Home Synthesis and crystal structure (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C11H12BrNO2
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Synthesis and crystal structure (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C11H12BrNO2

  • Zhang-Chao Dong ORCID logo , Liang-Liang Zheng , Bo-Wen Pan , Yang Shi EMAIL logo and Ying Zhou EMAIL logo
Published/Copyright: May 16, 2023

Abstract

C11H12BrNO2, monoclinic, P21/n (no. 14), a = 7.5143(12) Å, b = 11.8968(15) Å, c = 12.9852(13) Å, β = 105.575(14)°, V = 1118.2(3) Å3, Z = 4, R gt (F) = 0.0607, wR ref (F 2) = 0.1615, T = 293.00(10) K.

CCDC no.: 2253645

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.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.14 × 0.13 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 3.66 mm−1
Diffractometer, scan mode: SuperNova, ω
θ max, completeness: 25.0°, 98 %
N(hkl)measured, N(hkl)unique, R int: 3793, 1923, 0.065
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 1392
N(param)refined: 140
Programs: CrysAlis pro [1], Olex2 [2], SHELX [3]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
Br1 0.60408 (9) 0.34817 (6) 0.02383 (4) 0.0722 (5)
O1 0.5602 (6) 0.1999 (3) 0.3877 (3) 0.0593 (11)
H1 0.573260 0.216583 0.452123 0.089*
O2 0.6404 (6) 0.3130 (3) 0.5522 (3) 0.0612 (11)
N1 0.8419 (5) 0.5746 (3) 0.7461 (3) 0.0395 (10)
C1 0.6671 (6) 0.3910 (4) 0.3899 (4) 0.0367 (11)
C2 0.6031 (6) 0.2888 (4) 0.3360 (4) 0.0400 (11)
C3 0.5835 (6) 0.2786 (4) 0.2271 (4) 0.0439 (12)
H3 0.541040 0.210133 0.191096 0.053*
C4 0.6261 (7) 0.3684 (4) 0.1721 (4) 0.0430 (12)
C5 0.6860 (7) 0.4690 (4) 0.2204 (4) 0.0458 (12)
H5 0.713781 0.530146 0.180306 0.055*
C6 0.7050 (7) 0.4794 (4) 0.3291 (4) 0.0418 (12)
H6 0.745121 0.549111 0.363050 0.050*
C7 0.6883 (7) 0.3972 (4) 0.5070 (4) 0.0416 (12)
C8 0.7604 (6) 0.4951 (4) 0.5669 (4) 0.0411 (11)
H8 0.792463 0.559849 0.533003 0.049*
C9 0.7819 (6) 0.4929 (4) 0.6753 (4) 0.0386 (11)
H9 0.749958 0.424307 0.703253 0.046*
C10 0.8916 (7) 0.6846 (4) 0.7133 (4) 0.0484 (13)
H10A 0.985486 0.675882 0.674109 0.073*
H10B 0.940964 0.731393 0.776673 0.073*
H10C 0.781734 0.720705 0.666994 0.073*
C11 0.8584 (7) 0.5556 (5) 0.8589 (4) 0.0495 (13)
H11A 0.777038 0.607759 0.883121 0.074*
H11B 0.986570 0.568283 0.900231 0.074*
H11C 0.822765 0.478129 0.869390 0.074*

1 Source of material

To a suspension of the (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one (1.0 mmol, 0.86 g), in toluene (4 mL) was added N,N–dimethylformamide dimethyl acetal (1.05 mL, 8.0 mmol) at 80 °C and stirred for 6 h. Then, the crude product was subjected to flash column chromatography on silica gel (dichloromethane/ethyl acetate = 25:1) to afford the product.

2 Comment

Ketoamine compounds have good application potential in the field of organic synthesis, are intermediates [4, 5] used in many compounds, and have anti-inflammatory [6] and other pharmacological effects, therefore, the synthesis of arylketoamine has been a hot topic.

The title compound consisted of a basic structure similar to dopamine and a bromine atom, and a dimethylaminoacetone group. The bond lengths and angles derived from the title structure are within normal ranges and consistent with those reported previously in similar structures [79]. The C=C bond was determined at the distance of 1.372 (6) Å (C8–C9). The keto group was confirmed by the distance of 1.262(6) Å (C7–O2), and the alcohol hydroxyl group was identified by the distance of 1.338(6) Å (C2–O1), respectively. The bromine atom was determined at the distance of 1.902(5) Å (Br1–C4).


Corresponding authors: Yang Shi and Ying Zhou, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, P.R. China, E-mail: ,

Funding source: Guizhou Provincial Science and Technology Projects

Award Identifier / Grant number: Qian Ke He Zi ZK [2022] general 480 and [2023] general 404

Funding source: Key Disciplines of Traditional Chinese Medicine and Ethnic Medicine in Guizhou Province

Award Identifier / Grant number: QZYYZDXK(JS)-2021–03

Funding source: Projects of Guizhou Province

Award Identifier / Grant number: Qian Jiao He KY Zi [2022]253, gzwkj2022–232 and gzwkj2022–467

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was financially supported by Guizhou Provincial Science and Technology Projects (Qian Ke He Zi ZK [2022] general 480 and [2023] general 404), Key Disciplines of Traditional Chinese Medicine and Ethnic Medicine in Guizhou Province during the 14th Five–Year Plan (QZYYZDXK(JS)-2021–03) and the Projects of Guizhou Province (Qian Jiao He KY Zi [2022]253, gzwkj2022–232 and gzwkj2022–467).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Rigaku, O. D. CrysAlisPro Software; Rigaku Oxford Diffraction [CP/DK]: Japan, 2015.Search in Google Scholar

2. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

4. Gaspar, F. V. 1,3–Dipolar cycloaddition reactions of enaminones and azides: synthesis of 4-acyl-1,2,3-triazoles and mechanistic studies. Tetrahedron 2022, 120, 132856; https://doi.org/10.1016/j.tet.2022.132856.Search in Google Scholar

5. Wang, F., Fu, R., Chen, J. Metal-free synthesis of gem-difluorinated heterocycles from enaminones and difluorocarbene precursors. Chem. Commun. 2022, 58, 3477–3480; https://doi.org/10.1039/d2cc00383j.Search in Google Scholar PubMed

6. Zhao, Q., Xiang, H., Xiao, J. A. Selectfluor-triggered tandem cyclization of o-hydroxyarylenaminones to access difluorinated 2-amino-substituted chromanones. J. Org. Chem. 2017, 82, 9837–9843.10.1021/acs.joc.7b01339Search in Google Scholar PubMed

7. Kaiser, C., Jain, T. Dopamine receptors: functions, subtyper and emerging concepts. Med. Res. Rev. 1985, 5, 145–229; https://doi.org/10.1002/med.2610050202.Search in Google Scholar PubMed

8. Cheng, D., Yu, C., Pu, Y. DDQ-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene. Tetrahedron Lett. 2022, 90, 153609; https://doi.org/10.1016/j.tetlet.2021.153609.Search in Google Scholar

9. Attia, M. H., Elrazaz, E. Z., El-Emam, S. Z. Synthesis and in-vitro anti-proliferative evaluation of some pyrazolo [1,5-a] pyrimidines as novel larotrectinib analogs. Bioorg. Chem. 2020, 94, 103458; https://doi.org/10.1016/j.bioorg.2019.103458.Search in Google Scholar PubMed

Received: 2023-04-12
Accepted: 2023-05-01
Published Online: 2023-05-16
Published in Print: 2023-08-28

© 2023 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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