(2Z,5Z)-5-(3-Chloro-4-((R)-2,3-dihydroxypropoxy)benzylidene)-2-(propylimino)-3-(O-tolyl)thiazolidin-4-one

C₂₃H₂₅ClN₂O₄SCAS 854107-55-4460.97 g/mol

Open in Covalent MOL file

Alcohol Alkene Amide Aryl halide Ether Lactam Sulfide

Properties

Molecular formula: C₂₃H₂₅ClN₂O₄S
Molar mass: 460.97 g/mol
Exact mass: 460.1224 Da
logP: 4.27Crippen estimate
Polar surface area: 82.4 Å²
H-bond donors / acceptors: 2 / 6
Rotatable bonds: 8
Stereocentres: Rin SMILES atom order
Double bonds: ZE/Z, in SMILES order

Hazards

No GHS classification is on file for this compound. That is not evidence that it is harmless.

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Identifiers

CAS number

854107-55-4

SMILES

CCCN=C1N(C(=O)/C(=C/C2=CC(=C(C=C2)OC[C@@H](CO)O)Cl)/S1)C3=CC=CC=C3C

InChIKey

LPAUOXUZGSBGDU-ULCCENQXSA-N

InChI

InChI=1S/C23H25ClN2O4S/c1-3-10-25-23-26(19-7-5-4-6-15(19)2)22(29)21(31-23)12-16-8-9-20(18(24)11-16)30-14-17(28)13-27/h4-9,11-12,17,27-28H,3,10,13-14H2,1-2H3/b21-12-,25-23?/t17-/m1/s1

Characterization data

Calculated from the structure, in the form journals print them.

¹H NMR

Predicted ¹H NMR (400 MHz, CDCl₃) δ 7.48 (s, 1H), 7.37 (dd, J = 7.7, 1.6 Hz, 1H), 7.36 (d, J = 1.6 Hz, 1H), 7.24 (dd, J = 7.7, 1.6 Hz, 1H), 7.11 (dd, J = 7.7, 1.6 Hz, 1H), 7.08 (m, J = 7.7, 1.6 Hz, 1H), 6.97 (m, J = 7.7, 1.6 Hz, 1H), 6.83 (d, J = 7.7 Hz, 1H), 4.88 (quint, J = 7.0 Hz, 1H), 4.36 (d, J = 7.0 Hz, 2H), 3.98 (d, J = 7.0 Hz, 2H), 3.60 (t, J = 7.0 Hz, 2H), 2.35 (s, 3H), 2.00 (br s, 1H), 2.00 (br s, 1H), 1.44 (sext, J = 7.0 Hz, 2H), 0.86 (t, J = 7.0 Hz, 3H).

¹³C NMR

Predicted ¹³C NMR (101 MHz, CDCl₃) δ 169.0, 162.0, 159.3, 138.8, 130.8, 129.6, 129.5, 129.3, 127.3, 125.7, 125.1, 123.9, 121.9, 120.4, 120.2, 115.0, 75.9, 75.1, 66.9, 44.5, 27.2, 19.8, 11.1.

[M + H]+

[M + H]+ Calcd for C23H26ClN2O4S 461.1296

[M + Na]+

[M + Na]+ Calcd for C23H25ClN2NaO4S 483.1116

[M − H]−

[M − H]− Calcd for C23H24ClN2O4S 459.1151

Elemental analysis

Anal. Calcd for C23H25ClN2O4S: C, 59.93; H, 5.47; N, 6.08; S, 6.95.