論文目次 |
中文摘要 .......................................................................................................... i
英文摘要 ........................................................................................................ iii
謝誌 ................................................................................................................ v
目錄 ................................................................................................................ vi
圖目錄 .......................................................................................................... xvi表目錄 ......................................................................................................... xvii
縮寫對照表 ................................................................................................ xviii
一、 緒 論 ..................................................................................................... 1
二、 結 果 ..................................................................................................... 7
2-1 合成新化合物N-Benzyl-β-amino Alcohols 13a .......................... 7
2-2 合成新化合物N-Benzyl-β-amino Alcohols 13b與13c ............... 9
2-3 合成新化合物3-Isopropyl-5-(naphthalen-1-yloxy)methyl-
1,3-thiazolidine-2-thione (17) ..................................................... 11
2-4 合成新化合物Thiazolidine-2-thiones 18a–c與
Oxazolidine-2-thiones 19a–c ...................................................... 12
2-5 合成烯類化合物1-(Allyloxy)naphtalene (20) ........................... 13
2-6 合成烯類化合物2-Methyl-3-(4-benzyloxy)phenylpropene (21a)
與2-Phenyl-1-butene (21b) ........................................................ 14
2-7 合成新化合物2-(Hydroxymethyl)indolines 24a–d ................... 16
2-8 合成新化合物9,9a-Dihydro-1H-thiazolo[3,4-a]indole-3-thiones
25a–d ...................................................................................... 18
2-9 合成新化合物3-(2-Allylphenyl)-1,3-benzothiazol-2-ones
26a–d與[N-(2-Allylphenyl)-2-imino]-l,3-benzodithioles
27a–d ...................................................................................... 20
三、 討 論 ................................................................................................... 22
3-1 探討胺基醇β碳上之取代基數目對於反應的影響 ................. 22
3-2 探討胺基醇β碳為 4 級碳時對於反應的影響 ..................... 23
3-2-1 取代基大小所影響的產率結果 ...................................... 23
3-2-2 由分子模擬輔助探討反應機構 ...................................... 26
3-2-3 胺基醇類化合物中β碳具有四取代基之反應機構 ........ 29
3-3 探討 Thiazolidine-2-thiones 四號位置具不同數目之取代基
與苯炔反應情形 ............................................................. 30
3-4 探討電子效應對合成Thiazolo[3,4-a]indole-3-thiones 25之
影響 ........................................................................................... 32
3-5 Thiazolidine-2-thiones與苯炔反應的兩種途徑 ....................... 33
四、 結 論 ................................................................................................... 36
五、 實 驗 部 分 ....................................................................................... 38
2-Benzylamino-3-[4-(benzyloxy)phenyl]-2-methylpropanol (13a) ..... 39
2-Benzylamino-2-phenylbutanol (13b) ................................................ 40
2-Benzylamino-2,2-diphenylethanol (13c) .......................................... 41
3-Isopropyl-5-(naphthalen-1-yloxy)methyl-1,3-thiazolidine-
2-thione (17) ................................................................................... 42
3-Benzyl-4-[4-(benzyloxy)benzyl]-4-methyl-1,3-thiazolidine-
2-thione (18a) ................................................................................. 43
3-Benzyl-4-[4-(benzyloxy)benzyl]-4-methyl-1,3-oxazolidine-
2-thione (19a) ................................................................................. 43
3-Benzyl-4-ethyl-4-phenyl-1,3-thiazolidine-2-thione (18b) ................ 44
3-Benzyl-4-ethyl-4-phenyl-1,3-oxazolidine-2-thione (19b) ................ 44
3-Benzyl-4,4-diphenyl-1,3-oxazolidine-2-thione (19c) ....................... 45
2-Hydroxymethyl-5-methoxyindoline (24a) ........................................ 46
2-Hydroxymethyl-5-methylindoline (24b) ........................................... 46
2-Hydroxymethyl-5-chloroindoline (24c) ............................................ 47
2-Hydroxymethyl-5-fluoroindoline (24d) ............................................ 47
9,9a-Dihydro-7-methoxy-1H-thiazolo[3,4-a]indole-3-thione (25a) .... 48
