Phụ lục đính kèm về cây an điền hoa nhỏ

Phụ lục đính kèm về cây an điền hoa nhỏ

PHỤ LỤC

SF 500.1300157 MHz

SI 32768 F2 − Processing parameters SFO1 500.1335009 MHz PL1 −3.00 dB P1 10.50 usec NUC1 1H

======== CHANNEL f1 ======== MCWRK 0.01500000 sec MCREST 0.00000000 sec D1 1.00000000 sec

DS 0

NS 16 SOLVENT CDCl3

TD 65536 PULPROG zg30 PROBHD 5 mm Multinucl INSTRUM av500 Time 9.43 Date_ 20090428 F2 − Acquisition Parameters PROCNO 1 EXPNO 1 NAME 111TENE.C2 Current Data Parameters

11

4 12 9 5 1

28, 29, 30

1.6 1.7

1.8 1.9

2.0 2.1

SF 500.1300157 MHz

SI 32768 F2 − Processing parameters SFO1 500.1335009 MHz PL1 −3.00 dB P1 10.50 usec NUC1 1H

======== CHANNEL f1 ======== MCWRK 0.01500000 sec MCREST 0.00000000 sec D1 1.00000000 sec

DS 0

NS 16 SOLVENT CDCl3

TD 65536 PULPROG zg30 PROBHD 5 mm Multinucl INSTRUM av500 Time 9.43 Date_ 20090428 F2 − Acquisition Parameters PROCNO 1 EXPNO 1 NAME 111TENE.C2 Current Data Parameters

SF 125.7577825 MHz

SI 32768F2 − Processing parametersSFO2 500.1320005 MHzPL13 22.00 dBPL12 14.68 dBPL2 −3.00 dBPCPD2 88.00 usecNUC2 1HCPDPRG2 waltz16

======== CHANNEL f2 ========SFO1 125.7703643 MHzPL1 −1.00 dBP1 10.50 usecNUC1 13C

======== CHANNEL f1 ========MCWRK 0.01500000 secMCREST 0.00000000 secDELTA 1.89999998 secd11 0.03000000 secD1 2.00000000 sec

DS 2

NS 128SOLVENT CDCl3

TD 65536PULPROG zgpg30PROBHD 5 mm MultinuclINSTRUM av500Time 11.30Date_ 20090502F2 − Acquisition ParametersPROCNO 1EXPNO 2NAME 111TENE.C2Current Data Parameters

10 6 2

3

7 11

9 5 12

4 8

1 30

28 29

25.654

26.751 26.857

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160 170

180 190

200

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160 170

180 190

200

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160 170

180 190

20 25 30 35 40 45 50 55 60 65 70 75 80 85 90 95 100 105 110 115 120 125 130

20 25 30 35 40 45 50 55 60 65 70 75 80 85 90 95 100 105 110 115 120 125 130

20 25 30 35 40 45 50 55 60 65 70 75 80 85 90 95 100 105 110 115 120 125 130

SF 500.1299893 MHz

SI 32768 F2 − Processing parameters SFO1 500.1335009 MHz PL1 −1.00 dB P1 7.80 usec NUC1 1H

======== CHANNEL f1 ======== MCWRK 0.01500000 sec MCREST 0.00000000 sec D1 1.00000000 sec

DS 0

NS 16 SOLVENT CDCl3

TD 65536 PULPROG zg30 PROBHD 5 mm TXI 1H−13 INSTRUM av500 Time 11.24 Date_ 20090115 F2 − Acquisition Parameters PROCNO 1 EXPNO 1 NAME 111TENE.PE2 Current Data Parameters

5.237 5.244 5.251

SF 125.7577932 MHz

SI 32768F2 − Processing parametersSFO2 500.1320005 MHzPL13 20.50 dBPL12 19.62 dBPL2 −1.00 dBPCPD2 80.00 usecNUC2 1HCPDPRG2 waltz16

