Additional file 4
Full spectral data of synthesized compounds
(E)-4-phenylbut-3-en-2-one (2a, C10H10O) CAS : 1896-62-4 To a solution of
benzaldehyde (1 equiv, 0.47 mmol), in acetone (13.6 equiv, 6.4 mmol) was
added an aqueous solution of NaOH (28.2 mg / 47 mm3 of water). The mixture
was stirred under microwaves irradiation. After work-up, the (E)-4-phenylbut-3en-2-one was isolated as a yellow oil. Yield : 69 mg, Qtf. Rf = 0.40 SiO2
(CH2Cl2).1H NMR (CDCl3, 400 MHz) δ (ppm) = 2.38 (s, 3H, H1), 6.72 (d, 1H,
J2-3 = 16.28 Hz, H3), 7.38-7.42 (m, 3H, H7, H7’, H8), 7.51 (d, 1H, J3-4 = 16.4 Hz,
H4), 7.53-7.56 (m, 2H, H6, H6’).13C NMR (CDCl3, 400 MHz) δ (ppm) = 27.6
(C1), 127.2 (C3), 128.3 (C6, C6’), 129.0 (C7, C7’), 130.6 (C8), 134.5 (C5), 143.5
(C4), 198.5 (C=O). GC/MS : method 80; tR = 6.09 min, m/z: [M]+ (146), 131 [MCH3]+, 103 [M-COCH3]+. IR (ATR):
= 3061, 3029 (ʋcsp2-H), 1666 (ʋ
C=O),
1607 (ʋ C=C).
(E)-4-p-tolylbut-3-en-2-one (2b, C11H12O) CAS : 4023-84-1. To a solution of 4methylbenzaldehyde (1 equiv, 0.42 mmol), in acetone (13.6 equiv, 5.8 mmol)
was added an aqueous solution of NaOH (25.2 mg / 42 mm3 of water). The
mixture was stirred under microwaves irradiation. After work-up, the (E)-4-ptolylbut-3-en-2-one was isolated as a yellow oil. Yield : 64 mg (96%), Rf = 0.31
SiO2 (CH2Cl2).1H NMR (CDCl3, 400 MHz) δ (ppm) = 2.36 (s, 3H, H1), 2.37 (s,
3H, H9), 6.67 (d, 1H, J3-4=16.3 Hz, H3), 7.19 (d, 2H, Jortho=7.9 Hz, H6, H6’), 7.44
(d, 2H, Jortho= 8.3 Hz, H7, H7’), 7.47 (d, 1H, J3-4 = 16.3 Hz, H4).13C NMR (CDCl3,
S1
400 MHz) δ (ppm) = 21.5 (C1), 27.5 (C9), 126.3 (C3), 128.3 (C7, C7’ ), 129.7 (C6,
C6’), 131.7 (C5), 141.0 (C8), 143.5 (C4), 198.5 (C=O). GC/MS : method 80; tR =
7.53 min, m/z: [M]+ (160), 145 [M-CH3]+, 117 [M-COCH3]+. IR (ATR):
=
3025 (ʋcsp2-H), 2922 (ʋcsp3-H), 1663 (ʋ C=O), 1608(ʋ C=C), 798 (δcsp2-H, p-disubstitution).
