30.1671,found: 230.1670.
[0060] 實施例13(Z)-2_ 丁基-3_(4-甲基芐基)-2_戊烯醛(013)的合成
[0062]按實施例1所述的方法,不同的是所用底物和試劑為:2-丁基-4_(4-甲基苯基)_2, 3-丁二稀酸(0 · 2141g,1 · Ommol),甲苯(20mL),二乙基鋅溶液(1 · 2mL,2 · OM in toluene, 2.4mmol)和乙酸(2mL)得到(Z)-2-丁基-3-(4-甲基芐基)-2_戊烯醛(0.2098g,86%)(石油 醚(30-60°C)/乙酸乙酯= 100:1):液體;1H NMR(300MHz,CDC13)S10.18(s,1H,CH0),7.10 (d,J = 8. IHz,2H,ArH),7.03(d,J = 7.8Hz,2H,ArH),3.89(s,2H,CH2),2· 37-2.27(m,5H, Ofeand CH2),2.22(q,J = 7.6Hz,2H,CH2),1.44-1.27(m,4H,CH2X2),1.06(t,J = 7.7Hz,3H, CH3),0.92(t,J = 6.8Hz,3H,CH3) ;13C 匪R(75MHz,CDC13)S191.8,160.8,138.1,136.1, 135.3a29.3a28.3,34.5,31.7,26.9,25.1,23.0,20.8a3.9a2.6;IR(neat)v(cm _1)3048, 3021,2958,2931,2872,2757,1667,1620,1513,1460,1398,1377,1335,1278,I185,I151, 1118,1105,1072,1043,1021 ;MS(70ev,EI)m/z(%)244(M+,16.09),187(100);HRMS calcd for Ci7H24〇[M+] : 244.1827,found: 244.1829.
[0063] 實施例14(Z)-2-烯丙基-3-乙基-2-十三碳烯醛(014)的合成
[0064]
[0065]按實施例1所述的方法,不同的是所用底物和試劑為:2-烯丙基-2,3_十三碳二烯 酸(0·2343g,1 ·Ommol),甲苯(20mL),二乙基鋅溶液(1 ·6mL,1 ·5M in toluene,2·4mmol)和 乙酸(2mL)得到(Z)-2-烯丙基-3-乙基-2-十三碳烯醛(0.23248,88%)(石油醚(30-60°〇/ 乙酸乙酯= 100:1):液體;1H NMR(300MHz,CDCl3)Sl0.09(s,lH,CH0),5.85-5.68(m,lH,= CH),4.99-4.87(m,2H,=CH2),3.02(dd,Ji = 5.7Hz,J2 = O.9Hz,2H,CH2),2.58(t,J = 8.0Hz, 2H,CH2),2.29(q,J = 7.4Hz,2H,CH2),1.60-1.45(m,2H,CH2),1.43-1.18(m,14H,CH2X7), 1.09(t,J = 7.7Hz,3H,CH3),0.88(t,J = 6.2Hz,3H,CH3) ;13C 匪R(75MHz,CDC13)S190.6, 165·8,135·8,133·4,114·3,31·7,30·7,30·2,29·6,29·40,29·36,29·2,29·I,28·8,27·6, 22.5a3.9a2.3;IR(neat)v(cm _1)3079,2957,2925,2855,2752a67ia638a619a467, 1396,1378,1328,1153,1068 ;MS(70ev,EI)m/z(%)264(M+,6.56),123(100);HRMS calcd for Ci8H32OtM+] : 264.2453,found: 264.2452.
