Conformational study on 2-acyl-1-alkylidene-1,2,3,4-tetrahydroisoquinolines

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 6, 1996, Pages 1695-1700

  Kitamura, Masato ^a   Tsukamoto, Masaki ^a   Takaya, Hidemasa ^b   Noyori, Ryoji ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; INFRARED SPECTROPHOTOMETRY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE;

EID: 0030004127     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.1695     Document Type: Article

References (30)

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11. For structural studies of the amide linkage in crystalline state or solution, see: C. J. Brown, Acta Crystallogr., 21, 442 (1966); B. F. Pedersen, Acta Chem. Scand., 21, 1415 (1967); G. V. Garner, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc. C, 1971, 1234; T. Kojima, T. Kido, H. Itoh, T. Yamane, and T. Ashida, Acta Crystallogr., Sect. B, B36, 326 (1980); E. Subramanian and R. Parthasarathy, Int. J. Pept. Protein Res., 33, 345 (1989); A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo, Tetrahedron Lett., 30, 6177 (1989); Q.-P. Wang, A. J. Bennet, R. S. Brown, and B. D. Santarsiero, J. Am. Chem. Soc., 113, 5757 (1991); A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo, J. Am. Chem. Soc., 114, 10649 (1992); A. Greenberg and C. A. Venanzi, J. Am. Chem. Soc., 115, 6951 (1993). For theoretical studies, see: S. Tsuzuki and K. Tanabe, J. Chem. Soc., Perkin Trans. 2, 1991, 1255; K. B. Wiberg and C. M. Breneman, J. Am. Chem. Soc., 114, 831 (1992); S. Saito, Y. Toriumi, N. Tomioka, and A. Itai, J. Org. Chem., 60, 4715 (1995). Reviews: L. Pauling, "The Nature of the Chemical Bond," Cornell University Press, Ithaca (1948); J. Zabicky, "The Chemistry of Amides," Interscience Publishers, London (1970).
12. For structural studies of the amide linkage in crystalline state or solution, see: C. J. Brown, Acta Crystallogr., 21, 442 (1966); B. F. Pedersen, Acta Chem. Scand., 21, 1415 (1967); G. V. Garner, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc. C, 1971, 1234; T. Kojima, T. Kido, H. Itoh, T. Yamane, and T. Ashida, Acta Crystallogr., Sect. B, B36, 326 (1980); E. Subramanian and R. Parthasarathy, Int. J. Pept. Protein Res., 33, 345 (1989); A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo, Tetrahedron Lett., 30, 6177 (1989); Q.-P. Wang, A. J. Bennet, R. S. Brown, and B. D. Santarsiero, J. Am. Chem. Soc., 113, 5757 (1991); A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo, J. Am. Chem. Soc., 114, 10649 (1992); A. Greenberg and C. A. Venanzi, J. Am. Chem. Soc., 115, 6951 (1993). For theoretical studies, see: S. Tsuzuki and K. Tanabe, J. Chem. Soc., Perkin Trans. 2, 1991, 1255; K. B. Wiberg and C. M. Breneman, J. Am. Chem. Soc., 114, 831 (1992); S. Saito, Y. Toriumi, N. Tomioka, and A. Itai, J. Org. Chem., 60, 4715 (1995). Reviews: L. Pauling, "The Nature of the Chemical Bond," Cornell University Press, Ithaca (1948); J. Zabicky, "The Chemistry of Amides," Interscience Publishers, London (1970).
