17790-74-8|Ethyl 2-methyl-4-oxocyclopent-2-enecarboxylate| Ambeed

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Quality Control of [ 17790-74-8 ] Purity: 95% SDS Specification

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Product Details of [ 17790-74-8 ]

CAS No. :	17790-74-8
Formula :	C₉H₁₂O₃
M.W :	168.19
SMILES Code :	O=C1C=C(C)C(C(OCC)=O)C1
MDL No. :	MFCD24688643
InChI Key :	FIOFMYNFIRAGTI-UHFFFAOYSA-N
Pubchem ID :	11332690

Safety of [ 17790-74-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 17790-74-8 ]

* 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 [ 17790-74-8 ]

[ 17790-74-8 ] Synthesis Path-Downstream 1~35

1
[ 17790-74-8 ]
[ 2758-18-1 ]

References: [1]Journal of the Chemical Society,1952,p. 1127,1131.

2
[ 17790-69-1 ]
[ 17790-74-8 ]

References: [1]Journal of Organic Chemistry,1968,vol. 33,p. 4508 - 4511.
[2]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 4977 - 4982.

3
[ 128590-34-1 ]
[ 17790-74-8 ]

References: [1]Journal of the Chemical Society. Chemical communications,1990,p. 526 - 527.
[2]Journal of the Chemical Society. Perkin transactions I,1993,p. 2269 - 2274.

5
[ 17790-74-8 ]
[ 544-97-8 ]
[ 74-88-4 ]
2,2,3-trimethyl-4-oxocyclopentanecarboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 323 - 326.
[2]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 4977 - 4982.

6
[ 17790-74-8 ]
trans-ethyl-4-hydroxy-2-methylcyclopent-2-enecarboxylate [ No CAS ]
ethyl cis-4-hydroxy-2-methylcyclopent-2-ene-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%; 46%		A round-bottom flask was charged with <strong>[17790-74-8]ethyl 2-methyl-4-oxocyclopent-2-enecarboxylate</strong> (2.04 g, 12.1 mmol, Preparation No.CC.1), MeOH (30 mL), and cerium(III) chloride heptahydrate (5.65 g, 15.2 mmol) followed by portion-wise addition of sodium borohydride (0.574 g, 15.2 mmol). The suspension was stirred at room temperature over about 16 h. Saturated aqueous NH4Cl solution (50 mL) was added. The mixture was stirred for about 10 min and Et2O (60 mL) was added. The layers were separated and the aqueous layer was extracted with Et2O (3×30 mL). The combined organic layers were washed with saturated aqueous NaHCO3, dried over anhydrous MgSO4, filtered, and concentrated to dryness under reduced pressure. The residue was purified via silica gel chromatography eluting with 20-60% EtOAc/pentane to yield cis-ethyl 4-hydroxy-2-methylcyclopent-2-enecarboxylate (0.96 g, 46%): 1H NMR (400 MHz, CDCl3) delta 5.77-5.71 (m, 1H), 4.63 (m, 1H), 4.28-4.11 (m, 2H), 3.27-3.20 (m, 1H), 2.59 (bs, 1H), 2.41-2.30 (m, 1H), 2.00 (d, J=14.2 Hz, 1H), 1.79 (d,=1.2 Hz, 3H), 1.30 (t, J=7.1 Hz, 3H) and trans-ethyl 4-hydroxy-2-methylcyclopent-2-enecarboxylate (0.69 g, 33%): 1H NMR (400 MHz, CDCl3) delta 5.63 (dd, J=1.8, 3.4 Hz, 1H), 4.98 (m, 1H), 4.20-4.11 (m, 2H), 3.60-3.53 (m, 1H), 2.57 (ddd, J=4.4, 7.1, 13.9 Hz, 1H), 1.98 (ddd, J=3.5, 8.4, 13.9 Hz, 1H), 1.80 (d, J=1.4, 3H), 1.46 (bs, 1H), 1.27 (t, J=7.1 Hz, 3H).

References: [1]European Journal of Organic Chemistry,2003,p. 92 - 98.
[2]Patent: US2009/312338,2009,A1 .Location in patent: Page/Page column 131.

7
[ 17790-74-8 ]
[ 4294-57-9 ]
2-methyl-4-oxo-2-p-tolylcyclopentanecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron Asymmetry,2003,vol. 14,p. 2413 - 2418.

8
[ 17790-74-8 ]
[ 70548-79-7 ]
ethyl 2-(2-methoxy-5-methylphenyl)-2-methyl-4-oxocyclopentanecarboxylate [ No CAS ]

References: [1]European Journal of Organic Chemistry,2004,p. 5092 - 5099.

9
[ 17790-74-8 ]
ethyl 4-hydroxy-2-(2-methoxy-5-methylphenyl)-2-methylcyclopentanecarboxylate [ No CAS ]

References: [1]European Journal of Organic Chemistry,2004,p. 5092 - 5099.

10
[ 17790-74-8 ]
(+)-(1S,2S)-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron Asymmetry,2003,vol. 14,p. 2413 - 2418.

11
[ 17790-74-8 ]
[ 613669-95-7 ]

References: [1]Tetrahedron Asymmetry,2003,vol. 14,p. 2413 - 2418.

12
[ 17790-74-8 ]
4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron Asymmetry,2003,vol. 14,p. 2413 - 2418.

13
[ 17790-74-8 ]
[ 613669-91-3 ]

References: [1]Tetrahedron Asymmetry,2003,vol. 14,p. 2413 - 2418.

14
[ 17790-74-8 ]
(+)-(1S,2S,4R)-2-methyl-4-methylsulfanylthiocarbonyloxy-2-p-tolylcyclopentanecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron Asymmetry,2003,vol. 14,p. 2413 - 2418.

15
[ 17790-74-8 ]
ethyl (1R,4S)-4-acetoxy-2-methylcyclopent-2-ene-1-carboxylate [ No CAS ]

References: [1]European Journal of Organic Chemistry,2003,p. 92 - 98.

16
[ 29310-37-0 ]
[ 17790-74-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 2269 - 2274.
[2]Journal of the Chemical Society. Chemical communications,1990,p. 526 - 527.

17
[ 17790-74-8 ]
(S,S)-(+)-(3,4,5,5-tetramethylcyclopent-2-en-1-yl)methyl 2-methylpropanoate [ No CAS ]

References: [1]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 4977 - 4982.
[2]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 4977 - 4982.

18
[ 17790-74-8 ]
(3,4,5,5-tetramethylcyclopent-2-enyl)methanol [ No CAS ]

References: [1]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 4977 - 4982.
[2]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 4977 - 4982.

19
[ 17790-74-8 ]
2,2,3-trimethyl-4-methylenecyclopentanecarboxylic acid ethyl ester [ No CAS ]