Stereoselective Synthesis of 3,6-Disubstituted-3,6-dihydropyridin-2-ones as Potential Diketopiperazine Mimetics Using Organocopper-Mediated anti-S~N~2' Reactions and Their Use in the Preparation of Low-Molecule CXCR4 Antagonists
Ayumu Niida; Hiroaki Tanigaki; Eriko Inokuchi; Yoshikazu Sasaki; Shinya Oishi; Hiroaki Ohno; Hirokazu Tamamura; Zixuan Wang; Stephen C. Peiper; Kazuo Kitaura; Akira Otaka; Nobutaka Fujii; Journal of Organic Chemistry 71 (2006) 3942–3951; doi:10.1021/jo060390t

data_4021692
_publ_section_title
;
 Stereoselective Synthesis of
 3,6-Disubstituted-3,6-dihydropyridin-2-ones as Potential
 Diketopiperazine Mimetics Using Organocopper-Mediated
 anti-S~N~2' Reactions and Their Use in the Preparation of
 Low-Molecule CXCR4 Antagonists
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3942
_journal_page_last               3951
_journal_paper_doi               10.1021/jo060390t
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C20 H21 N O '
_chemical_formula_sum            'C20 H21 N O'
_chemical_formula_weight         291.39
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             'Wed Oct 23 15:46:29 2002'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.914(2)
_cell_length_b                   12.872(2)
_cell_length_c                   14.088(2)
_cell_measurement_reflns_used    15711
_cell_measurement_temperature    98.2
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.1
_cell_volume                     1616.5(4)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'teXsan (MSC & Rigaku, 1999)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'teXsan (MSC & Rigaku, 1999)'
_computing_structure_refinement  'teXsan (MSC & Rigaku, 1999)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9899
_diffrn_measured_fraction_theta_max 0.9899
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18750
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.19
_refine_ls_abs_structure_details
;
Determined relative to the S cofiguration of C1 already known.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2648
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^) + (0.00200(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0623
_reflns_number_gt                1743
_reflns_number_total             2648
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo060390tsi20060326_071749.cif
_cod_original_sg_symbol_H-M      'P 21 21 21   '
_cod_original_formula_sum        'C20 H21 N O '
_cod_database_code               4021692