10886
A. Sugimoto et al. / Tetrahedron 60 (2004) 10883–10886
with styrene. This compound was prepared by the
hydrogenation of 3-(9-phenanthryl)-1-phenylpropene (mp
105–107.5 8C) which was obtained by 3 steps from
9-phenanthrylethenyl phenyl ketone (mp 136.5–138 8C),
mp 84–85 8C (from pentane); lmax (hexane)/nm 211, 253,
277, 286, and 298 (log 3 4.57, 4.77, 4.13, 4.02, and 4.07); d
(CDCl3) 2.15 (2H, quintet, JZ7.7 Hz, CH2), 2.79 (2H, t,
JZ7.7 Hz, CH2), 3.13 (2H, t, JZ7.7 Hz, CH2), 7.15–7.36
(2H, m, ArH), 7.50–7.68 (5H, m, ArH), 7.51–7.65 (5H, m,
ArH), 7.81 (1H, d, JZ7.5 Hz, ArH), 8.01 (1H, d, JZ7.9 Hz,
ArH), 8.63 (1H, d, JZ8.2 Hz, ArH), 8.72 (1H, d, JZ8.2 Hz,
ArH); d (CDCl3) 31.89, 33.10, 36.12, 122.48, 123.25.
124.42, 125.88, 125.96, 126.11, 126.15, 126.52, 126.62,
128.05, 128.40, 128.56, 129.67, 130.73, 131.26, 131.91,
136.40, 142.17; m/z 296 (MC, 44%), 192 (100), and 191
(42). Found: C, 93.15; H, 6.8. Calcd for C23H20: C, 93.2; H,
6.8%.
for the Promotion of Science and Technology and by a
Grant-in-Aid for Scientific Research (Nos. 15350026 and
16655018) and by a Grant-in-Aid for Scientific Research on
Priority Areas (417) (No. 15033264) from the Ministry of
Education, Science, Sports, and Culture of Japan.
References and notes
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3.2.5. 1-(9-Phenanthryl)-2-benzylpropane 8. Ene-adduct
with 1-phenylpropene. This compound was prepared by the
following route: propiophenone to 1-(9-phenanthryl)-2-
benzoylpropane (mp 140–140.5 8C) and from this to 8, mp
112–115 8C (from pentane); lmax (hexane)/nm 211, 253,
277, 286, and 298 (log 3 4.56, 4.75, 4.12, 4.03 and 4.12); d
(CDCl3) 0.93 (3H, d, JZ7.6 Hz, CH3), 2.27 (1H, m, CH),
2.61 (1H, dd, JZ7.7, 13.7 Hz, CH2), 2.78 (2H, dd, JZ8.8,
13.8 Hz, CH2), 3.25 (1H, dd, JZ5.2, 13.7 Hz, CH2), 7.17–
7.34 (5H, m, ArH), 7.50–7.66 (5H, m, ArH), 7.78–7.84 (2H,
m, ArH), 8.64 (1H, d, JZ8.2 Hz, ArH), 8.71 (1H, d, JZ
8.2 Hz, ArH); d (CDCl3) 20.15, 36.11, 41.01, 44.26, 122.49,
123.22, 124.73, 125.95, 125.96, 126.07, 126.42, 126.62,
127.52, 128.07, 128.26, 129.36, 129.75, 130.80, 131.45,
131.75, 135.41, 141.19; m/z 310 (MC, 45%), 192 (100),
and 191 (73). Found: C, 92.53; H, 6.94. Calcd for C24H22: C,
92.86; H, 7.14%.
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3.2.6. 9-Hexylphenanthrene.26 The hydrogenated product
of 9, which corresponds to the ene-adduct with 1,3-
pentadiene. This was prepared from 9-phenanthrene-
carbaldehyde by the reaction with pentylmagnesium
bromide followed by dehydration and hydrogenation, mp
78–79 8C (from pentane); lmax (hexane)/nm 253, 277, 285,
and 298 (log 3 4.76, 4.13, 4.00 and 4.06); d (CDCl3) 0.90
(3H, t, JZ7.1 Hz, CH3), 1.25–1.41 (4H, m, CH2CH2), 1.43–
1.54 (2H, m, CH2), 1.81 (2H, quintet, JZ7.7 Hz, CH2), 3.11
(2H, t, JZ7.8 Hz, CH2), and 7.52–7.71 (5H, m, ArH), 7.78–
7.84 (1H, m, ArH), 8.03–8.14 (1H, m, ArH), 8.65 (1H, d,
JZ8.4 Hz, ArH), and 8.61–8.76 (1H, m, ArH); d (CDCl3)
14.40, 22.94, 29.81, 30.49, 32.03, 33.73, 122.48, 123.25,
124.54, 125.86, 125.96, 126.09, 126.48, 126.59, 128.04,
129.63, 130.73, 131.39, 132.00, 137.05; m/z 262 (MC,
60%), 191 (100), and 179 (28). Found: C, 91.51; H, 8.66.
Calcd for C20H22: C, 91.55; H, 8.45%.
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This work is partially supported by Tokyo Ohka Foundation