探討β胺醇之α碳上立體障礙與電子效應對苯炔誘導形成碳與碳雙鍵反應之影響

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張軒愷(Shiuan-kai Chang) 查詢紙本館藏

畢業系所

化學學系

論文名稱

探討β胺醇之α碳上立體障礙與電子效應對苯炔誘導形成碳與碳雙鍵反應之影響
(Steric and Electronic Effects around the α-Carbon on β-Amino Alcohols in the Benzyne-Induced Olefination)

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摘要(中)

由本實驗室所開發的烯類化合物之新型合成途徑：以β-amino alcohols作為起始物，在鹼性環境下加入二硫化碳進行合環反應，形成中間產物1,3-thiazolidine-2-thiones，再由氟化銫和2-(trimethylsilyl)phenyl trifluoromethanesulfonate生成的苯炔進行[3 + 2]加成反應，開環脫去副產物N-benzyl-2-imino-1,3-benzodithioles後，即可生成具有高度立體專一性之碳與碳雙鍵產物。羥基的位向、不同取代基、立體障礙、電子效應關係著二硫化碳進行分子內親核取代反應之反應性，進而影響生成1,3-thiazolidine-2-thione之產率。實驗室過去的初期研究，僅止於利用β-amino alcohol羥基之碳原子上為沒有取代基或是單取代苯基和甲基兩種基團進行此新型烯化反應，在此特別設計各式不同型態之β-amino alcohols以利增加此烯化反應的應用性與廣泛度，並探討各種效應對於反應之影響。
　　本論文於β-amino alcohols連接羥基之碳原子上，置換上九種不同型態的官能基團，雙取代有雙甲基及雙苯甲基，單取代基有苯甲基、乙烯基、正戊烷基、異丙基、methoxyphenyl、chlorophenyl、及phenol官能基團，對此九種官能基團進行本實驗的雙鍵合成探討，並做出結論。

摘要(英)

A new, stereospecific olefin synthesis from β-Amino alcohols: β-Amino alcohols was treated with CS2 in acetonitrile to produce 1,3-thiazolidine-2-thiones. 1,3-Thiazolidine-2-thiones was then added to a solution of 2-(trimethylsilylphenyl) trifluoromethanesulfonate and CsF in acetonitrile at room temperature. This would make [3 + 2] cycloaddition to give olefin products, along with side product N-benzyl-2-imino-1,3-benzodithioles. There are various factors like stereospecificity, hinderance of substituents, and electronic repulsion effect the olefination reaction.
　　In the early stages of research, we carried out olefination reaction by use of no substitute and single substitute like phenyl and methyl groups. My research project focused on study of olefination pathway by use of different substituent groups. We used various functional groups like benzyl, vinyl, n-hexyl, isopropyl, methoxyphenyl, chlorophenyl, and phenol, which were attached to the α-carbon on β-amino alcohols.
　　Finally in our laboratory we successfully synthesized eight olefin compounds by use of β-amino alcohols with various functional groups.　Overall yield of olefination products indicated benzyne-induced olefination applicable in the all no substitute and single substitute around the α-carbon on β-amino alcohols.

關鍵字(中)

★ 雙鍵合成

關鍵字(英)

