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鐭ユ湁姗�(j墨)鐗╃殑绲�(ji茅)妲�(g貌u)銆�
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纰冲師瀛� sp
3
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纰崇殑 sp
2
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鈶犵祼(ji茅)妲�(g貌u)锛氱⒊鐨� sp 闆滃寲鍜岀⒊-纰充笁閸�锛泂p 闆滃寲锛宻p
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闆滃寲 鍜� sp
3
闆滃寲鐨勭⒊鐨勯浕璨�(f霉)鎬х殑宸暟鍙婄浉鎳�(y墨ng)鍖栧悎鐗╃殑
鍋舵サ鐭�銆�
鈶″悓鍒嗙暟妲�(g貌u)楂�
鈶㈠寲瀛�(xu茅)鎬ц唱(zh矛)锛氭湯绔倲鐑寸殑閰告€у強鐩搁棞(gu膩n)鐨勫弽鎳�(y墨ng)锛涗笁閸电殑鍔犳垚锛氬偓鍖栧姞姘�锛岃Κ闆诲姞鎴�锛岃Κ鏍稿姞鎴�锛涚⒊鈥旂⒊
涓夐嵉鑸� H2/Lindlar 鍌寲鍔戝弽鎳�(y墨ng)锛堥爢寮忕儻鐑达級锛涚⒊鈥旂⒊涓夐嵉鑸� Na/娑叉皑鐨勫弽鎳�(y墨ng)锛堝弽寮忕儻鐑达級锛涘姞楣电礌锛涘姞 HX锛堥Μ
姘忚(gu墨)鍓囷級锛涘姞 H2O锛堢景鍩哄寲鍚堢墿鐨勫舰鎴愶級锛涘姞 HBr/閬�(gu貌)姘у寲鐗�锛涚〖姘寲鈥旀哀鍖�锛涘姞 HCN 鍙婁箼鐐旂殑浜岃仛锛涙哀鍖�
鍙嶆噳(y墨ng)锛欿MnO4 姘у寲鍜岃嚟姘у寲銆�
2锛� 浜岀儻鐑�
鈶犲叡杌涗簩鐑兇鐨勭┅(w臎n)瀹氭€э細閸佃兘鍜岄嵉闀�(zh菐ng)骞冲潎鍖栵紝鍏辫粵鏁堟噳(y墨ng)銆�
鈶′簩鐑兇鐨勫寲瀛�(xu茅)鍙嶆噳(y墨ng)锛�1锛�2-鍔犳垚鍜� 1锛�4-鍔犳垚锛堝弽鎳�(y墨ng)姗�(j墨)鐞嗭級锛涘弽鎳�(y墨ng)鐨勫嫊(d貌ng)鍔涘(xu茅)鎺у埗鍜岀啽鍔涘(xu茅)鎺у埗锛堝弽鎳�(y墨ng)
閬�(gu貌)绋嬩腑鐨勮兘閲忚畩鍖栵級锛涚儻涓欏瀷纰虫闆㈠瓙鐨勭┅(w臎n)瀹氭€э紙p-?鍏辫粵锛�锛汥iels-Alder 鍙嶆噳(y墨ng)銆�
锛堜簲锛夋尝璀滃垎鏋�
1锛� 绱鍏夎瓬
鐞嗚В鍚勭ó韬嶉伔锛�????锛宯???锛�????锛宯???锛夊拰鍚勮嚜鐨勫惛鏀惰兘閲忔尝闀�(zh菐ng)锛涚櫦(f膩)鑹插湗(tu谩n)鍜屽姪鑹插湗(tu谩n)锛涙憾鍔戞晥
鎳�(y墨ng)锛涙渶閲嶈鐨勬槸鑳藉寰炰竴寮� UV 璀滃湒涓緱鍒版湁鐢ㄧ殑淇℃伅锛堝垽鏂风祼(ji茅)妲�(g貌u)锛夛紙涓嶈姹傚埄鐢ㄧ稉(j墨ng)椹�(y脿n)瑕�(gu墨)鍓囧幓瑷�(j矛)绠楁煇鍖栧悎
鐗╀箣鍚告敹娉㈤暦(zh菐ng)锛�銆�
2锛� 绱呭鍏夎瓬