(E)-4-(4-tert-butylphenyl)but-3-en-2-one (2c, C14H18O) CAS : 55047-62-6 To a
solution of 4-tert-butylbenzaldehyde (1 equiv, 0.31 mmol), in acetone (13.6
equiv, 4.2 mmol) was added an aqueous solution of NaOH (18.6 mg / 31 mm3 of
water). The mixture was stirred under microwaves irradiation. After work-up,
the (E)-4-(4-tert- butylphenyl)but-3-en-2-one was isolated as a yellow oil. Yield
: 63 mg, Qtf. Rf = 0.33 SiO2 (cyclohexane/EtOAc : 9/1). 1H NMR (CDCl3, 400
MHz) δ (ppm) = 1.33 (s, 9H, H10), 2.37 (s, 3H, H1), 6.70 (d, 1H, J3-4= 16.3 Hz,
H3), 7.42 (d, 2H, Jortho= 8.6 Hz, H6, H6’), 7.48 (d, 2H, Jortho= 8.3 Hz, H7, H7’),
7.50 (d, 1H, J4-3 = 16.7 Hz, H4).13C NMR (CDCl3, 400 MHz) δ (ppm) = 27.4
(C1), 31.6 (C10,), 34.9 (C9), 125.9 (C6, C6’), 126.4 (C3), 128.1 (C7, C7’), 131.6
(C5), 143.5 (C4), 154.2 (C8), 198.6 (C=O). GC/MS : method 80; tR = 10.28 min,
m/z: [M]+ (202), 187 [M-CH3]+, 159 [M-COCH3]+. IR (ATR):
= 3031 (ʋcsp2-H),
2961 (ʋcsp3-H), 1666 (ʋ C=O), 1604(ʋ C=C), 815 (δcsp2-H, p-disubstitution).
(E)-4-(4-fluorophenyl)but-3-en-2-one (2d, C10H9FO) CAS : 65300-29-0 To a
solution of 4-fluorobenzaldehyde (1 equiv, 0.40 mmol), in acetone (13.6 equiv,
5.4 mmol) was added an aqueous solution of NaOH 24 mg / 40 mm3 of water).
The mixture was stirred under microwaves irradiation. After work-up, the (E)-4(4-fluorophenyl)but-3-en-2-one was isolated as a yellow oil. Yield : 52.5 mg
S2
(80%) Rf = 0.13 SiO2 (cyclohexane/EtOAc :9/1).1H NMR (CDCl3, 400 MHz) δ
(ppm) = 2.35 (s, 3H, H1), 6.62 (d, 1H, J3-4= 16.2 Hz, H3), 7.07 (dd, 2H, Jortho=
JH-F = 8.6 Hz, H7, H7’), 7.45 (d, 1H, J4-3 = 16.3 Hz, H4) ,7.51 (ddd, 2H, Jortho= 8.9
Hz, JH-F = 5.4 Hz, Jpara= 0.48 Hz).13C NMR (CDCl3, 400 MHz) δ (ppm) = 27.6
(C1), 116.1 (d, 2C, JC-F = 21.8 Hz, C7, C7’), 116.2 (C3), 130.1 (d, 2C, JC-F = 8.5
Hz, C6, C6’), 130.6 (d, 1H, JC-F = 3.2 Hz, C5), 142.09 (C4), 164.0 (d, 1H, JC-F =
250.4 Hz, C9), 198.2 (C=O). GC/MS : method 80; tR = 6.23 min, m/z: [M]+
(164), 149 [M-CH3]+, 121 [M-COCH3]+. IR (ATR):
= 3025 (ʋcsp2-H), 2926
(ʋcsp3-H), 1666 (ʋ C=O),1597, 1507 (ʋ C=C), 1225 (ʋ C-F ), 815 (δcsp2-H, p-disubstitution).
(E)-4-(4-bromophenyl)but-3-en-2-one (2e, C10H9BrO) CAS : 3815-31-4 To a
solution of 4-bromobenzaldehyde (1 equiv, 0.27 mmol), in acetone (13.6 equiv,
3.7 mmol) was added an aqueous solution of NaOH 16.2 mg / 27 mm3 of water).
The mixture was stirred under microwaves irradiation. After work-up, the (E)-4(4-bromophenyl)but-3-en-2-one was isolated as a yellow oil. Yield: 48.3 mg
(79%) Rf = 0.22 SiO2 (cyclohexane/EtOAc :9/1).1H NMR (CDCl3, 400 MHz) δ
(ppm) = 2.38 (s, 3H, H1), 6.69 (d, 1H, J3-4= 16.2 Hz, H3), 7.40 (d, 2H, Jortho= 8.7
Hz, H6, H6’), 7.43 (d, 1H, J4-3 = 16.5 Hz, H4) ,7.54 (d, 2H, Jortho= 8.7 Hz, H7, H7’).
