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鍙嬫儏鎻愮ず锛氭湰绔欐彁渚涘叏鍦�400澶氭墍楂樼瓑闄㈡牎鎷涙敹纰╁＋銆佸崥澹爺绌剁敓鍏ュ鑰冭│姝峰勾鑰冪爺鐪熼銆佽€冨崥鐪熼銆佺瓟妗�锛岄儴鍒嗗鏍℃洿鏂拌嚦2012骞�锛�2013骞�锛涘潎鎻愪緵鏀惰不涓嬭級銆� 涓嬭級娴佺▼锛� 鑰冪爺鐪熼 榛炴搳鈥�鑰冪爺瑭﹀嵎鈥濃€濅笅杓�; 鑰冨崥鐪熼 榛炴搳鈥�鑰冨崥瑭﹀嵎搴�鈥� 涓嬭級
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涓湅绉戝闄㈠ぇ瀛哥ⅸ澹爺绌剁敓鍏ュ鑰冭│
銆婃湁姗熷寲瀛搞€嬭€冭│澶х侗
鏈€婃湁姗熷寲瀛搞€嬭€冭│澶х侗閬╃敤浜庝腑鍦嬬瀛搁櫌澶у鏈夋鍖栧銆佽棩鐗╁寲瀛哥瓑灏堟キ(y猫)鍙婁互鏈�
姗熷悎鎴愮偤涓昏鎵嬫鐨勫叾浠栫浉闂�(gu膩n)灏堟キ(y猫)濡傜敓鐗╁寲瀛革紙鍖栧鐢熺墿瀛革級銆佹湁姗熷厜闆绘潗鏂�銆佹湁姗熷皫
闆绘潗鏂�銆佽静(n贸ng)钘ュ悎鎴�銆佺簿绱板寲宸ョ瓑鐮旂┒鏂瑰悜鎴�?q奴)顥滻(y猫)鐨勭ⅸ澹爺绌剁敓鍏ュ鑰冭│銆傛湁姗熷寲瀛告槸鍖�
瀛哥殑閲嶈鍒嗘灊锛屾槸瑷卞瀛哥灏堟キ(y猫)鐨勫熀绀�(ch菙)鐞嗚珫瑾茬▼锛屽畠鐨勫収(n猫i)瀹硅睈瀵�锛岃姹傝€冪敓灏嶅叾鍩烘湰姒�
蹇垫湁杓冩繁鍏ョ殑浜嗚В锛岃兘澶犵郴绲�(t菕ng)鍦版帉鎻″悇椤炲寲鍚堢墿鐨勫懡鍚嶃€佺祼(ji茅)妲�(g貌u)鐗归粸鍙婄珛楂旂暟妲�(g貌u)銆佷富瑕佹€�
璩�(zh矛)銆佸弽鎳�銆佷締婧愬拰鍚堟垚鍒跺倷鏂规硶绛夊収(n猫i)瀹�锛涜兘瀹屾垚鍙嶆噳銆佺祼(ji茅)妲�(g貌u)閼掑畾銆佸悎鎴愮瓑鍚勯鍟忛锛涚啛
缈掑吀鍨嬬殑鍙嶆噳姝风▼鍙婃蹇�锛涗簡瑙ｅ寲瀛搁嵉鐞嗚珫姒傚康銆侀亷娓℃厠(t脿i)鐞嗚珫锛屽垵姝ユ帉鎻＄⒊姝ｉ洟瀛�銆佺⒊
璨犻洟瀛�銆佺⒊娓搁洟鍩虹瓑涓枔楂旂殑鐩稿皪娲绘€у強鍏跺湪鏈夋鍙嶆噳閫茬▼涓殑浣滅敤锛涜兘鎳夌敤闆诲瓙鏁堟噳
鍜岀┖闁撴晥鎳変締瑙ｉ噵涓€浜涙湁姗熷寲鍚堢墿鐨勭祼(ji茅)妲�(g貌u)鑸囨€ц兘鐨勯棞(gu膩n)绯�锛涗簡瑙ｆ牳纾佸叡鎸瓬銆佺磪澶栧厜璀溿€�
绱鍏夎瓬銆佽唱(zh矛)璀滅瓑鐨勫熀鏈師鐞嗗強鍏跺湪娓畾鏈夋鍖栧悎鐗╃祼(ji茅)妲�(g貌u)涓殑鎳夌敤銆傚叿鏈夌稖鍚堥亱鐢ㄦ墍瀛�
鐭ヨ瓨鍒嗘瀽鍟忛鍙婅В姹哄晱椤岀殑鑳藉姏銆�
涓€銆佽€冭│鍏�(n猫i)瀹�
锛�銆佹湁姗熷寲鍚堢墿鐨勫悓鍒嗙暟妲�(g貌u)銆佸懡鍚嶅強鐗╂€�
锛�1锛夋湁姗熷寲鍚堢墿鐨勫悓鍒嗙暟妲�(g貌u)鐝�(xi脿n)璞�
锛�2锛夋湁姗熷寲鍚堢墿绲�(ji茅)妲�(g貌u)寮忕殑鍚勭ó琛ㄧず鏂规硶
锛�3锛夋湁姗熷寲鍚堢墿鐨勬櫘閫氬懡鍚嶅強鍦嬮殯 IUPAC 鍛藉悕鍘熷墖鍜屼腑鍦嬪寲瀛告渻鍛藉悕鍘熷墖鐨勯棞(gu膩n)绯�
锛�4锛夋湁姗熷寲鍚堢墿鐨勭墿鐞嗘€ц唱(zh矛)鍙婂叾绲�(ji茅)妲�(g貌u)闂�(gu膩n)绯�
2銆佹湁姗熷寲瀛稿弽鎳�
锛�1锛夐噸瑕佸畼鑳藉湗鍖栧悎鐗╃殑鍏稿瀷鍙嶆噳鍙婄浉浜掕綁(zhu菐n)鎻涚殑甯哥敤鏂规硶
閲嶈瀹樿兘鍦樺寲鍚堢墿锛氱兎鐑�銆佺儻鐑淬€佺倲鐑�銆侀沟浠ｇ兇銆佽姵鐑淬€侀唶銆侀厷銆侀啔銆侀啗銆侀叜銆�
閱�銆佺晶閰稿強鍏惰鐢熺墿銆佽兒鍙婂叾浠栧惈姘寲鍚堢墿銆佺啊鍠殑闆滅挵(hu谩n)楂旂郴
锛�2锛変富瑕佹湁姗熷弽鎳夛細鍙栦唬鍙嶆噳銆佸姞鎴愬弽鎳�銆佹秷闄ゅ弽鎳夈€佺府鍚堝弽鎳�銆佹哀鍖栭倓鍘熷弽鎳�銆侀噸
鎺掑弽鎳夈€佽嚜鐢卞熀鍙嶆噳銆佸懆鐠�(hu谩n)鍙嶆噳銆�
3銆佹湁姗熷寲瀛哥殑鍩烘湰鐞嗚珫鍙婂弽鎳夋鐞�
锛�1锛夎獦灏庢晥鎳�銆佸叡杌涙晥鎳�銆佽秴鍏辫粵鏁堟噳銆佺珛楂旀晥鎳�
锛�2锛夌⒊姝ｉ洟瀛�銆佺⒊璨犻洟瀛�銆佺⒊鑷敱鍩恒€佸崱璩�銆佽嫰鐐旂瓑娲绘€т腑闁撻珨
锛�3锛夊叡鎸珫绨′粙銆佹湁姗熷弽鎳夊嫝鑳藉湒鍙婄浉闂�(gu膩n)姒傚康
锛�4锛夋湁姗熷弽鎳夋鐞嗙殑琛ㄩ仈
4銆佹湁姗熷悎鎴�
2
锛�1锛夊畼鑳藉湗灏庡叆銆佽綁(zhu菐n)鎻�銆佷繚璀枫€�
锛�2锛夌⒊纰抽嵉褰㈡垚鍙婃柗瑁傜殑鍩烘湰鏂规硶
锛�3锛夐€嗗悜鍚堟垚鍒嗘瀽鐨勫熀鏈榛炲強鍏跺湪鏈夋鍚堟垚涓殑鎳夌敤
5銆佹湁姗熺珛楂斿寲瀛�
锛�1锛夊咕浣曠暟妲�(g貌u)銆佸皪鏄犵暟妲�(g貌u)銆佹(g貌u)璞＄暟妲�(g貌u)绛夐潨鎱�(t脿i)绔嬮珨鍖栧鐨勫熀鏈蹇�
锛�2锛夊娑堟棆楂旂殑鎷嗗垎鏂规硶銆佷笉灏嶇ū鍚堟垚绨′粙
