Assignment of Structural Elucidation

for Fourth Year Students

Prof. Nahla Ayoub

It will be submitted for the TAs in the labs next week

Wednesday 30. 11 2011

Concerning the given spectral data elucidate the structures of

the following

Compound 1
Rf-values (x 100)

UV data

lmax (nm)

H2O HOAc-15 BAW

MeOH(a) (a)+NaOAc,(b) (b)+H3BO3 (a)+AlCl3 (a)+NaOMe

(1)

67

41

38

255, 268sh
357

255, 376
360

272, 363
363

(1)

19

58

63

256, 263sh
350

273, 323sh
373

260, 302sh 276, 305sh 270, 326

309
333, 430
393

1
1

H and 13C NMR spectral data of flavonoid (1)

-----------H-6
---H-8
---------H-2
------H-5
H-6
H-1
H-2*
H-3*
H-4*
H-5*
----

13

(1)

C-2
C-3
C-4
C-5
C-6
C-7
C-8
C-9
C-10
C-1
C-2
C-3
C-4
C-5
C-6
C-1
C-2
C-3
C-4
C-5
C-6

156.4
134.0
177.6
160.8
98.0
164.7
93.7
157.4
103.6
120.4
115.4
144.8
148.5
114.4
121.0
102.8
71.6
74.0
76.49
76.49
169.7

(1)

6.2 (d, J = 2.5 Hz)

6.45 (d, J = 2.5 Hz)

7.55 (d, J = 2.55 Hz)

6.86 (d, J = 8 Hz)

7.60 (dd, J = 2.5 & 8 Hz)
5.50 (d, J = 9 Hz)

271, 350
394

272, 354,
406

Compound 2
Rf-values and UV epectral data of flavonoid (2)
Rf-values (x 100)
H2O
BAW
20

1
1

HOAc-15 MeOH(a)
52

70

259, 297sh
348

UV data

lmax (nm)

(a)+NaOAc,(b)

(b)+H3BO3

(a)+AlCl3

276, 372

272, 383

268, 352
408

H NMR data of flavonoid (2)

H-6
H-8
H-2
H-5
H-6
H-1
H-2
H-3
H-4
H-5
H-6

(2)
6.25 (d, J = 2.14 Hz)
6.46 (d, J = 2.14 Hz)
7.49 (d, J = 2.13 Hz)
6.98 (d, J = 8.12 Hz)
7.39 (dd, J = 2.13 & 8.12 Hz)
5.50 (d, J = 1.5 Hz)
4.20 (dd, J = 1.50 Hz & 3.40 Hz)
3.71 (dd, J = 8.94 Hz & 3.42 Hz)
3.32 (t, J = 8.94 Hz)
3.40 (m, 1H)
0.90 (d, J = 5.98 Hz)

(a)+NaOMe
270, 355
402

Compound 3
Rf-values and UV specral data of flavonoid (3)
Rf-values (x 100)
H2O
BAW
19

1
1

UV data

lmax (nm)

HOAc-15 MeOH(a) (a)+NaOAc,(b) (b)+H3BO3 (a)+AlCl3 (a)+NaOMe

38

60

258, 267*,
356

256, 374,
362

H NMR data of flavonoid (3)

H-6
H-8
H-2
H-5
H-6
H-1
H-2.-.H-6

(3)
6.20 (d, J = 2.5 Hz)
6.45 (d, J = 2.5 Hz
7.57 (m))
6.84 (d, J = 8. Hz)
7.57 (m)
5.52 (d, J = 8 Hz)
3.20 - 3.70 (m)

265*, 272,
380, 420**

263,
430

275,
470

Compound 4 and 5
Rf-values and UV specral data of flavonoid (4)and its aglycone , (5)
Rf-values (x 100)
H2O
BAW

UV data

lmax (nm)

HOAc-15 MeOH(a) (a)+NaOAc,(b) (b)+H3BO3 (a)+AlCl3 (a)+NaOMe

(4)

20

42

68

267,
353

268,
355

271,
355

272,
408

275, 310,
402

(5)

02

04

79

253sh, 266
322sh, 367

272,
387

276, 297sh
320sh, 372

260, 269
350, 424

278,
416,(dec)

