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Chemical Structure| 930-30-3 Chemical Structure| 930-30-3
Chemical Structure| 930-30-3

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Synonyms: Cyclopent-2-enone

4.5 *For Research Use Only !

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Product Details of 2-Cyclopentenone

CAS No. :930-30-3
Formula : C5H6O
M.W : 82.10
SMILES Code : O=C1C=CCC1
Synonyms :
Cyclopent-2-enone
MDL No. :MFCD00001401
InChI Key :BZKFMUIJRXWWQK-UHFFFAOYSA-N
Pubchem ID :13588

Safety of 2-Cyclopentenone

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225
Precautionary Statements:P210-P403+P235
Class:3
UN#:1224
Packing Group:

Application In Synthesis of 2-Cyclopentenone

* 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.

  • Downstream synthetic route of [ 930-30-3 ]

[ 930-30-3 ] Synthesis Path-Downstream   1~13

  • 2
  • [ 930-30-3 ]
  • [ 17642-18-1 ]
  • endo-6-(Carbomethyloxy)-6-vinylbicyclo<3.1.0>hexan-2-one [ No CAS ]
  • exo-6-(Carbomethyloxy)-6-vinylbicyclo<3.1.0>hexan-2-one [ No CAS ]
  • 3
  • [ 930-30-3 ]
  • [ 3027-21-2 ]
  • [ 64145-51-3 ]
  • 4
  • [ 930-30-3 ]
  • [ 73672-37-4 ]
  • hydroxy(5-oxocyclopent-1-enyl)(pyridin-3-yl)acetic acid ethyl ester [ No CAS ]
  • 5
  • [ 930-30-3 ]
  • [ 6414-69-3 ]
  • [ 92015-98-0 ]
  • 6
  • [ 50820-65-0 ]
  • [ 930-30-3 ]
  • [ 863885-65-8 ]
YieldReaction ConditionsOperation in experiment
79% With tin(II) chloride dihdyrate; In isopropyl alcohol; at 20℃; for 16h;Inert atmosphere; To a solution of <strong>[50820-65-0]methyl 1H-indole-6-carboxylate</strong> (17.5 g, 99.9 mmol, 1.0 eq) in i-PrOH (200 mL) was added cyclopent-2-en-1-one (16.4 g, 199.8 mmol, 16.7 mL, 2.0 eq) and SnCl2*2H2O (2.25 g, 9.99 mmol, 831.8 µL, 0.1 eq) under N2. After addition, the mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated and diluted with DCM (250 mL). The organic layer was separated and washed with H2O (200 mL), brine (200 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2) to give compound 03-4-1 (22.4 g, 79% yield).1H NMR (CDCl3, 400 MHz): δ 8.38 (s, 1 H) 8.17 (s, 1 H) 7.84 (d, J=8.8 Hz, 1 H) 7.66 (d, J=8.8 Hz, 1 H) 7.19 (d, J=2.01 Hz, 1 H) 3.97 (s, 3 H) 3.74-3.77 (m, 1 H) 2.77-2.83 (m, 1 H) 2.58-2.59 (m, 1 H) 2.39-2.48 (m, 3 H) 2.15-2.17 (m, 1 H).
70% ytterbium(III) triflate; In acetonitrile; for 16h;Heating / reflux; Step 2:; The methyl ester 1-2 from step 1 (3.31 g, 18.9 mmol) was dissolved in MeCN (50 mL) and a catalytic amount of Yb (OT3 (586 mg, 0.95 mmol) was added. 2-Cyclopenten- 1-one (7.76 mL, 94.5 mmol) was added and the reaction mixture was stirred at reflux for 16 h. The MeCN solvent was removed under vacuum, the residue was re- dissolved in EtOAc (-200 mL) and extracted with aqueous saturated NaHC03 (-100 mL), H2O (50 mL) and brine (50 mL). The organic layer was dried over anhydrous MgS04 and concentrated to dryness under vacuum. After purification of the residue by flash column chromatography, using 40% EtOAc in hexane as the solvent gradient, the desired cyclopentanone adduct 1-3 was isolated as isolated as a beige-colored powder (3.4 g, 70% yield).