9,9a-Dihydro-7-methyl-1H-thiazolo[3,4-a]indole-3-thione (25b) ....... 49
7-Chloro-9,9a-dihydro-1H-thiazolo[3,4-a]indole-3-thione (25c) ........ 49
9,9a-Dihydro-7-fluoro-1H-thiazolo[3,4-a]indole-3-thione (25d) ........ 50
1-(Allyloxy)naphthalene (20) ............................................................... 51
2-Methyl-3-(4-benzyloxy)phenylpropene (21a) .................................. 51
2-Phenyl-1-butene (21b) ...................................................................... 52
3-(2-Allyl-4-methoxyphenyl)-1,3-benzothiazol-2-one (26a) ............... 52
[N-(2-Allyl-4-methoxyphenyl)]-2-imino-l,3-benzodithiole (27a) ....... 52
3-(2-Allyl-4-methylphenyl)-1,3-benzothiazol-2-one (26b) ................. 53
[N-(2-Allyl-4-methylphenyl)]-2-imino-l,3-benzodithiole (27b) .......... 53
3-(2-Allyl-4-chlorophenyl)-1,3-benzothiazol-2-one (26c) ................... 54
[N-(2-Allyl-4-chlorophenyl)]-2-imino-l,3-benzodithiole (27c) ........... 54
3-(2-Allyl-4-fluorophenyl)-1,3-benzothiazol-2-one (26d) .................. 55
[N-(2-Allyl-4-fluorophenyl)]-2-imino-l,3-benzodithiole (27d) ........... 55
Methyl 3-[4-(Benzyloxy)phenyl]-2-[tert-butoxycarbonyl)amino]-
2-methylpropanoate (11) ................................................................ 56
tert-Butyl 3-[4-(Benzyloxy)phenyl]-1-hydroxy-2-methylpropan-
2-ylcarbamate (12) ......................................................................... 56
六、 參 考 文 獻 ....................................................................................... 58
七、 光 譜 ................................................................................................... 61
2-Benzylamino-3-[4-(benzyloxy)phenyl]-2-methylpropanol (13a)
1H NMR spectrum .......................................................................... 62
2-Benzylamino-3-[4-(benzyloxy)phenyl]-2-methylpropanol (13a)
13C NMR spectrum ......................................................................... 62
2-Benzylamino-3-[4-(benzyloxy)phenyl]-2-methylpropanol (13a)
IR spectrum .................................................................................... 63
2-Benzylamino-2-phenylbutanol (13b) 1H NMR spectrum ................. 63
2-Benzylamino-2-phenylbutanol (13b) 13C NMR spectrum ................ 64
2-Benzylamino-2-phenylbutanol (13b) IR spectrum ........................... 64
2-Benzylamino-2,2-diphenylethanol (13c) 1H NMR spectrum ........... 65
2-Benzylamino-2,2-diphenylethanol (13c) 13C NMR spectrum .......... 65
2-Benzylamino-2,2-diphenylethanol (13c) IR spectrum ...................... 66
3-Isopropyl-5-(naphthalen-1-yloxy)methyl-1,3-thiazolidine-
2-thione (17) 1H NMR spectrum .................................................... 66
3-Isopropyl-5-(naphthalen-1-yloxy)methyl-1,3-thiazolidine-
2-thione (17) 13C NMR spectrum ................................................... 67
3-Isopropyl-5-(naphthalen-1-yloxy)methyl-1,3-thiazolidine-
2-thione (17) IR spectrum .............................................................. 67
3-Benzyl-4-[4-(benzyloxy)benzyl]-4-methyl-1,3-thiazolidine-
2-thione (18a) 1H NMR spectrum .................................................. 68
3-Benzyl-4-[4-(benzyloxy)benzyl]-4-methyl-1,3-thiazolidine-
2-thione (18a) 13C NMR spectrum ................................................. 68
3-Benzyl-4-[4-(benzyloxy)benzyl]-4-methyl-1,3-thiazolidine-
2-thione (18a) IR spectrum ............................................................ 69
3-Benzyl-4-[4-(benzyloxy)benzyl]-4-methyl-1,3-oxazolidine-
2-thione (19a) 1H NMR spectrum ................................................... 69
3-Benzyl-4-[4-(benzyloxy)benzyl]-4-methyl-1,3-oxazolidine-
2-thione (19a) 13C NMR spectrum ................................................. 70
3-Benzyl-4-[4-(benzyloxy)benzyl]-4-methyl-1,3-oxazolidine-
2-thione (19a) IR spectrum ............................................................. 70
3-Benzyl-4-ethyl-4-phenyl-1,3-thiazolidine-2-thione (18b)
1H NMR spectrum .......................................................................... 71
3-Benzyl-4-ethyl-4-phenyl-1,3-thiazolidine-2-thione (18b)
13C NMR spectrum ......................................................................... 71
3-Benzyl-4-ethyl-4-phenyl-1,3-thiazolidine-2-thione (18b)
IR spectrum .................................................................................... 72
3-Benzyl-4-ethyl-4-phenyl- 1,3-oxazolidine-2-thione (19b)