[0066]實施例153-乙基-2芐基-2-戊烯醛(015)的合成
[0068]按實施例1所述的方法,不同的是所用底物和試劑為:2-芐基-2,3-戊二烯醛 (0 · 1718g,1 ·Ommol),甲苯(20mL),二乙基鋅溶液(1 ·6mL,1 · 5M in toluene,2 ·4mmol)和乙 酸(2mL)得到3-乙基-2芐基-2-戊烯醛(0.17778,88%)(石油醚(30-60°〇/乙酸乙酯=50: 1):液體; 1H NMR(300MHz,CDC13)S10.18(s,1H,CH0),7.27-7.18(m,2H,ArH),7.17-7 ·07(ι?, 3H,ArH),3.65(s,2H,CH2),2.64(q,J = 7.6Hz,2H,CH2),2.31(q,J = 7.5Hz,2H,CH2),l. 19 (t,J = 7.7Hz,3H,CH3),0.99(t,J = 7.5Hz,3H,CH3);13C NMR(75MHz,CDC13)S191.2,167.8, 140.2,134.3,128.2,127.9,125.6,30.1,27.7,23.3,15.3,12.1;IR(neat)v(cm _1)3084, 3061,3027,2972,2935,2875,2755,1667,1617,1494,1453,1378,1328,1281,1246,I153, 1074,1042,1030;MS(70ev,EI)m/z(%)202(M +,59.88),91(100);HRMS calcd for Ci4HisO[M +]:202.1358,found:202.1360.
[0069] 實施例16(Z)-2-丙基-3-丁基-2-^碳烯醛(016)的合成
[0071 ]按實施例1所述的方法,不同的是所用底物和試劑為:2-丙基-2,3-十一碳二烯醛 (0 · 2079g,1 ·Ommol),甲苯(20mL),二丁基鋅溶液(2 ·4mL,1 · OM in toluene,2 ·4mmol)和乙 酸(2mL)得到(Z)-2-丙基-3-丁基-2-^碳烯醛(0.2387g,90% )(石油醚(30_60°C)/乙酸 乙酯= 100:1):液體;1H M1R(300MHz,CDC13)S10.07(s,1H,CH0),2.52(t,J = 7.8Hz,2H, CH2),2.33-2.14(m,4H,CH2X2),1.57-1.17(m,18H,CH2X9),1.00-0.83(m,9H,CH 3X3);13C NMR(75MHz,CDC13)S191.6,163.5,136.6,34.5,31.8,31.0,30.6,29.7,29.3,29.1,27.2, 23. l,22.7,22.6a4.2a4.〇a3.9;IR(neat)v(cm_1)2958,2927,2858,2753a668a616, 1465,1397,1378,1348,1154,1083;MS(70ev,EI)m/z(% )266(M+,37.72),126(100);HRMS calcd for Ci8H34OtM+]:266.2610,found:266.2611.
[0072] 實施例17 (Z) -2-丙基-3-丁基-2-十四碳烯醛(017)的合成
[0074]按實施例1所述的方法,不同的是所用底物和試劑為:2_丙基_2,3_十四碳二烯醛 (0 · 2502g,1 ·Ommol),甲苯(20mL),二丁基鋅溶液(2 ·4mL,1 · OM in toluene,2 ·4mmol)和乙 酸(2mL)得到(Z)-2-丙基-3-丁基-2-十四碳烯醛(0.271(^,88%)(石油醚(30-60°〇/乙酸 乙酯= 200:1):液體;1H M1R(300MHz,CDC13)S10.07(s,1H,CH0),2.53(t,J = 8.0Hz,2H, CH2),2.3h2.15(m,4H,CH2X2),1.57-1.21(m,24H,CH2X12),1.00-0.83(m,9H,CH 3X3);13C 匪R(75MHz,CDC13)S191.5,163.4,136.6,34.5,31.8,31.0,30.57,30.55,29.6,29.52, 29.45,29.32,29.26,27.2,23.1,22.7,22.6a4.2a4.〇a3.8;IR(neat)v(cm _1)2958,2926, 2855,2752,1670,1615,1464,1397,1378,1348,131I,1271,1229,I152,1081;MS(70ev,EI) m/z(% )308(M+,25.06) ,43(100) ;HRMS calcd for C2iH4〇0[M+] : 308.3079 , found : 308.3080.