鐞嗚В IR 鍏夎瓬涔嬪熀鏈師鐞嗭紝鏈€閲嶈鐨勬槸鍒╃敤 IR 鍏夎瓬锛堢祼(ji茅)鍚堝叾瀹冩尝璀滐級鎺ㄦ脯(c猫)鏈夋(j墨)鍒嗗瓙鐨勭祼(ji茅)妲�(g貌u)锛岄€欏氨瑕佹眰
灏�(du矛)鍚勯(l猫i)瀹樿兘鍦�(tu谩n)鐨勭磪澶栧惛鏀惰寖鍦嶆湁娓呮鐨勪簡瑙�锛屽苟娓呮褰遍熆宄颁綅缃畩鍖栫殑鍥犵礌銆�
3锛� 鏍哥鍏辨尟璀滐紙
1
H NMR锛夛紙纰宠瓬涓嶈姹傦級
浜嗚В鍩烘湰鍘熺悊锛涘熀鏈蹇碉細鍖栧(xu茅)浣嶇Щ锛屽収(n猫i)妯�(bi膩o)锛屽妯�(bi膩o)锛屽伓鍚�锛屽伓鍚堝父鏁�(sh霉)锛屽睆钄�锛屽幓灞忚斀绛�銆傛竻妤氫笉鍚岄(l猫i)
鍨嬬殑鏋濊唱(zh矛)瀛愮殑鍖栧(xu茅)浣嶇Щ鑼冨湇鍙婂奖闊垮洜绱�锛涙渶閲嶈鐨勬槸鍒╃敤 NMR 璀滐紙绲�(ji茅)鍚堝叾瀹冩尝璀滐級鎺ㄦ脯(c猫)鏈夋(j墨)鍒嗗瓙鐨勭祼(ji茅)妲�(g貌u)銆�
4锛� 璩�(zh矛)璀�
浜嗚В鍩烘湰鍘熺悊锛涘咕绋噸瑕佺殑闁�(k膩i)瑁傛柟寮忥紙鍖呮嫭閲嶈鐨勯噸鎺掗枊(k膩i)瑁傚楹�?zh菙n)鐜板槒?锛�?Diels-Alder 閲嶆帓绛夛級锛涙渶
閲嶈鐨勬槸鍒╃敤 MS 寰楀嚭鐨勫垎瀛愰洟瀛愬嘲锛堝苟绲�(ji茅)鍚堝叾瀹冩尝璀滄柟娉曪級鎺ㄦ脯(c猫)鏈夋(j墨)鍒嗗瓙鐨勭祼(ji茅)妲�(g貌u)銆�
鏈珷鏈€閲嶈鐨勬槸鍒╃敤骞剧ó娉㈣瓬鏂规硶绲�(ji茅)鍚堟帹娓�(c猫)鏈夋(j墨)鍒嗗瓙鐨勭祼(ji茅)妲�(g貌u)銆�
锛堝叚锛夎姵棣欑兇
1锛� 鑻殑绲�(ji茅)妲�(g貌u)鍜岃姵棣欐€�
鐞嗚В鑺抽鎬х殑姒傚康鍜屽垽鏂疯姵棣欐€х殑 H眉ckel 瑕�(gu墨)鍓�锛岃兘鐢ㄦ瑕�(gu墨)鍓囧垽鏂蜂竴绲﹀畾鐨勫垎瀛愶紙鎴栭洟瀛愶級鏄惁鏄姵棣�
鎬х殑銆�
2锛� 鑻殑鐣版(g貌u)锛屽悓绯荤墿鍜屽懡鍚�
3锛� 鑻強鍏跺悓绯荤墿鐨勭墿鐞嗘€ц唱(zh矛)鍜屾尝璀滄€ц唱(zh矛)
涓昏浜嗚В鍏舵尝璀滅壒寰侊紝渚嬪鑺抽鐑寸殑 NMR 璀滃(xu茅)鐗瑰緛锛屼笉鍚屽彇浠ｈ嫰鍦� IR 鎸囩磱鍗€(q奴)鐨勭壒寰佺瓑銆�
4锛� 鍖栧(xu茅)鎬ц唱(zh矛)
瑕浕鍙栦唬鍙嶆噳(y墨ng)鍙婃(j墨)鐞�锛涘倕姘忓弽鎳�(y墨ng)鐨勭壒榛�(di菐n)鍙婂眬闄愶紱姘敳鍩哄寲鍙嶆噳(y墨ng)锛汫atterman-Koch 鍙嶆噳(y墨ng)锛涜姵棣欑挵(hu谩n)涓婂彇浠�
鍩虹殑瀹氫綅鏁堟噳(y墨ng)锛涘叾瀹冨弽鎳�(y墨ng)锛氬伌(c猫)閺堟哀鍖栵紱鍋�(c猫)閺堝彇浠�锛涜姵棣欑挵(hu谩n)涓婄殑閭勫師锛氬偓鍖栧姞姘�锛孊irch 閭勫師銆�
5锛� 钀樼殑绲�(ji茅)妲�(g貌u)鍜屽寲瀛�(xu茅)鎬ц唱(zh矛)
锛堜竷锛夌珛楂斿寲瀛�(xu茅)
1锛� 鍩烘湰姒傚康
灏�(du矛)鏄犵暟妲�(g貌u)锛堥珨锛�锛涙墜鎬у垎瀛�锛涢彙鍍�锛涙棆鍏夋€�锛屾棆鍏夊害锛涘皪(du矛)鏄犻珨锛涢潪灏�(du矛)鏄犻珨锛涘樊鍚戠暟妲�(g貌u)楂�锛涘収(n猫i)娑堟棆楂�锛�
澶栨秷鏃嬮珨锛涙墜寰佹€�锛涙墜鎬т腑蹇�銆�
2锛� 灏�(du矛)鏄犵暟妲�(g貌u)楂旀(g貌u)鍨嬬殑琛ㄧず娉�
R/S 娉曪紙娆″簭瑕�(gu墨)鍓囷級銆�
3锛� 鐔熸倝鍚勯(l猫i)鎵嬫€у垎瀛�
鍚� 1鈥�3 鍊�(g猫)鎵嬫€х⒊鍘熷瓙鐨勬墜鎬у垎瀛�锛涗笉鍚墜鎬х⒊鍘熷瓙鐨勬墜鎬у垎瀛愶紱鐠�(hu谩n)鐙€鍖栧悎鐗�銆�
4锛� 绔嬮珨鐣版(g貌u)楂旂殑鍒跺倷鍜屽弽鎳�(y墨ng)
鐔熸倝鑳界敘(ch菐n)鐢熺珛楂旂暟妲�(g貌u)楂旂殑鍖栧(xu茅)鍙嶆噳(y墨ng)鍙婃(j墨)鐞�锛岃薄鐑兇鑸囬沟绱犵殑鍙嶅紡鍔犳垚锛岀挵(hu谩n)姘т箼鐑风殑闁�(k膩i)鐠�(hu谩n)锛岀景鍩哄寲鍚堢墿
鐨勫姞鎴愶紙Cram 瑕�(gu墨)鍓囷級绛夌瓑銆�
锛堝叓锛夐沟浠ｇ兇
1锛� 鐣版(g貌u)锛屽垎椤�(l猫i)锛屽懡鍚�
2锛� 娉㈣瓬鎬ц唱(zh矛)锛屽挨鍏舵槸 NMR 璀�
3锛� 鍖栧(xu茅)鎬ц唱(zh矛)
瑕牳鍙栦唬鍙嶆噳(y墨ng)鍙婃(j墨)鐞嗭紙SN1锛孲N2锛�锛涘奖闊胯Κ鏍稿彇浠ｅ強姗�(j墨)鐞嗙殑鍥犵礌锛涜Κ鏍歌│鍔戠殑瑕牳鎬�锛汼N2 鍙嶆噳(y墨ng)鐨勭珛楂�
鍖栧(xu茅)锛汼N1 鍙嶆噳(y墨ng)涓殑閲嶆帓锛涢劙鍩哄弮鑸�銆�
娑堥櫎鍙嶆噳(y墨ng)鍙婃(j墨)鐞嗭紙E1锛孍2锛孍1cb锛夛細娑堥櫎鍙嶆噳(y墨ng)鐨勫彇鍚戯紙Saytzeff 瑕�(gu墨)鍓囷級鍜岀珛楂斿寲瀛�(xu茅)锛涙秷闄ゅ弽鎳�(y墨ng)鍜屽彇浠ｅ弽
鎳�(y墨ng)鐨勭(j矛ng)鐖�(zh膿ng)銆�
楣典唬鐑磋垏 Mg锛孡i锛孨a 绛夌殑鍙嶆噳(y墨ng)锛欸rignard 瑭﹀姂銆佹湁姗�(j墨)閶拌│鍔戝強鍏舵噳(y墨ng)鐢�銆�
锛堜節锛夐唶銆侀厷銆侀啔
1锛� 绲�(ji茅)妲�(g貌u)銆佸垎椤�(l猫i)銆佸懡鍚�
2锛� 閱囩殑鐗╃悊鎬ц唱(zh矛)鍜屽厜璀滄€ц唱(zh矛)
姘嵉灏�(du矛)鍏剁墿鐞嗘€ц唱(zh矛)鐨勫奖闊�锛汭R 鍏夎瓬鍜� NMR 璀滅殑鐗瑰緛銆�
3锛� 閱囩殑鍖栧(xu茅)鎬ц唱(zh矛)
閱囩殑閰告€э紙鑸囧叾瀹冮(l猫i)鍨嬪寲鍚堢墿濡� H2O锛岄厷锛岀晶閰�?閰告€х殑姣旇純锛�锛涜垏閰告€ф湁闂�(gu膩n)鐨勫弽鎳�(y墨ng)锛堣垏閲戝爆濡� Na锛�
Mg锛孉l?鐨勫弽鎳�(y墨ng)锛夛紱閱囩殑姘у寲锛堝舰鎴愰啗/閰�锛岀晶閰革級锛涚啛鎮夊悇绋哀鍖栧姂锛涢唶鐨勬垚閰弽鎳�(y墨ng)锛氳垏鐒�(w煤)姗�(j墨)閰告垚閰�锛岃垏
鏈夋(j墨)閰告垚閰紙姗�(j墨)鐞嗭級锛涢沟鍖栧弽鎳�(y墨ng)锛涚敤 SOCl2 楣靛寲鐨勭珛楂斿寲瀛�(xu茅)鍙婃(j墨)鐞嗭紱鐢� HX 鐨勯沟浠ｅ弽鎳�(y墨ng)锛圠ucas 瑭﹀姂鐢ㄤ締(l谩i)鍗€(q奴)