锛�3锛夊彇浠ｃ€佸姞鎴�銆佹秷闄ゃ€侀噸鎺�銆佸懆鐠�(hu谩n)鍙嶆噳鐨勭珛楂斿寲瀛�
6銆佹湁姗熷寲鍚堢墿鐨勫父鐢ㄧ殑鍖栧銆佺墿鐞嗛憭瀹氭柟娉�
锛�1锛夊父瑕嬪畼鑳藉湗鐨勭壒寰佸寲瀛搁憭鍒ユ柟娉�
锛�2锛夊父瑕嬫湁姗熷寲鍚堢墿鐨勬牳纾佸叡鎸瓬锛圚NMR銆丆NMR锛�銆佺磪澶栧厜璀�(IR)銆佺传澶栧厜璀�(UV)
鍜岃唱(zh矛)璀�(MS)鐨勮瓬瀛哥壒寰�
锛�3锛夐亱鐢ㄥ寲瀛告柟娉曞強鍥涘ぇ娉㈣瓬灏嶇啊鍠湁姗熷寲鍚堢墿閫茶绲�(ji茅)妲�(g貌u)閼掑畾
7銆侀洔鐠�(hu谩n)鍖栧悎鐗╁強鍏冪礌鏈夋鍖栧
鍚� N锛孲锛孫 绛夌殑浜�銆佸叚鍏冮洔鐠�(hu谩n)鍖栧悎鐗�銆佸強鍏跺畠绲�(ji茅)妲�(g貌u)鐨勬湁姗熺～銆佺７銆佺鍖栧悎鐗�
8銆佺⒊姘村寲鍚堢墿銆佹补鑴傘€佹皑鍩洪吀銆佽泲鐧借唱(zh矛)銆佽悳椤炪€佺斁鏃忕瓑澶╃劧鐢�(ch菐n)鐗╃殑绲�(ji茅)妲�(g貌u)銆佹€ц唱(zh矛)鍜岀敤閫�
浜�銆佽€冭│瑕佹眰锛堣姹傛帉鎻″拰浜嗚В鐨勫悇绔犲収(n猫i)瀹癸級
绗竴绔� 绶掕珫
浜嗚В鏈夋鍖栧悎鐗╁拰鏈夋鍖栧鐨勬兜缇�銆佹湁姗熷寲瀛哥殑閲嶈鎬�銆佷竴鑸殑鐮旂┒鏂规硶鍙婂垎椤�
鎺屾彙浜嗚В鏈夋鍖栧悎鐗╃壒鎬�
1.1 浜嗚В鏈夋鍖栧悎鐗╃殑娑电京銆佹湁姗熷寲瀛稿強鍏剁櫦(f膩)灞曠啊鍙�銆佹湁姗熷寲瀛哥殑閲嶈鎬�
1.2 鐔熸倝骞舵帉鎻℃湁姗熷寲鍚堢墿鐨勭祼(ji茅)妲�(g貌u)鑸囩壒鎬�
1.2.1 鍏卞児閸电殑鏈唱(zh矛)锛堝児閸垫硶銆佸垎瀛愯粚閬撴硶銆侀畱鏋楀叡鎸珫绨′粙锛�
1.2.2 鍏卞児閸电殑鍙冩暩(sh霉)锛氶嵉闀�銆侀嵉瑙�銆侀嵉鑳�銆佸厓绱犵殑闆昏矤鎬у拰閸电殑妤垫€�
1.2.3 鏈夋鍖栧悎鐗╃殑鐗规€э細鐗╃悊鐗规€�銆佺珛楂旂暟妲�(g貌u)锛屽畼鑳藉湗鐣版(g貌u)锛屽悓鍒嗙暟妲�(g貌u)鐝�(xi脿n)璞★紙楂旓級锛�
妲�(g貌u)鍨嬭垏妲�(g貌u)璞★紝Kekule A (鍑卞韩鍕�)鍙� Couper A(鍙ゆ煆鐖�)鐨勫叐鍊嬮噸瑕佸熀鏈(gu墨)鍓�銆�
1.2.4 鍏卞児閸垫柗瑁傛柟寮忓拰鏈夋鍙嶆噳椤炲瀷
1.2.5 鏈夋鍖栧悎鐗╃殑閰稿牽姒傚康
1.3 浜嗚В鐮旂┒鏈夋鍖栧悎鐗╃殑涓€鑸柟娉�
1.4 浜嗚В鏈夋鍖栧悎鐗╃殑鍒嗛锛氭寜纰宠兂鍒嗛锛屾寜瀹樿兘鍦樺垎椤�
绗簩绔� 鐑风兇鍜岃剛鐠�(hu谩n)鐑风兇
2.1 鎺屾彙鐑风兇鐨勫垎椤�銆佸懡鍚嶃€佺祼(ji茅)妲�(g貌u)銆佸悓绯诲垪鍜屽悓鍒嗙暟妲�(g貌u)鐝�(xi脿n)璞★紙纰冲師瀛愬拰姘師瀛愮殑椤炲瀷锛�銆�
鐣版(g貌u)銆佹(g貌u)璞″強妲�(g貌u)璞＄暟妲�(g貌u)楂�銆佺墿鐞嗘€ц唱(zh矛)璁婂寲瓒ㄥ嫝锛涗簡瑙ｇ敳鐑风殑绲�(ji茅)妲�(g貌u)锛氱⒊鍘熷瓙鐨勫洓闈㈤珨
姒傚康 SP3
闆滃寲銆佄� 閸碉紙妲�(g貌u)鍨嬫蹇碉級锛涗簡瑙ｄ箼鐑枫€佷竵鐑风殑妲�(g貌u)璞″強鐩镐簰杞�(zhu菐n)璁婇棞(gu膩n)绯�
3
2.2 浜嗚В鐑风兇鐨勯噸瑕佺墿鐞嗘€ц唱(zh矛)锛氱啍榛�銆佹哺榛炪€佸瘑搴�銆佹憾瑙ｅ害銆佹姌鍏夌巼銆�
鎺屾彙鍒嗗瓙绲�(ji茅)妲�(g貌u)灏嶇墿鐞嗗寲瀛告€ц唱(zh矛)鐨勫奖闊�锛涚┅(w臎n)瀹氭€�銆侀沟浠�銆佹哀鍖栵紙瀹屽叏姘у寲鍜屾帶鍒舵哀鍖栵級銆�
瑁傚寲鍜岃瑙�銆佺暟妲�(g貌u)鍖栫瓑銆�
2.3 鐞嗚В鐑风兇鐨勫弽鎳�銆佺敳鐑风殑楣典唬鍙嶆噳姝风▼銆佹父闆㈠熀銆侀€ｉ帠鍙嶆噳銆佽兘閲忔洸绶�銆侀亷娓＄媭鎱�(t脿i)銆�
娓搁洟鍩虹殑绌�(w臎n)瀹氭€у拰楣典唬鍙嶆噳鐨勫彇鍚戯細鑷敱鍩哄彇浠ｅ弽鎳夈€佺⒊鑷敱鍩哄舰鎴愬強鎬ц唱(zh矛)銆侀張鍙�
鎳夌殑寮曠櫦(f膩)鑸囩祩姝�
2.4 浜嗚В鐑风兇鐨勪締婧愬強鍒跺倷
2.5 浜嗚В鐠�(hu谩n)鐑风兇鍛藉悕鍙婂弽鎳夊強鐠�(hu谩n)宸辩兎宸ユキ(y猫)渚嗘簮锛涙帉鎻″皬鐠�(hu谩n)鐨勫嫉鍔涘強绌�(w臎n)瀹氭€�銆佹寮�/鑸瑰紡妲�(g貌u)
鍨嬨€佸彇浠ｇ挵(hu谩n)宸茬兎鍜屽崄姘寲钀樼殑妲�(g貌u)璞★細鑸瑰紡銆佹寮忋€乤 閸�銆乪 閸�銆�
绗笁绔� 鐑�
鎺屾彙鍠儻鐑寸殑閲嶈鍖栧鎬ц唱(zh矛)鍙婂弽鎳夎(gu墨)寰�
鎺屾彙鍠儻鐑寸殑鍒嗛銆佸懡鍚�銆佺祼(ji茅)妲�(g貌u)鍙婂悓鍒嗙暟妲�(g貌u)鐝�(xi脿n)璞�
3.1 鐔熸倝鐑殑鍛藉悕銆佺祼(ji茅)妲�(g貌u)銆佺暟妲�(g貌u)楂�銆佺墿鐞嗘€ц唱(zh矛)
3.1.1 鐞嗚В鐑兇鐨勭祼(ji茅)妲�(g貌u) SP2
