Wang & Zhang
FULL PAPER
43.39; IR (KBr) ν: 2833, 1725, 1636, 1598, 1505, 1401,
1130, 923, 815, 746 cm- 1; HRMS (EI+) calcd for
C15H13O79Br (M+) 288.0150, found 288.0147, calcd for
C15H13O81Br (M+) 290.0129, found 290.0148.
4H, ArH), 5.81—5.71 (m, 1H, CH), 5.42—5.38 (m, 1H,
CH2), 3.26—3.18 (m, 1H, CH), 2.10—1.41 (m, 6H, 3
CH2); 13C NMR (CDCl3, 100 MHz) δ: 190.68, 135.08,
133.14, 131.30, 130.84, 128.85, 128.85, 125.89, 80.36,
43.89, 26,42, 25,17,21.93; IR (KBr) ν: 2936, 1726, 1639,
1591, 1539, 1491, 1014, 902, 824 cm ; HRMS (EI )
calcd for C14H14O79Br35Cl (M + ) 311.9917, found
311.9914.
2-Bromo-2-(naphthalen-1-yl)pent-4-enal
(2j)
-
+
1
1
Yield 52%; yellow oil. H NMR (CDCl3, 400 MHz) δ:
9.63 (s, 1H, CHO), 8.00—7.24 (m, 7H, ArH), 5.72—
5.61 (m, 1H, CH), 5.05—4.97 (m, 2H, CH2), 3.48—3.43
(m, 2H, CH2); 13C NMR (CDCl3, 100 MHz) δ: 191.18,
134.65, 132.38, 131.35, 130.86, 130.05, 129.74, 128.94,
126.93, 126.21, 125.18, 124.67, 119.84, 75.83, 42.18;
IR (KBr) ν: 2836, 1722, 1635, 1597, 1510, 1397, 991,
2-Bromo-2-(4-bromophenyl)-2-(cyclohex-2-enyl)-
1
acetaldehyde (4c) Yield 35%; yellow oil. H NMR
(CDCl3, 400 MHz) δ: 9.45 (s, 1H, CHO), 7.52—7.35 (m,
4H, ArH), 5.82—5.71 (m, 1H, CH), 5.45—5.38 (m, 1H,
CH2), 3.25—3.15 (m, 1H, CH), 2.03—1.44 (m, 6H,
3CH2); 13C NMR (CDCl3, 100 MHz) δ: 190.57, 133.69,
131.78, 131.28, 131.09, 125.84, 123.29, 80.36, 43.84,
26.39, 25.13, 21.90; IR (KBr) ν: 2939, 1725, 1636, 1584,
-
+
+
1
924, 775 cm ; HRMS (EI ) calcd for C15H13O79Br (M )
288.0150, found 288.0148.
2-Chloro-2-(4-chlorophenyl)pent-4-enal
(2k)
Yield 40%; colorless oil. 1H NMR (CDCl3, 400 MHz) δ:
9.39 (s, 1H, CHO), 7.40—7.35 (m, 4H, ArH), 5.70—
5.61 (m, 1H, CH), 5.13—5.08 (m, 2H, CH2), 3.01 (d,
J=6.8 Hz, 2H, CH2); 13C NMR (CDCl3, 100 MHz) δ:
191.92, 135.47, 134.09, 131.26, 129.48, 129.08, 120.83,
77.18, 42.91; IR (KBr) ν: 2723, 1732, 1640, 1595, 1492,
-
+
1
1488, 1396, 1009, 916, 821 cm ; HRMS (EI ) calcd
for C14H14O81Br79Br (M+) 357.9391, found 357.9389,
calcd for C11H10O81Br2 (M+) 359.9370, found 359.9350.
2-Bromo-2-(cyclooct-2-enyl)-2-phenylacetaldehyde
1
(4d) Yield 27%; colorless oil. H NMR (CDCl3, 400
-
+
1
1400, 1012, 924, 824 cm ; HRMS (EI ) calcd for
C11H1035Cl2O (M+) 228.0109, found 228.0112, calcd for
C11H1035Cl37ClO (M+) 230.0079, found 230.0141.
2-Allyl-2-bromooctanal (2l) Yield 41%; colorless
MHz) δ: 9.42 (s, 1H, CHO), 7.48—7.29 (m, 5H, ArH),
5.63—5.60 (m, 1H, CH), 5.35—5.30 (m, 1H, CH2), 3.50
—3.60 (m, 1H, CH), 2.27—1.31 (m, 10H, 5CH2); 13C
NMR (CDCl3, 100 MHz) δ: 191.08, 135.08, 130.88,
129.14, 129.10, 128.81, 128.75, 82.12, 43.21, 33.73,
1
oil. H NMR (CDCl3, 400 MHz) δ: 9.39 (s, 1H, CHO),
5.84—5.74 (m, 1H, CH), 5.21—5.17 (m, 2H, CH2), 2.77
(t, J=6.8 Hz, 2H, CH2), 2.01—1.91 (m, 2H, CH2),
1.29—1.45 (m, 8H, 4CH2), 0.88 (t, J=7.2 Hz, 3H, Me);
13C NMR (CDCl3, 100 MHz) δ: 193.71, 132.18, 119.98,
73.07, 40.46, 36.41, 31.59, 29.36, 25.28, 22.64, 14.15;
IR (KBr) ν: 2956, 2929, 2859, 1728, 1463, 1378, 995,
29.40, 26.89, 26.82, 25.60; IR (KBr) ν: 2846, 1728,
1640, 1595, 1511, 1449, 989, 914, 764, 695 cm-
;
1
HRMS (EI+) calcd for C16H1979BrO (M+) 306.0619,
found 306.0617, calcd for C16H1981BrO (M+) 308.0599,
found 308.0580.