13. For structural studies of the amide linkage in crystalline state or solution, see: C. J. Brown, Acta Crystallogr., 21, 442 (1966); B. F. Pedersen, Acta Chem. Scand., 21, 1415 (1967); G. V. Garner, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc. C, 1971, 1234; T. Kojima, T. Kido, H. Itoh, T. Yamane, and T. Ashida, Acta Crystallogr., Sect. B, B36, 326 (1980); E. Subramanian and R. Parthasarathy, Int. J. Pept. Protein Res., 33, 345 (1989); A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo, Tetrahedron Lett., 30, 6177 (1989); Q.-P. Wang, A. J. Bennet, R. S. Brown, and B. D. Santarsiero, J. Am. Chem. Soc., 113, 5757 (1991); A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo, J. Am. Chem. Soc., 114, 10649 (1992); A. Greenberg and C. A. Venanzi, J. Am. Chem. Soc., 115, 6951 (1993). For theoretical studies, see: S. Tsuzuki and K. Tanabe, J. Chem. Soc., Perkin Trans. 2, 1991, 1255; K. B. Wiberg and C. M. Breneman, J. Am. Chem. Soc., 114, 831 (1992); S. Saito, Y. Toriumi, N. Tomioka, and A. Itai, J. Org. Chem., 60, 4715 (1995). Reviews: L. Pauling, "The Nature of the Chemical Bond," Cornell University Press, Ithaca (1948); J. Zabicky, "The Chemistry of Amides," Interscience Publishers, London (1970).
14. For structural studies of the amide linkage in crystalline state or solution, see: C. J. Brown, Acta Crystallogr., 21, 442 (1966); B. F. Pedersen, Acta Chem. Scand., 21, 1415 (1967); G. V. Garner, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc. C, 1971, 1234; T. Kojima, T. Kido, H. Itoh, T. Yamane, and T. Ashida, Acta Crystallogr., Sect. B, B36, 326 (1980); E. Subramanian and R. Parthasarathy, Int. J. Pept. Protein Res., 33, 345 (1989); A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo, Tetrahedron Lett., 30, 6177 (1989); Q.-P. Wang, A. J. Bennet, R. S. Brown, and B. D. Santarsiero, J. Am. Chem. Soc., 113, 5757 (1991); A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo, J. Am. Chem. Soc., 114, 10649 (1992); A. Greenberg and C. A. Venanzi, J. Am. Chem. Soc., 115, 6951 (1993). For theoretical studies, see: S. Tsuzuki and K. Tanabe, J. Chem. Soc., Perkin Trans. 2, 1991, 1255; K. B. Wiberg and C. M. Breneman, J. Am. Chem. Soc., 114, 831 (1992); S. Saito, Y. Toriumi, N. Tomioka, and A. Itai, J. Org. Chem., 60, 4715 (1995). Reviews: L. Pauling, "The Nature of the Chemical Bond," Cornell University Press, Ithaca (1948); J. Zabicky, "The Chemistry of Amides," Interscience Publishers, London (1970).
15. For structural studies of the amide linkage in crystalline state or solution, see: C. J. Brown, Acta Crystallogr., 21, 442 (1966); B. F. Pedersen, Acta Chem. Scand., 21, 1415 (1967); G. V. Garner, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc. C, 1971, 1234; T. Kojima, T. Kido, H. Itoh, T. Yamane, and T. Ashida, Acta Crystallogr., Sect. B, B36, 326 (1980); E. Subramanian and R. Parthasarathy, Int. J. Pept. Protein Res., 33, 345 (1989); A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo, Tetrahedron Lett., 30, 6177 (1989); Q.-P. Wang, A. J. Bennet, R. S. Brown, and B. D. Santarsiero, J. Am. Chem. Soc., 113, 5757 (1991); A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo, J. Am. Chem. Soc., 114, 10649 (1992); A. Greenberg and C. A. Venanzi, J. Am. Chem. Soc., 115, 6951 (1993). For theoretical studies, see: S. Tsuzuki and K. Tanabe, J. Chem. Soc., Perkin Trans. 2, 1991, 1255; K. B. Wiberg and C. M. Breneman, J. Am. Chem. Soc., 114, 831 (1992); S. Saito, Y. Toriumi, N. Tomioka, and A. Itai, J. Org. Chem., 60, 4715 (1995). Reviews: L. Pauling, "The Nature of the Chemical Bond," Cornell University Press, Ithaca (1948); J. Zabicky, "The Chemistry of Amides," Interscience Publishers, London (1970).
