Home Cart Sign in  
Chemical Structure| 37905-03-6 Chemical Structure| 37905-03-6

Structure of 37905-03-6

Chemical Structure| 37905-03-6

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 37905-03-6 ]

CAS No. :37905-03-6
Formula : C12H20O3
M.W : 212.29
SMILES Code : OC/C(C)=C/CC/C(C)=C/COC(C)=O
MDL No. :MFCD31391065
InChI Key :HZIJXISIZGWHAY-NXAIOARDSA-N
Pubchem ID :10375891

Safety of [ 37905-03-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362

Application In Synthesis of [ 37905-03-6 ]

* 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 [ 37905-03-6 ]

[ 37905-03-6 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 37905-02-5 ]
  • [ 37905-03-6 ]
YieldReaction ConditionsOperation in experiment
1.517 g With sodium tetrahydroborate; ethanol; at 0℃; for 1h; General procedure: SeO2 (602 mg, 5.43 mmol) was added to a solution of geranyl acetate (Compound 29, 1.0 ml, 4.7 mmol) in EtOH (20 ml) at room temperature, and the mixture was refluxed for one hour. The reaction solution was allowed to warm to room temperature, and was filtered through celite. The filtrate was concentrated, and EtOH (20 ml) was then added to the residue. The mixture was cooled to 0C. NaBH4 (58 mg, 1.5 mmol) was added to this cooled mixture followed by stirring for one hour. A 2 M aqueous HCl solution (2 ml) was added to the reaction solution followed by stirring for 5 minutes. The mixture was then poured into H2O (30 ml). After extraction with EtOAc, the combined organic layer was washed with a saturated aqueous NaCl solution, and was dried over Na2SO4. After evaporation of the solvent, the residue was subjected to column chromatography on silica gel (Hexane:EtOAc= 2:1) to yield a partially purified primary alcohol (Compound 30) (1.517 g).
160.0 mg With sodium tetrahydroborate; In dichloromethane; at 0℃; for 0.5h;Inert atmosphere; A suspension of selenium dioxide (5.6 mg, 1.0 mmol) tert-butyl hydroperoxide (0.24 mL, 2.5 mmol), salicylic acid (12 mol%, 16.6 mg) in anhydrous dichloromethane (20 mL) was stirred for 20 min at room temperature, and then silica gel (230-400 mesh, 72.0 mg) was added. After 30 min, the geranyl acetate 9 (196.3 mg,1.0 mmol) was slowly added. The mixture was stirred for 26 h, filtered through Celite, and washed with 10% potassium hydroxide and brine. The extract was dried over Na2SO4 and concentrated under vacuum. The resulting dark orange residue was dissolved in 4 mL of ethanol and cooled to 0 C, and sodium borohydride (37.8 mg, 1.0 mmol) was added in several portions. After 30 min, a saturated solution of NH4Cl (5 mL), brine, and ethyl acetate was added. The mixture was extracted with ethyl acetate and once with dichloromethane, dried, and concentrated. The residue was purified by flash chromatography eluting with hexane/AcOEt (9/1, v/v) to give alcohol 10 as a yellow oil (160.0 mg, 75%). 1H NMR (400 MHz, CDCl3): δ (ppm)5.38-5.28 (m, 2H), 4.55 (2H, d, J 7.2), 3.96 (2H, s), 2.28-2.06 (5H,m), 2.05 (3H, s), 1.70 (3H, s), 1.60 (3H, s).
  • 2
  • [ 105-87-3 ]
  • [ 37905-03-6 ]
  • [ 37905-02-5 ]
YieldReaction ConditionsOperation in experiment
45%; 19% With selenium(IV) oxide; tert-butyl hydroperoxide; In dichloromethane; at 0℃; for 5h;Inert atmosphere; General procedure: Starting material (1.00 mmol) was added to a solution of selenium dioxide (44 mg, 0.40 mmol) and t-BuOOH (453 mg, 3.10 mmol) in dichloromethane (5 mL) at 0C. After stirring under nitrogen at 0C for a time t (vide infra), the mixture was diluted with ethyl acetate (15 mL), and washed successively with water (2 x 10 mL), saturated NaHCO3 (10 mL), water (10 mL) and brine (10 mL). The organic layer was then dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by chromatography on silica gel (hexanes / ethyl acetate).
With selenium(IV) oxide; In ethanol; for 1h;Reflux; SeO2 (4.34 g, 37.9 mmol) was added to a solution of geranyl acetate (Compound 29, 7.7 ml, 36 mmol) in EtOH (20 ml) at room temperature, and the mixture was refluxed for one hour. The reaction solution was allowed to warm to room temperature, and was filtered through celite. The filtrate was concentrated, and the residue was then subjected to column chromatography on silica gel (Hexane:EtOAc = 1:1). The fractions containing alcohol (Compound 30) and aldehyde (Compound 31) were collected. After evaporation of the solvent, the residue was dissolved in Et2O (100 ml). MnO2 (85% purity, 22.5 g, 220 mmol) was added to this solution followed by stirring for 15 hours. The reaction solution was filtered through celite, and the filtrate was washed with a saturated aqueous NaCl solution, and was dried over Na2SO4. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (Hexane:EtOAc = 4:1) to yield the aldehyde (Compound 31) (2.142 g, 28%).
  • 3
  • [ 37905-03-6 ]
  • [ 37905-02-5 ]
YieldReaction ConditionsOperation in experiment
With manganese(IV) oxide; In diethyl ether; for 15h; SeO2 (4.34 g, 37.9 mmol) was added to a solution of geranyl acetate (Compound 29, 7.7 ml, 36 mmol) in EtOH (20 ml) at room temperature, and the mixture was refluxed for one hour. The reaction solution was allowed to warm to room temperature, and was filtered through celite. The filtrate was concentrated, and the residue was then subjected to column chromatography on silica gel (Hexane:EtOAc = 1:1). The fractions containing alcohol (Compound 30) and aldehyde (Compound 31) were collected. After evaporation of the solvent, the residue was dissolved in Et2O (100 ml). MnO2 (85% purity, 22.5 g, 220 mmol) was added to this solution followed by stirring for 15 hours. The reaction solution was filtered through celite, and the filtrate was washed with a saturated aqueous NaCl solution, and was dried over Na2SO4. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (Hexane:EtOAc = 4:1) to yield the aldehyde (Compound 31) (2.142 g, 28%).
  • 4
  • [ 37905-03-6 ]
  • [ 98-55-5 ]
 

Historical Records

Technical Information

Categories