페닐기 및 메틸기를 포함하는 새로운 lactone의 합성

장승현; 문상칠; 김학희; 이갑득; 정광보

Journal of the Korean Industrial and Engineering Chemistry, Vol.9, No.6, 842-845, November, 1998

Export Citation

페닐기 및 메틸기를 포함하는 새로운 lactone의 합성

Syntheses of New Lactones Containing Phenyl or Methyl Groups

장승현, 문상칠, 김학희, 이갑득, 정광보

초록

디히드록시 화합물과 oxalyl chloride의 반응에 의해 4가지 새로운 lactone류와 α,ω-dibromo 화합물과의 반응에 의해 dibenzo crown ether를 합성하였다. 5,6,11,12- Tetracarbonyl-2,2,3,3,8,8,9,9-octaphenyl-1,4,7,10-tetraoxacyclododecane(1), 5,6,11,12- tetracarbonyl-2,2,3,3,8,8,9,9-octamethyl-1,4,7,10-tetraoxacyclododecane(2), 7,8,15,16- tetracarbonyl-1,6,9,14-tetraoxacylclohexadecane(3), 5,6,11,12-tetracarbonyl-2,3,8,9- tetraphenyl-1,4,7,10-tetraoxacyclododecane(4)는 pyridine 존재 하에서 각각 benzopinacol, pinacol, 2,2'-dihydroxybiphenyl, hydrobenzoin과 oxalyl chloride의 반응에 의해 합성하였다. Dibenzo-13-crown-4(5)는 catechol과 1,3-dibromopropane/1,2-dibromoethane의 반응에 의해 각각 25%, 12%, 20%, 75%, 25%의 수율로 합성하였다.

Four new lactones and one dibenzo crown ether were synthesized by reaction of dihydroxy compound with oxalyl chloride and with α,ω-dibromo compound, respectively. 5,6,11,12-Tetracarbonyl-2,2,3,3,8,8,9,9-octaphenyl-1,4,7,10-tetraoxacyclodode- cane(1), 5,6,11,12-tetracarbonyl-2,2,3,3,8,8,9,9-octamethyl-1,4,7,10-tetraoxacyclododecane(2), 7,8,15,16-tetracarbonyl-1,6,9,14-tetraoxacylclohexadecane(3), and 5,6,11,12-tetracarbonyl- 2,3,8,9- tetraphenyl-1,4,7,10-tetraoxacyclododecane(4) were prepared by reaction of oxalyl chloride with benzopinacol, pinacol, 2,2'-dihydroxybiphenyl and hydrobenzoin, respectively, in the presence of pyridine. Dibenzo-13-crown-4 (5) was obtained by reaction of catechol with 1,3-dibromopropane/1,2-dibromoethane.

Keywords:Lactones;Crown Ether;Dihydroxy Compound;Oxalyl Chloride;Dibromo Compound

[References]

Pedersen CJ, J. Am. Chem. Soc., 89, 7017 (1967)
Pedersen CJ, J. Am. Chem. Soc., 89, 2495 (1967)
Dietrich B, Lehn JM, Sauvage JP, Tetrahedron Lett., 2885 (1969)
Dietrich B, Lehn JM, Sauvage JP, Blanzat J, Tetrahedron, 29, 1629 (1973)
Cram DJ, Cram JM, Science, 83, 803 (1974)
Vogtle F, Weber E, "Host Guest Chemistry Macrocycles," Springer Verlag Berlin, Heidelberg, New York (1985)
Beer PD, "Chemical Sensors," T. Edmonds Ed., Champman and Hall, New York (1988)
Wastson JD, Crick FHC, Nature, 171, 737 (1953)
Goke GW, Oscar M, Accounts Chem. Res., 29, 425 (1996)
Chang SH, Kim JY, Chung KB, J. Korean Chem. Soc., 40, 635 (1996)
Chang SH, Yoen AS, Chung KB, J. Korean Chem. Soc., 40, 117 (1996)
Kang TJ, Chang SH, Kim DJ, Mol. Cryst. Liq. Cryst., 278, 181 (1996)
Chang SH, Kim JY, J. Korean Chem. Soc., 38, 377 (1994)
Diederich F, Angew. Chem.-Int. Edit., 27, 362 (1988)
Frensch JS, Thompson MD, J. Org. Chem., 43, 2456 (1979)
Crawford LMR, Drewes SE, Sutton DA, J. Am. Chem. Soc., 101, 2759 (1979)
Lamb JD, Izatt RM, Swain CS, J. Am. Chem. Soc., 102, 479 (1980)
Frensch K, Vogtle F, Tetrahedron Lett., 2573 (1977)
Vogtle F, Dunwald T, Schmidt T, Accounts Chem. Res., 29, 451 (1996)
Bradshaw JS, Mass GE, Izatt RM, Christensen JJ, Chem. Rev., 79, 37 (1979)
Izatt RM, Lamb JD, Asay RE, Bradshaw JS, Chrisfensen JJ, J. Am. Chem. Soc., 99, 2365 (1977)
Cram DJ, Angew. Chem.-Int. Edit., 25, 1039 (1986)
Shinkai S, Nakaji T, Ogawa J, Shigenmatau K, Manabe O, J. Am. Chem. Soc., 103, 111 (1981)
Lehn JM, Sauvage JP, J. Am. Chem. Soc., 97, 6700 (1975)
Jackson MD, Gilkerson WR, J. Am. Chem. Soc., 101, 328 (1979)
Ehrlich BE, Diamond JM, J. Membr. Biol., 52, 187 (1980)
Pedersen CJ, Angew. Chem.-Int. Edit., 27, 1021 (1988)