★ carbon-carbon double bond

論文目次

中文摘要 i
英文摘要 iii
謝　誌 iv
縮寫對照表 v
目　錄 vi
圖　目　錄 xv
表　目　錄 xv
一、緒論（Introduction） 1
二、結果（Results） 8
2-1 製備α位置雙取代官能基之β-Amino Alcohols起始物 (4a and 4b) 8
2-2 製備α碳上單取代官能基之β-Amino Alcohols化合物 (9a–d) 9
2-3 製備α碳上單取代官能基之β-Amino Alcohols化合物 (9e and 9f) 10
2-4 利用苯炔誘導烯化反應合成二取代與三取代之烯類化合物(11a–f, 14, and 22) 12
三、討論（Discussion） 16
3-1　利用NMR判定化合物 11a–f 之結構及其立體位向之確認 16
3-2　α碳上單取代官能基之β-Amino Alcohols進行Olefination反應，合成雙取代烯類之立體障礙探討 18
3-3　α碳上具有單取代苯甲基之β-Amino Alcohol進行Olefination反應，合成雙取代烯類之雙鍵位移探討 20
3-4　α碳上具有單取代乙烯基之β-Amino Alcohol進行Olefination，合成出共軛烯類化合物之探討 20
3-5　應用α碳上具有單取代之p-Methoxyphenyl或p-Chlorophenyl Groups之β-Amino Alcohols進行Olefination，探討合成雙取代烯類化合物時，電子效應之影響 22
3-6　α碳上雙取代與三取代官能基之β-Amino Alcohols進行Olefination，合成雙取代以及三取代烯類之立體障礙探討 23
3–7　β-Amino Alcohol帶有可與苯炔反應之官能基進行Olefination之探討 27
3–8　具各種不同取代基之β-Amino Alcohols與苯炔進行Olefination兩部反應總產率探討 28
3–9　嘗試將β-Amino Alcohols轉換成Azides中間體 30
3–10　嘗試將β-Amino Alcohols轉換成β-Chloro Amines中間體 31
四、結論（Conclusion） 32
五、實驗部分（Experimental Section） 34
(S)-3-Amino-2-methyl-4-phenylbutan-2-ol (3a) 37
(S)-3-Amino-2-benzyl-1,4-diphenylbutan-2-ol (3b) 37
(S)-3-Benzylamino-2-methyl-4-phenylbutan-2-ol (4a) 38
(S)-2-Benzyl-3-benzylamino-1,4-diphenyl-butan-2-ol (4b) 39
(S)-2-[N-(tert-Butoxycarbonyl)amino]-1-phenylnonan-3-one (7a) 40
(S)-3-[N-(tert-Butoxycarbonyl)amino]-1,4-diphenylbutan-2-one (7b) 41
(S)-4-[N-(tert-Butoxycarbonyl)amino]-3-oxo-5-phenyl-pent-1-ene (7c) 41
(S)-2-[N-(tert-Butoxycarbonyl)amino]-4-methyl-1-phenylpentan-3-one (7d) 42
(S)-2-[N-(tert-Butoxycarbonyl)amino]-1-(4-methoxyphenyl)-3-
phenylpropan-1-one (7e) 43
(S)-2-[N-(tert-Butoxycarbonyl)amino]-1-(4-chlorophenyl)-3-
phenylpropan-1-one (7f) 44
(2S,3R)-2-[N-(tert-Butoxycarbonyl)amino]-1-phenylnonan-3-ol (8a) 44
(2R,3S)-3-[N-(tert-Butoxycarbonyl)amino]-1,4-diphenyl-butan-2-ol
(8b) 45
(4S)-4-[N-(tert-Butoxycarbonyl)amino]-5-phenylpent-1-en-3-ol (8c) 46
(2S,3R)-2-[N-(tert-Butoxycarbonyl)amino]-4-methyl-1-phenylpentan-3-ol (8d) 46
(2S)-1-[N-(tert-Butoxycarbonyl)amino]-1-(4-methoxyphenyl)-3-
phenylpropan-1-ol (8e) 47
(2S)-2-N-(tert-Butoxycarbonyl)amino]-1-(4-chlorophenyl)-3-
phenylpropan-1-ol (8f) 48
(2S,3R)-2-Benzylamino-1-phenylnonan-3-ol (9a) 49
(2S,3R)-3-Benzylamino-1,4-diphenylbutan-2-ol (9b) 49
(S)-4-Benzylamino-5-phenylpent-1-en-3-ol (9c) 50
(2S,3R)-2-Benzylamino-4-methyl-1-phenylpentan-3-ol (9d) 51
(1S,2S)-2-Benzylamino-1-(4-methoxyphenyl)-3-phenylpropan-1-ol (9e) 52
(1S,2S)-2-Benzylamino-1-(4-chlorophenyl)-3-phenylpropan-1-ol (9f) 53
(4S,5S)-3,4-Dibenzyl-5-hexylthiazolidine-2-thione (10a) 54
(4S,5S)-3,4,5-Tribenzyl-1,3-thiazolidine-2-thione (10b) 55
(4S)-3,4-Dibenzyl-5-vinylthiazolidine-2-thione (10c) 56
(4S,5S)-3,4-Dibenzyl-5-isopropyl-1,3-thiazolidine-2-thione (10d) 57