闆滃寲銆佅€ 閸�
3.1.2 鎺屾彙鐑兇鐨勫悓鍒嗙暟妲�(g貌u)楂斿拰鍛藉悕锛氱⒊鑳崇暟妲�(g貌u)銆佷綅缃暟妲�(g貌u)銆侀爢鍙嶇暟妲�(g貌u)銆佺郴绲�(t菕ng)鍛藉悕娉�
锛堢儻鍩虹殑鍛藉悕锛�銆侀爢鍙嶇暟妲�(g貌u)楂旂殑鍛藉悕銆侀爢/鍙�銆乑/E
3.1.3 浜嗚В鐗╃悊鎬ц唱(zh矛)
3.2 鐑殑鍙嶆噳
鎺屾彙瑕浕鍔犳垚鍙嶆噳姝风▼銆佹捍閹撻洟瀛�銆佽Κ闆昏│鍔戙€佺⒊姝ｉ洟瀛愬強鍏剁┅(w臎n)瀹氭€�銆侀Μ姘忚(gu墨)鍓�銆�
瑾樺皫鏁堟噳锛屾父闆㈠熀鍔犳垚鍙嶆噳姝风▼銆侀亷姘у寲鐗╂晥鎳夌殑瑙ｉ噵棣埦鍙凹鍙か瑕�(gu墨)鍓囥€佸姞鎴愬弽
鎳変腑鐨勭⒊姝ｉ洟瀛�銆佺⒊姝ｉ洟瀛愮殑绲�(ji茅)妲�(g貌u)鍙婃€ц唱(zh矛)銆佷簩鐑殑 1锛�4 鍔犳垚 Diels-Alder[2+4]鐠�(hu谩n)鍔�
鎴愬弽鎳�
3.2.1 鍔犳垚鍙嶆噳锛氬偓鍖栧姞姘€佽垏涔欑〖鐑风殑鍔犳垚銆佸姞 X2銆佽垏閰哥殑鍔犳垚銆愬姞 HX銆乕棣皬
锛圡arkovnikow锛夎(gu墨)鍓�銆侀亷姘у寲鐗╂晥鎳塢銆佸姞 H2SO4銆�銆侀吀鍌寲鍔� H2O銆佽垏鏈夋
閰搁唶閰氬姞鎴�銆佸姞 HOCl銆佽嚜鐢卞熀鍔犳垚銆�
3.2.2 鑸囧崱璩撶殑鍙嶆噳銆佺儻鐑寸殑闋嗗弽鐣版(g貌u)鍙嶆噳
3.2.3 姘у寲锛氱挵(hu谩n)姘у寲銆侀珮閷抽吀閴€姘у寲鍜岃嚟姘у寲
3.2.4 伪 鈥旀矮鍘熷瓙鐨勯沟浠ｅ弽鎳�
3.2.5 浜嗚В鑱氬悎鍙嶆噳
3.3 鐑殑渚嗘簮鍜屽埗鍌�
3.3.1 鎺屾彙閱囩殑鑴按銆侀沟浠ｇ兇鑴沟鍖栨矮銆侀劙浜岄沟浠ｇ兎鑴沟绱�
3.3.2 鎺屾彙涔欑儻銆佷笝鐑殑绲�(ji茅)妲�(g貌u)鐗归粸鍙婂埗鍌欐柟娉曘€佷富瑕佺敤閫�
3.3.3 浜嗚В鐭虫补鐨勮瑙ｅ拰鐔辫姘ｇ殑鍒嗛洟
3.3.4 浜嗚В閲嶈鐨勭儻鐑达細涔欑儻銆佷笝鐑�
3.4 鎺屾彙鍏辫粵浜岀儻鐑寸壒鍒ユ槸 1锛�3鈥斾竵浜岀儻鐨勬€ц唱(zh矛)銆佺祼(ji茅)妲�(g貌u)鐗归粸鍙婄敤閫�
3.4.1 鍒嗛鍜屽懡鍚�銆佸叡杌涗簩鐑兇鐨勫垎瀛愮祼(ji茅)妲�(g貌u)锛氶洟鍩熼嵉銆侀洟鍩熻兘銆佸叡杌涙晥鎳�
4
3.4.2 鍏辫粵浜岀儻鐑寸殑鍖栧鐗规€э細鍔犳垚鍙嶆噳锛�1锛�2 鍜� 1锛�4鈥斿姞鎴愶級銆佺媱鑰虫柉鈥旈樋鐖惧痉锛圖iels
锛岮lder锛夌挵(hu谩n)鍔犳垚鍙嶆噳銆佽仛鍚堝弽鎳�
3.4.3 閲嶈鐨勪簩鐑兇锛氫竵浜岀儻鍜岀暟鎴婁簩鐑締婧愯垏鍙嶆噳
绗洓绔� 鐐旂兇
4.1 鎺屾彙鐐旂兇鐨勫垎椤�銆佸懡鍚�锛岀祼(ji茅)妲�(g貌u)锛坰p 闆滃寲绛夛級鍙婂悓鍒嗙暟妲�(g貌u)鐝�(xi脿n)璞�
4.2 鎺屾彙鐐旂兇閲嶈鐗╃悊鍖栧鎬ц唱(zh矛)銆佸埗鍌欐柟娉曞強鍙嶆噳瑕�(gu墨)寰�, 濡傜倲鐨勫弽鎳夛細鍔犳垚銆佹哀鍖栧強鏈�
绔� H 鐨勬椿鎬х瓑
4.2.1 鍔犳垚鍙嶆噳锛氬偓鍖栧姞姘€佷箼纭肩兎銆佸姞 X2銆佸姞 HX銆佸姞 H2O銆丠CN銆丠OCl锛涜垏鍚�
鈥滄椿鎬ф矮鈥濈殑鏈夋鐗╃殑瑕牳鍔犳垚锛涜垏鍫块噾灞紙K,Na,Li锛夊強娑叉皑閭勫師鍔犳垚锛�
4.2.2 鑱氬悎鍙嶆噳锛堜簩鑱�銆佷笁鑱氾級
4.2.3 姘у寲鍙嶆噳
4.2.4 鐐旈嵉纰充笂鐨勬矮鍘熷瓙鐨勬€ц唱(zh矛)鍜岄憭瀹氾細寮遍吀鎬с€侀噾灞倲鍖栫墿鍙婄兇鍖栵紙纰宠矤闆㈠瓙锛�
4.2.5 鎺屾彙鐐旂兇鍜岀儻鐑寸殑鍒跺倷鍙婂弽鎳夋椿鎬х殑鍗€(q奴)鍒ヨ垏鍏卞悓榛�
4.3 浜嗚В鐐旂殑鍒跺倷锛岀壒鍒ユ槸涔欑倲鐨勬€ц唱(zh矛)銆佸埗鍌欐柟娉曞強鐢ㄩ€�
绗簲绔� 鑻強鑺抽鐑�
鎺屾彙鑺抽鐑撮鍖栧悎鐗╃殑鍛藉悕鍜岀祼(ji茅)妲�(g貌u)锛圫P2
闆滃寲锛夌壒鍒ユ槸鑻殑鐗规€э紙鑺抽鎬э級鍙婄祼(ji茅)妲�(g貌u)鐗瑰緛
鎺屾彙鑺崇兇椤炲寲鍚堢墿鐨勯噸瑕佹€ц唱(zh矛)锛氳嫰鍙婂悓鍒嗙墿鐨勫弽鎳�锛屽彇浠ｅ弽鎳夌殑瀹氫綅瑕�(gu墨)寰�銆佸彇浠ｆ晥鎳夌殑
瑙ｉ噵锛屽苟鑳芥噳鐢ㄥ湪鏈夋鍚堟垚涓�銆�
浜嗚В鑻€佺敳鑻�銆佽悩鐨勬€ц唱(zh矛)鍙婇噸瑕佺敤閫�锛屼簡瑙ｅ鐠�(hu谩n)鑺抽鍖栧悎鐗╁拰闈炶嫰鑺抽楂旂郴
5.1 鑺抽鐑�
5.1.1 鐔熸倝鑻殑鍒嗗瓙绲�(ji茅)妲�(g貌u)锛氬嚤搴嫆锛圞ekule锛夊紡銆佸垎瀛愯粚閬撴硶銆佸叡鎸珫绨′粙锛岃姵棣欐€цВ
閲�
5.1.2 浜嗚В鍠挵(hu谩n)鑺抽鐑寸殑鐣版(g貌u)鐝�(xi脿n)璞″拰鍛藉悕
5.1.3 鎺屾彙鑻強鍏跺悓绯荤墿鐨勭墿鐞嗗拰鍖栧鎬ц唱(zh矛)