1
1

H NMR data of flavonoid (4)

H-6
H-8
H-2, H-6
H-3, H-5
H-1
H-2.-.H-6

(4)
6.24 (d, J = 2.5 Hz)
6.44 (d, J = 2.5 Hz
8.08 (d, J = 8 Hz)
6.92 (d, J = 8. Hz)
5.44 (d, J = 7.50 Hz)
3.20 - 3.70 (m)

Compound (6)
Rf-values and UV specral data of flavonoid (6), its aglycone (6)
Rf-values (x 100)

UV data

lmax (nm)

H2O HOAc-15 BAW MeOH(a) (a)+NaOAc,(b) (b)+H3BO3 (a)+AlCl3 (a)+NaOMe

(6)

39

67

41

253, 265 sh
355

253,265 sh,
355, 420 sh

254,
357

(6)

01

02

68

253, 267sh
326, 370

260sh, 274
320, 393

255, 270sh 264, 304sh

320, 377 361, 431

1
1

269, 300 sh,

370 sh, 405

H and 13C-NMR data of flavonoid (6)

-----------H-6
---H-8
---------H-2
------H-5
H-6
3-OCH3

6.46 (d, J = 2.5 Hz)

6.85 (d, J = 2.5 Hz)

7.95 (d, J = 8 Hz)

6.95 (d, J = 8 Hz)

7.57 (d, J = 8 Hz)
3.84 (d, J = 6 Hz)

H of glucose
H-1
H-2*
H-3*
H-4*
H-5*
H-6*

13

(6)

C-2
C-3
C-4
C-5
C-6
C-7
C-8
C-9
C-10
C-1
C-2
C-3
C-4
C-5
C-6
3-OCH3

155.97
133.32
177.60
160.90
98.50
161.60
95.00
156.76
105.90
120.90
113.80
149.63
146.95
115.50
122.30
56.00

(6)

13

C of glucose
C-1
C-2
C-3
C-4
C-5
C-6

5.58 (d, J = 8 Hz)

101.8
74.50
77.50
69.90
76.20
60.80

270,
415
240sh, 271
328, 435

H of Rhamnose
H-1*
H-2*
H-3*
H-4*
H-5*
H-6*

13

C of Rhamnose
C-1
C-2
C-3
C-4
C-5
C-6

5.55 (s, Dn1/2 = 4 Hz)

1.12 (d, J = 6 Hz)

99.70
69.90
69.90
72.80
69.90
18.5

Compound (7)
Rf-values and UV specral data of flavonoid (7)
Rf-values (x 100)
H2O
BAW
10
1
1

UV data

HOAc-15 MeOH(a)
25

74

269,
333

lmax (nm)
(a)+NaOAc,(b)
267, 355
385

H-NMR spectral data of flavonid (7)

H-3
H-6
H-8
H-2, H-6
H-3, H-5
H-1
H-2.-.H-6

(7)
6.88 (s)
6.42 (d, J = 2.5 Hz)
6.81 (d, J = 2.5 Hz
7.94 (d, J = 8 Hz)
6.94 (d, J = 8. Hz)
5.05 (d, J = 7.50 Hz)
3.15- 3.50 (m)

(b)+H3BO3

(a)+AlCl3

268,
337

275, 303,
345, 385

(a)+NaOMe
270.
389

Compound (8)
Rf-values and UV specral data of flavonoid (8)
Rf-values (x 100)
H2O
BAW
08
1
1

UV data

HOAc-15 MeOH(a)
18

54

255, 267*
346

lmax (nm)
(a)+NaOAc,(b)

(b)+H3BO3

259, 265*,
360, 398

260, 370,

H NMR data of flavonoid (8)

H-3
H-6
H-8
H-2
H-5
H-6
H-1
H-2.-.H-6

(8)
6.88 (s)
6.44 (d, J = 2.5 Hz)
6.81 (d, J = 2.5 Hz)
7.50 (d, J = 2.5 Hz)
6.94 (d, J = 8. Hz)
7.45 (dd, J = 8 Hz & J = 2.5 Hz)
5.10 (d, J = 7.50 Hz)
3.30- 3.80 (m )

(a)+AlCl3
272, 300*,
330, 430

(a)+NaOMe
264, 300
3 98