13
C NMR (CDCl3, 400 MHz) δ (ppm) = 27.7 (C1), 124.8 (C5), 127.5 (C3), 129.6
(C6, C6’), 131.8 (C5), 132.2 (C7, C7’), 141.9 (C4), 196.6 (C=O). GC/MS : method
80; tR = 9.41 min, m/z: [M]+ (226), 165 [M-CH3]+, 183 [M-COCH3]+. IR (ATR):
= 3050 (ʋcsp2-H), 2920 (ʋcsp3-H), 1655 (ʋ
C=O),1607,
1585, 1486, (ʋ
C=C),804
(δcsp2-H, p-disubstitution).
S3
(E)-4-(4-methoxyphenyl)but-3-en-2-one (2f, C11H12O2) CAS : 3815-30-3 To a
solution of 4-methoxybenzaldehyde (1 equiv, 0.37 mmol), in acetone (13.6
equiv, 5.0 mmol) was added an aqueous solution of NaOH (22.2 mg / 37 mm3 of
water). The mixture was stirred under microwaves irradiation. After work-up,
the (E)-4-(4-methoxyphenyl)but-3-en-2-one was isolated as a yellow oil. Yield :
65 mg, Qtf. Rf = 0.53 SiO2 (cyclohexane/EtOAc :9/1) 1H NMR (CDCl3, 400
MHz) δ (ppm) = 2.33 (s, 3H, H1), 3.81 (s, 3H, H9), 6.58 (d, 1H, J3-4=16.2 Hz,
H2), 6.88 (d, 2H, Jortho=8.8 Hz, H7, H7’), 7.45 (d, 1H, J4-3 = 16.6 Hz, H4) , 7.47 (d,
2H, Jortho = 8.9 Hz, H6, H6’).13C NMR (CDCl3, 400 MHz) δ (ppm) = 27.4 (C1),
55.4 (C9), 114.4 (C7, C7’), 125.0 (C3), 127.0 (C5), 129.9 (C6, C6’), 143.5 (C4),
161.6 (C8), 198.5 (C=O). GC/MS : method 80; tR = 9.49 min, m/z: [M]+ (176),
161 [M-CH3]+, 133 [M-COCH3]+. IR (ATR):
2840 (ʋ
O-Me),
1680 (ʋ
C=O),
1662 (ʋ
C=C),
= 3005 (ʋcsp2-H), 2919 (ʋcsp3-H),
1588, 1575, 1509,1464 (ʋcsp2ar-C), 816
(δcsp2-H, p-disubstitution).
(E)-4-(3-chlorophenyl)but-3-en-2-one (2g, C10H9ClO) CAS 30626-02-9 To a
solution of 3-chlorobenzaldehyde (1 equiv, 0.36 mmol), in acetone (13.6 equiv,
4.8 mmol) was added an aqueous solution of NaOH 21.3 mg / 36 mm3 of water).
The mixture was stirred under microwaves irradiation. After work-up, the (E)-4(3-chlorophenyl)but-3-en-2-one was isolated as a yellow oil. Yield : 56.1 mg
(85%), Rf = 0.49 SiO2(cyclohexane/EtOAc :8/2). 1H NMR (CDCl3, 400 MHz) δ
(ppm) = 2.38 (s, 3H, H1), 6.70 (d, 1H, J3-4= 16.3 Hz, H3), 7.34-7.38 (m, 2H, H7,
H8), 7.40 (m, 1H, H6) ,7.43 (d, 1H, J4-3= 16.2 Hz, H4), 7.52 (m, 1H, H10). NMR
data are in agreement with those previously reported [22]. GC/MS : method 80;
tR = 5.89 min, m/z: [M]+ (180), 165 [M-CH3]+, 137 [M-COCH3]+. IR (ATR):
S4
= 3063 (ʋcsp2-H), 2923 (ʋcsp3-H), 1667 (ʋ C=O),1594, 1568,1475 (ʋ C=C), 780 (δcsp2-H,
m-disubstitution).