2-Bromo-2-(4-bromophenyl)-2-(cyclooct-2-enyl)-
-
+
+
924 cm ; HRMS (EI ) calcd for C11H1981BrO (M )
248.0599, found 248.0952, calcd for C11H1979BrO (M+)
248.0619, found 248.0674.
acetaldehyde (4e) Yield 30%; yellow oil. H NMR
1
1
(CDCl3, 400 MHz) δ: 9.40 (s, 1H, CHO), 7.50—7.33 (m,
4H, ArH), 5.64—5.61 (m, 1H, CH), 5.31—5.25 (m, 1H,
CH2), 3.52—3.46 (m, 1H, CH), 2.24—1.31 (m, 10H, 5
CH2); 13C NMR (CDCl3, 100 MHz) δ: 191.01, 134.32,
131.92, 131.44, 130.84, 128.77, 123.27, 81.48, 43.26,
33.82, 29.42, 26.94, 25.61; IR (KBr) ν: 2843, 1711, 1640,
1,1-Dibromo-2-phenylpent-4-en-2-ol (3) Yellow
oil. 1H NMR(CDCl3, 400 MHz) δ: 7.49—7.33 (m, 5H,
ArH), 6.00 (s, 1H, CH), 5.58—5.46 (m, 1H, CH),
5.18—5.08 (m, 2H, CH2), 2.94 (d, J=6.8 Hz, 2H, CH2),
2.78 (s, 1H, OH); 13C NMR (CDCl3, 100 MHz) δ:
140.46, 132.28, 128.50, 128.26, 126.47, 120.45, 78.87,
57.49, 43.78; IR (KBr) ν: 3440, 2915, 1595, 1497, 1440,
962, 913, 743, 714 cm- 1; HRMS (EI+ ) calcd for
C8H779Br81BrO (M+-C3H5) 278.8843, found 278.8813.
2-Bromo-2-(cyclohex-2-enyl)-2-phenylacetaldehyde
-
+
1
1593, 1504, 1441, 986, 907, 826 cm ; HRMS (EI )
calcd for C16H18O79Br2 (M+) 383.9724, found 383.9722,
calcd for C16H18O81Br79Br (M + ) 385.9704, found
385.9665.
2-Bromo-2,3-diphenylpent-4-enal (4f) dr=3∶5.
1
Yield 23%; yellow oil. H NMR (CDCl3, 400 MHz) δ:
1
(4a) Yield 32%; colorless oil. H NMR (CDCl3, 400
9.55—9.42 (m, 1H, CHO), 7.40—6.90 (m, 10H, ArH),
6.31—5.88 (m, 1H, CH), 5.32—5.10 (m, 2H, CH2),
4.45—4.35 (m, 1H, CH); 13C NMR (CDCl3, 100 MHz)
δ: 190.07, 189.47, 138.43, 138.13, 137.36, 136.13,
133.84, 130.61, 130.24, 129.43, 129.00, 128.83, 128.26,
128.18, 127.92, 127.85, 127.50, 127.24, 126.17, 119.47,
MHz) δ: 9.46 (s, 1H, CHO), 7.50—7.33 (m, 5H, ArH),
5.77—5.73 (m, 1H, CH), 5.45—5.40 (m, 1H, CH2), 3.22
—3.29 (m, 1H, CH), 2.05—1.52 (m, 6H, 3CH2); 13C
NMR (CDCl3, 100 MHz) δ: 191.09, 134.71, 130.99,
129.61, 129.16, 128.98, 126.56, 81.71, 44.05, 26.80,
25.42, 22.26; IR (KBr) ν: 2836, 1724, 1642, 1597, 1532,
118.93, 77.90, 57.31, 56.23; IR (KBr) ν: 2738, 1702,
-
+
1445, 987, 913, 752, 696 cm ; HRMS (EI ) calcd for
C14H1579BrO (M+) 278.0306, found 278.0304, calcd for
C14H1581BrO (M+) 280.0286, found 280.0255.
1639, 1593, 1553, 1484, 996, 904, 779, 698 cm-
;
1
1
HRMS (EI+) calcd for C16H18O81Br (M+) 316.0286,
found 316.0255.
2-Bromo-2-(4-chlorophenyl)-2-(cyclohex-2-enyl)-
acetaldehyde (4b) Yield 30%; yellow oil. H NMR
(CDCl3, 400 MHz) δ: 9.45 (s, 1H, CHO), 7.45—7.34 (m,
2-Bromo-2-(4-bromophenyl)-3-phenylpent-4-enal
(4g) dr=3∶2. Yield 25%; yellow oil. 1H NMR
(CDCl3, 400 MHz) δ: 9.50—9.43 (m, 1H, CHO), 7.48—
1
98
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2012, 30, 96—102