======== CHANNEL f2 ========SFO1 125.7703643 MHzPL1 −5.00 dBP1 13.00 usecNUC1 13C

======== CHANNEL f1 ========MCWRK 0.01500000 secMCREST 0.00000000 secDELTA 1.89999998 secd11 0.03000000 secD1 2.00000000 sec

DS 2

NS 2048SOLVENT CDCl3

TD 65536PULPROG zgpg30PROBHD 5 mm TXI 1H−13INSTRUM av500Time 11.52Date_ 20090115F2 − Acquisition ParametersPROCNO 1EXPNO 2NAME 111TENE.PE2Current Data Parameters

SF 500.1299796 MHz

SI 32768 F2 − Processing parameters SFO1 500.1335009 MHz PL1 −3.00 dB P1 10.50 usec NUC1 1H

======== CHANNEL f1 ======== MCWRK 0.01500000 sec MCREST 0.00000000 sec D1 1.00000000 sec

DS 0

NS 16 SOLVENT CDCl3

TD 65536 PULPROG zg30 PROBHD 5 mm Multinucl INSTRUM av500 Time 14.38 Date_ 20090629 F2 − Acquisition Parameters PROCNO 1 EXPNO 1 NAME 111TENE.C5 Current Data Parameters

SF 125.7577598 MHz

SI 32768 F2 − Processing parameters SFO2 500.1320005 MHz PL13 22.00 dB PL12 14.68 dB PL2 −3.00 dB PCPD2 88.00 usec NUC2 1H CPDPRG2 waltz16

======== CHANNEL f2 ======== SFO1 125.7716224 MHz PL1 −1.00 dB P1 10.50 usec NUC1 13C

======== CHANNEL f1 ======== MCWRK 0.01500000 sec MCREST 0.00000000 sec DELTA 1.89999998 sec d11 0.03000000 sec D1 2.00000000 sec

DS 2

NS 2048 SOLVENT CDCl3

TD 65536 PULPROG zgpg30 PROBHD 5 mm Multinucl INSTRUM av500 Time 16.07 Date_ 20090705 F2 − Acquisition Parameters PROCNO 1 EXPNO 2 NAME 111TENE.C5 Current Data Parameters

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160 170

180

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160 170

180

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160 170

15 20

25 30

35 40

45 50

15 20

25 30

35 40

45 50

15 20

25 30

35 40

45 50

SF 500.1299785 MHz

SI 32768 F2 − Processing parameters SFO1 500.1335009 MHz PL1 −3.00 dB P1 10.50 usec NUC1 1H

======== CHANNEL f1 ======== MCWRK 0.01500000 sec MCREST 0.00000000 sec D1 1.00000000 sec

DS 0

NS 16 SOLVENT CDCl3

TD 65536 PULPROG zg30 PROBHD 5 mm Multinucl INSTRUM av500 Time 14.33 Date_ 20090629 F2 − Acquisition Parameters PROCNO 1 EXPNO 1 NAME 111TENE.C4 Current Data Parameters

12

2

3 18

3.381 3.384 3.387

3.626 3.635 3.648 3.654 3.667 3.676

5.369

2.281

4.389

0.962 1.158

SF 125.7577733 MHz

SI 32768 F2 − Processing parameters SFO2 500.1320005 MHz PL13 22.00 dB PL12 14.68 dB PL2 −3.00 dB PCPD2 88.00 usec NUC2 1H CPDPRG2 waltz16

======== CHANNEL f2 ======== SFO1 125.7716224 MHz PL1 −1.00 dB P1 10.50 usec NUC1 13C

======== CHANNEL f1 ======== MCWRK 0.01500000 sec MCREST 0.00000000 sec DELTA 1.89999998 sec d11 0.03000000 sec D1 2.00000000 sec