(E)-4-(4-nitrophenyl)but-3-en-2-one (2h, C10H9NO3) CAS : 30625-98-0 To a
solution of 4-nitrobenzaldehyde (1 equiv, 0.33 mmol), in acetone (13.6 equiv,
4.5 mmol) was added an aqueous solution of NaOH 19.8 mg / 33 mm3 of water).
The mixture was stirred under microwaves irradiation. After work-up, the
residue was purified by chromatography column (cyclohexane/EtOAc :7/3) and
the (E)-4-(4-nitrophenyl)but-3-en-2-one was isolated as a yellow oil. Yield : 29
mg (46%), Rf = 0.33 SiO2 (cyclohexane/EtOAc :9/1).1H NMR (CDCl3, 400
MHz) δ (ppm) = 2.43 (s, 3H, H1), 6.82 (d, 1H, J3-4= 16.3 Hz, H3), 7.53 (d, 1H, J43=
16.3 Hz, H4), 7.7 (d, 2H, J6-6’ = 8.9 Hz, H6, H6’), 8.26 (d, 2H, J7-7’= 8.7 Hz,
H7, H7’). GC/MS: method 80; tR = 6.90 min, m/z: [M]+ (191), 176 [M-CH3]+. IR
(ATR):
= 3084 (ʋcsp2-H), 2923 (ʋcsp3-H), 1591, (ʋ Car=Car), 1512 (ʋ asNO2), 1342 (ʋ
sNO2).
(E)-4-(4-(trifluoromethyl)phenyl)but-3-en-2-one (2i, C11H9F3O) CAS :11566592-4 To a solution of 4-(trifluoromethyl)benzaldehyde (1 equiv, 0.29 mmol), in
acetone (13.6 equiv, 3.9 mmol) was added an aqueous solution of NaOH 17.4
mg / 29 mm3 of water). The mixture was stirred under microwaves irradiation.
After work-up, the (E)-4-(4-(trifluoromethyl)phenyl)but-3-en-2-one was isolated
as a yellow oil. Yield : 47.8 mg (77%) Rf = 0.49 SiO2 (cyclohexane/EtOAc
:9/1).1H NMR (CDCl3, 400 MHz) δ (ppm) = 2.39 (s, 3H, H1), 6.76 (d, 1H, J3-4=
16.3 Hz, H3), 7.47 (d, 2H, J6-6’= 8.0 Hz, H6, H6’), 7.51 (d, 1H, J4-3 = 16.3 Hz, H4)
S5
,7.59 (d, 2H, J7-7’= 8.0 Hz, H7,H7’), 7.46 (s,CF3). 1H NMR data are in agreement
with those previously reported [23].GC/MS : method 80; tR = 4.54 min, m/z:
[M]+ (214), 199 [M-CH3]+, 171 [M-COCH3]+. IR (ATR):
=3051 (ʋcsp2-H),
2976 (ʋcsp3-H), 1321 (ʋ C-F).
(E)-4-(3,4-dimethoxyphenyl)but-3-en-2-one (2j, C12H14O3) CAS 60234-90-4 To
a solution of 3,4-dimethoxybenzaldehyde (1 equiv, 0.30 mmol), in acetone (13.6
equiv, 4.1 mmol) was added an aqueous solution of NaOH 18 mg / 30 mm3 of
water). The mixture was stirred under microwaves irradiation. After work-up,
the (E)-4-(3,4-dimethoxyphenyl)but-3-en-2-one was isolated as a yellow oil.
