Phosphine-catalyzed reaction of cyclopropenones with water: divergent synthesis of highly functionalized γ-butenolides, trisubstituted α,β-unsaturated acids and anhydride.
Li, Fujuan; Yang, Danna; Qu, Hongyan; Zhu, Mingqi; Zheng, Suqing; Organic & biomolecular chemistry 23 (2025) 5582–5589; doi:10.1039/d5ob00306g

data_7160559
_publ_section_title
;
 Phosphine-catalyzed reaction of cyclopropenones with water: divergent
 synthesis of highly functionalized &#x3b3;-butenolides, trisubstituted
 &#x3b1;,&#x3b2;-unsaturated acids and anhydride.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5582
_journal_page_last               5589
_journal_paper_doi               10.1039/d5ob00306g
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C45 H32 O4'
_chemical_formula_sum            'C45 H32 O4'
_chemical_formula_weight         636.70
_chemical_name_systematic
'(E)-2-((E)-1,2-diphenylvinyl)-5-oxo-3,4-diphenyl-2,5-dihydrofuran-2-yl 2,3-diphenylacrylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-20
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-20 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                108.644(2)
_cell_angle_beta                 93.890(2)
_cell_angle_gamma                101.156(2)
_cell_formula_units_Z            4
_cell_length_a                   11.7242(5)
_cell_length_b                   14.3519(7)
_cell_length_c                   22.1388(10)
_cell_measurement_reflns_used    5486
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      22.003
_cell_measurement_theta_min      2.462
_cell_volume                     3429.1(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker D8 Venture, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker D8 Venture, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      223.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1037
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            74988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.039
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1158 before and 0.0767 after correction.
The Ratio of minimum to maximum transmission is 0.9372.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             1336
_exptl_crystal_recrystallization_method
'Petroleum ether and ethyl acetate mixed solvent recrystallized'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     883
_refine_ls_number_reflns         15726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0533P)^2^+0.6293P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1552
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8781
_reflns_number_total             15726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00306g2.cif
_cod_data_source_block           mo_20240809_wq_240807147900_0m
_cod_depositor_comments          'Adding full bibliography for 7160559.cif.'
_cod_database_code               7160559
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C16(H16), C33(H33), C65(H65), C20(H20), C12(H12), C61(H61),
 C90(H90), C24(H24), C78(H78), C63(H63), C57(H57), C71(H71), C26(H26), C6(H6),
 C15(H15), C69(H69), C86(H86), C41(H41), C10(H10), C55(H55), C30(H30), C60(H60),
  C39(H39), C58(H58), C66(H66), C13(H13), C59(H59), C45(H45), C67(H67),
 C68(H68), C89(H89), C23(H23), C21(H21), C51(H51), C87(H87), C72(H72), C29(H29),
  C35(H35), C88(H88), C14(H14), C80(H80), C73(H73), C27(H27), C42(H42),
 C28(H28), C22(H22), C75(H75), C84(H84), C43(H43), C44(H44), C9(H9), C54(H54),
 C36(H36), C8(H8), C7(H7), C53(H53), C52(H52), C74(H74), C81(H81), C38(H38),
 C37(H37), C82(H82), C83(H83)
;
_shelx_res_checksum              26723
_shelx_hkl_checksum              54961
_olex2_submission_original_sample_id zsq-1
_olex2_submission_special_instructions 'No special instructions were received'