DS 2

NS 4096 SOLVENT CDCl3

TD 65536 PULPROG zgpg30 PROBHD 5 mm Multinucl INSTRUM av500 Time 10.50 Date_ 20090705 F2 − Acquisition Parameters PROCNO 1 EXPNO 2 NAME 111TENE.C4 Current Data Parameters

Phụ lục 10c: Phổ C-NMR của hợp chất TENE.C4 13

Phụ lục 11a: Phổ DEPT-NMR của hợp chất TENE.C4

TENE.C4−CDCl3&MeOD−C13CPD

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160 170

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160 170

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160 170

Phụ lục 11b: Phổ DEPT-NMR của hợp chất TENE.C4

TENE.C4−CDCl3&MeOD−C13CPD

20 25

30 35

40 45

50

20 25

30 35

40 45

50

20 25

30 35

40 45

SF 500.1300047 MHz

SI 32768 F2 − Processing parameters SFO1 500.1335009 MHz PL1 −3.00 dB P1 10.50 usec NUC1 1H

======== CHANNEL f1 ======== MCWRK 0.01500000 sec MCREST 0.00000000 sec D1 1.00000000 sec

DS 0

NS 16 SOLVENT DMSO

TD 65536 PULPROG zg30 PROBHD 5 mm Multinucl INSTRUM av500 Time 10.11 Date_ 20090428 F2 − Acquisition Parameters PROCNO 1 EXPNO 1 NAME 111TENE.C1 Current Data Parameters

6

1'

1'

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160

20 30

40 50

60 70

80 90

100 110

120 130

140 150

SF 500.1300008 MHz

SI 32768 F2 − Processing parameters SFO1 500.1335009 MHz PL1 −3.00 dB P1 10.50 usec NUC1 1H

======== CHANNEL f1 ======== MCWRK 0.01500000 sec MCREST 0.00000000 sec D1 1.00000000 sec

DS 0

NS 16 SOLVENT MeOD

TD 65536 PULPROG zg30 PROBHD 5 mm Multinucl INSTRUM av500 Time 10.40 Date_ 20090615 F2 − Acquisition Parameters PROCNO 1 EXPNO 1 NAME 111TENE.C3 Current Data Parameters

6'a 6'b

-OCH 3

3' 4' 5'

2'

3

4.951 4.982

5.077 5.095

6.041 6.044

SF 125.7576139 MHz

SI 32768 F2 − Processing parameters SFO2 500.1320005 MHz PL13 22.00 dB PL12 14.68 dB PL2 −3.00 dB PCPD2 88.00 usec NUC2 1H CPDPRG2 waltz16

======== CHANNEL f2 ======== SFO1 125.7703643 MHz PL1 −1.00 dB P1 10.50 usec NUC1 13C

======== CHANNEL f1 ======== MCWRK 0.01500000 sec MCREST 0.00000000 sec DELTA 1.89999998 sec d11 0.03000000 sec D1 2.00000000 sec

DS 2

NS 128 SOLVENT CDCl3

TD 65536 PULPROG zgpg30 PROBHD 5 mm Multinucl INSTRUM av500 Time 10.44 Date_ 20090615 F2 − Acquisition Parameters PROCNO 1 EXPNO 2 NAME 111TENE.C3 Current Data Parameters

3' 2'4' 6'

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160 170

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160 170

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160 170

3' 2' 4' 10 6'

2 3

4 5

6 7

10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160

TENE.C3−MeOD−HSQC

1

1' 10b

6'a 6'b

-OCH 3

3' 4' 2'

10a 6

5'

-CH 3 3

2 3

4 5

6 7

20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180

5.0 5.5

6.0 6.5

7.0 7.5

100 105 110 115 120 125 130 135 140 145 150 155 160 165 170 175

6.0 6.2

6.4 6.6

6.8 7.0

7.2 7.4

3.0 3.5

4.0 4.5

2 3

4 5

6 7

SF 500.1300478 MHzMC2 States−TPPI

SI 1024F1 − Processing parameters

PC 1.00

GB 0

LB 0.00 HzSSB 2WDW QSINE

SF 500.1300057 MHz

SI 1024F2 − Processing parametersFnMODE States−TPPI

SW 11.000 ppmFIDRES 21.489479 HzSFO1 500.1323 MHz

TD 256ND0 1F1 − Acquisition parametersSFO1 500.1322506 MHzPL1 −3.00 dBP1 10.50 usecNUC1 1H

