Molecules 2020, 25, 1590
9 of 14
(E)-2-(benzo [d] [
solid (61 mg, 88% yield); H NMR (500 MHz, CDCl3)
,
]dioxol-5-ylmethylene)-3,4-dihydronaphthalen-1(2H)-one (Scheme 2, 3l) [27], Yellow
1
δ 8.11 (dd, J = 7.8, 0.9 Hz, 1H), 7.79 (s, 1H),
7.49–7.46 (m, 1H), 7.35 (t, J = 7.5 Hz, 1H), 7.27–7.23 (m, 1H), 6.99–6.95 (m, 2H), 6.86 (d, J = 8.0 Hz, 1H),
6.00 (s, 2H), 3.13–3.11 (m, 2H), 2.96–2.93 (m, 2H); 13C NMR (125 MHz, CDCl3)
δ
187.8, 148.0, 147.8,
143.1, 136.7, 134.0, 133.6, 133.2, 129.9, 128.2, 127.0, 125.1, 115.0, 109.8, 108.5, 101.4, 28.8, 27.3.
(E)-2-(furan-2-ylmethylene)-3,4-dihydronaphthalen-1(2H)-one (Scheme 2, 3m) [27], Yellow solid (48 mg,
85% yield); 1H NMR (500 MHz, CDCl3)
δ 8.11 (dd, J = 7.8, 1.3 Hz, 1H), 7.60–7.56 (m, 2H), 7.50–7.46 (m,
1H), 7.37–7.33 (m, 1H), 7.27 (d, J = 7.5 Hz, 1H), 6.71 (d, J = 3.5 Hz, 1H), 6.52 (dd, J = 3.4, 1.8 Hz, 1H),
3.36–3.31 (m, 2H), 3.03–2.99 (m, 2H); 13C NMR (125 MHz, CDCl3)
133.1, 131.9, 128.1, 127.0, 122.8, 116.6, 115.0, 112.2, 28.4, 26.7.
δ 187.4, 152.5, 144.3, 143.5, 133.6,
(E)-2-(cyclohexylmethylene)-3,4-dihydronaphthalen-1(2H)-one (Scheme 2, 3n), Yellow solid (41 mg, 69%
yield); 1H NMR (500 MHz, CDCl3)
8.02 (dd, J = 7.8, 1.0 Hz, 1H), 7.40–7.36 (m, 1H), 7.25 (t, J = 7.5 Hz,
1H), 7.16 (d, J = 7.5 Hz, 1H), 6.70 (d, J = 9.7 Hz, 1H), 2.89–2.86 (m, 2H), 2.74–2.71 (m, 2H), 2.36–2.27 (m,
1H), 1.72–1.68 (m, 2H), 1.63–1.58 (m, 3H), 1.28–1.14 (m, 5H); 13C NMR (125 MHz, CDCl3)
186.9, 144.1,
δ
δ
142.7, 132.7, 132.3, 131.9, 127.2, 127.1, 125.8, 36.2, 31.2, 28.3, 24.9, 24.8, 24.6. HRMS (ESI): Calculated for
[C17H21O]+ 241.1587; Found 241.1589.
(E)-2-(cyclopropylmethylene)-3,4-dihydronaphthalen-1(2H)-one (Scheme 2, 3o) [63], White solid (39 mg,
78% yield); 1H NMR (500 MHz, CDCl3)
δ 8.01 (dd, J = 7.8, 1.1 Hz, 1H), 7.39–7.37 (m, 1H), 7.26 (t, J = 7.5
Hz, 1H), 7.18 (d, J = 7.6 Hz, 1H), 6.27 (d, J = 10.9 Hz, 1H), 2.93–2.86 (m, 2H), 2.86–2.83 (m, 2H), 1.67–1.60
(m, 1H), 0.97–0.93 (m, 2H), 0.68–0.65 (m, 2H); 13C NMR (125 MHz, CDCl3)
132.8, 132.7, 128.2, 128.1, 126.8, 29.0, 25.5, 11.8, 9.0.