16. For structural studies of the amide linkage in crystalline state or solution, see: C. J. Brown, Acta Crystallogr., 21, 442 (1966); B. F. Pedersen, Acta Chem. Scand., 21, 1415 (1967); G. V. Garner, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc. C, 1971, 1234; T. Kojima, T. Kido, H. Itoh, T. Yamane, and T. Ashida, Acta Crystallogr., Sect. B, B36, 326 (1980); E. Subramanian and R. Parthasarathy, Int. J. Pept. Protein Res., 33, 345 (1989); A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo, Tetrahedron Lett., 30, 6177 (1989); Q.-P. Wang, A. J. Bennet, R. S. Brown, and B. D. Santarsiero, J. Am. Chem. Soc., 113, 5757 (1991); A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo, J. Am. Chem. Soc., 114, 10649 (1992); A. Greenberg and C. A. Venanzi, J. Am. Chem. Soc., 115, 6951 (1993). For theoretical studies, see: S. Tsuzuki and K. Tanabe, J. Chem. Soc., Perkin Trans. 2, 1991, 1255; K. B. Wiberg and C. M. Breneman, J. Am. Chem. Soc., 114, 831 (1992); S. Saito, Y. Toriumi, N. Tomioka, and A. Itai, J. Org. Chem., 60, 4715 (1995). Reviews: L. Pauling, "The Nature of the Chemical Bond," Cornell University Press, Ithaca (1948); J. Zabicky, "The Chemistry of Amides," Interscience Publishers, London (1970).
17. For structural studies of the amide linkage in crystalline state or solution, see: C. J. Brown, Acta Crystallogr., 21, 442 (1966); B. F. Pedersen, Acta Chem. Scand., 21, 1415 (1967); G. V. Garner, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc. C, 1971, 1234; T. Kojima, T. Kido, H. Itoh, T. Yamane, and T. Ashida, Acta Crystallogr., Sect. B, B36, 326 (1980); E. Subramanian and R. Parthasarathy, Int. J. Pept. Protein Res., 33, 345 (1989); A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo, Tetrahedron Lett., 30, 6177 (1989); Q.-P. Wang, A. J. Bennet, R. S. Brown, and B. D. Santarsiero, J. Am. Chem. Soc., 113, 5757 (1991); A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo, J. Am. Chem. Soc., 114, 10649 (1992); A. Greenberg and C. A. Venanzi, J. Am. Chem. Soc., 115, 6951 (1993). For theoretical studies, see: S. Tsuzuki and K. Tanabe, J. Chem. Soc., Perkin Trans. 2, 1991, 1255; K. B. Wiberg and C. M. Breneman, J. Am. Chem. Soc., 114, 831 (1992); S. Saito, Y. Toriumi, N. Tomioka, and A. Itai, J. Org. Chem., 60, 4715 (1995). Reviews: L. Pauling, "The Nature of the Chemical Bond," Cornell University Press, Ithaca (1948); J. Zabicky, "The Chemistry of Amides," Interscience Publishers, London (1970).
18. For structural studies of the amide linkage in crystalline state or solution, see: C. J. Brown, Acta Crystallogr., 21, 442 (1966); B. F. Pedersen, Acta Chem. Scand., 21, 1415 (1967); G. V. Garner, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc. C, 1971, 1234; T. Kojima, T. Kido, H. Itoh, T. Yamane, and T. Ashida, Acta Crystallogr., Sect. B, B36, 326 (1980); E. Subramanian and R. Parthasarathy, Int. J. Pept. Protein Res., 33, 345 (1989); A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo, Tetrahedron Lett., 30, 6177 (1989); Q.-P. Wang, A. J. Bennet, R. S. Brown, and B. D. Santarsiero, J. Am. Chem. Soc., 113, 5757 (1991); A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo, J. Am. Chem. Soc., 114, 10649 (1992); A. Greenberg and C. A. Venanzi, J. Am. Chem. Soc., 115, 6951 (1993). For theoretical studies, see: S. Tsuzuki and K. Tanabe, J. Chem. Soc., Perkin Trans. 2, 1991, 1255; K. B. Wiberg and C. M. Breneman, J. Am. Chem. Soc., 114, 831 (1992); S. Saito, Y. Toriumi, N. Tomioka, and A. Itai, J. Org. Chem., 60, 4715 (1995). Reviews: L. Pauling, "The Nature of the Chemical Bond," Cornell University Press, Ithaca (1948); J. Zabicky, "The Chemistry of Amides," Interscience Publishers, London (1970).