1H NMR spectrum .......................................................................... 72
3-Benzyl-4-ethyl-4-phenyl- 1,3-oxazolidine-2-thione (19b)
13C NMR spectrum ......................................................................... 73
3-Benzyl-4-ethyl-4-phenyl- 1,3-oxazolidine-2-thione (19b)
IR spectrum .................................................................................... 73
3-Benzyl-4,4-diphenyl-1,3-oxazolidine-2-thione (19c)
1H NMR spectrum .......................................................................... 74
3-Benzyl-4,4-diphenyl-1,3-oxazolidine-2-thione (19c)
13C NMR spectrum ......................................................................... 74
3-Benzyl-4,4-diphenyl-1,3-oxazolidine-2-thione (19c)
IR spectrum .................................................................................... 75
2-Hydroxymethyl-5-methoxyindoline (24a) 1H NMR spectrum ......... 75
2-Hydroxymethyl-5-methoxyindoline (24a) 13C NMR spectrum ........ 76
2-Hydroxymethyl-5-methoxyindoline (24a) IR spectrum ................... 76
2-Hydroxymethyl-5-methylindoline (24b) 1H NMR spectrum ........... 77
2-Hydroxymethyl-5-methylindoline (24b) 13C NMR spectrum .......... 77
2-Hydroxymethyl-5-methylindoline (24b) IR spectrum ...................... 78
2-Hydroxymethyl-5-chloroindoline (24c) 1H NMR spectrum ............. 78
2-Hydroxymethyl-5-chloroindoline (24c) 13C NMR spectrum ............ 79
2-Hydroxymethyl-5-chloroindoline (24c) IR spectrum ....................... 79
2-Hydroxymethyl-5-fluoroindoline (24d) 1H NMR spectrum ............. 80
2-Hydroxymethyl-5-fluoroindoline (24d) 13C NMR spectrum ............ 80
2-Hydroxymethyl-5-fluoroindoline (24d) IR spectrum ....................... 81
9,9a-Dihydro-7-methoxy-1H-thiazolo[3,4-a]indole-3-thione (25a)
1H NMR spectrum .......................................................................... 81
9,9a-Dihydro-7-methoxy-1H-thiazolo[3,4-a]indole-3-thione (25a)
13C NMR spectrum ......................................................................... 82
9,9a-Dihydro-7-methoxy-1H-thiazolo[3,4-a]indole-3-thione (25a)
IR spectrum .................................................................................... 82
9,9a-Dihydro-7-methyl-1H-thiazolo[3,4-a]indole-3-thione (25b)
1H NMR spectrum .......................................................................... 83
9,9a-Dihydro-7-methyl-1H-thiazolo[3,4-a]indole-3-thione (25b)
13C NMR spectrum ......................................................................... 83
9,9a-Dihydro-7-methyl-1H-thiazolo[3,4-a]indole-3-thione (25b)
IR spectrum .................................................................................... 84
7-Chloro-9,9a-dihydro-1H-thiazolo[3,4-a]indole-3-thione (25c)
1H NMR spectrum .......................................................................... 84
7-Chloro-9,9a-dihydro-1H-thiazolo[3,4-a]indole-3-thione (25c)
13C NMR spectrum ......................................................................... 85
7-Chloro-9,9a-dihydro-1H-thiazolo[3,4-a]indole-3-thione (25c)
IR spectrum .................................................................................... 85
9,9a-Dihydro-7-fluoro-1H-thiazolo[3,4-a]indole-3-thione (25d)
1H NMR spectrum .......................................................................... 86
9,9a-Dihydro-7-fluoro-1H-thiazolo[3,4-a]indole-3-thione (25d)
13C NMR spectrum ......................................................................... 86
9,9a-Dihydro-7-fluoro-1H-thiazolo[3,4-a]indole-3-thione (25d)
IR spectrum .................................................................................... 87
1-(Allyloxy)naphtalene (20) 1H NMR spectrum .................................. 87
1-(Allyloxy)naphtalene (20) 13C NMR spectrum ................................. 88
2-Methyl-3-(4-benzyloxy)phenylpropene (21a) 1H NMR spectrum ... 88
2-Methyl-3-(4-benzyloxy)phenylpropene (21a) 13C NMR spectrum .. 89
2-Methyl-3-(4-benzyloxy)phenylpropene (21a) IR spectrum ............. 89
2-Phenyl-1-butene (21b) 1H NMR spectrum ....................................... 90
3-(2-Allyl-4-methoxyphenyl)-1,3-benzothiazol-2-one (26a)
1H NMR spectrum .......................................................................... 90
3-(2-Allyl-4-methoxyphenyl)-1,3-benzothiazol-2-one (26a)
13C NMR spectrum ......................................................................... 91