[1] Pedersen CJ, J. Am. Chem. Soc., 89, 7017 (1967)

[2] Pedersen CJ, J. Am. Chem. Soc., 89, 2495 (1967)

[3] Dietrich B, Lehn JM, Sauvage JP, Tetrahedron Lett., 2885 (1969)

[4] Dietrich B, Lehn JM, Sauvage JP, Blanzat J, Tetrahedron, 29, 1629 (1973)

[5] Cram DJ, Cram JM, Science, 83, 803 (1974)

[6] Vogtle F, Weber E, "Host Guest Chemistry Macrocycles," Springer Verlag Berlin, Heidelberg, New York (1985)

[7] Beer PD, "Chemical Sensors," T. Edmonds Ed., Champman and Hall, New York (1988)

[8] Wastson JD, Crick FHC, Nature, 171, 737 (1953)

[9] Goke GW, Oscar M, Accounts Chem. Res., 29, 425 (1996)

[10] Chang SH, Kim JY, Chung KB, J. Korean Chem. Soc., 40, 635 (1996)

[11] Chang SH, Yoen AS, Chung KB, J. Korean Chem. Soc., 40, 117 (1996)

[12] Kang TJ, Chang SH, Kim DJ, Mol. Cryst. Liq. Cryst., 278, 181 (1996)

[13] Chang SH, Kim JY, J. Korean Chem. Soc., 38, 377 (1994)

[14] Diederich F, Angew. Chem.-Int. Edit., 27, 362 (1988)

[15] Frensch JS, Thompson MD, J. Org. Chem., 43, 2456 (1979)

[16] Crawford LMR, Drewes SE, Sutton DA, J. Am. Chem. Soc., 101, 2759 (1979)

[17] Lamb JD, Izatt RM, Swain CS, J. Am. Chem. Soc., 102, 479 (1980)

[18] Frensch K, Vogtle F, Tetrahedron Lett., 2573 (1977)

[19] Vogtle F, Dunwald T, Schmidt T, Accounts Chem. Res., 29, 451 (1996)

[20] Bradshaw JS, Mass GE, Izatt RM, Christensen JJ, Chem. Rev., 79, 37 (1979)

[21] Izatt RM, Lamb JD, Asay RE, Bradshaw JS, Chrisfensen JJ, J. Am. Chem. Soc., 99, 2365 (1977)

[22] Cram DJ, Angew. Chem.-Int. Edit., 25, 1039 (1986)

[23] Shinkai S, Nakaji T, Ogawa J, Shigenmatau K, Manabe O, J. Am. Chem. Soc., 103, 111 (1981)

[24] Lehn JM, Sauvage JP, J. Am. Chem. Soc., 97, 6700 (1975)

[25] Jackson MD, Gilkerson WR, J. Am. Chem. Soc., 101, 328 (1979)

[26] Ehrlich BE, Diamond JM, J. Membr. Biol., 52, 187 (1980)

[27] Pedersen CJ, Angew. Chem.-Int. Edit., 27, 1021 (1988)