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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/閬庢哀鍖栫墿锛涚〖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細閸佃兘鍜岄嵉闀峰钩鍧囧寲锛屽叡杌涙晥鎳�(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)
閬庣▼涓殑鑳介噺璁婂寲锛夛紱鐑笝鍨嬬⒊姝ｉ洟瀛愮殑绌�(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凤紱鐧�(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)椹楄(gu墨)鍓囧幓瑷堢畻鏌愬寲鍚�
鐗╀箣鍚告敹娉㈤暦锛夈€�
2锛� 绱呭鍏夎瓬
鐞嗚В IR 鍏夎瓬涔嬪熀鏈師鐞�锛屾渶閲嶈鐨勬槸鍒╃敤 IR 鍏夎瓬锛堢祼(ji茅)鍚堝叾瀹冩尝璀滐級鎺ㄦ脯鏈夋(j墨)鍒嗗瓙鐨勭祼(ji茅)妲�(g貌u)锛岄€欏氨瑕佹眰
灏嶅悇椤炲畼鑳藉湗(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)锛屽伓鍚堬紝鍋跺悎甯告暩(sh霉)锛屽睆钄斤紝鍘诲睆钄界瓑銆傛竻妤氫笉鍚岄
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狅紱鏈€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嬭鏂瑰紡锛堝寘鎷噸瑕佺殑閲嶆帓闁嬭濡傞亥?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)鍚堟帹娓湁姗�(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�锛屼緥濡傝姵棣欑兇鐨� 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)鐞嗭紱鍌呮皬鍙嶆噳(y墨ng)鐨勭壒榛�(di菐n)鍙婂眬闄�锛涙隘鐢插熀鍖栧弽鎳�(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
灏嶆槧鐣版(g貌u)锛堥珨锛夛紱鎵嬫€у垎瀛�锛涢彙鍍忥紱鏃嬪厜鎬�锛屾棆鍏夊害锛涘皪鏄犻珨锛涢潪灏嶆槧楂旓紱宸悜鐣版(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� 灏嶆槧鐣版(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� 鐔熸倝鍚勯鎵嬫€у垎瀛�
鍚� 1鈥�3 鍊嬫墜鎬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�锛涚挵(hu谩n)鐙€鍖栧悎鐗┿€�
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箼鐑风殑闁嬬挵(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)锛屽垎椤烇紝鍛藉悕
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)鐨勭鐖�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�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)
姘嵉灏嶅叾鐗╃悊鎬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�锛涢唶鐨勬哀鍖栵紙褰㈡垚閱�/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℃(j墨)閰告垚閰紝鑸�
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�锛涚敤 HX 鐨勯沟浠ｅ弽鎳�(y墨ng)锛圠ucas 瑭﹀姂鐢ㄤ締鍗€(q奴)
鍒ュ叚鍊嬬⒊鍘熷瓙浠ヤ笅 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€�锛涢噸鎺�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�锛岀：鍖栵紱鍏跺畠瑕浕鍙栦唬锛氳垏閱涚殑
浣滅敤锛涜垏 CO2 鐨勪綔鐢�锛汻eimer-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�锛汣laisen 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€嬬⒊鍘熷瓙浠ヤ笅鐨勭挵(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�
RCOCH3
NaO X
RCOO Na CHX3+
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�
鈶犵兇椤炴哀鍖�
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℃(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
RC H2
O HRCO O 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
RCOC 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╄垏缇ュ熀鐨勭浉灏嶄綅缃湁闂�(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 HXCO 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�
CH2
(COOC2
H5
)2
RCH(COOC2
H5
)2 RC H2
COO H
CO2
R2
C(COOC2
H5
)2 R2
C HCOO 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 NHCO C 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�锛屼箼閰板寲锛涒憽鍛嬪杻鏄撶櫦(f膩)鐢燂紱Diels-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€э紱鈶ゅ悺鍟剁殑姘у寲銆侀倓鍘熸€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)涓粚閬撳皪绋辨€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 灏嶇ū
4n+2 灏嶆棆 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
CH2
=C H C
H2
C H2
C H2
=C H
6锛� Claisen 閲嶆帓
O-CH 2
-CH=CH 2
OH
C H 2
-CH=CH 2
O-CH 2
-CH=CH 2
CH 3
CH 3 CH 3
CH 3
OH
CH 2
-CH=CH 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)鍨嬪紡鐨勫娉曪細缇板熀蹇呴爤瀵湪涓婄锛涒憽妲�(g貌u)鍨嬶細绶ㄨ櫉鏈€澶ф墜鎬х⒊鍘熷瓙涓� OH 鍦ㄨ睅绶氬彸閭婄偤 D-
鍨�锛屽湪宸﹂倞鐐� L-鍨�锛涒憿Haworth 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�锛岀敤绋€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€旀垚鑴庛€�
锛堝崄鍏級姘ㄥ熀閰�銆佸鑲姐€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熀閰革紝鍙湁 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)鏅傛皑鍩洪吀浠ュ叐鎬ч洟瀛愬瓨鍦紝姘ㄥ熀閰告憾瑙ｅ害鏈€??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ｏ紝c. 浜屼笝閰搁叝鍚堟垚
娉�锛涒懃澶氳偨鐨勫悎鎴愭柟娉�銆�
锛堝崄涔濓級钀滈鍜岀斁楂斿寲鍚堢墿
鈶犳帉鎻¤悳椤炲寲鍚堢墿鐨勫熀鏈祼(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鍔冨垎钀滈鍖栧悎鐗╀腑鐨勭暟鎴婁簩鐑柈浣�銆�
鈶℃帉鎻′竴浜涢噸瑕佺殑钀滈澶╃劧鐢�(ch菐n)鐗╁父瑕�(gu墨)鎬ц唱(zh矛)锛氬娉曞凹閱�锛涚墰鍏掗叜锛涙鐗涘厭濂�锛涘北閬撳勾锛涚董鐢熺礌 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悳椤炲拰鐢鹃珨鍖栧悎鐗╃殑鐢熺墿鍚堟垚銆�
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�锛岃珛鑱�(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€嬩汉瑙€榛�(di菐n)锛岃垏鏈恫(w菐ng)绔欑劇闂�(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)鏈珯璀夊锛屽皪鏈枃浠ュ強鍏朵腑鍏ㄩ儴鎴栬€呴儴鍒嗗収(n猫i)瀹�銆佹枃瀛楃殑鐪熷鎬�銆佸畬鏁存€�銆佸強鏅傛€ф湰绔欎笉浣滀换浣曚繚璀夋垨鎵胯锛岃珛璁€鑰呭儏浣滃弮鑰冿紝骞惰珛鑷鏍稿鐩搁棞(gu膩n)鍏�(n猫i)瀹�銆�
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鏂囩珷鎼滅储
鎮ㄧ従(xi脿n)鍦ㄧ殑浣嶇疆锛� 
