The diketo form of (+)-(1R, 4R)-3-benzoylcamphor

被引:1
|
作者
Seo, Jang Woo [1 ]
Niemeyer, Mark [1 ]
机构
[1] Univ Stuttgart, Inst Anorgan Chem, D-70569 Stuttgart, Germany
关键词
D O I
10.1107/S1600536806039808
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
Molecules of the title compound, (+)-(1R,4R)-3-benzoyl-1,7,7-trimethylbicyclo[ 2.2.1] heptan-2-one, C17H20O2, crystallize in the diketo form. One of the carbonyl groups is involved in a weak intramolecular C-H center dot center dot center dot O interaction [C center dot center dot center dot O = 2.778 (3) angstrom]. 3-Benzoylcamphor is a rare example of a structurally characterized beta-diketone that crystallizes both in the diketo and the enol forms. According to density functional theory (DFT) calculations, the diketo tautomer is destabilized by 17.4 kJ mol(-1) over the previously reported [Niemeyer & Gan (2005). Acta Cryst. E61, o2363-o2365] enol form.
引用
收藏
页码:O4850 / O4852
页数:3
相关论文
共 50 条
  • [21] 3R, 1R or 3R+1R? The Teachers' Dilemma
    Liu, Ong Puay
    Ting, Helen
    Tee, Ong Puay
    Hoon, Ong Puay
    INTERNATIONAL CONFERENCE ON LEARNER DIVERSITY 2010, 2010, 7 : 191 - 200
  • [22] SYNTHESIS AND REACTIONS OF SOME 1R,1R',2,3,4,5-TETRAPHENYL-1-SILACYCLOPENTADIENES
    JUTZI, P
    KARL, A
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 214 (03) : 289 - 302
  • [23] SYNTHESIS AND REACTIONS OF SOME 1R,1R',2,3,4,5-TETRAPHENYL-1-GERMACYCLOPENTADIENES
    JUTZI, P
    KARL, A
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 215 (01) : 19 - 25
  • [24] (+)-(3R,4R)-bis(diphenylphosphino)-1-benzylpyrrolidine
    Sugi, K
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2005, 63 (06) : 655 - 657
  • [25] (1R,4R)-1-(hydroxydiphenylmethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one
    Gao, Yu-Xing
    Tang, Guo
    Zhao, Yu-Fen
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O4521 - O4522
  • [26] (1R,4R,10R)-1,4-EPOXYCADINANE, A NEW SESQUITERPENOID FROM THE BROWN ALGA DILOPHUS-FASCIOLA
    FATTORUSSO, E
    MAGNO, S
    MAYOL, L
    GAZZETTA CHIMICA ITALIANA, 1979, 109 (10-1): : 589 - 590
  • [27] IMPROVED PROCEDURES FOR THE PREPARATION OF (+)-(1R,2S,4R)-4-AMINO-2-HYDROXY-1-HYDROXYMETHYL CYCLOPENTANE
    BRAY, BL
    DOLAN, SC
    HALTER, B
    LACKEY, JW
    SCHILLING, MB
    TAPOLCZAY, DJ
    TETRAHEDRON LETTERS, 1995, 36 (25) : 4483 - 4486
  • [28] INVESTIGATION OF A CHIRAL MASKED KETENE SYNTHON SYNTHESIS OF THE (+)-(1R,4R) AND (-)-(1S,4S) ENANTIOMERS OF DEHYDRONORCAMPHOR
    MAIGNAN, C
    RAPHAEL, RA
    TETRAHEDRON, 1983, 39 (20) : 3245 - 3249
  • [29] Biotransformation of (-)-(1R,4S)-Menthone and (+)-(1S,4R)-Menthone by the Common Cutworm Spodoptera litura Larvae
    Marumoto, Shinsuke
    Okuno, Yoshiharu
    Hagiwara, Yuki
    Miyazawa, Mitsuo
    JOURNAL OF OLEO SCIENCE, 2017, 66 (08) : 883 - 888
  • [30] Electrochemical reduction of (1R,2r,3S,4R,5r,6S)-hexachlorocyclohexane (Lindane) at carbon cathodes in dimethylformamide
    Merz, Jordan P.
    Gamoke, Benjamin C.
    Foley, Matthew P.
    Raghavachari, Krishnan
    Peters, Dennis G.
    JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2011, 660 (01) : 121 - 126