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[ CAS No. 760-58-7 ] {[proInfo.proName]}

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Chemical Structure| 760-58-7
Chemical Structure| 760-58-7
Structure of 760-58-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 760-58-7 ]

CAS No. :760-58-7 MDL No. :MFCD22377852
Formula : C7H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JYFREZOLRUHBAQ-ZZXKWVIFSA-N
M.W : 139.15 Pubchem ID :5956093
Synonyms :

Calculated chemistry of [ 760-58-7 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.43
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.81
TPSA : 61.09 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) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.26
Log Po/w (XLOGP3) : 1.3
Log Po/w (WLOGP) : 1.18
Log Po/w (MLOGP) : 0.54
Log Po/w (SILICOS-IT) : 0.46
Consensus Log Po/w : 0.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.39
Solubility : 5.67 mg/ml ; 0.0408 mol/l
Class : Very soluble
Log S (Ali) : -2.18
Solubility : 0.913 mg/ml ; 0.00656 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.23
Solubility : 82.9 mg/ml ; 0.596 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.33

Safety of [ 760-58-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 760-58-7 ]

* 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 [ 760-58-7 ]
  • Downstream synthetic route of [ 760-58-7 ]

[ 760-58-7 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 372-09-8 ]
  • [ 78-84-2 ]
  • [ 760-58-7 ]
YieldReaction ConditionsOperation in experiment
83% With ammonium acetate In tolueneReflux Step 1 - 2-Cyano-4-methyl-2-pentenoic acidA stirred suspension of cyanoacetic acid (42.5g, 0.5 mol), ammonium acetate(1 .56g, 0.02 mol, 4 molpercent) and isobutyraldehyde (55ml, 39.66g, 0.55 mol, 1 .1 eq) in toluene (130ml) was heated to reflux with Dean-Stark removal of water. When generation of water ceased, the reaction mixture was cooled to room temperature and concentrated under reduced pressure to give a yellow solid (79.5g). Hexane (150ml) was added and the suspension was stirred at 400rpm for 1 hour. The solid was filtered, washed with hexane (2 x 50ml) and dried to provide the title compound as a yellow crystalline solid (58.5g, 83percent yield).
11.2 g
Stage #1: for 30 h;
Stage #2: With piperidine In methanol for 1 h;
To a solution of 2-cyanoacetic acid (8.7g, 102 mmol) in methanol (200mL) was added 2-methylpropanal (18.6 mL, 204 mmol) and the solution was stirred with a slight exotherm noted. After 30 minutes, added piperidine (1 1.1 mL, 1 12 mmol) and continued stirring for 1 h before removing solvent in vacuo with gentle heating. The thick material was diluted with ether and washed with 125mL of 1.0M HC1 and then washed with brine. The organic phase was dried over sodium sulfate and concentrated to afford a colorless oil weighing 11.2 g of 2- cyano-4-methylpent-2-enoic acid which precipitated on standing.
Reference: [1] Organic Process Research and Development, 2014, vol. 18, # 1, p. 109 - 121
[2] Patent: WO2012/25861, 2012, A1, . Location in patent: Page/Page column 22
[3] Journal of the Chemical Society, 1932, p. 445,453[4] Journal of the Chemical Society, 1933, p. 613
[5] Patent: WO2014/39899, 2014, A1, . Location in patent: Page/Page column 52
[6] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 101, p. 67 - 72
  • 2
  • [ 372-09-8 ]
  • [ 590-86-3 ]
  • [ 760-58-7 ]
Reference: [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 8, p. 1878 - 1882
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