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Chemical Structure| 51716-62-2 Chemical Structure| 51716-62-2

Structure of 51716-62-2

Chemical Structure| 51716-62-2

Cis-tetrahydro-1'H-spiro[[1,3]dioxolane-2,2'-pentalen]-5'(3'H)-one

CAS No.: 51716-62-2

4.5 *For Research Use Only !

Cat. No.: A473844 Purity: 97%

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Product Details of [ 51716-62-2 ]

CAS No. :51716-62-2
Formula : C10H14O3
M.W : 182.22
SMILES Code : O=C1C[C@]2([H])CC3(C[C@]2([H])C1)OCCO3
MDL No. :MFCD28348036

Safety of [ 51716-62-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 51716-62-2 ]

* 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 [ 51716-62-2 ]

[ 51716-62-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 51716-63-3 ]
  • [ 107-21-1 ]
  • [ 51716-62-2 ]
YieldReaction ConditionsOperation in experiment
56% With toluene-4-sulfonic acid; In benzene;Heating / reflux; Preparation of 7,7-(ethylidene acetal)bicyclo[3.3.0] octane-3-one 1; bIn a 250 ml round bottom flask equipped with a water segregator, tetrahydro-pentalene-2,5-dione 1a (3 g, 21 mmol) and ethane-1,2-diol (1.03 mL, 18.5 mmol) were dissolved in 150 mL benzene under stirring, then 4-methylbenzenesulfonic acid (50 mg, 0.21 mmol) was added. Upon completion of the addition, the reaction mixture was heated to reflux overnight and then cooled to room temperature. The solvent of benzene was removed under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound 7,7-(ethylidene acetal)bicyclo[3.3.0] octane-3-one 1b (1.8 g, yield 56%) as a colorless oil.MS m/z (ESI): 183.5 [M+1].
40% With toluene-4-sulfonic acid; In toluene; at 100℃; for 10h; To (3as, 6as) -tetrahydropentadiene-2,5 (1H, 3H) -dione 1a (100 g, 725 mmol), ethylene glycol (40.4 g, 652 mmol), to the mixture with toluene (1.6 L), p-toluenesulfonic acid (12.4 g, 72.4 mmol) was added and the reaction mixture was heated to 100 C and stirred for 10 hours. Cool to room temperature and remove the solvent under reduced pressure. The residue was added with water and extracted with ethyl acetate (500 mL × 3). The combined organic phases were dried over anhydrous sodium sulfate, filtered to remove the drying agent, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 3/1) to obtain the target product (3aR,6aS)-tetrahydro-1H-spiro[pentalene-2,2'-[1,3]dioxolane]-5(3H)-one 1b (53 g, yellow oil), yield: 40%.
With toluene-4-sulfonic acid; In toluene; at 130℃; for 3h; Step 1 : To a solution of (3as,6as)-tetrahydropentalene-2,5(1 y,3H)-dione (500 mg, 3.62 mmol) in toluene (60 mL) was added ethylene glycol (226 mg, 3.65 mmol) and TsOH (20 mg) and the mixture was stirred at 130C for 3h, diluted with water and extracted with EtOAc. The organic portion was washed with brine, dried over Na2S04, filtered and concentrated to give (3a'R,6a'S)- tetrahydro-1 '/-/-spiro[[1 ,3]dioxolane-2,2'-pentalen]-5'(3'/-/)-one lnt-11a-1
  • 2
  • [ 51716-63-3 ]
  • [ 51716-62-2 ]
 

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