δ 186.7, 145.6, 143.6, 133.7,
2-butyl-3,4-dihydronaphthalen-1(2H)-one (Scheme 2, 3p) [64], Pale yellow liquid (36 mg, 70% yield); 1H
NMR (500 MHz, CDCl3) 7.96 (dd, J = 7.8, 1.0 Hz, 1H), 7.40–7.36 (m, 1H), 7.23 (d, J = 7.6 Hz, 1H), 7.16
δ
(d, J = 7.6 Hz, 1H), 2.94–2.86 (m, 3H), 2.42–2.38 (m, 1H), 2.20–2.14(m, 1H), 1.90–1.80 (m, 2H), 1.44–1.40
(m, 1H), 1.36–1.28 (m, 3H), 0.85 (t, J = 7.0 Hz, 3H); 13C NMR (125 MHz, CDCl3)
δ 199.5, 143.0, 132.0,
131.6, 127.6, 126.4, 125.5, 46.5, 28.2, 28.1, 27.3, 27.2, 21.8, 13.0.
2-pentyl-3,4-dihydronaphthalen-1(2H)-one (Scheme 2, 3q) [65], Pale yellow liquid (29 mg, 53% yield); 1H
NMR (400 MHz, CDCl3) 7.96 (d, J = 7.8 Hz, 1H), 7.40–7.36 (m, 1H), 7.23 (t, J = 7.5 Hz, 1H), 7.16 (d,
δ
J = 7.5 Hz, 1H), 2.98–2.84 (m, 3H), 2.44–2.37 (m, 1H), 2.20–2.13 (m, 1H), 1.91–1.78 (m, 2H), 1.35–1.21 (m,
6H), 0.83 (t, J = 6.6 Hz, 3H); 13C NMR (100 MHz, CDCl3)
δ 199.5, 142.9, 132.0, 131.5, 127.6, 126.4, 125.5,
46.5, 30.9, 28.3, 27.3, 27.1, 25.7, 21.6, 13.1.
(E)-2-benzylidenecycloheptan-1-one (Scheme 2, 4a) [66], Colorless liquid (29 mg, 58% yield); 1H NMR
(400 MHz, CDCl3) δ 7.45 (s, 1H), 7.34–7.29 (m, 2H), 7.28–7.22 (m, 3H), 2.66–2.61 (m, 4H), 1.77–1.68 (m,
6H); 13C NMR (100 MHz, CDCl3) δ 205.0, 140.8, 136.1, 135.7, 129.5, 128.5, 43.5, 31.4, 30.0, 27.7, 25.5.
1
(E)-2-benzylidenecyclooctanone (Scheme 2, 4b) [66], Colorless liquid (27 mg, 50% yield); H NMR
(500 MHz, CDCl3)
δ 7.40 (s, 1H), 7.31 (dd, J = 10.4, 2.8 Hz, 4H), 7.28–7.24 (m, 1H), 2.76–2.74 (m, 2H), 2.65
(dd, J = 7.3, 5.5 Hz, 2H), 1.81–1.76 (m, 2H), 1.71–1.66 (m, 2H), 1.60–1.55 (m, 2H), 1.48–1.43 (m, 2H); 13
C
NMR (125 MHz, CDCl3) δ 206.6, 139.5, 135.5, 135.1, 128.6, 127.4, 127.4, 38.3, 29.1, 28.6, 25.5, 24.9, 24.5.
1
(E)-2-benzylidenecyclopentadecanone (Scheme 2, 4c), Colorless liquid (24 mg, 31% yield); H NMR
(500 MHz, CDCl3)
δ 7.43–7.41 (m, 5H), 7.37–7.34 (m, 1H), 2.84–2.81 (m, 2H), 2.65 (t, J = 7.0 Hz, 2H),
2.44 (t, J = 6.7 Hz, 1H), 1.78–1.75 (m, 2H), 1.49 (dd, J = 9.1, 6.2 Hz, 2H), 1.39–1.29 (m, 17H); 13C NMR
(125 MHz, CDCl3) δ 204.0, 143.3, 137.2, 136.1, 129.2, 128.5, 128.2, 42.1, 37.6, 28.6, 27.8, 27.6, 27.5, 26.8,
26.7, 26.5, 26.4, 26.2, 26.1, 24.3, 23.5. HRMS (ESI): Calculated for [C22H33O]+ 313.2526; Found 241.2528.
(E)-2-benzylidene-7-methoxy-3,4-dihydronaphthalen-1(2H)-one (Scheme 2, 4d) [66], Yellow solid (48 mg,
1
72% yield); H NMR (500 MHz, CDCl3)
δ 7.89 (s, 1H), 7.66 (d, J = 2.8 Hz, 1H), 7.48–7.43 (m, 4H),
7.40–7.37 (m, 1H), 7.19 (d, J = 8.3 Hz, 1H), 7.10 (dd, J = 8.3, 2.8 Hz, 1H), 3.90 (s, 3H), 3.15–3.13 (m, 2H),