[0075] 實施例18 (Z) -2-丙基-3-苯乙基-2-庚烯醛(018)的合成
[0077]按實施例1所述的方法,不同的是所用底物和試劑為:2-丙基-5-苯基-2,3-戊二烯 酸(0· 1998g,1 ·Ommol),甲苯(20mL),二丁基鋅溶液(2·4mL,1 ·OM in toluene,2·4mmol)和 乙酸(2mL)得到(Z)-2-丙基-3-苯乙基-2-庚烯醛(0.22968,89%)(石油醚(30-60°〇/乙酸 乙酯= 50:1):液體;1H NMR(300MHz,CDCl3)S9.87(s,lH,CH0),7.31-7.23(m,2H,ArH),7.23-7.09(m,3H,ArH),2.88-2.73(m,4H,CH2X2),2.3h2.13(m,4H,CH2X2),1.54-1.21(m,6H, CH2X3),1· 10-0.85(m,6H,CH3X2);13C 匪R(75MHz,CDC13)S191.1,160.9,140.4,137.3, 128.4,128.3,126.3,36.6,34.2,32.3,30.5,27.3,23.0,22.6,14.2,13.8 ;IR(neat)v(cm-〇 3085,3063,3027,2959,2931,2871,2756,1668,1614,1496,1464,1454,1397,1379,1379, 1347,I150,1097,1075,1031;MS(70ev,EI)m/z(%)258(Μ+,4·46),91(100);HRMS calcd for Ci8H26OtM+] : 258.1984,found: 258.1985.
[0078] 實施例19(Z)-2-丙基-3-丁基-7-氯-2-庚烯醛(019)的合成 [0079]
[0080]按實施例1所述的方法,不同的是所用底物和試劑為:2-丙基-7-氯-2,3-庚二烯醛 (0 · 1865g,1 ·Ommol),甲苯(20mL),二丁基鋅溶液(2 ·4mL, 1 · OM in toluene,2 ·4mmol)和乙 酸(2mL)得到(Z)-2-丙基-3-丁基-7-氯-2-庚烯醛(0.2107g,86 % )(石油醚(30-60°C)/乙酸 乙酯= 30:1):液體;1H NMR(300MHz,CDCl3)Sl0.07(s,lH,CH0),3.56(t,J = 6.3Hz,2H,CH2), 2.58(t,J = 8.0Hz,2H,CH2),2.32-2.14(m,4H,CH2X2),1.90-1.76(m,2H,CH2),1.74-1.59 (m,2H,CH2),1.52-1.23(m,6H,CH2X3),1.00-0.85(m,6H,CH 3X2);13C NMR(75MHz,CDC13)S 191.2,162.0,137.0,44.4,34.3,32.1,30.5,29.6,27.8,27.2,23.0,22.6,14.1,13.8;IR (neat)v(cm_1)2959,2929,2871,2756,1667,1616,1464,1399,1378,1347,1311,1269,1228, 1153,1080;MS(70ev,EI)m/z(%)246(M +(37Cl),8.05),244(M+(35Cl),24.25),55(100);HRMS calcd for CwH25O35Cl[M+] :244.1594,found:244.1597.
[00811 實施例20(Z)-3-丁基-2-烯丙基-2-十三碳烯醛(020)的合成
[0083]按實施例1所述的方法,不同的是所用底物和試劑為:2-烯丙基-2,3-十三碳二烯 酸(0·2341g,1 ·Ommol),甲苯(20mL),二丁基鋅溶液(2·4mL,1 ·OM in toluene,2·4mmol)和 乙酸(2mL)得到(Z)-3-丁基-2-烯丙基-2-十三碳烯醛(0.25988,89%)(石油醚(30-60°〇/ 乙酸乙酯= 100:1):液體;1H NMR(300MHz,CDCl3)Sl0.08(s,lH,CH0),5.84-5.68(m,lH,= CH),4.99-4.87(m,2H,=CH2),3.02(dt,Ji = 5.9Hz,j2 = 1.6Hz,2H,CH2),2.57(t,J = 8.0Hz, 2H,C