Identification | Back Directory | [Name]
3-(BENZYLOXY)CYCLOBUTANONE | [CAS]
30830-27-4 | [Synonyms]
30830-27-4 3- (benzyloxy) -1-butanone 3-(BENZYLOXY)CYCLOBUTANONE 3-(Benzyloxy)cyclobutan-1... Cyclobutanone, 3-(benzyloxy)- 3-(Benzyloxy)cyclobutan-1-one 3-phenylmethoxycyclobutan-1-one Cyclobutanone, 3-(phenylmethoxy)- 3-(Benzyloxy)cyclobutan-1-one 97+% 3-(BENZYLOXY)CYCLOBUTANONE###30830-27-4 https://www.chemicalbook.com/productlist.aspxcbn=CB32460661 1-(Benzyloxy)-3-oxocyclobutane, {[(3-Oxocyclobut-1-yl)oxy]methyl}benzene | [EINECS(EC#)]
800-316-6 | [Molecular Formula]
C11H12O2 | [MDL Number]
MFCD09755991 | [MOL File]
30830-27-4.mol | [Molecular Weight]
176.22 |
Chemical Properties | Back Directory | [Boiling point ]
285℃ | [density ]
1.11 | [refractive index ]
1.5225 | [Fp ]
126℃ | [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [form ]
clear liquid | [color ]
Colorless to Yellow | [InChI]
InChI=1S/C11H12O2/c12-10-6-11(7-10)13-8-9-4-2-1-3-5-9/h1-5,11H,6-8H2 | [InChIKey]
GPPSQLLIFNWNSB-UHFFFAOYSA-N | [SMILES]
C1(=O)CC(OCC2=CC=CC=C2)C1 |
Hazard Information | Back Directory | [Uses]
3-(Benzyloxy)cyclobutanone is used as a reactant for the synthesis of cyclobutyl derivatives of 2''-deoxyadenosine 5''-triphosphate as inhibitors of HIV-1 reverse transcriptase. | [Synthesis]
The general procedure for the synthesis of 3-(benzyloxy)-1-cyclobutanone from the compound (CAS: 917887-34-4) was as follows: 26.5 L of diethyl ether was added to a 30-35 L reactor and the reactor was water cooled at the beginning of the addition. 1.064 kg of compound (VII) was added to the reactor. 0.932 L of perchloric acid (60%) was pre-diluted with 0.664 L of water and added slowly to the reactor over 20-30 minutes at 10°C. After addition of the acid, cooling was stopped and the reaction was stirred vigorously overnight at about 20°C. The reaction was quenched by the addition of 900 g of NaHCO3 dissolved in 8 L of water until the pH was about 7. The aqueous phase was discarded and the reaction mixture was washed with an additional 7 L of water. The ether was removed under vacuum, 2 L of toluene was added, and the crude mixture was azeotropically dried. The crude product was diluted to about 2 L with toluene and loaded onto a silica gel pad. The pad was wet packed and pre-eluted with toluene. For the separation of 1.5 kg batches, a silica gel pad with a diameter of 40 cm and a height of 22 cm was used. After the crude product was applied to the pad, it was eluted with eluent in the following order: 3 x 10 L toluene; 9 x 10 L toluene: ethyl acetate (95:5). The product grades were collected and the solvent was evaporated under vacuum. High vacuum was required to remove the last 5% of toluene. Final isolation gave 533 g of product (yield = 77%).GC analysis showed 95% product purity. The 1H NMR (500 MHz, CDCl3) data for compound (VIII) were as follows: δH 7.40-7.29 (m, 5H), 4.53 (s, 2H), 4.38 (tt, J = 6.6, 4.7Hz, 1H), 3.3-3.1 (m, 4H). | [References]
[1] Patent: WO2013/11115, 2013, A1. Location in patent: Paragraph 00059-00061 [2] Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 6, p. 1637 - 1642 [3] Patent: US2009/233903, 2009, A1. Location in patent: Page/Page column 58 [4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 12, p. 4064 - 4067 [5] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 3, p. 643 - 652 |
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