3-(2-Allyl-4-methoxyphenyl)-1,3-benzothiazol-2-one (26a)
IR spectrum .................................................................................... 91
[N-(2-Allyl-4-methoxyphenyl)]-2-imino-l,3-benzodithiole (27a)
1H NMR spectrum .......................................................................... 92
[N-(2-Allyl-4-methoxyphenyl)]-2-imino-l,3-benzodithiole (27a)
13C NMR spectrum ......................................................................... 92
N-(2-Allyl-4-methoxyphenyl)]-2-imino-l,3-benzodithiole (27a)
IR spectrum .................................................................................... 93
3-(2-Allyl-4-methylphenyl)-1,3-benzothiazol-2-one (26b)
1H NMR spectrum .......................................................................... 93
3-(2-Allyl-4-methylphenyl)-1,3-benzothiazol-2-one (26b)
13C NMR spectrum ......................................................................... 94
3-(2-Allyl-4-methylphenyl)-1,3-benzothiazol-2-one (26b)
IR spectrum .................................................................................... 94
[N-(2-Allyl-4-methylphenyl)]-2-imino-l,3-benzodithiole (27b)
1H NMR spectrum .......................................................................... 95
[N-(2-Allyl-4-methylphenyl)]-2-imino-l,3-benzodithiole (27b)
13C NMR spectrum ......................................................................... 95
[N-(2-Allyl-4-methylphenyl)]-2-imino-l,3-benzodithiole (27b)
IR spectrum .................................................................................... 96
3-(2-Allyl-4-chlorophenyl)-1,3-benzothiazol-2-one (26c)
1H NMR spectrum .......................................................................... 96
3-(2-Allyl-4-chlorophenyl)-1,3-benzothiazol-2-one (26c)
13C NMR spectrum ......................................................................... 97
3-(2-Allyl-4-chlorophenyl)-1,3-benzothiazol-2-one (26c)
IR spectrum .................................................................................... 97
[N-(2-Allyl-4-chlorophenyl)]-2-imino-l,3-benzodithiole (27c)
1H NMR spectrum .......................................................................... 98
[N-(2-Allyl-4-chlorophenyl)]-2-imino-l,3-benzodithiole (27c)
13C NMR spectrum ......................................................................... 98
[N-(2-Allyl-4-chlorophenyl)]-2-imino-l,3-benzodithiole (27c)
IR spectrum .................................................................................... 99
3-(2-Allyl-4-fluorophenyl)-1,3-benzothiazol-2-one (26d)
1H NMR spectrum .......................................................................... 99
3-(2-Allyl-4-fluorophenyl)-1,3-benzothiazol-2-one (26d)
13C NMR spectrum ....................................................................... 100
3-(2-Allyl-4-fluorophenyl)-1,3-benzothiazol-2-one (26d)
IR spectrum .................................................................................. 100
[N-(2-Allyl-4-fluorophenyl)]-2-imino-l,3-benzodithiole (27d)
1H NMR spectrum ........................................................................ 101
[N-(2-Allyl-4-fluorophenyl)]-2-imino-l,3-benzodithiole (27d)
13C NMR spectrum ....................................................................... 101
[N-(2-Allyl-4-fluorophenyl)]-2-imino-l,3-benzodithiole (27d)
IR spectrum .................................................................................. 102
Methyl 3-[4-(Benzyloxy)phenyl]-2-[tert-butoxycarbonyl)amino]-
2-methylpropanoate (11) 1H NMR spectrum ............................... 102
Methyl 3-(4-(Benzyloxy)phenyl)-2-[tert-butoxycarbonyl)amino]-
2-methylpropanoate (11) 13C NMR spectrum .............................. 103
Methyl 3-(4-(Benzyloxy)phenyl)-2-[tert-butoxycarbonyl)amino]-
2-methylpropanoate (11) IR spectrum .......................................... 103
tert-Butyl 3-[4-(Benzyloxy)phenyl]1-hydroxy-2-methylpropan-
2-ylcarbamate (12) 1H NMR spectrum ......................................... 104
tert-Butyl 3-[4-(Benzyloxy)phenyl]1-hydroxy-2-methylpropan-
2-ylcarbamate (12) 13C NMR spectrum ........................................ 104
tert-Butyl 3-[4-(Benzyloxy)phenyl]1-hydroxy-2-methylpropan-
2-ylcarbamate (12) IR spectrum ................................................... 105
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