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[ CAS No. 59669-59-9 ] {[proInfo.proName]}

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Chemical Structure| 59669-59-9
Chemical Structure| 59669-59-9
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Product Details of [ 59669-59-9 ]

CAS No. :59669-59-9 MDL No. :MFCD05266697
Formula : C7H12N2O Boiling Point : -
Linear Structure Formula :- InChI Key :APHNQOGPYLTSFX-UHFFFAOYSA-N
M.W : 140.18 Pubchem ID :2095694
Synonyms :

Calculated chemistry of [ 59669-59-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.57
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.18
TPSA : 52.05 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) : -5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 1.73
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 0.87
Log Po/w (SILICOS-IT) : 1.12
Consensus Log Po/w : 1.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.11 mg/ml ; 0.00789 mol/l
Class : Soluble
Log S (Ali) : -2.44
Solubility : 0.51 mg/ml ; 0.00364 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.06
Solubility : 1.21 mg/ml ; 0.00865 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.55

Safety of [ 59669-59-9 ]

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 [ 59669-59-9 ]

* 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 [ 59669-59-9 ]
  • Downstream synthetic route of [ 59669-59-9 ]

[ 59669-59-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 59997-51-2 ]
  • [ 59669-59-9 ]
YieldReaction ConditionsOperation in experiment
76% With sodium hydroxide; hydroxylamine hydrochloride In water at 50℃; for 3 h; To an aqueous solution of sodium hydroxide solution (40.00 g, 1 mol, in 200 ml of water) was added hydroxylamine hydrochloride (24.00 g, 346 mmol) and pivaloylacetonitrile (40.00 g, 320 mmol).
The resulting solution was stirred at 50° C. for 3 hrs.
The reaction mixture cooled and the resultant white crystalline solid filtered, washed with water and dried to provide 3-t-butylisoxazol-5-amine as a white crystalline solid (34 g, yield 76percent yield).
1H NMR (DMSO-d6) δ 6.41 (brs, 2H), 4.85 (s, 1H), 1.18(s, 9H): LC-MS (ES, m/z, M+H) 141.3.
Reference: [1] Heterocycles, 1991, vol. 32, # 6, p. 1153 - 1158
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 3, p. 1082 - 1105
[3] Patent: US2008/261961, 2008, A1, . Location in patent: Page/Page column 16
[4] Organic Letters, 2018, vol. 20, # 9, p. 2774 - 2777
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 18, p. 8293 - 8305
[6] Chemische Berichte, 1932, vol. 65, p. 1857,1862
[7] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 18, p. 2047 - 2050
[8] Patent: WO2010/77836, 2010, A2, . Location in patent: Page/Page column 131
[9] Molecules, 2014, vol. 19, # 2, p. 2004 - 2028
[10] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3436 - 3441
  • 2
  • [ 59997-51-2 ]
  • [ 59669-59-9 ]
  • [ 121449-41-0 ]
Reference: [1] Dyes and Pigments, 2010, vol. 86, # 1, p. 42 - 49
  • 3
  • [ 3938-95-2 ]
  • [ 59669-59-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3436 - 3441
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 18, p. 8293 - 8305
  • 4
  • [ 59669-54-4 ]
  • [ 59669-59-9 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 7, p. 2736 - 2744
[2] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 7, p. 2736 - 2744
  • 5
  • [ 59669-59-9 ]
  • [ 15673-05-9 ]
  • [ 55809-36-4 ]
YieldReaction ConditionsOperation in experiment
52% With lithium hydroxide; hydroxylamine hydrochloride In ethanol; water EXAMPLE 2
Preparation of 3-amino-5-(t-butyl)isoxazole
In a 1 l.
3-neck round bottom flask there was placed 30 g. of pivalyl acetonitrile, 13.5 g. of lithium hydroxide, 394 ml. of water and 281 ml. of ethanol.
This mixture was heated to reflux and there was added thereto over a period of 10 minutes 94 ml. of an aqueous solution of 22.2 g. of hydroxylamine hydrochloride.
The pH of the reaction mixture after the addition was complete was about 7.3.
This pH was adjusted to about pH 6.7 using concentrated aqueous hydrochloric acid.
After 30 minutes the pH was about 6.1.
After 1 hour the pH was about 6.3.
The pH was checked again at 2 hours and at 3 hours after the addition was complete and the pH at those times was about 6.6.
A recheck of the pH at 4 hours, 5 hours, and 6 hours revealed the pH to be at about 6.7.
The reaction mixture was then refluxed overnight.
The following morning the pH was about 6.8.
The reaction mixture was cooled and the ethanol removed from the mixture on the rotovapor at room temperature.
A solid which separated was filtered off and dried.
It weighed 18.65 g. and it was determined by vpc that the product contained 97percent of the desired 3-amino-5-(t-butyl)isoxazole, and 1.6percent of 5-amino-3-(t-butyl)isoxazole. Yield: 52percent of desired isomer.
Reference: [1] Patent: US4259501, 1981, A,
  • 6
  • [ 59669-59-9 ]
  • [ 121449-41-0 ]
  • [ 55809-36-4 ]
  • [ 136320-07-5 ]
  • [ 75914-61-3 ]
Reference: [1] Heterocycles, 1991, vol. 32, # 6, p. 1153 - 1158
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