======== CHANNEL f1 ========ST1CNT 128MCWRK 0.75000000 secMCREST 0.00000000 secIN0 0.00018178 secD8 0.60000002 secD1 1.50000000 secd0 0.00007752 sec

DS 4

NS 32SOLVENT MeOD

TD 2048PULPROG noesyphPROBHD 5 mm MultinuclINSTRUM av500Time 14.40Date_ 20090727F2 − Acquisition ParametersPROCNO 1EXPNO 9NAME 111TENE.C3Current Data Parameters

1 1' 10b

5'

-CH 3

10a 6

1

1' 10b

6'a 6'b -OCH 3

5 9

3' 4' 2' 5' -CH 3

3

7 10a 6

3.0 3.5

4.0 4.5

5.0 5.5

SF 500.1300478 MHzMC2 States−TPPI

SI 1024F1 − Processing parameters

PC 1.00

GB 0

LB 0.00 HzSSB 2WDW QSINE

SF 500.1300057 MHz

SI 1024F2 − Processing parametersFnMODE States−TPPI

SW 11.000 ppmFIDRES 21.489479 HzSFO1 500.1323 MHz

TD 256ND0 1F1 − Acquisition parametersSFO1 500.1322506 MHzPL1 −3.00 dBP1 10.50 usecNUC1 1H

======== CHANNEL f1 ========ST1CNT 128MCWRK 0.75000000 secMCREST 0.00000000 secIN0 0.00018178 secD8 0.60000002 secD1 1.50000000 secd0 0.00007752 sec

DS 4

NS 32SOLVENT MeOD

TD 2048PULPROG noesyphPROBHD 5 mm MultinuclINSTRUM av500Time 14.40Date_ 20090727F2 − Acquisition ParametersPROCNO 1EXPNO 9NAME 111TENE.C3Current Data Parameters

1

1' 10b

6

1

1' 10b

6'a

6'b -OCH 3

5 9

3'

4' 2' 5'

7

10a 6

SF 500.1300008 MHz

SI 32768 F2 − Processing parameters SFO1 500.1335009 MHz PL1 −3.00 dB P1 10.50 usec NUC1 1H

======== CHANNEL f1 ======== MCWRK 0.01500000 sec MCREST 0.00000000 sec D1 1.00000000 sec

DS 0

NS 32 SOLVENT MeOD

TD 65536 PULPROG zg30 PROBHD 5 mm Multinucl INSTRUM av500 Time 9.29 Date_ 20090813 F2 − Acquisition Parameters PROCNO 1 EXPNO 1 NAME 111TENEC7 Current Data Parameters

3

1'

10a 10b 6'a 6'b

-OCH 3

4.462 4.493 4.555

4.702 4.718 4.733 4.749 4.794 4.843 4.898

4.990

5.072 5.090

6.043 6.045

SF 125.7576139 MHz

SI 32768 F2 − Processing parameters SFO2 500.1320005 MHz PL13 22.00 dB PL12 14.68 dB PL2 −3.00 dB PCPD2 88.00 usec NUC2 1H CPDPRG2 waltz16

======== CHANNEL f2 ======== SFO1 125.7716224 MHz PL1 −1.00 dB P1 10.50 usec NUC1 13C

======== CHANNEL f1 ======== MCWRK 0.01500000 sec MCREST 0.00000000 sec DELTA 1.89999998 sec d11 0.03000000 sec D1 2.00000000 sec

