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[ CAS No. 626-35-7 ] {[proInfo.proName]}

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Chemical Structure| 626-35-7
Chemical Structure| 626-35-7
Structure of 626-35-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 626-35-7 ]

CAS No. :626-35-7 MDL No. :MFCD00007403
Formula : C4H7NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :FTKASJMIPSSXBP-UHFFFAOYSA-N
M.W : 133.10 Pubchem ID :69379
Synonyms :

Calculated chemistry of [ 626-35-7 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 30.73
TPSA : 72.12 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) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.94
Log Po/w (XLOGP3) : 0.48
Log Po/w (WLOGP) : -0.17
Log Po/w (MLOGP) : -0.9
Log Po/w (SILICOS-IT) : -1.55
Consensus Log Po/w : -0.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.7
Solubility : 26.3 mg/ml ; 0.198 mol/l
Class : Very soluble
Log S (Ali) : -1.56
Solubility : 3.63 mg/ml ; 0.0273 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.11
Solubility : 102.0 mg/ml ; 0.769 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.13

Safety of [ 626-35-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P210-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P403+P235 UN#:N/A
Hazard Statements:H315-H319-H227 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 626-35-7 ]

* 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 [ 626-35-7 ]
  • Downstream synthetic route of [ 626-35-7 ]

[ 626-35-7 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 110-91-8 ]
  • [ 1010117-23-3 ]
  • [ 626-35-7 ]
  • [ 37714-64-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2007, vol. 80, # 12, p. 2413 - 2417
  • 2
  • [ 626-35-7 ]
  • [ 14337-43-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1923, vol. 434, p. 30
  • 3
  • [ 67-56-1 ]
  • [ 626-35-7 ]
  • [ 2483-57-0 ]
Reference: [1] Chirality, 2012, vol. 24, # 2, p. 112 - 118
  • 4
  • [ 1010117-23-3 ]
  • [ 75-65-0 ]
  • [ 626-35-7 ]
  • [ 32864-38-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2007, vol. 80, # 12, p. 2413 - 2417
  • 5
  • [ 626-35-7 ]
  • [ 31599-60-7 ]
  • [ 5724-56-1 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 23, p. 6108 - 6111
  • 6
  • [ 626-35-7 ]
  • [ 623-33-6 ]
Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 32, p. 3415 - 3418
  • 7
  • [ 626-35-7 ]
  • [ 107-19-7 ]
  • [ 123770-62-7 ]
YieldReaction ConditionsOperation in experiment
81% With 1,4-diaza-bicyclo[2.2.2]octane In ethanol at 80℃; for 72 h; Ace pressure tube INTERMEDIATE 4 - PREPARATION OF Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate.; To a mixture of propargyl alcohol (1.0 ml
16.76 mmol) and ethyl 2-nitroacetate (3.79 ml
33.52 mmol) in ethanol (23.5 ml.) in an Ace pressure tube was added 1 ,4- diazobicyclo[2.2.2]octane (DABCO, 0.194 g; 1.68 mmol). The tube was heated at 800C for 72 h. After cooling, the mixture was evaporated to dryness and the residue was purified by flash chromatography on silica gel (eluent: 0 to 6percent methanol in dichloromethane) to yield 2.32 g (81 percent) of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate as an oil. ESI/APCI(+): 172 (M+H).
180 g With 1,4-diaza-bicyclo[2.2.2]octane In ethanol at 80℃; for 16 h; Reference Production Example 42 (0684) Ethyl nitroacetate (198 mL, 1.78 mmol), propargyl alcohol (100 g, 1.78 mmol) and 1,4-diazabicyclo[2.2.2]octane (20.0 g, 178.3 mmol) were added to ethanol (1 L), and the mixture was heated at 80°C for 16 hours. Thereafter, the mixture was cooled to room temperature, and the solvent was concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 180 g of ethyl 5-hydroxymethylisoxazole-3-carboxylate represented by the following formula. 1H-NMR (CDCl3, TMS, δ (ppm)) : 6.67 (s, 1H), 4.83(d, 2H), 4.43 (q, 2H), 2.65 (brs, 1H), 1.41 (t, 3H)
Reference: [1] European Journal of Organic Chemistry, 2007, # 26, p. 4352 - 4359
[2] Journal of the American Chemical Society, 2014, vol. 136, # 48, p. 16792 - 16799
[3] Patent: WO2010/142801, 2010, A1, . Location in patent: Page/Page column 147
[4] Chemistry - A European Journal, 2012, vol. 18, # 7, p. 2081 - 2093
[5] European Journal of Organic Chemistry, 2016, vol. 2016, # 27, p. 4643 - 4655
[6] Patent: EP2952096, 2015, A1, . Location in patent: Paragraph 0684
  • 8
  • [ 530-48-3 ]
  • [ 626-35-7 ]
  • [ 163520-33-0 ]
Reference: [1] Tetrahedron Asymmetry, 2008, vol. 19, # 24, p. 2850 - 2855
  • 9
  • [ 626-35-7 ]
  • [ 6746-94-7 ]
  • [ 21080-81-9 ]
YieldReaction ConditionsOperation in experiment
92% With 1,4-diaza-bicyclo[2.2.2]octane In ethanol at 150℃; for 0.333333 h; Microwave irradiation INTERMEDIATE 15 - PREPARATION OF Ethyl δ-cyclopropylisoxazole-S-carboxylate.; A solution of ethynylcyclopropane (0.40 ml
4.58 mmol), ethyl 2-nitroacetate (1.30 ml
1 1.46 mmol), and 1 ,4-diazobicyclo[2.2.2]octane (DABCO, 0.053 g; 0.458 mmol) in ethanol(3 ml.) was irradiated in a microwave oven at 150 0C for 20 min and was then evaporated.The residue was dissolved in ethyl acetate and the solution was washed with water. The organic layer was evaporated and the residue was purified by flash chromatography on silica gel (eluent: 20 to 100percent of dichloromethane in heptane) to afford 0.765 g (92 percent) of ethyl 5-cyclopropylisoxazole-3-carboxylate as a yellow oil.ESI/APCI(+): 182 (M+H).
0.4 g With 1,4-diaza-bicyclo[2.2.2]octane In ethanol at 150℃; for 0.5 h; Inert atmosphere A mixture of ethyl 2-nitroacetate (1.0 g, 7.6 mmol, 2.5 eq), ethynylcyclopropane (0.2 g, 3.0 mmol, 1 eq),DABCO (33.9 mg, 303 imol, 0.1 eq) in 2 mL of EtOH was degassed and purged with N2 three times. The mixture was stirred at 150 °C for 30 mm under microwave condition. It was evaporated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02 eluting with petroleum ether:ethyl acetate = 30:1) to give 0.4 g of ethyl 5 -cyclopropylisoxazole-3 -carboxylate as a colorless liquid.
Reference: [1] Patent: WO2010/142801, 2010, A1, . Location in patent: Page/Page column 151
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 27, p. 4643 - 4655
[3] Patent: WO2018/119395, 2018, A1, . Location in patent: Page/Page column 211; 212
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