(4S,5R)-3,4-Dibenzyl-5-(4-methoxyphenyl)thiazolidine-2-thione (10e) and (4S,5R)-3,4-Dibenzyl-5-(4-methoxyphenyl)oxazolidine-2-thione (12) 58
(4S,5R)-3,4-Dibenzyl-5-(4-chlorophenyl)thiazolidine-2-thione (10f) and (4S,5R)-3,4-Dibenzyl-5-(4-chlorophenyl)oxazolidine-2-thione (13) 59
trans-1-Phenylnon-2-ene (11a) 60
trans-1,4-Diphenyl-2-butene (11b) 61
trans-5-Phenylpenta-1,3-diene (11c) 61
trans-4-Methyl-1-phenylpentan-2-ene (11d) 62
cis-1-(4-Methoxyphenyl)-3-phenylprop-2-ene (11e) 62
cis-1-(4-Chlorophenyl)-3-phenylprop-1-ene (11f) and trans-1-(4-Chlorophenyl)-3-phenylprop-1-ene (14) 63
(S)-3,4-Dibenzyl-5,5-dimethylthiazolidine-2-thione (15) and (S)-3,4-Dibenzyl-5,5- dimethyloxazolidine-2-thione (16) 64
3-Methyl-1-phenyl-penta-2-ene (17) 65
(S)-3,4,5,5-Tetrabenzyloxazolidine-2-thione (18) 66
(5S)-5-(3-Hydroxyphenyl)-3-methylthiazolidine-2-thione (21) 67
1-Phenoxy-3-vinylbenzene (22) 67
六、參考文獻（Reference） 69
七、光譜 72
(S)-3-Benzylamino-2-methyl-4-phenylbutan-2-ol (4a)
1H NMR spectrum 73
(S)-3-Benzylamino-2-methyl-4-phenylbutan-2-ol (4a)
13C NMR spectrum 73
(S)-3-Benzylamino-2-methyl-4-phenylbutan-2-ol (4a)
IR spectrum 74
(S)-2-Benzyl-3-benzylamino-1,4-diphenyl-butan-2-ol (4b)
1H NMR spectrum 74
(S)-2-Benzyl-3-benzylamino-1,4-diphenyl-butan-2-ol (4b)
13C NMR spectrum 75
(S)-2-Benzyl-3-benzylamino-1,4-diphenyl-butan-2-ol (4b)
IR spectrum 75
(S)-4-[N-(tert-Butoxycarbonyl)amino]-1-phenylnonan-3-one (7a) 1H NMR spectrum 76
(S)-4-[N-(tert-Butoxycarbonyl)amino]-1-phenylnonan-3-one (7a)
13C NMR spectrum 76
(S)-4-[N-(tert-Butoxycarbonyl)amino]-1-phenylnonan-3-one (7a)
IR spectrum 77
(S)-2-[N-(tert-Butoxy)carbonyl)amino]-4-methyl-1-phenylpentan-3-one (7d) 1H NMR spectrum 77
(S)-2-[N-(tert-Butoxy)carbonyl)amino]-4-methyl-1-phenylpentan-3-one (7d) 13C NMR spectrum 78
(S)-2-[N-(tert-Butoxycarbonyl)amino]-4-methyl-1-phenylpentan-3-one (7d) IR spectrum 78
(S)-2-[N-(tert-Butoxycarbonyl)amino]-1-(4-methoxyphenyl)-3-phenylpropan-1- one (7e) 1H NMR spectrum 79
(S)-2-[N-(tert-Butoxycarbonyl)amino]-1-(4-methoxyphenyl)-3-phenylpropan-1- one (7e) 13C NMR spectrum 79
(S)-2-[N-(tert-Butoxycarbonyl)amino]-1-(4-methoxyphenyl)-3-phenylpropan-1- one (7e) IR spectrum 80
(S)-2-[N-(tert-Butoxycarbonyl)amino]-1-(4-chlorophenyl)-3-phenylpropan-1-one (7f) 1H NMR spectrum 80
(S)-2-[N-(tert-Butoxycarbonyl)amino]-1-(4-chlorophenyl)-3-phenylpropan-1-one (7f) 13C NMR spectrum 81
(S)-2-[N-(tert-Butoxycarbonyl)amino]-1-(4-chlorophenyl)-3-phenylpropan-1-one (7f) IR spectrum 81
(2S,3R)-2-[N-(tert-Butoxycarbonyl)amino]-1-phenylnonan-3-ol (8c)
1H NMR spectrum 82
(2S,3R)-2-[N-(tert-Butoxycarbonyl)amino]-1-phenylnonan-3-ol (8c)
13C NMR spectrum 82
(2S,3R)-2-[N-(tert-Butoxycarbonyl)amino]-1-phenylnonan-3-ol (8c)
IR spectrum 83
(2S,3R)-2-[N-(tert-Butoxycarbonyl)amino]-4-methyl-1-phenylpentan-3-ol (8d) 1H NMR spectrum 83