DS 2

NS 3072 SOLVENT MeOD

TD 65536 PULPROG zgpg30 PROBHD 5 mm Multinucl INSTRUM av500 Time 9.51 Date_ 20090813 F2 − Acquisition Parameters PROCNO 1 EXPNO 2 NAME 111TENEC7 Current Data Parameters

11

8

7

1' 3

1

6 5' 3' 2' 4' 6' 10

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160

20 30

40 50

60 70

80 90

100 110

120 130

140 150

160

20 30

40 50

60 70

80 90

100 110

120 130

140 150

1

6 5' 3' 2'

4'

6' 10

-OCH 3 9 4

5

2.5 3.0

3.5 4.0

4.5 5.0

5.5 6.0

6.5 7.0

SF 500.1299982 MHzMC2 QF

SI 1024F1 − Processing parameters

PC 1.40

GB 0

LB 0.00 HzSSB 0WDW SINE

SF 500.1299999 MHz

SI 1024F2 − Processing parametersFnMODE QF

SW 9.997 ppmFIDRES 31.250000 HzSFO1 500.1323 MHz

TD 256ND0 1F1 − Acquisition parametersP16 1000.00 usecGPZ2 10.00 %GPZ1 10.00 %GPY2 0.00 %GPY1 0.00 %GPX2 0.00 %GPX1 0.00 %GPNAM2 SINE.100GPNAM1 SINE.100

====== GRADIENT CHANNEL =====SFO1 500.1322506 MHzPL1 −3.00 dBP1 10.50 usecP0 10.50 usecNUC1 1H

======== CHANNEL f1 ========MCWRK 1.48689198 secMCREST 0.00000000 secIN0 0.00020000 secD16 0.00015000 secd13 0.00000400 secD1 1.48689198 secd0 0.00000300 sec

DS 8

NS 16SOLVENT MeOD

TD 2048PULPROG cosygpqfPROBHD 5 mm MultinuclINSTRUM av500Time 12.00Date_ 20090816F2 − Acquisition ParametersPROCNO 1EXPNO 5NAME 111TENEC7Current Data Parameters

1' 10a 10b 6'a 6'b

-OCH 3

3'

5' 2' 6

3

7

1 1' 10a 10b 6'a 6'b -OCH 3

5 9

3' 4' 2'

6

3 5'

2.5 3.0

3.5 4.0

4.5 5.0

5.5 6.0

40 45 50 55 60 65 70 75 80 85 90 95 100 105 110 115 120 125 130 135

TENE.C7−MeOD−HSQC

1' 10a 10b 6'a

2.5 3.0 3.5

4.0 4.5

5.0 5.5 6.0

6.5 7.0

7.5

30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190

TENE.C7−MeOD−HMBC

3

1' 10a 10b

6'a 6'b

-OCH 3

3'

5' 2' 6

3.0 3.5

4.0 4.5

100 105 110 115 120 125 130 135 140 145 150 155 160 165 170

2.6 2.8 3.0 3.2 3.4 3.6 3.8 4.0 4.2 4.4 4.6 4.8

4' 2' 6

RT [min] Area % 1.9 63628129 71.1388 2.6 25814088 28.8612

SF 500.1300008 MHz

SI 32768 F2 − Processing parameters SFO1 500.1335009 MHz PL1 −3.00 dB P1 10.50 usec NUC1 1H

======== CHANNEL f1 ======== MCWRK 0.01500000 sec MCREST 0.00000000 sec D1 1.00000000 sec

DS 0

NS 16 SOLVENT MeOD

TD 65536 PULPROG zg30 PROBHD 5 mm Multinucl INSTRUM av500 Time 11.31 Date_ 20090910 F2 − Acquisition Parameters PROCNO 1 EXPNO 1 NAME 111TENE.C10 Current Data Parameters

-CH

7

6

1 3 1'

10a 10b

6'a 6'b

-OCH 3

5 9

3'

4' 5' 4 2'

3