ethyl 2-(oxetan-3-ylidene)acetate Chemical Properties

Boiling point:

207℃

Density 

1.228

Flash point:

78℃

storage temp. 

Sealed in dry,Store in freezer, under -20°C

form 

liquid

color 

Colourless to light yellow

InChI

InChI=1S/C7H10O3/c1-2-10-7(8)3-6-4-9-5-6/h3H,2,4-5H2,1H3

InChIKey

CVZGHWOZWYWLBL-UHFFFAOYSA-N

SMILES

C(OCC)(=O)/C=C1\COC\1

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36

HS Code 

29329990

ethyl 2-(oxetan-3-ylidene)acetate Usage And Synthesis

Uses

Ethyl 2-(Oxetan-3-ylidene)acetate is a CBL-?B inhibitors which is used in the treatment of cancer.

Synthesis

Oxetan-3-one (500 mg, 6.938 mmol) was dissolved in dichloromethane (15.00 mL) at 0 °C, followed by the addition of ethoxycarbonylmethylene triphenylphosphine (2.659 g, 7.632 mmol). The reaction system was slowly warmed to room temperature and stirred continuously for 15 minutes. Upon completion of the reaction, the reaction mixture was filtered through a pad of silica gel (using 30% ethyl acetate/petroleum ether as eluent) and the filtrate was concentrated under reduced pressure to afford ethyl 2-(oxetan-3-ylidene)acetate as a colorless viscous oil (815 mg, 79% yield). [00346] 1H NMR (400 MHz, CDCl3): δ 1.29 (t, 3H), 4.18 (q, 2H), 5.32-5.34 (m, 2H), 5.52-5.54 (m, 2H), 5.64-5.66 (m, 1H) ppm.

References

[1] Patent: WO2013/61205, 2013, A2. Location in patent: Page/Page column 67
[2] MedChemComm, 2016, vol. 7, # 10, p. 1925 - 1931
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3227 - 3246
[4] Tetrahedron Letters, 2014, vol. 55, # 28, p. 3805 - 3808
[5] Patent: WO2014/141118, 2014, A1. Location in patent: Page/Page column 42

ethyl 2-(oxetan-3-ylidene)acetate(922500-91-2)Related Product Information

• oxetan-3-ylidene-acetaldehyde
• 1-(oxetan-3-yl)hydrazine dihydrochloride
• oxetane-2-carboxylic acid ethyl ester
• oxetane-2-carboxylic acid methyl ester
• 3-Oxetanemethanol
• Oxetan-3-ol
• methyl oxetane-3-carboxylate
• oxetan-3-yl-acetic acid ethyl ester