(2S,3R)-2-[N-(tert-Butoxycarbonyl)amino]-4-methyl-1-phenylpentan-3-ol (8d) 13C NMR spectrum 84
(2S,3R)-2-[N-(tert-Butoxycarbonyl)amino]-4-methyl-1-phenylpentan-3-ol (8d) IR spectrum 84
(2S)-2-[N-(tert-Butoxycarbonyl)amino]-1-(4-methoxyphenyl)-3-phenylpropan-1-ol (8e) 1H NMR spectrum 85
(2S)-2-[N-(tert-Butoxycarbonyl)amino]-1-(4-methoxyphenyl)-3-phenylpropan-1-ol (8e) 13C NMR spectrum 85
(2S)-2-[N-(tert-Butoxycarbonyl)amino]-1-(4-methoxyphenyl)-3-phenylpropan-1-ol (8e) IR spectrum 86
(2S)-2-[N-(tert-Butoxycarbonyl)amino]-1-(4-chlorophenyl)-3-phenylpropan-1-ol (8f) 1H NMR spectrum 86
(2S)-2-[N-(tert-Butoxycarbony)lamino]-1-(4-chlorophenyl)-3-phenylpropan-1-ol (8f) 13C NMR spectrum 87
(2S)-2-[N-(tert-Butoxycarbonyl)amino]-1-(4-chlorophenyl)-3-phenylpropan-1-ol (8f) IR spectrum 87
(2S,3R)-2-Benzylamino-1-phenylnonan-3-ol (9a)
1H NMR spectrum 88
(2S,3R)-2-Benzylamino-1-phenylnonan-3-ol (9a)
13C NMR spectrum 88
(2S,3R)-2-Benzylamino-1-phenylnonan-3-ol (9a)
IR spectrum 89
(2S,3R)-3-Benzylamino-1,4-diphenylbutan-2-ol (9b)
1H NMR spectrum 89
(2S,3R)-3-Benzylamino-1,4-diphenylbutan-2-ol (9b)
13C NMR spectrum 90
(2S,3R)-3-Benzylamino-1,4-diphenylbutan-2-ol (9b)
IR spectrum 90
(2S,3R)-2-Benzylamino-4-methyl-1-phenylpentan-3-ol (9d)
1H NMR spectrum 91
(2S,3R)-2-Benzylamino-4-methyl-1-phenylpentan-3-ol (9d)
13C NMR spectrum 91
(2S,3R)-2-Benzylamino-4-methyl-1-phenylpentan-3-ol (9d)
IR spectrum 92
(1S,2S)-2-Benzylamino-1-(4-methoxyphenyl)-3-phenylpropan-1-ol (9e) 1H NMR spectrum 92
(1S,2S)-2-Benzylamino-1-(4-methoxyphenyl)-3-phenylpropan-1-ol (9e) 13C NMR spectrum 93
(1S,2S)-2-Benzylamino-1-(4-methoxyphenyl)-3-phenylpropan-1-ol (9e) IR spectrum 93
(1R,2S)-2-Benzylamino-1-(4-methoxyphenyl)-3-phenylpropan-1-ol (9e’) 1H NMR spectrum 94
(1R,2S)-2-Benzylamino-1-(4-methoxyphenyl)-3-phenylpropan-1-ol (9e’) 13C NMR spectrum 94
(1R,2S)-2-Benzylamino-1-(4-methoxyphenyl)-3-phenylpropan-1-ol (9e’) IR spectrum 95
(1S,2S)-2-Benzylamino-1-(4-chlorophenyl)-3-phenylpropan-1-ol (9f)
1H NMR spectrum 95
(1S,2S)-2-Benzylamino-1-(4-chlorophenyl)-3-phenylpropan-1-ol (9f)
13C NMR spectrum 96
(1S,2S)-2-Benzylamino-1-(4-chlorophenyl)-3-phenylpropan-1-ol (9f)
IR spectrum 96
(1R,2S)-2-Benzylamino-1-(4-chlorophenyl)-3-phenylpropan-1-ol (9f’) 1H NMR spectrum 97
(1R,2S)-2-Benzylamino-1-(4-chlorophenyl)-3-phenylpropan-1-ol (9f’) 13C NMR spectrum 97
(1R,2S)-2-Benzylamino-1-(4-chlorophenyl)-3-phenylpropan-1-ol (9f’) IR spectrum 98
(4S,5S)-3,4-Dibenzyl-5-hexylthiazolidine-2-thione (10a)
1H NMR spectrum 98
(4S,5S)-3,4-Dibenzyl-5-hexylthiazolidine-2-thione (10a)
13C NMR spectrum 99
(4S,5S)-3,4-Dibenzyl-5-hexylthiazolidine-2-thione (10a)
IR spectrum 99
(4S,5S)-3,4,5-Tribenzyl-1,3-thiazolidine-2-thione (10b)
1H NMR spectrum 100
(4S,5S)-3,4,5-Tribenzyl-1,3-thiazolidine-2-thione (10b)
13C NMR spectrum 100