鍒ュ叚鍊�(g猫)纰冲師瀛愪互涓� 1?锛�2?鍜� 3?閱囷級锛沇agner-Meerwein 閲嶆帓銆�
閱囩殑鑴按鍙嶆噳(y墨ng)锛氬弽鎳�(y墨ng)姗�(j墨)鐞�/鎵庝緷鍒囧か瑕�(gu墨)寰�锛涘弽鎳�(y墨ng)娲绘€э紱閲嶆帓锛涘垎瀛愰枔鑴按鎴愰啔銆�
澶氬厓閱囩殑鍙嶆噳(y墨ng)锛氳垏 HIO4 鎴� Pb锛圤Ac锛�4 鐨勫弽鎳�(y墨ng)锛涚墖鍚堕唶閲嶆帓鍙嶆噳(y墨ng)鍙婃(j墨)鐞�銆�
4锛� 閰氱殑鐗╃悊鎬ц唱(zh矛)鍜屽厜璀滄€ц唱(zh矛)
5锛� 閰氱殑鍖栧(xu茅)鎬ц唱(zh矛)
閰告€у強鑸囦箣鐩搁棞(gu膩n)鐨勫弽鎳�(y墨ng)锛汧ries 閲嶆帓锛涜姵鐠�(hu谩n)涓婄殑瑕浕鍙栦唬锛氶沟浠�锛岀鍖栵紝纾哄寲锛涘叾瀹冭Κ闆诲彇浠ｏ細鑸囬啗鐨�
浣滅敤锛涜垏 CO2 鐨勪綔鐢紱Reimer-Tiemann 鍙嶆噳(y墨ng)锛涢厷鐨勬哀鍖栧弽鎳�(y墨ng)銆�
6锛� 閰氱殑鍒跺倷鏂规硶
鐣颁笝鑻哀鍖栨硶锛涙隘鑻按瑙ｆ硶锛涜嫰纾洪吀鍫跨啍娉�銆�
7锛� 閱氱殑鍙嶆噳(y墨ng)
鑸� HX 鐨勫弽鎳�(y墨ng)锛堥啔閸垫柗瑁傦級鍙婃(j墨)鐞嗭紱Claisen 閲嶆帓锛涚挵(hu谩n)姘т箼鐑风殑鍙嶆噳(y墨ng)銆�
8锛� 閱氱殑鍚堟垚鏂规硶
Williamson 鍚堟垚娉�銆�
锛堝崄锛夐啗鍜岄叜
1锛� 閱涢叜鐨勫弽鎳�(y墨ng) 鈶犲姞鎴愬弽鎳�(y墨ng)锛岃Κ鏍稿姞鎴�
OC C N OC
C N
H2 O
+
_ _
O HC
C N
+ O H
_
OC Na HSO3
O HC
SO3
Na
+
浠ヤ笂鍙嶆噳(y墨ng)閬╃敤浜庨啗銆佽剛鑲棌鐢插熀閰拰鍏€�(g猫)纰冲師瀛愪互涓嬬殑鐠�(hu谩n)閰�銆�
OC R Mg X O Mg XC
R
+ O HC
R
OC H2
NB NC+
H,H2
O
+
B
B= -O H,-NHC6
H5
,-NHCO NH2
,-Ar 绛�
OC RO H+ C(O R)2
2
鈶�?鈥旂⒊鍘熷瓙涓�
2 RC H2
C HO
O H
RC H2
C HO H
C HC HOR
RC H2
C H=CC HO
R
_
_
H2 O
楣典豢鍙嶆噳(y墨ng)锛�
RCO C H3
NaO X
RCO O Na C HX3+
鈶㈡哀鍖栧拰閭勫師
RC HO
[O ]
RCO O H
OC
OC
[H]
C HO H
[Zn Hg+ HCl]
[NH2
NH2
+ NaO H]
C H2鎴�
2锛� 閱涢叜鐨勫埗娉�
鈶犵兇椤�(l猫i)姘у寲
CH3
CH O
[O ]
鈶￠唶鐨勬哀鍖栧強鍘绘矮
RC H2
O H RC HO
RC HO HR' RCOR'
[O]
[O]
鈶riedel-Crafts ?锛涱嚞纾�?y墨ng)
C6
H5
COCl C6
H6
AlCl3
C6
H5
COC6
H5+
3锛�?锛�?鈥斾笉椋藉拰閱�銆侀叜鐨勫弽鎳�(y墨ng)锛�
C=C C=O R Mg X
C=C C-O Mg X
R
C=C C=O
+
C=C C-O H
R
H2 O
C-O Mg X
H2 O
C
R
C C=OC
R
C H
HC N
C=O
C N
C HC
1,2-鍔� 鎴�
1,4-鍔� 鎴�
锛堝崄涓€锛夌晶閰稿強鍏惰鐢熺墿
1锛� 缇ч吀鐨勫弽鎳�(y墨ng)锛�
鈶犻吀鎬э細缇ч吀鐨勯吀鎬ф瘮纰抽吀寮�(qi谩ng)锛屾瘮鐒�(w煤)姗�(j墨)閰稿急銆�
鈶＄晶閰镐腑缇ュ熀鐨勫彇浠ｅ弽鎳�(y墨ng)
_
RCO O H PCl3
RCO Cl
RCO O H R'O H RCO O R'
NH3 RCO O NH4
RCO NH2
RCO O H
+
+
+ H2 O
鈶㈤倓鍘�
LiAlH4
RCH2
OHRCOO H +
2锛� 缇ч吀鐨勫埗娉�
鈶犳哀鍖栨硶
RC H2
O H
RC HO
[O ]
RCO O H
RCO C H3
ArC H3
K MnO4
,H
ArCO O H
RCO O H
楣� 浠� 鍙� 鎳�(y墨ng)
+
鈶℃按瑙ｆ硶
++RCN
H
RCOO H NH4
+
H2 O
+
鈶rignard 瑭﹀姂鑸囦簩姘у寲纰充綔鐢�
RCO O H+R Mg X CO2
RCO O Mg X
H2 O
3锛� 缇ч吀琛嶇敓鐗╃殑鍙嶆噳(y墨ng)
鈶犳按瑙ｉ兘鐢熸垚缇ч吀
鈶￠唶瑙� 閰版隘銆侀吀閰愬拰閰殑閱囪В閮界敓鎴愰叝锛岄叝鑸囬唶浣滅敤鐢熸垚鍘熼吀閰垨閰�銆�
鈶㈡皑瑙� 閰版隘銆侀吀閰愬拰閰殑姘ㄨВ閮界敓鎴愰叞鑳�
鈶ｉ吀瑙� 鐢熸垚骞宠 娣峰悎鐗�
4锛� 缇ч吀琛嶇敓鐗╃殑鍒舵硶
鈶犻叞姘細缇ч吀鑸囩劇(w煤)姗�(j墨)閰版隘浣滅敤锛涒憽閰搁厫锛氶叞姘垏缇ч吀楣戒綔鐢�锛涒憿閰細鐩存帴閰寲锛� 鈶ｉ叞鑳猴細缇ч吀鐨勯姩
楣藉幓姘存垨閰殑姘ㄨВ锛涒懁鑵堬細閰拌兒鍘绘按鎴栭沟浠ｇ兇鑸囨鞍鍖栭垑浣滅敤銆�
锛堝崄浜岋級鍙栦唬缇ч吀
1锛� 楣典唬閰哥殑鍙嶆噳(y墨ng)
鈶犺垏鍫跨殑鍙嶆噳(y墨ng)锛岀敘(ch菐n)鐗╄垏楣电礌鍜岀晶鍩虹殑鐩稿皪(du矛)浣嶇疆鏈夐棞(gu膩n)銆�
?-楣典唬閰�?缇ュ熀閰�
?-楣典唬閰�??锛�?-涓嶉＝鍜岄吀
?鎴�?-楣典唬閰�?鍏�(n猫i)閰�
鈶arzen 鍙嶆噳(y墨ng)
R2
C=O XCH2
COOC2
H5
B
O
R2
C CHCOOC2
H5
+
_
2锛� 瑾樺皫(d菐o)鏁堟噳(y墨ng)
+
Y CR3
H CR3
X CR3
I I
(C H3
)3
N F Cl Br C H3
O
(C H3
)3
C (C H2
)2
C H C H3
C H2
CH3
_
+
+
I
I
_
:
: > > > >
> > >
妯�(bi膩o) 婧�(zh菙n)
3锛� 鍏辫粵鏁堟噳(y墨ng)
_
+
_
:
:
>
>N O
O
+
> > >OC C=N
> >
C=C NC
N
.. ...