5.1.3.1 鍙栦唬鍙嶆噳锛氶沟浠�銆佺鍖�銆佺：鍖�銆佸倕鈥斿厠锛團ridel-Crafts锛夊弽鎳�锛涜嫰鐠�(hu谩n)瑕浕鍙栦唬
鍙嶆噳姝风▼锛埼� 鈥旂怠(lu貌)鍚堢墿锛�锛涜嫰鐠�(hu谩n)涓婂彇浠ｅ弽鎳夌殑瀹氫綅瑕�(gu墨)寰嬶紙鐞嗚珫瑙ｉ噵鍜屽悎鎴愪笂
鐨勬噳鐢級銆佽秴鍏辫粵鏁堟噳銆�
5.1.3.2 楣电礌锛圕l锛夌敳鍩哄寲鍙嶆噳,鍔犵壒鏇�(Gatterman)-绉戣但(Koch)鍙嶆噳
5.1.3.3 浼锛圔irch锛夐倓鍘熷弽鎳�
5.1.3.4 姘у寲鍙嶆噳锛氳嫰鐠�(hu谩n)姘у寲銆佸伌(c猫)閺堟哀鍖�
5.1.3.5 閲嶈鐨勫柈鐠�(hu谩n)鑺崇兇锛氳嫰銆佺敳鑻€佷簩鐢茶嫰銆佽嫰涔欑儻
5.2 澶氱挵(hu谩n)鍙婄鐠�(hu谩n)鑺崇兇
5.2.1 浜嗚В涓夎嫰鐢插熀鍖栧悎鐗╁強鍏堕洟瀛愬拰鑷敱鍩虹殑绌�(w臎n)瀹氭€�锛岃伅(li谩n)鑻壒鎬у強鍚堟垚
5.2.2 鎺屾彙钀橈細 绲�(ji茅)妲�(g貌u)鎬ц唱(zh矛)鍙婂叾鍙栦唬鍙嶆噳銆佸姞鎴愬弽鎳�銆佹哀鍖栧弽鎳�
5.2.3 浜嗚В钂藉拰鑿诧細绲�(ji茅)妲�(g貌u)鍜屾€ц唱(zh矛)锛�9銆�10 浣嶇殑娲绘綉鎬э級
5
5.2.4 浜嗚В鍏朵粬绋犵挵(hu谩n)鑺崇兇锛堣嚧鐧岀兇锛�
5.3 浜嗚В鑺抽鐑寸殑渚嗘簮锛氱叅鐒︽补鐨勫垎闆�銆佺煶娌圭殑鑺虫(g貌u)鍖栧拰閲嶆暣
鐭虫补锛氱煶娌圭殑鎴愬洜銆佺祫鎴愬拰鍒嗛锛涚煶娌圭殑鐓夊埗鍜岀煶娌瑰姞宸�
锛�1锛� 鐭虫补鐨勪竴娆″姞宸ワ細甯�銆佹笡澹撹捀椁�
锛�2锛� 鐭虫补鐨勪簩娆″姞宸ワ細瑁傝В鍜岄噸鏁�
姹芥补鍜屾煷娌癸細杈涚兎鍊�銆佹姉鐖嗗姂銆佸崄鍏兎鍊�
5.4 涓€鑸簡瑙ｉ潪鑻姵鐑达細浼戝厠鑰筹紙Huckel锛夎(gu墨)鍓囧強鍏舵噳鐢ㄣ€佷簩鑼傞惖
绗叚绔� 楣典唬鐑�
浜嗚В楣典唬鐑寸殑鍒嗛鍜岀墿鐞嗘€ц唱(zh矛)
鎺屾彙楣典唬鐑寸殑鍛藉悕鍙婇噸瑕佸寲瀛告€ц唱(zh矛)
鎺屾彙骞剧ó閲嶈鐨勯沟浠ｇ兇鍒跺倷鏂规硶,浜嗚В鍏舵€ц唱(zh矛)鍙婃噳鐢�
6.1 楣典唬鐑寸殑鍒嗛鍙婂懡鍚�銆佺祼(ji茅)妲�(g貌u)銆佸悓鍒嗙暟妲�(g貌u)
6.2 楣典唬鐑寸殑鐗╃悊鍖栧鎬ц唱(zh矛)
6.2.1 鎺屾彙鍖栧鎬ц唱(zh矛): 楣典唬鐑寸殑鍙嶆噳濡傚彇浠ｃ€佹秷闄�銆侀倓鍘熺瓑
6.2.1.1 鍙栦唬鍙嶆噳锛氭按瑙ｃ€侀唶瑙�銆佹皑瑙�銆佽垏纭濋吀閵€鍙婃鞍鍖栭垑鐨勫弽鎳�
6.2.1.2 娑堝幓鍙嶆噳锛氭湱渚濆垏澶紙Saytzeff锛夎(gu墨)鍓�
6.2.1.3 鑸囬噾灞弽鎳夛細鏍兼皬锛圙rignard锛夎│鍔�銆佹湁姗熼嫲瑭﹀姂銆佹鎱堬紙Wurtz锛�
鍙嶆噳锛堟湁姗熼噾灞寲鍚堢墿鐨勬蹇碉級
6.2.2 鎺屾彙椋藉拰纰冲師瀛愪笂鐨勮Κ鏍稿彇浠ｅ弽鎳�
6.2.2.1 鍙栦唬鍙嶆噳鐨勯洟瀛愭鐞� SN1銆丼N2; 娑堥櫎鍙嶆噳鐨勬鐞� E1銆丒2
6.2.2.2 瑕牳鍙栦唬鐨勭珛楂斿寲瀛�
6.2.2.3 鐑村熀绲�(ji茅)妲�(g貌u)銆侀洟鍘诲熀鍦樺皪瑕牳鍙栦唬鍙嶆噳閫熷害鐨勫奖闊�
6.2.2.4 绲�(ji茅)妲�(g貌u)鑸囧弽鎳夋椿鎬х殑闂�(gu膩n)绯伙紙鑴傝偑鐑磋垏鑺抽鐑村皪姣�,浼徊鍙斿皪姣旓級
6.3 鎺屾彙涓€鑸沟浠ｇ兇鐨勫埗娉曪細鐢辩兇鍒跺倷銆佺敱閱囧埗鍌�銆侀沟浠ｇ兇鐨勪簰鎻�
6.4 浜嗚В閲嶈楣典唬鐑达細姘箼鐑€佹隘鑻�銆佹隘鑺�銆佷笁姘敳鐑枫€佸洓姘寲纰�銆佹盁閲屾槀銆佸洓姘熶箼鐑�銆�
绗竷绔� 閱囥€侀厷鍜岄啔
鐔熸倝閱�銆侀厷銆侀啔鐨勫垎椤炪€佸懡鍚�銆佺祼(ji茅)妲�(g貌u)鍚屽垎鐣版(g貌u)锛堝畼鑳藉湗鐣版(g貌u)锛夊拰鍏夎瓬鐗规€�
鎺屾彙閱囥€侀厷銆侀啔鐨勯噸瑕佹€ц唱(zh矛)鍜屽弽鎳夎(gu墨)寰嬶細姘嵉鈥旈唶鑸囬啔灏嶆瘮銆侀唶鑸囬厷鐨勯吀鎬у皪姣�锛�
閱囩殑鍙嶆噳銆侀啔鐨勫弽鎳�銆佺浠垮弽鎳�锛岄唶鐨勯憭鍒ワ細Lucas 瑭﹀姂鍜岄壔閰愮～閰告按娉�
浜嗚В閱�銆侀厷銆侀啔涓噸瑕佺殑鍖栧悎鐗╃殑鎬ц唱(zh矛)銆佸悎鎴愭柟娉曞強鎳夌敤
7.1 閱�
7.1.1 閱囩殑鐗╃悊鍜屽寲瀛告€ц唱(zh矛)
鐔熸倝鎺屾彙鍏跺寲瀛告€ц唱(zh矛)锛氳垏娲绘綉閲戝爆鍙嶆噳锛岃垏楣靛寲纾凤紙鎴栦簽纭叞姘級鍙嶆噳锛岃垏鐒�
姗熼吀锛堟矮楣甸吀銆佺～閰�銆佺閰革級锛岄叞姘拰閰搁厫绛夌殑鎴愰叝鍙嶆噳锛岃劔姘村弽鎳�锛屾哀鍖栧拰鑴�
6