Yield : 61 mg (98%) Rf = 0.19 SiO2(cyclohexane/EtOAc : 8/2)
1
H NMR
(CDCl3, 400 MHz) δ (ppm) = 2.56 (s, 3H, H1), 4.11 (s, 6H, H8, H9), 6.79 (d, 1H,
J3-4= 16.2 Hz, H3), 7.06 (d, 1H, J7-6= 8.3 Hz, H7, H6) ,7.26 (m, 1H, H10), 7.31
(d,1H, J6-7= 8.3 Hz, H6, H7), 7.65 (d, 1H, J4-3= 16.2 Hz, H4). NMR data are in
agreement with those previously reported [22]. GC/MS : method 80; tR = 8.01
min, m/z: [M]+ (206), 191 [M-CH3]+, 163 [M-COCH3]+. IR (ATR):
(ʋcsp2-H), 2945-2919 (ʋcsp3-H), 2841 (ʋ OMe), 1666 (ʋ
Car=Car),
C=O),
= 3012
1594, 1510,1453 (ʋ
802 (δcsp2-H).
(E)-4-(5-chloro-2-nitrophenyl)but-3-en-2-one (2k, C10H8ClNO3) CAS 95905878-7 To a solution of 5-chloro-2-nitrobenzaldehyde (1 equiv, 0.27 mmol), in
acetone (13.6 equiv, 3.7 mmol) was added an aqueous solution of NaOH 16.2
mg / 27 mm3 of water). The mixture was stirred under microwaves irradiation.
After work-up, (E)-4-(5-chloro-2-nitrophenyl)but-3-en-2-one was isolated as a
S6
yellow oil. Yield : 54.8 mg (90%) Rf = 0.19 SiO2(cyclohexane/EtOAc : 8/2).
1
H NMR (CDCl3, 400 MHz) δ (ppm) = 2.36 (s, 3H, H1), 6.49 (d, 1H, J3-4= 16.2
Hz, H3), 7.25 (m, 2H, J= 8.8 Hz, H6, H8),7.88 (d, 1H, J4-3= 16.2 Hz, H4), 8.00
(d,1H, J= 8.8 Hz, H9). NMR data are in agreement with those previously
reported [24]. GC/MS : method 80; tR = 7.80 min, m/z: 182 [M-COCH3]+. IR
(ATR):
Car=Car),
= 3074 (ʋcsp2-H), 2925 (ʋcsp3-H), 1715 (ʋ
C=O),
1600, 1563, 1521 (ʋ
902, 822 (δcsp2-H).
(E)-4-(naphthalen-1-yl)but-3-en-2-one (2l, C14H12O) To a solution of 1naphtaldehyde (1 equiv, 0.32 mmol), in acetone (13.6 equiv, 4.4 mmol) was
added an aqueous solution of NaOH 19.2 mg / 32 mm3 of water). The mixture
was stirred under microwaves irradiation. After work-up, the (E)-4-(naphthalen1-yl)but-3-en-2-one was isolated as a yellow oil. Yield : 63 mg, Qtf. Rf = 0.55
SiO2 (cyclohexane/EtOAc : 8/2) 1H NMR (CDCl3, 400 MHz) δ (ppm) = 2.46 (s,
3H, H1), 6.81 (d, 1H, J3-4= 15.9 Hz, H3), 7.26-7.61 (m, 3H, H12, H13, H14) ,7.77
(d, 1H, J= 7.1 Hz, H10), 7.89 (d, 2H, J= 8.3 Hz, H8,H9), 8.17 (d, 1H, J= 8.4 Hz,
H7), 8.37 (d, 1H, J4-3= 15.9 Hz, H4). 1H NMR data are in agreement with those
previously reported [23]. GC/MS: method 80; tR = 8.05 min, m/z: [M]+ (196),
181 [M-CH3]+, 153 [M-COCH3]+. IR (ATR):
= 3049 (ʋcsp2-H), 2971 (ʋcsp3-H),
1668 (ʋ C=O), 1599, 1510 (ʋ Car=Car), 778, 729 (δcsp2-H).
S7