70% ytterbium(III) triflate; In acetonitrile; for 16h;Heating / reflux; Step 2; The methyl ester 1-2 from step 1 (3.31 g, 18.9 mmol) was dissolved in MeCN (50 ml_)and a catalytic amount of Yb(OTf)3 (586 mg, 0.95 mmol) was added. 2-Cyclopenten-1-one (7.76 ml, 94.5 mmol) was added and the reaction mixture was stirred at reflux for16 h. The MeCN solvent was removed under vacuum, the residue was re-dissolved inEtOAc (-200 ml_) and extracted with aqueous saturated NaHCO3 (-100 ml_), H2O (50ml_) and brine (50 ml_). The organic layer was dried over anhydrous MgSO4 andconcentrated to dryness under vacuum. After purification of the residue by flashcolumn chromatography, using 40% EtOAc in hexane as the solvent gradient, thedesired cyclopentanone adduct 1-3 was isolated as isolated as a beige-coloredpowder (3.4 g, 70% yield).
  • 7
  • [ 930-30-3 ]
  • [ 17356-08-0 ]
  • [ 53051-97-1 ]
YieldReaction ConditionsOperation in experiment
40% With iodine; at 100℃; A mixture of cyclopentanone (8.4 g, 0.1 mol), thiourea (15.22 g, 0.2 mol) and iodine (25.38 g, 0.1 mol) was heated overnight at 100 C., then isopropyl ether was added and the mixture heated at reflux for an additional 30 minutes. The solid was collected via filtration, washed with ether, and then dissolved in hot water. The solution was left to cool to RT, was then basified with concentrated ammonia, and extracted with ethyl acetate. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to give the desired product (5.56 g 40% yield). ESIMS (m/z) 141.0 (MH+).
  • 8
  • [ 930-30-3 ]
  • [ 380430-57-9 ]
  • C12H15NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium hydroxide;(eta6-1,4-dihydroxybenzene)(eta2,eta2-cyclooctadiene-1,5)rhodium tetrafluoroborate; In 1,2-dimethoxyethane; water; at 50℃; General procedure ETo a solution of 2-cyclopenten-l-one (400 mumol) in 400 mul_ DME were added boronic acid (480 mumol, 1.2 eq.), (COD)Rh(l,4-dihydroquinone)BF4 (1 mol%) in 100 muL DME, and LiOH (4 mol%) in 600 muL water. After shaking the mixture overnight at 50 0C, the solvent was removed in vacuo. The crude intermediate ketone was dissolved in DCE containing acetic acid (1.2 eq.). An amine (1 eq.) in DCE was added followed by NaBH(OAc)3 (1.2 eq.) The mixture was shaken overnight at r. t., filtered and the solvents were removed in vacuo. The residue was redissolved in 750 muL DMSO and purified by preparative HPLC-MS.; Example 55. (lR)-(N)-[(lR/S,3R/S)-3-[4-acetamidophenyl]cyclopentyl]-l-(3- methoxyphenyl)ethanamine (mixture of stereoisomers) (compound 1054)General procedure E was followed using (4-acetylaminophenyl)boronic acid as the boronic acid and (R)-l-(3-methoxyphenyl)ethylamine as the amine. LC-MS (method B): RT = 3.99, M = 352.
  • 9
  • [ 930-30-3 ]
  • [ 1184919-69-4 ]
  • 10
  • [ 930-30-3 ]
  • [ 13725-38-7 ]
  • 12
  • [ 19063-55-9 ]
  • [ 930-30-3 ]
  • [ 42201-84-3 ]
  • ethyl 2-(6-bromo-2-oxo-3-(3-oxocyclopentyl)chroman-4-yl)acetate [ No CAS ]
  • ethyl 2-(6-bromo-2-oxo-3-(3-oxocyclopentyl)chroman-4-yl)acetate [ No CAS ]
  • 13
  • [ 930-30-3 ]
  • [ 475250-52-3 ]
  • 2-(4-methoxybenzyl)cyclopentanone [ No CAS ]
 

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