姘弽鎳�锛岀浉閯颁簩閱囩壒鏈夌殑鍙嶆噳 Cu(OH)2銆丠IO4銆佺墖鍚堕唶锛坧inacol锛夐噸鎺�銆佺茎鍩鸿
缃彌鍙嶆噳锛堥劙鍩哄弮鑸囨晥鎳夛級
7.1.2 鎺屾彙娑堝幓鍙嶆噳姝风▼
a)尾 鈥旀秷鍘诲弽鎳夛細鍙嶆噳姝风▼ E1銆丒2锛� 娑堥櫎鍙嶆噳鐨勫彇鍚戯細鏈緷鍒囧か瑕�(gu墨)鍓囩殑瑙ｉ噵锛�
鑸囪Κ鏍稿彇浠ｅ弽鎳夌殑绔剁埈
b)伪 鈥旀秷鍘诲弽鎳夛細鍗¤硴鐨勭祼(ji茅)妲�(g貌u)鍜屾€ц唱(zh矛)
7.1.3 鎺屾彙閱囩殑鍒舵硶锛氶沟浠ｇ兇姘磋В锛岄啗銆侀叜鐨勯倓鍘�锛岀敱鏍兼皬瑭﹀姂鍚堟垚锛岀儻鐑寸殑缇ユ睘鍖�銆�
7.1.4 浜嗚В閲嶈鐨勯唶锛氱敳閱�銆佷箼閱�銆佷笁鍗佺兎閱囥€佽嫰鐢查唶銆佷箼浜岄唶銆佷笝涓夐唶锛堢敇娌圭殑鍖�
瀛稿紡锛夈€佽倢閱�
7.2 閰�
7.2.1 鎺屾彙閰氱殑鐗╃悊鎬ц唱(zh矛)銆佸寲瀛告€ц唱(zh矛)鍙婂弽鎳�
锛�1锛� 閰氱茎鍩虹殑鎬ц唱(zh矛)锛氬急閰告€�銆侀厷閱氱殑鐢熸垚銆侀’鑹插弽鎳夛紙FeCl3锛�
锛�2锛� 鑻挵(hu谩n)涓婅Κ闆诲彇浠ｅ弽鎳�锛屾哀鍖栧弽鎳�
7.2.2 浜嗚В閲嶈鐨勯厷: 鑻厷锛堢暟涓欒嫰姘у寲鍒跺倷鍜岀敤閫旓級銆佺敳鑻厷銆佽嫰浜岄厷銆佽悩閰�
7.3 閱�
7.3.1 鎺屾彙閱氱殑鍒舵硶锛� 閱囩殑鑴按锛屽▉寤夊閬滐紙Williamson锛�
7.3.2 鎺屾彙閱氱殑鐗╃悊鍖栧鎬ц唱(zh矛)鍙婂弽鎳夛細楣界殑鐢熸垚銆侀啔閸电殑鏂疯銆侀亷姘у寲鐗╃殑鐢熸垚
7.3.3 浜嗚В骞剧ó閲嶈鐨勯啔鐨勬€ц唱(zh矛)鍜屾噳鐢細涔欓啔銆佷簩鑻啔锛堝偝鐔辫級楂旓級銆佺挵(hu谩n)姘т箼鐑枫€佸啝
閱氾紙鐩歌綁(zhu菐n)绉诲偓鍖栵級
绗叓绔� 閱�銆侀叜椤炵景鍩哄寲鍚堢墿
鎺屾彙閱�銆侀叜鍖栧悎鐗╃殑鍒嗛銆佸懡鍚�銆佺祼(ji茅)妲�(g貌u)鍙婄暟妲�(g貌u)銆佺墿鎬у強鍏夎瓬鐗规€�
鎺屾彙閱�銆侀叜椤炵景鍩哄寲鍚堢墿鐨勯噸瑕佹€ц唱(zh矛)鍜屽弽鎳夎(gu墨)寰�
鐔熸倝閲嶈閱�銆侀叜鍖栧悎鐗╃殑鎬ц唱(zh矛)銆佸悎鎴愭柟娉曞拰鎳夌敤
8.1 閱�銆侀叜椤炵景鍩哄寲鍚堢墿鐨勭墿鐞嗗寲瀛告€ц唱(zh矛)
8.1.1 鐔熸倝骞舵帉鎻¤垏鍚哀銆佸惈纭�銆佸惈纰炽€佸惈姘Κ鏍歌│鍔戠殑鍔犳垚鍙嶆噳鍙婂弽鎳夋绋�锛屽姞鎴�
鈥旀秷鍘诲弽鎳夋绋�锛屽奖闊跨景鍩烘椿鎬х殑鍥犵礌锛氬姞 HCN銆丯aHSO3銆丷SH銆丷MgX銆�
ROH銆丠2O锛岃垏鏈夋鑳哄強鍏惰鐢熺墿鐨勫姞鎴愮府鍚堝弽鎳�锛岃垏姘ㄧ殑琛嶇敓鐗╃殑鍙嶆噳銆�
8.1.2 伪 鈥旀矮鍘熷瓙鐨勫弽鎳夛細楣典唬锛堥沟浠垮弽鎳夛級銆佺茎閱涚府鍚�
8.1.3 鎺屾彙鍏舵哀鍖栭倓鍘熷弽鎳�
a)姘у寲锛涙墭鍊紙Tollens锛夎│鍔�銆佽不鏋楋紙Fehling锛夎│鍔�銆佸挤姘у寲鍔�
b)閭勫師锛氬埄鐢� H2,銆丩iAlH4銆丯aBH4銆丅2H6銆丮e2CHOAl銆乑n/Hg/H+
銆丯H2NH2/KOH
绛夎│鍔戞浠堕倓鍘熸垚閱囷紙闆欏垎瀛愰倓鍘燂級銆侀倓鍘熸垚鐑�銆佸厠閲岄杸閬滐紙Clemmensen锛夊弽
鎳�銆佹鐖惧か鈥旈枊姝囩磵锛圵ollf-Kishner锛夆€旈粌槌撮緧锛圚uang Minlon锛夊弽鎳�
c)姝у寲锛氬悍灏兼煡缇咃紙Cannizzaro锛夊弽鎳�銆�
8.1.4 浜嗚В閱涚殑鑷韩鍔犳垚鑱氬悎
8.1.5 浜嗚В閱涚殑椤壊鍙嶆噳锛氬笇澶紙Schiff锛夎│椹�
7
8.2 鎺屾彙閱�銆侀叜鐨勫埗娉曪細閱囩殑姘у寲銆佺兇鐨勬哀鍖栵紝鍋曚簩楣典唬鐗╃殑姘磋В锛屽倕鈥斿厠閰板熀鍖栧弽鎳�锛�
鐐旂兇鐨勭景鍩哄寲锛岀晶閰稿強鍏惰鐢熺墿鐨勯倓鍘�銆�
8.3 鐔熸倝閲嶈鐨勯啗銆侀叜锛氱敳閱�銆佷箼閱涳紙涔欑儻姘у寲鍚堟垚涔欓啗锛変笁姘箼閱�銆佽嫰鐢查啗锛堝畨鎭
绺悎锛夈€佷笝閰�銆佷竵浜岄叜锛堥幊瑭﹀姂锛�銆佺挵(hu谩n)宸遍叜[璨濆厠鏇硷紙Bechmann锛塢閲嶆帓
8.4 浜嗚В涔欑儻閰�銆侀唽绛変笉椋藉拰缇板熀鍖栧悎鐗╋紝鐔熸倝伪 锛屛� 鈥斾笉椋藉拰閱涢叜鐨勭壒鎬э細1锛�4鈥斿姞
鎴愩€佹彃鐑(gu墨)寰�銆�
绗節绔� 缇ч吀鍙婄晶閰歌鐢熺墿
浜嗚В缇ч吀鍙婂叾琛嶇敓鐗╃殑鍒嗛鍜屽懡鍚�
鎺屾彙缇ч吀鍙婂叾琛嶇敓鐗╃殑閲嶈鎬ц唱(zh矛)
鐔熸倝鎺屾彙涔欓叞涔欓吀涔欓叝鍜屼笝浜岄吀浜屼箼閰湪鏈夋鍖栧悎鐗╃殑鎳夌敤
9.1 缇ч吀鐨勫懡鍚�銆佺墿鎬у強鍏夎瓬鐗规€�
9.2 鐔熸倝缇ч吀鐨勭祼(ji茅)妲�(g貌u)鑸囬吀鎬э紙瑾樺皫鏁堟噳锛屽叡杌涙晥鎳夊強鍫存晥鎳夌殑褰遍熆锛�
9.3 鐔熸倝缇ч吀鐨勫埗鍌欙細鐢辩兇銆佷集閱囨垨閱涚殑姘у寲銆佺敱閰埗鍌欍€佺敱鑵堟按瑙ｅ強閲戝爆鏈夋瑭﹀姂鍚�
鎴愬鏍兼皬瑭﹀姂鍒跺倷
9.4 鎺屾彙缇ч吀鐨勫弽鎳�
閰告€х晶鍩轰腑姘師瀛愮殑鍙嶆噳锛堝彇浠ｅ熀灏嶉吀鎬х殑褰遍熆銆佽獦灏庢晥鎳夛級銆佸舰鎴愰吀楣�銆侀叝銆侀叞
鑳�銆佽劔缇�銆佄� 鈥擧 鐨勯沟浠ｅ弽鎳�銆侀倓鍘燂紙琚矮鍖栭媮閶伴倓鍘燂級銆侀叝鍖栧弽鎳夌殑姗熺悊锛氱晶閰�
涓殑缇у熀鐨勫弽鎳夛紙閰寲鍙嶆噳鐨勬绋嬶細闂℃槑姗熺悊鐨勫悓浣嶇礌娉曪級
9.5 浜嗚В閲嶈鐨勭晶閰革細鐢查吀銆佷箼閰�銆佷笝鐑吀銆佽嫰鐢查吀銆佽悩涔欓吀銆�
浜嗚В閲嶈浜屽厓缇ч吀鐗╃悊鍖栧鎬ц唱(zh矛)锛氫箼浜岄吀銆佸繁浜岄吀銆佺櫢浜岄吀銆佷竵鐑簩閰�銆佽嫰浜岀敳閰�
9.6 鐔熸倝缇ч吀琛嶇敓鐗╅叞楣�銆侀叝銆侀叞鑳�銆佽厛鐨勫垎椤�銆佸懡鍚�銆佺祼(ji茅)妲�(g貌u)姣旇純銆佺墿鐞嗗拰鍖栧鎬ц唱(zh矛)銆�
鍙嶆噳鍜屽埗鍌�锛涙帉鎻＄晶閰歌鐢熺墿鐨勫寲瀛稿弽鎳夊強鍏剁浉浜掕綁(zhu菐n)鍖栵細瑕牳鍙栦唬鍙嶆噳锛堝姞鎴愨€旀秷
闄ゅ弽鎳夋绋嬶級銆佹按瑙�銆侀唶瑙�銆佹皑瑙ｉ叝鐨勬按瑙ｅ強姝风▼锛涜垏閲戝爆瑭﹀姂鐨勫弽鎳�锛涚晶閰歌鐢�
鐗╃殑閭勫師锛涢叝绺悎鍙嶆噳锛涢叞姘ㄧ殑鑴按鍜岄湇澶浖锛圚offfmann锛夐檷瑙ｅ弽鎳�銆�
9.7 鐔熸倝骞舵帉鎻′箼閰颁箼閰镐箼閰拰涓欎簩閰镐簩涔欓叝鐨勫埗鍌欒垏鎳夌敤
a)涔欓叞涔欓吀涔欓叝锛氬埗鍌�銆佷簰璁婄暟妲�(g貌u)鍙婂叾鍦ㄥ悎鎴愪笂鐨勬噳鐢�
b)涓欎簩閰镐簩涔欓叝鍙婂叾鍦ㄥ悎鎴愪笂鐨勬噳鐢�
c)纰抽吀鍙婅鐢熺墿锛氬厜姘�銆佸翱绱犮€佹皑鍩虹敳閰搁叝
9.8 涔欑儻閰�
9.9 鐔熸倝鍙栦唬缇ч吀锛堝楣典唬閰�銆佺茎閰�銆侀叜閰革級鐨勫悎鎴愯垏鍙嶆噳锛屼簡瑙ｅ鍏冪晶閰哥殑鎬ц唱(zh矛)
9.10 浜嗚В鍕曠墿鑸囨鐗╄剛鑲殑鍗€(q奴)鍒ワ細娌硅剛銆佽牊鍙婂悎鎴愭礂婊屽姂鍘绘薄鍘熺悊
鐗瑰垾鏄补鑴傜殑绲勬垚鑸囩祼(ji茅)妲�(g貌u)鍙婃€ц唱(zh矛)锛氱殏鍖�銆佸姞鎴愬弽鎳�銆佹补鑴傞吀?銆傘剫宥傛媴鈹栭€忓皻?br/>绗崄绔� 绔嬮珨鍖栧锛氱祼(ji茅)妲�(g貌u)鐣版(g貌u)鍜岀珛楂旂暟妲�(g貌u)
10.1 浜嗚В灏嶆槧鐣版(g貌u)( enantiomers )鐝�(xi脿n)璞�銆佺墿璩�(zh矛)鐨勬棆鍏夋€ц垏鍒嗗瓙绲�(ji茅)妲�(g貌u)鐨勯棞(gu膩n)绯伙細鎵嬫€�(Chiral)銆�
8
灏嶇ū鍥犵礌锛堝皪绋遍潰銆佸皪绋变腑蹇冿級銆佸钩闈㈠亸鎸厜鍜屾棆鍏夋€�銆佹棆鍏夊剙鍜屾瘮鏃嬪厜搴�
10.2 鐔熸倝鍚湁鎵嬫€х⒊鍘熷瓙鍖栧悎鐗╃殑灏嶆槧鐣版(g貌u)
a)鍚湁涓€鍊嬫墜鎬х⒊鍘熷瓙鍖栧悎鐗╃殑灏嶆槧鐣版(g貌u)銆佸皪鏄犻珨銆佸娑堟棆楂�銆佽不姝囩埦锛團ischer锛�
鎶曞奖寮�
b)灏嶆槧鐣版(g貌u)楂旂殑妲�(g貌u)鍨嬶細鐩稿皪妲�(g貌u)鍨嬪拰绲曞皪妲�(g貌u)鍨�銆佹帉鎻℃(g貌u)鍨嬬殑 R/S 娉曪紙娆″簭瑕�(gu墨)鍓囷級銆佷簡
瑙� D/L 娉�
c)鍚叐鍊嬫墜鎬х⒊鍘熷瓙鍖栧悎鐗╃殑灏嶆槧鐣版(g貌u)锛氶潪灏嶆槧楂斻€佸収(n猫i)娑堟棆楂�
d)鐠�(hu谩n)鐙€鐨勫寲鍚堢墿灏嶆槧鐣版(g貌u)
10.3 鎺屾彙鐑兇鍖栧悎鐗╃殑骞句綍鐣版(g貌u)楂旓細闋嗗弽鐣版(g貌u)鍙婃€ц唱(zh矛)銆�
10.4 浜嗚В鍚墜鎬ц桓鎴栧惈鎵嬫€ч潰鐨勫寲鍚堢墿鐨勭珛楂旂暟妲�(g貌u)楂旓紝浜嗚В涓嶅惈鎵嬫€х⒊鍘熷瓙鍖栧悎鐗╃殑灏�
鏄犵暟妲�(g貌u)锛氫笝浜岀儻鍨�銆佽伅(li谩n)鑻瀷锛岃灪鏃嬪瀷鍖栧悎鐗�; 浜嗚В N, S 绛夋墜鎬у師瀛愮殑鍖栧悎鐗┿€�
10.5 浜嗚В澶栨秷鏃嬮珨銆佹媶鍒嗗拰涓嶅皪绋卞悎鎴�
10.6 鎺屾彙绔嬮珨鍖栧鍦ㄧ爺绌跺弽鎳夋绋嬩腑鐨勬噳鐢細鐑兇鐨勫姞婧�
绗崄涓€绔� 绱呭锛岀传澶栧厜璀�銆佹牳纾佸叡鎸瓬鍜岃唱(zh矛)璀�
鐔熸倝绱銆佺磪澶栧厜璀溿€佹牳纾佸叡鎸瓬鐨勫熀鏈師鐞嗗強鍦ㄦ湁姗熷寲鍚堢墿绲�(ji茅)妲�(g貌u)娓畾涓殑鎳夌敤
浜嗚В璩�(zh矛)璀滅殑鍩烘湰鍘熺悊鍙婃噳鐢�
閬斿埌鑳藉鍒╃敤鍚勭ó璀滃湒鐨勭稖鍚堜俊鎭苟绲�(ji茅)鍚堢啊鍠寲瀛稿弽鎳夊幓鍒ゆ柗杓冪偤寰╅洔鐨勫寲鍚堢墿鐨勭祼(ji茅)
妲�(g貌u)
11.1 绱呭鍏夎瓬
11.1.1 鍩烘湰鍘熺悊锛氬垎瀛愭尟鍕曢鍨�銆佺磪澶栧厜璀滃湒鐨勮〃绀烘柟娉�
11.1.2 鐔熸倝閲嶈瀹樿兘鍦樼殑鐗瑰緛鍚告敹宄�锛屽奖闊跨磪澶栧惛鏀朵俊铏熶綅绉荤殑鍥犵礌