.
.. ...
.O F Cl Br> >..
..
....
. . ...
..
I
.
C
C ..
4锛� 閱囬吀鐨勫弽鎳�(y墨ng)
鈶犲幓姘�锛岀敘(ch菐n)鐗╄垏缇ュ熀鐨勭浉灏�(du矛)浣嶇疆鏈夐棞(gu膩n)
?-閱囬吀?浜ら叝 ?-閱囬吀??锛�?-涓嶉＝鍜岄吀 ?-閱囬吀?鍏�(n猫i)閰�
鈶″垎瑙ｏ細
H2 ORCHO HCOO H
H2
SO4
RCHO CO2+ +
5锛� 涔欓叞涔欓吀涔欓叝鍦ㄥ悎鎴愪笂鐨勬噳(y墨ng)鐢�
鈶犲悎鎴愮敳鍩洪叜锛�
C H3
CO C H2
CO O C2
H5
C H3
CO C HRCO O C2
H5
C H3
CO C H2
R
鎴� 閰� 姘� 瑙�
鈶� 鈶2
H5
O Na R X
鈶″悎鎴愰叜閰�
C H3
CO C H2
CO O C2
H5
C2
H5
O Na,RC H XCO O C2
H5
C H3
CO C HCO O C2
H5
RC HCO O C2
H5
C H3
CO C H2
C HCO O H
R
6锛� 涓欎簩閰搁叝鍦ㄥ悎鎴愪笂鐨勬噳(y墨ng)鐢�
鈶犲悎鎴愪竴鍏冪晶閰�
C H2
(CO O C2
H5
)2
RC H(CO O C2
H5
)2 RC H2
CO O H
CO2
R2
C(CO O C2
H5
)2 R2
C HCO O H
姘� 瑙�
姘� 瑙�
_
_
CO2
鈶� 鈶2
H5
O Na R X
鈶″悎鎴愪簩鍏冪晶閰�
C H2
(CO O C2
H5
)2
CO2
姘� 瑙�
_
C H(CO O C2
H5
)2
RC HCO O C2
H5
C H2
CO O H
C HCO O HR
C H2
(CO O C2
H5
)2
C2
H5
O Na
CO2
姘� 瑙�
_
n+2(C H2
)
C H(CO O C2
H5
)2
C H(CO O C2
H5
)2
n+2(C H2
)
C H2
CO O H
C H2
CO O H
鈶� 鈶� RC HXCO O C2
H5
C2
H5
O Na鈶� 鈶� RC HXCO O C2
H5
锛堝崄涓夛級鑳哄拰鍚爱鍖栧悎鐗�
1锛� 鑳虹殑鍖栧(xu茅)鎬ц唱(zh矛)
鈶犲牽鎬�
_
R NH2 HX R N H3
X+ +
鈶＄兇鍖�
+
+
R NH2
R X
R X
R X
R2
NH
R3
N
R2
N H2
X
HXR3
N
R4
N X
+
+
+
+
_
_
_
鈶�?锛涱嚇鈩塱nsberg 鍙嶆噳(y墨ng)锛�
R NH2
R2
NH
R3
N
+
+
+
+
(C H3
CO)2
O R NHCOC H3
p-C H3
C6
H4
SO2
Cl
NaO H p-C H3
C6
H4
SO2
NR2
p-C H3
C6
H4
SO2
Cl p-C H3
C6
H4
SO2
N R Na
p-C H3
C6
