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[ CAS No. 591769-05-0 ] {[proInfo.proName]}

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Chemical Structure| 591769-05-0
Chemical Structure| 591769-05-0
Structure of 591769-05-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 591769-05-0 ]

CAS No. :591769-05-0 MDL No. :MFCD11857755
Formula : C8H11N Boiling Point : -
Linear Structure Formula :- InChI Key :VMELXYJYSXXORF-ZZXKWVIFSA-N
M.W : 121.18 Pubchem ID :21427952
Synonyms :

Calculated chemistry of [ 591769-05-0 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.62
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.73
TPSA : 23.79 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) : -5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 2.43
Log Po/w (WLOGP) : 2.26
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 2.1
Consensus Log Po/w : 2.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.06
Solubility : 1.06 mg/ml ; 0.00879 mol/l
Class : Soluble
Log S (Ali) : -2.57
Solubility : 0.324 mg/ml ; 0.00268 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.17
Solubility : 8.29 mg/ml ; 0.0684 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.56

Safety of [ 591769-05-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P264-P270-P301+P310-P405-P501 UN#:3276
Hazard Statements:H301 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 591769-05-0 ]

* 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 [ 591769-05-0 ]
  • Downstream synthetic route of [ 591769-05-0 ]

[ 591769-05-0 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 872-53-7 ]
  • [ 2537-48-6 ]
  • [ 591769-05-0 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃;
Stage #2: at 0 - 20℃; for 64 h;
Step 1.
(2E)- and (2Z)-3-Cyclopentylacrylonitrile
To a solution of 1.0 M potassium tert-butoxide in THF (235 mL) at 0 °C was added dropwise a solution of diethyl cyanomethylphosphonate (39.9 mL, 0.246 mol) in THF (300 mL).
The cold bath was removed and the reaction was warmed to room temperature followed by recooling to 0 °C, at which time a solution of cyclopentanecarbaldehyde (22.0 g, 0.224 mol) in THF (60 mL) was added dropwise.
The bath was removed and the reaction warmed to ambient temperature and stirred for 64 hours.
The mixture was partitioned between diethyl ether and water, the aqueous was extracted with three portions of ether, followed by two portions of ethyl acetate.
The combined extracts were washed with brine, then dried over sodium sulfate, filtered and concentrated in vacuo to afford a mixture containing 24.4 g of olefin isomers which was used without further purification (89percent).
1H NMR (400 MHz, CDCl3): δ 6.69 (dd, 1H, trans olefin), 6.37 (t, 1H, cis olefin), 5.29 (dd, 1H, trans olefin), 5.20 (d, 1H, cis olefin), 3.07-2.95 (m, 1H, cis product), 2.64-2.52 (m, 1H, trans product), 1.98-1.26 (m, 16H).
67%
Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 3 h; Cooling with ice
Stage #2: at 0 - 20℃;
Under ice-cooling conditions, 5.9g of diethyl cyanomethylphosphonate was dissolved in 100mL anhydrous tetrahydrofuran. 5.6g of potassium tert-butoxide was added portionwise in the solution and was stirred at room temperature for three hours. The temperature was reduced to 0°C and cyclopentanecarbaldehyde was added dropwise to the reaction solution and reacted overnight at room temperature. TLC was used to monitor reaction completion. 100ml of saturated ammonium chloride solution was added to quench the reaction. After distilling off the solvent, the residue was extracted with ethyl acetate then washed with water. The organic phase was washed with 100mL each of saturated sodium chloride solution 3 times. The organic phase was dried over anhydrous anhydrous magnesium sulfate overnight. The mixture was filtered and the solvent was distilled off under reduced pressure to give a crude product. The product was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 80:1) to give 2.5g of intermediate 5a as a colorless liquid, yield: 67percent.
46% With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 49 h; To a solution of Potassium t-butoxide (1.23 g, 10.37 mmol) in THF (20 mL) at 0 °C was added diethyl cyanomethylphosphonate 34b (1.96 g, 10.87 mmol) dropwise over a period of 10 mins. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 1 h. The reaction mixture was cooled to 0 °C and added a solution ofcyclopentanecarbaldehyde 34a (0.97 g, 9.88 mmol) in THF (10 mL). The reaction mixture was allowed to warm to room temperature and stirred for 48 h. The reaction was diluted with water (10 mL and extracted with ethyl acetate (3 x 30 ml). The ethyl acetate layers were combined and washed with brine (25 ml), dried concentrated in vacuum. The residue obtained was purified by flash column chromatography (silica gel 20 g, eluting with 0-50percent ethyl acetate in hexane) to furnish 3-cyclopentylacrylonitrile 34c (0.55 g, 46percent) as a colorless oil; 1HNMR (300 MHz, DMSO) δ 6.85 (dd, J= 8.1, 16.3, 0.4H), 6.66 - 6.51 (m, 0.6H), 5.67 (dd, J= 1.2, 16.3, 0.4H), 5.56 (dd, J= 0.6, 10.8, 0.6H), 2.86 (dq, J= 8.1, 16.5, 0.6H), 2.60 (dt, J= 8.3, 16.7, 0.4H), 1.79 (m, 2H), 1.70 - 1.50 (m, 4H), 1.42 - 1.29 (m, 2H).
Reference: [1] Journal of Catalysis, 2003, vol. 218, # 1, p. 191 - 200
[2] Patent: EP2349260, 2016, B1, . Location in patent: Paragraph 0111
[3] Patent: CN105418616, 2016, A, . Location in patent: Paragraph 0110; 0111
[4] Patent: WO2011/31554, 2011, A2, . Location in patent: Page/Page column 147-148
  • 2
  • [ 872-53-7 ]
  • [ 15898-47-2 ]
  • [ 591769-05-0 ]
YieldReaction ConditionsOperation in experiment
26.2%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 1 h; Inert atmosphere
Under nitrogen, a suspension of (cyanomethyl)triphenylphosphanium bromide (12 g, 31.49 mmol) in anhydrous THF (100 mL) was cooled to 0° C., a solution of 2.5 M n-BuLi in n-hexane (13 mL, 34.64 mmol) was added dropwise. The mixture was stirred at 0° C. for another 30 minutes, then cyclopentane-carbaldehyde (3.1 g, 31.49 mmol) was added, and the mixture was warmed to the room temperature and stirred for further 1 hour. The reaction was quenched with saturated aqueous ammonium chloride solution (50 mL), extracted with ethyl acetate (100 mL×3). The organic layers were combined, washed with water (60 mL×3) and saturated brine (60 mL) in sequence, dried over anhydrous sodium sulfate. The mixture was filtrated, the filtrate was concentrated in vacuum, the residue was purified by silica column chromatography (petroleum ether:ethyl acetate=10:1) to give colorless oil 3-b (1.0 g, yield: 26.2percent). LC-MS (ESI): m/z=122 [M+H]+.
Reference: [1] Patent: US2015/336982, 2015, A1, . Location in patent: Paragraph 0122; 0125; 0126
  • 3
  • [ 112-62-9 ]
  • [ 107-13-1 ]
  • [ 591769-05-0 ]
Reference: [1] ChemCatChem, 2018, vol. 10, # 13, p. 2868 - 2872
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