11.1.3 鎺屾彙閲嶈瀹樿兘鍦樼殑绱呭鍏夎瓬鐗瑰緛鍙婂吀鍨嬬啊鍠湁姗熷寲鍚堢墿鐨勭磪澶栧厜璀滃湒鐨勮В閲�
11.2 鏍哥鍏辨尟璀�
11.2.1 浜嗚В鏍哥鍏辨尟鐨勫熀鏈師鐞�,绛夊児璩�(zh矛)瀛愯垏闈炵瓑鍍硅唱(zh矛)瀛�, 鍋跺悎甯告暩(sh霉)
11.2.2 鎺屾彙绨″柈鍏稿瀷鍖栧悎鐗╃殑鏍哥鍏辨尟璀滃墫鏋愶細灞忚斀鏁堟噳鍜屽寲瀛镐綅绉�锛屽嘲闈㈢⿳鐨�
寮峰害鑸囪唱(zh矛)瀛愭暩(sh霉)锛岃嚜鏃嬪伓鍚堣垏鑷棆瑁傚垎
11.3 绱鍏夎瓬
11.3.1 绱鍏夎瓬鐨勫熀鏈師鐞�銆佺传澶栧厜璀滃湒,浜嗚В鍚勯鍖栧悎鐗╃殑闆诲瓙韬嶉伔锛岀传澶栧厜
璀滆垏鍒嗗瓙绲�(ji茅)妲�(g貌u)鐨勯棞(gu膩n)绯�
11.4 璩�(zh矛)璀滅啊浠�
11.4.1 璩�(zh矛)璀滅殑鍩烘湰鍘熺悊鑸囪唱(zh矛)璀滃剙锛岃唱(zh矛)璀滃湒闆㈠瓙鐨勪富瑕侀鍨嬨€佸舰鎴愬強鎳夌敤锛屽奖闊�
闆㈠瓙褰㈡垚鐨勫洜绱�锛屽悇椤炲寲鍚堢墿鐨勮唱(zh矛)璀滃湒鐗瑰緛
绗崄浜岀珷 鑳哄強鍏朵粬鍚爱鍖栧悎鐗�
鎺屾彙鑳洪鍖栧悎鐗╃殑绲�(ji茅)妲�(g貌u)銆佸垎椤�銆佸懡鍚嶅拰鐗╃悊鍖栧鎬ц唱(zh矛)銆佸弽鎳夎(gu墨)寰嬪拰閲嶈鍖栧悎鐗╃殑鎳夌敤
鎺屾彙纭濆熀鍖栧悎鐗╃殑绲�(ji茅)妲�(g貌u)銆佸垎椤�銆佸懡鍚嶅拰閲嶈鐨勫寲瀛告€ц唱(zh矛)
9
12.1 鑳虹殑鍒嗛銆佸懡鍚�銆佺祼(ji茅)妲�(g貌u)鐗╂€у拰鍏夎瓬鐗瑰緛
12.2 鐔熸倝骞舵帉鎻¤兒鐨勭墿鐞嗘€ц唱(zh矛)鍜屽寲瀛告€ц唱(zh矛)
12. 2. 1 鑳虹殑绲�(ji茅)妲�(g貌u)鍜屽牽鎬э紙绲�(ji茅)妲�(g貌u)鐗归粸銆佹墜鎬�銆佸牽鎬у強褰遍熆鍫挎€уぇ灏忕殑鍥犵礌锛�
12. 2. 2 鎴愰菇銆佸洓绱氶姩楣界殑褰㈡垚銆佺壒榛炲強鎳夌敤锛堝竟搴曠敳鍩哄寲鍙嶆噳銆佸洓绱氶姩鍫跨殑褰㈡垚锛�
鐩歌綁(zhu菐n)绉诲偓鍖栧姂锛夈€丠ofmann 娑堥櫎锛堣(gu墨)寰�銆佸弽鎳夋鐞嗭級
12.2.3 ?锛涱姮顕橀槀闃�锛�?銆侀叞楣�銆侀吀閰�銆佽嫰纾洪叞姘紙鑸堟柉鍫� Hinsberg 鍙嶆噳锛�
12.2.4 鑳虹殑姘у寲鍜� Cope 娑堥櫎锛堥爢鍨嬫秷闄わ級
12.2.5 鑳鸿垏浜炵閰哥殑鍙嶆噳锛堥噸姘寲鍙嶆噳锛岃拏鑺瓙鈥旀嵎濮嗘彋璜惧か Tiffeneau-Demjanov
鐨勭挵(hu谩n)鎿村ぇ閲嶆帓鍙嶆噳锛�
12.2.6 鑳虹殑鐗规畩鍙嶆噳锛氭槗姘у寲銆佽嫰鐠�(hu谩n)涓婃槗鍙栦唬锛� Mannich 鍙嶆噳鍙婂叾鎳夌敤
12.3 鐔熸倝鎺屾彙鑳虹殑鍒跺倷锛氭皑鎴栬兒鐨勭兇鍩哄寲銆佽姵楣电殑姘ㄨВ锛堣嫰鐐旓級; 钃嬪竷鐟炵埦锛圙abriei锛�
鍚堟垚娉�锛岀敤閱囧埗鍌�锛屽惈姘寲鍚堢墿鐨勯倓鍘�:纭濆熀鍖栧悎鐗╃殑閭勫師, 鑵�銆侀叞鑳�銆佽偀鐨勯倓鍘�, 閱�銆�
閰殑閭勫師鑳哄寲(濡傚妷鍗＄壒/Leuckart 鍙嶆噳锛屽焹鏂煁鍕掆€斿厠鎷夊厠/Eschweiler-Clarke 鍙嶆噳);
寰炵晶閰稿強鍏惰鐢熺墿鍒跺倷( 闇嶅か鏇� Hofmann 閲嶆帓銆佸厠鐖炬彁鏂� Curtius 閲嶆帓銆佹柦瀵嗙壒
Schmidt 閲嶆帓)
12.4 浜嗚В閲嶈鐨勮兒锛氳嫰鑳�銆佷簩鐢茶兒銆佷箼浜岃兒锛圗DTA锛�銆佸繁浜岃兒銆佸悇绋儻鑳哄寲鍚堢墿銆�
12.5 鎺屾彙閲嶆爱鍜屽伓姘寲鍚堢墿锛氶噸姘敳鐑峰強鍗¤硴銆佹爱鐑�銆佺枈姘寲鐗╃殑鍒跺倷銆佸弽鎳�
12.5.1 閲嶆爱楣界殑鍒舵硶
12.5.2 閲嶆爱楣界殑鎬ц唱(zh矛)锛氬幓姘弽鎳夛紙琚� H銆丱H銆乆銆丆N 绛夊彇浠ｅ熀鍙栦唬锛�銆佺暀姘弽鎳夛紙鍋�
鍚堝拰閭勫師锛�
12.5.3 浜嗚В鏌撴枡绲�(ji茅)妲�(g貌u)鑸囨€ц唱(zh矛)鍜岀敤閫旓細鍖栧悎鐗╅鑹插拰绲�(ji茅)妲�(g貌u)鐨勯棞(gu膩n)绯伙紙鐢熻壊鍩哄拰鍔╄壊鍩猴級銆�
鏌撴枡鐨勫垎椤炲強鍋舵爱鏌撴枡鍜屾寚绀哄姂锛堢敳鍩烘銆佸墰鏋滅磪锛�
12.6 纭濆熀鍖栧悎鐗�
12.6.1 浜嗚В鍒嗛銆佺祼(ji茅)妲�(g貌u)鍜屽懡鍚�
12.6.2 鎺屾彙鍏舵€ц唱(zh矛)锛氱鍩哄皪伪 鈥旀矮鍘熷瓙鐨勫奖闊匡紙浜掕畩鐣版(g貌u)锛夈€侀倓鍘�銆佺鍩哄皪鑻挵(hu谩n)涓婂彇
浠ｅ熀鐨勫奖闊�
12.6.3 鐔熸倝閲嶈鐨勭鍩哄寲鍚堢墿锛氱鍩鸿嫰銆佽嫤鍛抽吀銆乀NT
12.7 鑵堝拰鐣拌厛锛氬垎瀛愮祼(ji茅)妲�(g貌u)銆佹按瑙ｅ拰閭勫師鍙嶆噳
