Abstract
C16H12O3, orthorhombic, Pbca (no. 19), a = 3.9935(16) Å, b = 16.629(7) Å, c = 19.406(8) Å, V = 1288.7(9) Å3, Z = 4, Rgt(F) = 0.0387, wRref(F2) = 0.1084, T = 296(2) K.
The structure of the title compound showing 40% probability displacement ellipsoids and the atom-numbering scheme.
The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.
Data collection and handling.
| Crystal: | Colourless block |
| Size: | 0.32 × 0.28 × 0.24 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 0.09 mm−1 |
| Diffractometer, scan mode: | Bruker APEX-II, φ and ω |
| θmax, completeness: | 27.5°, >99% |
| N(hkl)measured, N(hkl)unique, Rint: | 14445, 2930, 0.046 |
| Criterion for Iobs, N(hkl)gt: | I > 2s(I), 2342 |
| N(param)refined: | 173 |
| Programs: | Bruker [1], SHELX [2] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| O1 | 0.0581(5) | 0.45567(9) | 0.71069(8) | 0.0831(6) |
| O2 | 0.3362(5) | 0.47637(9) | 0.61209(7) | 0.0693(5) |
| O3 | 0.3527(4) | 0.80804(9) | 0.61734(8) | 0.0717(5) |
| C1 | 0.2742(6) | 0.16495(12) | 0.54743(10) | 0.0564(5) |
| H1 | 0.364233 | 0.200526 | 0.515431 | 0.068* |
| C2 | 0.2484(6) | 0.08498(13) | 0.53169(11) | 0.0654(6) |
| H2 | 0.321996 | 0.066373 | 0.489106 | 0.078* |
| C3 | 0.1146(7) | 0.03219(14) | 0.57838(12) | 0.0695(7) |
| H3 | 0.094768 | −0.021968 | 0.567150 | 0.083* |
| C4 | 0.0102(6) | 0.05892(13) | 0.64145(12) | 0.0681(6) |
| H4 | −0.075234 | 0.022672 | 0.673434 | 0.082* |
| C5 | 0.0310(5) | 0.13927(13) | 0.65771(10) | 0.0585(5) |
| H5 | −0.045932 | 0.157453 | 0.700178 | 0.070* |
| C6 | 0.1665(5) | 0.19318(11) | 0.61096(9) | 0.0492(4) |
| C7 | 0.1872(6) | 0.27691(12) | 0.62753(10) | 0.0569(5) |
| C8 | 0.1999(6) | 0.34677(12) | 0.64120(11) | 0.0641(6) |
| C9 | 0.1870(6) | 0.43072(12) | 0.65996(10) | 0.0582(5) |
| C10 | 0.3325(6) | 0.56091(12) | 0.61879(10) | 0.0546(5) |
| C11 | 0.2015(6) | 0.60363(14) | 0.56481(10) | 0.0600(5) |
| H6 | 0.107468 | 0.576865 | 0.527453 | 0.072* |
| C12 | 0.2098(6) | 0.68617(13) | 0.56611(10) | 0.0609(5) |
| H7 | 0.118952 | 0.715420 | 0.529794 | 0.073* |
| C13 | 0.3528(5) | 0.72575(12) | 0.62125(10) | 0.0521(5) |
| C14 | 0.4847(6) | 0.68230(12) | 0.67511(10) | 0.0549(5) |
| H8 | 0.580232 | 0.708897 | 0.712397 | 0.066* |
| C15 | 0.4755(6) | 0.59918(12) | 0.67399(10) | 0.0555(5) |
| H9 | 0.565233 | 0.569610 | 0.710236 | 0.067* |
| C16 | 0.5085(7) | 0.85106(13) | 0.67193(14) | 0.0819(7) |
| H10 | 0.499909 | 0.907662 | 0.662337 | 0.123* |
| H11 | 0.737765 | 0.834378 | 0.676002 | 0.123* |
| H12 | 0.392982 | 0.840201 | 0.714300 | 0.123* |
Source of material
A 25 mL Schlenk tube was charged with phenylpropiolic acid (1.0 mmol), p-methoxyphenol (1.2 mmol), dimethylaminopyridine (0.5 eq), dicyclohexylcarbodiimide (1.5 eq) in 10 mL of dichloromethane step by step. The reaction mixture was stirred at room temperature for 24 h. Upon the reaction completion (monitored by TLC), the reaction mixture was filtered, quenched with 5 mL of water, extracted with EtOAc (5 mL), washed with brine. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated in vacuo and the residue was purified by chromatography on silica gel, using Hexane/EtOAc (10:1) as the eluent, give the 4-methoxyphenyl 3-phenylpropiolate as a colorless solid. The solid was dissolved in ethylene acetate and crystals of the title compound were obtained by slow evaporation within a week.
Experimental details
Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.
Comment
In recent decades, thousands of alkynyl-containing active ingredients have been isolated from traditional medicinal plants or other active organisms [3], [4]. These alkynyl-containing active ingredients exhibit abundant biological activities, such as anti-tumor [5], anti-inflammatory [6], antibacterial, anti-viral, etc [7], [8]. Acetylenic acid ester compounds as reactants in organic synthesis, in the core skeleton structure of conjugated structures has an important position [9]. Therefore, it is important to find a highly efficient and simple synthetic protokol of conjugated olefin derivatives for the supplement of active compounds [10].
There is one molecule in the asymmetric unit of the title structure (see the figure). The single crystal structure verifies that all bond lengths are in normal ranges and in accord with parameters reported in the literature [11], [12].
Funding source: Hunan University of Science and Engineering
Award Identifier / Grant number: XNZW16C07
Funding source: The plant of Yongzhou Science and Technology innovation guidance program
Award Identifier / Grant number: 2018ZD16
Funding source: Research Programs of Hunan University of Science and Engineering
Award Identifier / Grant number: 17XKY015
Funding statement: The work was supported by the opening project of key laboratory of comprehensive utilization of advantage plants resources in Hunan south, Hunan University of Science and Engineering (XNZW16C07), The plant of Yongzhou Science and Technology innovation guidance program (2018ZD16), Research Programs of Hunan University of Science and Engineering (17XKY015).
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©2019 Jun Pan et al., published by De Gruyter, Berlin/Boston
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