H4
SO2
Cl
R NH2
NaO H
NaO H
+
_
涓� 鐢� 鎴� 纾� 閰� 鑳�
鈶ｈ垏浜炵閰哥殑鍙嶆噳(y墨ng)
绛� +R NH2
HX Na NO2
RO H N2
ArNH2
HX Na NO2
ArN NX
R2
NH
R3
N
R2
N-N=OHX Na NO2
HX Na NO2
HX Na NO2
+
+
+
+
+ +
+
+
+
+
+
_
鍣诲惄>鍚″挴>鍛嬪杻
闆㈠煙鑳斤紙kJ/mol
鈥�1
锛� 150.6锛�121.3锛�87.6锛�66.9
3锛� 鍛嬪杻銆佸櫥鍚�銆佸悺鍜殑鎬ц唱(zh矛)
鈶犺Κ闆诲彇浠ｏ細楣典唬锛岀鍖�锛岀：鍖�锛屼箼?锛�?锛涒憽鍛嬪杻鏄撶櫦(f膩)鐢�锛汥iels-Alder 鍙嶆噳(y墨ng)锛涒憿鍚″挴鐨勫急鍫挎€�锛涒懀鍚�
鍟剁殑鍫挎€�锛涒懁鍚″暥鐨勬哀鍖栥€侀倓鍘熸€ц唱(zh矛)锛涒懃Fischer 鍚插摎鍚堟垚娉曞拰 Skraup 鍠瑰晧鍚堟垚娉�銆�
锛堝崄鍏級鍛ㄧ挵(hu谩n)鍙嶆噳(y墨ng)
1锛� 鍦ㄥ崝(xi茅)鍚屽弽鎳�(y墨ng)涓粚閬撳皪(du矛)绋�(ch膿ng)鎬у畧鎭�
2锛� 闆荤挵(hu谩n)鍖栧弽鎳�(y墨ng)鐨勯伕鎿囪(gu墨)寰�
?闆诲瓙鏁�(sh霉) 鍩烘厠(t脿i) 婵€鐧�(f膩)鎱�(t脿i)
4n 闋嗘棆 灏�(du矛)绋�(ch膿ng)
4n+2 灏�(du矛)鏃� 闋嗘棆
3锛� 鐠�(hu谩n)鍖栧姞鎴愬弽鎳�(y墨ng)鐨勯伕鎿囪(gu墨)寰嬶紙鍚屼竴閭婏級
?闆诲瓙鏁�(sh霉) 鍩烘厠(t脿i) 婵€鐧�(f膩)鎱�(t脿i)
4n 绂侀樆 鍏佽ū
4n+2 鍏佽ū 绂侀樆
4锛� ?閬风Щ鍙嶆噳(y墨ng)鐨勯伕鎿囪(gu墨)寰嬶紙鍚屼竴閭婏級
i+j 4n 4n+2
鍩烘厠(t脿i) 绂侀樆 鍏佽ū
5锛� Cope 閲嶆帓
C H2
-C H=C H2
C H2
-C H=C H2
C H2
=C H C
H2
C H2
C H2
=C H
6锛� Claisen 閲嶆帓
O-C H 2
-C H =C H 2
OH
C H 2
-C H =C H 2
O-C H 2
-C H =C H 2
C H 3
CH 3 CH 3
C H 3
OH
C H 2
-C H =C H 2
*
*
*
*
锛堝崄涓冿級纰虫按鍖栧悎鐗�
1锛� 鍠硸鐨勭祼(ji茅)妲�(g貌u)鑸囨(g貌u)鍨�
鈶燜ischer 妲�(g貌u)鍨嬪紡鐨勫(xi臎)娉曪細缇板熀蹇呴爤瀵�(xi臎)鍦ㄤ笂绔�锛涒憽妲�(g貌u)鍨嬶細绶ㄨ櫉(h脿o)鏈€澶ф墜鎬х⒊鍘熷瓙涓� OH 鍦ㄨ睅绶�(xi脿n)鍙抽倞鐐� D-
鍨�锛屽湪宸﹂倞鐐� L-鍨嬶紱鈶aworth 寮忥細宸遍啗绯栫殑 Haworth 寮忎腑 C1 涓婄殑 OH 鑸� C5 涓婄殑 CH2OH 鍦ㄧ挵(hu谩n)鍚屼竴閭婄偤?
