - 479
[3] Patent: WO2012/87833, 2012, A1, . Location in patent: Page/Page column 133
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9133 - 9153
[5] Patent: WO2008/127361, 2008, A2, . Location in patent: Page/Page column 89
[6] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1784 - 1795
[7] Patent: US2016/137639, 2016, A1, . Location in patent: Paragraph 3411
  • 5
  • [ 100-39-0 ]
  • [ 123320-44-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9133 - 9153
[2] Patent: US2016/137639, 2016, A1,
[3] Patent: WO2018/140809, 2018, A1,
[4] Patent: WO2012/87833, 2012, A1,
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