Home Physical Sciences Synthesis and crystal structure of 2-(3-oxo-3-phenylpropyl)isoindoline-1,3-dione, C17H13NO3
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Synthesis and crystal structure of 2-(3-oxo-3-phenylpropyl)isoindoline-1,3-dione, C17H13NO3

  • Ju-Mei Shi ORCID logo , Yong-Jia Hao , Lian-Hua Xu ORCID logo , Ying Zhou and Hua-Bin Wang ORCID logo EMAIL logo
Published/Copyright: September 5, 2023

Abstract

C17H13NO3, monoclinic, P21/c (no. 14), a = 9.5306(2) Å, b = 6.1971(2) Å, c = 23.3849(7) Å, β = 101.445(3)°, V = 1353.70(7) Å3, Z = 4, Rgt(F) = 0.0644, wR ref (F2) = 0.1909, T = 120 K.

CCDC no.: 2289192

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: Colorless block
Size: 0.16 × 0.14 × 0.12 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 0.78 mm−1
Diffractometer, scan mode: SuperNova, ω
θmax, completeness: 73.8°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 5078, 2663, 0.119
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2298
N(param)refined: 190
Programs: Olex2 [1], Bruker [2], SHELX [3]
Table 2:

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

Atom x y z Uiso*/Ueq
O1 0.66334 (17) −0.1034 (2) 0.46288 (7) 0.0390 (4)
O2 0.35215 (15) 0.5431 (2) 0.41648 (6) 0.0312 (4)
O3 0.70904 (14) 0.4709 (2) 0.31323 (6) 0.0307 (4)
N1 0.54492 (15) 0.4637 (2) 0.37370 (6) 0.0221 (4)
C1 0.84965 (17) 0.0300 (3) 0.53629 (7) 0.0225 (4)
C2 0.86915 (18) −0.1714 (3) 0.56318 (8) 0.0253 (4)
H2 0.809668 −0.288787 0.547528 0.030*
C3 0.9746 (2) −0.2017 (3) 0.61259 (8) 0.0306 (4)
H3 0.987496 −0.339592 0.630602 0.037*
C4 1.0616 (2) −0.0302 (3) 0.63578 (8) 0.0312 (5)
H4 1.133812 −0.050574 0.669712 0.037*
C5 1.04260 (19) 0.1707 (3) 0.60923 (9) 0.0305 (4)
H5 1.102275 0.287837 0.624913 0.037*
C6 0.93649 (18) 0.2011 (3) 0.55971 (8) 0.0262 (4)
H6 0.923361 0.339325 0.541864 0.031*
C7 0.73344 (19) 0.0535 (3) 0.48336 (7) 0.0241 (4)
C8 0.70255 (18) 0.2742 (3) 0.45596 (7) 0.0236 (4)
H8A 0.790176 0.332474 0.444926 0.028*
H8B 0.673377 0.374111 0.484511 0.028*
C9 0.58384 (19) 0.2580 (3) 0.40220 (8) 0.0256 (4)
H9A 0.614702 0.158636 0.373938 0.031*
H9B 0.498066 0.194683 0.413610 0.031*
C10 0.42799 (18) 0.5867 (3) 0.38238 (7) 0.0217 (4)
C11 0.41576 (16) 0.7686 (3) 0.34028 (7) 0.0205 (4)
C12 0.31797 (18) 0.9352 (3) 0.33008 (7) 0.0235 (4)
H12 0.243342 0.947361 0.351458 0.028*
C13 0.3328 (2) 1.0847 (3) 0.28732 (8) 0.0265 (4)
H13 0.266970 1.201028 0.279038 0.032*
C14 0.4436 (2) 1.0656 (3) 0.25636 (8) 0.0286 (4)
H14 0.452107 1.170100 0.227516 0.034*
C15 0.54208 (18) 0.8963 (3) 0.26693 (7) 0.0253 (4)
H15 0.617284 0.883088 0.245888 0.030*
C16 0.52517 (16) 0.7487 (3) 0.30940 (7) 0.0206 (4)
C17 0.60796 (17) 0.5499 (3) 0.33014 (7) 0.0222 (4)

1 Source of material

The 1-phenylprop-2-yn-1-ol (0.5 mmol) and isoindoline-1,3-dione (1.5 mmol) were dissolved in toluene (4 mL), and Ag2CO3 (0.075 mmol) and 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-α]azepine (2 mmol) were added to the mixed solution for reflux reaction at 363 K for 12 h. After the reaction is completed, the mixture is extracted three times with ethyl acetate, the organic layers are merged, dried with anhydrous sodium sulfate to remove water, filtered to obtain the organic layer, and concentrated. Rapid column chromatography on silica gel (Petroleum ether: ethyl ester = 5: 1, v/v), and recrystallized with methanol to obtain pale yellow needle crystals.

2 Experimental details

The carbon-bound hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

3 Comment

Phthalimide and its derivatives are important structures in medicinal chemistry and organic chemistry [4, 5]. Phthalimide-based drugs have been successfully repurposed for erythema nodosum leprosum, multiple myeloma and myelodysplasia [6]. N-(acyloxy)phthalimides (NHPI esters) have emerged as suitable precursors of the corresponding carbon centered radicals under reductive decarboxylative conditions [7], [8], [9]. Therefore, the synthesis and modification of phthalimide has been a hot topic.

The basic structure of the title compound is a phthalimide derivative, containing a phthalimide and a phenylacetone. The bond lengths and angles from the title structure are within the normal range, consistent with those previously reported in the similar structure [10], [11], [12]. There are three keto-groups in the structure with the distances 1.223(2) Å (C7–O1), 1.208(2) Å (C10–O2), 1.215(2) Å (C17–O3), respectively. The three bonds, in which the N atom participates, are 1.452(2) Å (N1–C9), 1.398(2) Å (N1–C10), and 1.388(2) Å (N1–C17).


Corresponding author: Hua-Bin Wang, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, P.R. China, E-mail:

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

  2. Research funding: Guizhou Administration of Traditional Chinese Medicine. (No.QZYY-2021-008). Guizhou Provincial Basic Research Program(Natural Science)(Qian Ke He Ji Chu-ZK[2023] Zhong Dian 047, Qian Ke He Ji Chu-ZK[2021] Yi Ban 561).

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

References

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Received: 2023-07-22
Accepted: 2023-08-17
Published Online: 2023-09-05
Published in Print: 2023-12-15

© 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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