浣嶇暟妲�(g貌u)楂�銆�
2锛� 鍠硸鐨勫弽鎳�(y墨ng)
鈶犳哀鍖栵細閱涚硸鐢ㄦ捍姘存哀鍖栫敓鎴愮硸閰革紝鐢ㄧ█纭濋吀姘у寲鐢熸垚绯栦簩閰�
鈶￠倓鍘燂細鐢� NaBH4 閭勫師鐢熸垚澶氬厓閱�
鈶㈣剮鐨勭敓鎴愶細绯栬垏鑻偧浣滅敤鈥斺€旀垚鑴�銆�
锛堝崄鍏級姘ㄥ熀閰�銆佸鑲�銆佽泲鐧借唱(zh矛)
1锛庘憼姘ㄥ熀閰哥殑鍩烘湰绲�(ji茅)妲�(g貌u)
C
CO O H
HNH2
R 澶╃劧鐨�?-姘ㄥ熀閰�锛屽彧鏈� R 鍙栦唬鍩虹殑宸垾銆�
鈶＄瓑闆婚粸(di菐n)锛氱瓑闆婚粸(di菐n)鏅�(sh铆)姘ㄥ熀閰镐互?x煤n)灏氬櫔x瀛愬瓨鍦�锛屾皑鍩洪吀婧惰В搴︽渶灏�锛涒憿姘ㄥ熀閰�-鑼氫笁閰殑椤壊鐨勫弽鎳�(y墨ng)锛涒懀Sanger
瑭﹀姂鍙婃噳(y墨ng)鐢�锛涒懁姘ㄥ熀閰哥殑鍒跺倷锛歛. ?-楣典唬閰哥殑姘ㄨВ锛宐. 閱涘拰閰垏姘�銆佹矮姘伴吀鍔犳垚鐗╂按瑙�锛宑. 浜屼笝閰搁叝鍚堟垚
娉曪紱鈶ュ鑲界殑鍚堟垚鏂规硶銆�
锛堝崄涔濓級钀滈(l猫i)鍜岀斁楂斿寲鍚堢墿
鈶犳帉鎻¤悳椤�(l猫i)鍖栧悎鐗╃殑鍩烘湰绲�(ji茅)妲�(g貌u)锛氱⒊楠ㄦ灦鐢辩暟鎴婁簩鐑柈浣嶇祫鎴愮殑锛涙渻(hu矛)鍔冨垎钀滈(l猫i)鍖栧悎鐗╀腑鐨勭暟鎴婁簩鐑柈浣�銆�
鈶℃帉鎻′竴浜涢噸瑕佺殑钀滈(l猫i)澶╃劧鐢�(ch菐n)鐗╁父瑕�(gu墨)鎬ц唱(zh矛)锛氬娉曞凹閱囷紱鐗涘厭閰�锛涙鐗涘厭濂э紱灞遍亾骞�锛涚董鐢熺礌 A锛涜憠缍�
閱�锛涜榀婄儻銆�?-鑳¤樋鍗滅礌銆�
鈶簡瑙ｇ斁楂斿寲鍚堢墿鐨勫洓鐠�(hu谩n)绲�(ji茅)妲�(g貌u)鍜屽懡鍚�銆�
鈶ｄ簡瑙ｈ悳椤�(l猫i)鍜岀斁楂斿寲鍚堢墿鐨勭敓鐗╁悎鎴�銆�
鍏嶈铂(z茅)鑱叉槑锛氭湰鏂囩郴杞�(zhu菐n)杓夎嚜缍�(w菐ng)绲�(lu貌)锛屽鏈変镜鐘紝璜�(q菒ng)鑱�(li谩n)绯绘垜鍊戠珛鍗冲埅闄�锛屽彟锛氭湰鏂囧儏浠ｈ〃浣滆€呭€�(g猫)浜鸿榛�(di菐n)锛岃垏鏈恫(w菐ng)绔欑劇(w煤)闂�(gu膩n)銆傚叾鍘熷壍(chu脿ng)鎬т互鍙婃枃涓櫝杩版枃瀛楀拰鍏�(n猫i)瀹规湭缍�(j墨ng)鏈珯璀夊(sh铆)锛屽皪(du矛)鏈枃浠ュ強鍏朵腑鍏ㄩ儴鎴栬€呴儴鍒嗗収(n猫i)瀹�銆佹枃瀛楃殑鐪熷(sh铆)鎬�銆佸畬鏁存€с€佸強鏅�(sh铆)鎬ф湰绔欎笉浣滀换浣曚繚璀夋垨鎵胯锛岃珛(q菒ng)璁€鑰呭儏浣滃弮鑰�锛屽苟璜�(q菒ng)鑷鏍稿(sh铆)鐩搁棞(gu膩n)鍏�(n猫i)瀹广€�
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鎮ㄧ従(xi脿n)鍦ㄧ殑浣嶇疆锛� 
