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Volumn , Issue 8, 2007, Pages 1274-1278

Lithium naphthalenide induced reductive selenenylation of α-cyano ketones: A regiocontrolled process for α-phenylseleno ketones and one-pot conversion into enone system

Author keywords

cyano ketones; phenylseleno ketones; Lithium naphthalenide; Reductive selenenylation; Regioselectivity

Indexed keywords

ALPHA CYANO KETONE DERIVATIVE; ALPHA PHENYLSELENO KETONE DERIVATIVE; KETONE; LITHIUM NAPHTHALENIDE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34249784824     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-977448     Document Type: Article
Times cited : (9)

References (35)
  • 2
    • 0001092045 scopus 로고    scopus 로고
    • Liotta, D.; Barnum, C.; Puleo, R.; Zima, G.; Bayer, C.; Kezar, H. S. III J. Org. Chem. 1981, 46, 2920.
    • (b) Liotta, D.; Barnum, C.; Puleo, R.; Zima, G.; Bayer, C.; Kezar, H. S. III J. Org. Chem. 1981, 46, 2920.
  • 11
    • 0038442808 scopus 로고    scopus 로고
    • In humans, 25 selenoproteins have been identified, many of which possess unknown functions and remain to be explored. For the leading references, see: (a) Kryukov, G. V.; Castellano, S.; Novoselov, S. V.; Lobanov, A. V.; Zehtab, O.; Guigo, R.; Gladyshev, V. N. Science 2003, 300, 1439.
    • In humans, 25 selenoproteins have been identified, many of which possess unknown functions and remain to be explored. For the leading references, see: (a) Kryukov, G. V.; Castellano, S.; Novoselov, S. V.; Lobanov, A. V.; Zehtab, O.; Guigo, R.; Gladyshev, V. N. Science 2003, 300, 1439.
  • 24
    • 0031592554 scopus 로고    scopus 로고
    • For preparing a stock solution of LN, see
    • For preparing a stock solution of LN, see: Liu, H. J.; Yip, J.; Shia, K. S. Tetrahedron Lett. 1997, 38, 2253.
    • (1997) Tetrahedron Lett , vol.38 , pp. 2253
    • Liu, H.J.1    Yip, J.2    Shia, K.S.3
  • 26
    • 34249823764 scopus 로고    scopus 로고
    • Satisfactory spectral and LC-MS or HRMS analytical data were obtained for all new compounds. A typical experiment is outlined as follows: To a solution of α-cyano ketone 1 (110 mg, 0.55 mmol) in THF (10 mL) at -40°C was added LN (7.5 mL, 0.365 M, 2.75 mmol) dropwise. The resulting dark green solution was stirred at the same temperature for 20 min followed by addition of phenylselenyl bromide (156 mg, 0.66 mmol) in one portion. The resulting mixture was continued to stir for additional 30 min at -40°C and then quenched with sat. aq NH4Cl and extracted with EtOAc (2 x 10 mL, The combined extracts were washed with brine, dried with Na2SO4, and concentrated to give the crude residue, which was subjected to flash chromatography on silica gel (EtOAc-n-hexane, 1:50) to afford the corresponding α-phenylseleno ketone 2 as a colorless oil (165 mg, 90, IR (neat, 1729, 1604, 1577 cm-1. 1HNMR 300 MHz, CDCl
    • +.
  • 30
    • 34249782083 scopus 로고    scopus 로고
    • 1-Benzoyl-4,6,6-trimethylcyclohex-3-enecarbonitrile (10, IR (KBr, 2232, 1692, 1596, 1578 cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.12 (s, 3 H, 1.21 (s, 3 H, 1.72 (br s, 3 H, 1.96 (d, J, 17.9 Hz, 1 H, 2.31 (d, J, 17.9 Hz, 1 H, 2.58 (br d, J, 17.8 Hz, 1 H, 2.90 (br d, J, 17.8 Hz. 1 H, 5.32 (br s, 1 H, 7.42-7.48 (tm, J, 7.3 Hz. 2 H) 7.52-7.58 (tm, J, 7.3 Hz, 1 H, 8.04-8.08 (dm, J, 7.3 Hz, 2 H, 13C NMR (75 MHz, CDCl3, δ, 22.7, 23.8, 27.7, 33.1, 36.7, 44.0, 53.2, 115.2, 121.7,128.4, 129.1, 132.9, 133.9, 137.5, 195.3. LC-MS (ES, m/z, 253 [M, 1-Benzoyl-3,4,6,6-tetramethylcyclohex-3-enecarbonitrile (11, IR (KBr, 2232, 1692, 1595, 1578 cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.08 (s, 3 H, 1.20 (s, 3 H, 1.66 (br s, 6 H, 1.90 (d, J, 17.8 Hz, 1 H, 2.38 br d, J, 18.0 Hz, 1 H
    • -.
  • 35
    • 34249828469 scopus 로고    scopus 로고
    • 2 containing a small portion of pyridine at 25°C gave rise to a mixture of the exo- and endocyclic enones in a ratio of 1:1.3.
    • 2 containing a small portion of pyridine at 25°C gave rise to a mixture of the exo- and endocyclic enones in a ratio of 1:1.3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.