19. For structural studies of the amide linkage in crystalline state or solution, see: C. J. Brown, Acta Crystallogr., 21, 442 (1966); B. F. Pedersen, Acta Chem. Scand., 21, 1415 (1967); G. V. Garner, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc. C, 1971, 1234; T. Kojima, T. Kido, H. Itoh, T. Yamane, and T. Ashida, Acta Crystallogr., Sect. B, B36, 326 (1980); E. Subramanian and R. Parthasarathy, Int. J. Pept. Protein Res., 33, 345 (1989); A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo, Tetrahedron Lett., 30, 6177 (1989); Q.-P. Wang, A. J. Bennet, R. S. Brown, and B. D. Santarsiero, J. Am. Chem. Soc., 113, 5757 (1991); A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo, J. Am. Chem. Soc., 114, 10649 (1992); A. Greenberg and C. A. Venanzi, J. Am. Chem. Soc., 115, 6951 (1993). For theoretical studies, see: S. Tsuzuki and K. Tanabe, J. Chem. Soc., Perkin Trans. 2, 1991, 1255; K. B. Wiberg and C. M. Breneman, J. Am. Chem. Soc., 114, 831 (1992); S. Saito, Y. Toriumi, N. Tomioka, and A. Itai, J. Org. Chem., 60, 4715 (1995). Reviews: L. Pauling, "The Nature of the Chemical Bond," Cornell University Press, Ithaca (1948); J. Zabicky, "The Chemistry of Amides," Interscience Publishers, London (1970).
20. For structural studies of the amide linkage in crystalline state or solution, see: C. J. Brown, Acta Crystallogr., 21, 442 (1966); B. F. Pedersen, Acta Chem. Scand., 21, 1415 (1967); G. V. Garner, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc. C, 1971, 1234; T. Kojima, T. Kido, H. Itoh, T. Yamane, and T. Ashida, Acta Crystallogr., Sect. B, B36, 326 (1980); E. Subramanian and R. Parthasarathy, Int. J. Pept. Protein Res., 33, 345 (1989); A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo, Tetrahedron Lett., 30, 6177 (1989); Q.-P. Wang, A. J. Bennet, R. S. Brown, and B. D. Santarsiero, J. Am. Chem. Soc., 113, 5757 (1991); A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo, J. Am. Chem. Soc., 114, 10649 (1992); A. Greenberg and C. A. Venanzi, J. Am. Chem. Soc., 115, 6951 (1993). For theoretical studies, see: S. Tsuzuki and K. Tanabe, J. Chem. Soc., Perkin Trans. 2, 1991, 1255; K. B. Wiberg and C. M. Breneman, J. Am. Chem. Soc., 114, 831 (1992); S. Saito, Y. Toriumi, N. Tomioka, and A. Itai, J. Org. Chem., 60, 4715 (1995). Reviews: L. Pauling, "The Nature of the Chemical Bond," Cornell University Press, Ithaca (1948); J. Zabicky, "The Chemistry of Amides," Interscience Publishers, London (1970).