(4S,5S)-3,4,5-Tribenzyl-1,3-thiazolidine-2-thione (10b)
IR spectrum 101
(4S)-3,4-Dibenzyl-5-vinylthiazolidine-2-thione (10c)
1H NMR spectrum 101
(4S)-3,4-Dibenzyl-5-vinylthiazolidine-2-thione (10c)
13C NMR spectrum 102
(4S)-3,4-Dibenzyl-5-vinylthiazolidine-2-thione (10c)
IR spectrum 102
(4S,5S)-3,4-Dibenzyl-5-isopropyl-1,3-thiazolidine-2-thione (10d)
1H NMR spectrum 103
(4S,5S)-3,4-Dibenzyl-5-isopropyl-1,3-thiazolidine-2-thione (10d)
13C NMR spectrum 103
(4S,5S)-3,4-Dibenzyl-5-isopropyl-1,3-thiazolidine-2-thione (10d)
IR spectrum 104
(4S,5R)-3,4-Dibenzyl-5-(4-methoxyphenyl)thiazolidine-2-thione (10e) 1H NMR spectrum 104
(4S,5R)-3,4-Dibenzyl-5-(4-methoxyphenyl)thiazolidine-2-thione (10e) 13C NMR spectrum 105
(4S,5R)-3,4-Dibenzyl-5-(4-methoxyphenyl)thiazolidine-2-thione (10e) IR spectrum 105
(4S,5R)-3,4-Dibenzyl-5-(4-chlorophenyl)thiazolidine-2-thione (10f)
1H NMR spectrum 106
(4S,5R)-3,4-Dibenzyl-5-(4-chlorophenyl)thiazolidine-2-thione (10f)
13C NMR spectrum 106
(4S,5R)-3,4-Dibenzyl-5-(4-chlorophenyl)thiazolidine-2-thione (10f)
IR spectrum 107
cis-1-(4-Chlorophenyl)-3-phenylprop-1-ene (11f)
1H NMR spectrum 107
cis-1-(4-Chlorophenyl)-3-phenylprop-1-ene (11f)
13C NMR spectrum 108
cis-1-(4-Chlorophenyl)-3-phenylprop-1-ene (11f)
IR spectrum 108
(4S,5R)-3,4-dibenzyl-5-(4-methoxyphenyl)oxazolidine-2-thione (12)
1H NMR spectrum 109
(4S,5R)-3,4-dibenzyl-5-(4-methoxyphenyl)oxazolidine-2-thione (12)
13C NMR spectrum 109
(4S,5R)-3,4-dibenzyl-5-(4-methoxyphenyl)oxazolidine-2-thione (12)
IR spectrum 110
(4S,5R)-3,4-Dibenzyl-5-(4-chlorophenyl)oxazolidine-2-thione (13)
1H NMR spectrum 110
(4S,5R)-3,4-Dibenzyl-5-(4-chlorophenyl)oxazolidine-2-thione (13)
13C NMR spectrum 111
(4S,5R)-3,4-Dibenzyl-5-(4-chlorophenyl)oxazolidine-2-thione (13)
IR spectrum 111
(S)-3,4-Dibenzyl-5,5-dimethylthiazolidine-2-thione (15)
1H NMR spectrum 112
(S)-3,4-Dibenzyl-5,5-dimethylthiazolidine-2-thione (15)
13C NMR spectrum 112
(S)-3,4-Dibenzyl-5,5-dimethylthiazolidine-2-thione (15)
IR spectrum 113
(S)-3,4-Dibenzyl-5,5- dimethyloxazolidine-2-thione (16)
1H NMR spectrum 113
(S)-3,4-Dibenzyl-5,5- dimethyloxazolidine-2-thione (16)
13C NMR spectrum 114
(S)-3,4-Dibenzyl-5,5-dimethyloxazolidine-2-thione (16)
IR spectrum 114
(S)-3,4,5,5-Tetrabenzyloxazolidine-2-thione (18)
1H NMR spectrum 115
(S)-3,4,5,5-Tetrabenzyloxazolidine-2-thione (18)
13C NMR spectrum 115
(S)-3,4,5,5-Tetrabenzyloxazolidine-2-thione (18)
IR spectrum 116
(5S)-5-(3-Hydroxyphenyl)-3-methylthiazolidine-2-thione (21)
1H NMR spectrum 116
(5S)-5-(3-Hydroxyphenyl)-3-methylthiazolidine-2-thione (21)
13C NMR spectrum 117
(5S)-5-(3-Hydroxyphenyl)-3-methylthiazolidine-2-thione (21)
IR spectrum 117

參考文獻

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指導教授

胡紀如(Jih-Ru Hwu)

審核日期

2012-7-26

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