Crystal structure of (+)-methyl (E)-3-[(2S,4S,5R)-2-amino-5-hydroxymethyl-2-trichloromethyl-1,3-dioxolan-4-yl]-2-methylprop-2-enoate

被引:0
|
作者
Oishi, Takeshi [1 ]
Yasushima, Daichi [2 ]
Yuasa, Kihiro [2 ]
Sato, Takaaki [2 ]
Chida, Noritaka [2 ]
机构
[1] Keio Univ, Sch Med, Kohoku Ku, Hiyoshi 4-1-1, Yokohama, Kanagawa 2238521, Japan
[2] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Hiyoshi 3-14-1, Yokohama, Kanagawa 2238522, Japan
来源
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS | 2016年 / 72卷
关键词
crystal structure; orthoamide; dioxolane; hydrogen bonding; hydroxy group; amino group; disorder;
D O I
10.1107/S2056989016002474
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
In the title compound, C10H14Cl3NO5, the five-membered dioxolane ring adopts an envelope conformation. The C atom at the flap, which is bonded to the hydroxymethyl substituent, deviates from the mean plane of other ring atoms by 0.357 (5) angstrom. There are two intramolecular hydrogen bonds (O-H center dot center dot center dot N and N-H center dot center dot center dot O) between the hydroxy and amino groups, so that O- and N-bound H atoms involved in these hydrogen bonds are each disordered with equal occupancies of 0.50. The methyl 2-methylprop-2-enoate substituent also shows a disordered structure over two sets of sites with refined occupancies of 0.482 (5) and 0.518 (5). In the crystal, molecules are connected into a dimer by an O-H center dot center dot center dot O hydrogen bond. The dimers are further linked by N-H center dot center dot center dot O, C-H center dot center dot center dot N and C-H center dot center dot center dot O interactions, extending a sheet structure parallel to ((1) over bar 01).
引用
收藏
页码:343 / +
页数:10
相关论文
共 50 条
  • [1] Effect of the β-substituent with respect to the azido group on the reactivity of methyl (2E)-3-[5-(azidomethyl)-2,2-diethyl-1,3-dioxolan-4-yl]-2-methylprop-2-enoate
    F. A. Gimalova
    G. M. Khalikova
    V. A. Egorov
    I. I. Fatkullina
    A. G. Mustafin
    M. S. Miftakhov
    Russian Journal of Organic Chemistry, 2013, 49 : 1047 - 1054
  • [2] Effect of the β-substituent with respect to the azido group on the reactivity of methyl (2E)-3-[5-(azidomethyl)-2,2-diethyl-1,3-dioxolan-4-yl]-2-methylprop-2-enoate
    Gimalova, F. A.
    Khalikova, G. M.
    Egorov, V. A.
    Fatkullina, I. I.
    Mustafin, A. G.
    Miftakhov, M. S.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 49 (07) : 1047 - 1054
  • [3] (S)-3-Dimethylamino-2-{(4S, 5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxypropanoic acid
    Jenkinson, Sarah F.
    Hotchkiss, David J.
    Cowley, Andrew R.
    Fleet, George W. J.
    Watkin, David J.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O294 - U5289
  • [4] Regioselective Intermolecular Cyclization of Methyl (E)-3-[(4S,5S)-5-Acetyl-2,2-dimethyl-1,3-dioxolan-4-yl)]prop-2-enoate
    Valiullina, Z. R.
    Ivanova, N. A.
    Lobov, A. N.
    Miftakhov, M. S.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (11) : 2043 - 2047
  • [5] Regioselective Intermolecular Cyclization of Methyl (E)-3-[(4S,5S)-5-Acetyl-2,2-dimethyl-1,3-dioxolan-4-yl)]prop-2-enoate
    Z. R. Valiullina
    N. A. Ivanova
    A. N. Lobov
    M. S. Miftakhov
    Russian Journal of Organic Chemistry, 2020, 56 : 2043 - 2047
  • [6] Crystal structure of (-)-(R,E)-3-(1,3-benzodioxol-5-yl)-5-[(4S,5R)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-N,N-dimethylpent-4-enamide
    Oishi, Takeshi
    Ishii, Koki
    Ishibashi, Mizuki
    Sato, Takaaki
    Chida, Noritaka
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2018, 74 : 825 - +
  • [7] (2S,4S)-4-azido-1-benzyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl] pyrrolidine
    Chesterton, Amy K. S.
    Jenkinson, Sarah F.
    Jones, Nigel A.
    Fleet, George W. J.
    Watkin, David J.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2006, 62 : O2983 - O2985
  • [8] (E)-2-((4R, 5R)-5-((Benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-ene-1,4-diol
    Carreras, Carlos R.
    Garcia, Celina E.
    Martin, Victor S.
    Tonn, Carlos E.
    Diaz Diaz, David
    Pedro Cenal, Juan
    MOLBANK, 2010, (02)
  • [9] IDENTIFICATION AND STEREOCHEMISTRY OF (2S, 4S, 5R) AND (2R, 4S, 5R)-2,3,4-TRIMETHYL-5-PHENYLOXAZOLIDINE, DEGRADATION PRODUCTS OF EPHEDRINE
    BECKETT, AH
    JONES, GR
    TETRAHEDRON, 1977, 33 (24) : 3313 - 3316
  • [10] Crystal structure of 4-[(1R, 2S, 5R)-2-isopropyl-5-methylcyclohexyl] 2-methyl (2S, 4S, 5R)-1[(2S, 3R, 5R)-5-methoxycarbonyl-2-(2-methylphenyl)pyrrolidine-3-carbonyl]-5-(2-methylphenyl)-pyrrolidine-2,4-dicarboxylate
    Ivantcova, Polina M.
    Sokolov, Mikhail N.
    Kudryavtsev, Konstantin, V
    Churakov, Andrei, V
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2019, 75 : 537 - +