21. For structural studies of the amide linkage in crystalline state or solution, see: C. J. Brown, Acta Crystallogr., 21, 442 (1966); B. F. Pedersen, Acta Chem. Scand., 21, 1415 (1967); G. V. Garner, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc. C, 1971, 1234; T. Kojima, T. Kido, H. Itoh, T. Yamane, and T. Ashida, Acta Crystallogr., Sect. B, B36, 326 (1980); E. Subramanian and R. Parthasarathy, Int. J. Pept. Protein Res., 33, 345 (1989); A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo, Tetrahedron Lett., 30, 6177 (1989); Q.-P. Wang, A. J. Bennet, R. S. Brown, and B. D. Santarsiero, J. Am. Chem. Soc., 113, 5757 (1991); A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo, J. Am. Chem. Soc., 114, 10649 (1992); A. Greenberg and C. A. Venanzi, J. Am. Chem. Soc., 115, 6951 (1993). For theoretical studies, see: S. Tsuzuki and K. Tanabe, J. Chem. Soc., Perkin Trans. 2, 1991, 1255; K. B. Wiberg and C. M. Breneman, J. Am. Chem. Soc., 114, 831 (1992); S. Saito, Y. Toriumi, N. Tomioka, and A. Itai, J. Org. Chem., 60, 4715 (1995). Reviews: L. Pauling, "The Nature of the Chemical Bond," Cornell University Press, Ithaca (1948); J. Zabicky, "The Chemistry of Amides," Interscience Publishers, London (1970).
22. For structural studies of the amide linkage in crystalline state or solution, see: C. J. Brown, Acta Crystallogr., 21, 442 (1966); B. F. Pedersen, Acta Chem. Scand., 21, 1415 (1967); G. V. Garner, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc. C, 1971, 1234; T. Kojima, T. Kido, H. Itoh, T. Yamane, and T. Ashida, Acta Crystallogr., Sect. B, B36, 326 (1980); E. Subramanian and R. Parthasarathy, Int. J. Pept. Protein Res., 33, 345 (1989); A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo, Tetrahedron Lett., 30, 6177 (1989); Q.-P. Wang, A. J. Bennet, R. S. Brown, and B. D. Santarsiero, J. Am. Chem. Soc., 113, 5757 (1991); A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo, J. Am. Chem. Soc., 114, 10649 (1992); A. Greenberg and C. A. Venanzi, J. Am. Chem. Soc., 115, 6951 (1993). For theoretical studies, see: S. Tsuzuki and K. Tanabe, J. Chem. Soc., Perkin Trans. 2, 1991, 1255; K. B. Wiberg and C. M. Breneman, J. Am. Chem. Soc., 114, 831 (1992); S. Saito, Y. Toriumi, N. Tomioka, and A. Itai, J. Org. Chem., 60, 4715 (1995). Reviews: L. Pauling, "The Nature of the Chemical Bond," Cornell University Press, Ithaca (1948); J. Zabicky, "The Chemistry of Amides," Interscience Publishers, London (1970).
23. For structural studies of the amide linkage in crystalline state or solution, see: C. J. Brown, Acta Crystallogr., 21, 442 (1966); B. F. Pedersen, Acta Chem. Scand., 21, 1415 (1967); G. V. Garner, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc. C, 1971, 1234; T. Kojima, T. Kido, H. Itoh, T. Yamane, and T. Ashida, Acta Crystallogr., Sect. B, B36, 326 (1980); E. Subramanian and R. Parthasarathy, Int. J. Pept. Protein Res., 33, 345 (1989); A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo, Tetrahedron Lett., 30, 6177 (1989); Q.-P. Wang, A. J. Bennet, R. S. Brown, and B. D. Santarsiero, J. Am. Chem. Soc., 113, 5757 (1991); A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo, J. Am. Chem. Soc., 114, 10649 (1992); A. Greenberg and C. A. Venanzi, J. Am. Chem. Soc., 115, 6951 (1993). For theoretical studies, see: S. Tsuzuki and K. Tanabe, J. Chem. Soc., Perkin Trans. 2, 1991, 1255; K. B. Wiberg and C. M. Breneman, J. Am. Chem. Soc., 114, 831 (1992); S. Saito, Y. Toriumi, N. Tomioka, and A. Itai, J. Org. Chem., 60, 4715 (1995). Reviews: L. Pauling, "The Nature of the Chemical Bond," Cornell University Press, Ithaca (1948); J. Zabicky, "The Chemistry of Amides," Interscience Publishers, London (1970).
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