12.8 鎺屾彙鍚爱鑺抽鍖栧悎鐗╃殑浠ヤ笅鏈夐棞(gu膩n)鍏�(n猫i)瀹�
12.8.1 鑺抽纭濆熀鍖栧悎鐗╃殑绲�(ji茅)妲�(g貌u)銆佺墿鐞嗗強鍖栧鎬ц唱(zh矛)
12.8.2 鑺宠兒鐨勫埗鍌欏拰鑺宠兒鐨勭壒鎬�
12.8.3 鑻倲鐨勫埗鍌欏拰鐠�(hu谩n)鍔犳垚鍙嶆噳
12.8.4 鑺宠兒鐨勯噸姘菇鍙婂弽鎳夊強鍏跺湪鍚堟垚涓婄殑鎳夌敤
绗崄涓夌珷 鍚～銆佺７銆佺鍖栧悎鐗�
鐔熸倝鍚～鍖栧悎鐗╃殑鍖栧鎬ц唱(zh矛)锛屼簡瑙ｅ叾鐗╃悊鎬ц唱(zh矛)
鐔熸倝鏈夋纾峰寲鍚堢墿鐨勫垎椤�銆佸懡鍚嶄互鍙婃湁姗熺７杈�(n贸ng)钘ョ殑鎬ц唱(zh矛)銆佹€ц兘鍜屾噳鐢�
10
浜嗚В鍚鍖栧悎鐗╃殑鐗╃悊鎬ц唱(zh矛)鍙婂寲瀛告€ц唱(zh矛)
13.1 纭�銆佺７鍏冪礌鍘熷瓙鐨勯浕瀛愭(g貌u)鍨嬪拰鎴愰嵉鐗瑰緛
13.2 鐔熸倝鍚～鍖栧悎鐗╃殑绲�(ji茅)妲�(g貌u)椤炲瀷鍜屽懡鍚嶅強鍚堟垚鑸囧弽鎳�
纭唶鍜岀～閰�銆佺～閱�銆佷簽鐮滃拰鐮�銆佺：閰稿強鍏惰鐢熺墿锛堢：鑳鸿棩鐗�銆佺硸绮撅級
13.3 鍚７鍖栧悎鐗�
鎺屾彙閲嶈鍙嶆噳锛氬舰鎴愬纾烽菇鐨勫弽鎳夈€侀瓘鎮岄尗锛圵ittig锛夎│鍔戝強鍏跺弽鎳�
13.4 浜嗚В鏈夋杈�(n贸ng)钘ュ垎椤�銆佽静(n贸ng)钘ョ殑鍔戝瀷銆佽棩鏁堝拰闃茶銆佹湁姗熺７杈�(n贸ng)钘ュ強鍏朵粬
13.5 浜嗚В甯歌楣典唬纭呯兎鍙婄閱�銆佺姘х兎鐨勫悎鎴愬強鍏舵噳鐢�
绗崄鍥涚珷 绺悎鍙嶆噳锛堢啛鎮夊拰鎺屾彙澶ч儴鍒嗗収(n猫i)瀹癸級
14.1 閱囥€侀啗鍨嬬府鍚堝弽鎳夛細婊垮凹璧� Mannich鈥旇兒鐢插熀鍖栧弽鎳�銆侀亥鍏嬬埦 Micheal 鍔犳垚銆侀璩�
閬� Robinson 澧炵挵(hu谩n)鍙嶆噳
14.2 閰殑?锛涱姮顕；顎備箮銈縮鍚堝弽鎳�(鍏嬭悐妫府鍚堝弽鎳�銆佹贩鍚堥叝绺悎銆佸垎瀛愬収(n猫i)鐨勯叝
绺悎鍙嶆噳锛堢媱鍏嬫浖 Dieckmann 绺悎鍙嶆噳锛�銆佺敤閰版隘鎴栭吀閰愰€茶?锛涱姮?br/>14.3 閰殑鐑峰熀鍖�銆�?锛涱姮顕；顎€鈷�?j墨ng)鐑兒鐑峰熀鍖栨垨?锛涱姮?br/>14.4 尾 -浜岀景鍩哄寲鍚堢墿鐨勭壒鎬у強鍦ㄥ悎鎴愪笂鐨勬噳鐢細尾 -浜岀晶鍩哄寲鍚堢墿鐨勭壒鎬� 銆佷笝浜岄吀閰�
鍚堟垚娉�銆佷箼閰颁箼閰镐箼閰悎鎴愭硶銆�1,3 - 浜岀晶鍩哄寲鍚堢墿鐨勎� -鐑峰熀鍖栧拰纬 -閰板熀鍖�銆侀叝
绺悎鐨勯€嗗悜鍙嶆噳
14.5 榄忔倢閷弽鎳夊強鍏堕浼煎弽鎳夛細钁夌珛寰凤紙ylide锛�銆佺７钁夌珛寰�銆佺～钁夌珛寰风瓑鐨勭祼(ji茅)妲�(g貌u)鑸囧埗鍌欍€�
榄忔倢閷弽鎳�銆侀瓘鎮岄尗鈥旈湇绱嶇埦锛圵ittig-Horner锛夊弽鎳夈€�
14.6 鑺抽啗鑸囬吀閰愯Κ鏍稿姞鎴愬弽鎳夛細钂茬埦閲戯紙Perkin锛夊弽鎳�銆佸厠鑵︽枃鏍硷紙Knoevenagel锛夊弽鎳�
14.7 閱�銆侀叜鑸� 伪锛嶉沟浠ｇ晶閰搁叝鐨勫弽鎳夛細閬斿弮锛圖arzens锛夊弽鎳�
14.8 鑻敳閱涚殑姘伴洟瀛愶紙CN-锛夊偓鍖栦笅锛氬畨鎭绺悎鍙嶆噳銆佸畨鎭閰搁噸鎺�
14.9 鍚堟垚鍓栨瀽锛氳ō(sh猫)瑷堜竴鍊嬪悎鎴愮殑渚嬭绋嬪簭锛昏瓨鍒ュ畼鑳藉湗锛屽垏鏂凤紙骞惧ぇ椤炴湁姗熷弽鎳�锛屽咕绋�
鍏稿瀷绲�(ji茅)妲�(g貌u)鐨勫垏鏂凤級锛屽師鏂欑殑閬告搰锛屽悎鎴愭椹熺殑瑷�(sh猫)瑷�锛岄伕鎿囨€у弽鎳夊強淇濊鍩虹殑鎳夌敤锛�
绔嬮珨鍖栧鎺у埗锛�
绗崄浜旂珷 闆滅挵(hu谩n)鍖栧悎鐗�
浜嗚В甯歌闆滅挵(hu谩n)鍖栧悎鐗╃殑绲�(ji茅)妲�(g貌u)鍜屽懡鍚嶆柟娉�
鐔熸倝闆滅挵(hu谩n)鍖栧悎鐗╃殑鑺抽鎬у拰鍚爱闆滅挵(hu谩n)鍖栧悎鐗╃殑閰稿牽鎬�
鎺屾彙鍛嬪杻銆佸櫥鍚┿€佸悺鍜瓑鐨勫悎鎴愬強鍖栧鎬ц唱(zh矛)锛堣Κ闆诲彇浠ｅ弽鎳夎(gu墨)寰嬶級
浜嗚В鍚″暥銆佸柟鍟夌瓑鐨勫寲瀛告€ц唱(zh矛)鍙婅Κ闆诲彇浠ｅ弽鎳夎(gu墨)寰�
15.1 鐠�(hu谩n)鍖栧悎鐗╃殑鍒嗛鍜屽懡鍚嶏紙闊宠娉曪級
15.2 鐔熸倝浜斿厓闆滅挵(hu谩n)鍖栧悎鐗╋細鍛嬪杻銆佸悺鍜�銆佸櫥鍚�銆佺碃閱涚殑绲�(ji茅)妲�(g貌u)銆佹€ц唱(zh矛)鍜屽埗鍌欏強绨″柈鍙嶆噳锛�
浜嗚В鍏惰鐢熺墿鎬ц唱(zh矛)锛圴B1銆侀潚闇夌礌绛夛級锛屼簡瑙ｅ崯鍟夎鐢熺墿锛氳绱呯礌銆佽憠缍犵礌銆乂B12銆�
15.3 浜嗚В鍏厓闆滅挵(hu谩n)鍖栧悎鐗�
15.3.1 鍚″暥鐨勭祼(ji茅)妲�(g貌u)鍙婂悺鍟惰鐢熺墿锛氱厵閰搞€乂B6銆佺暟鐓欒偧
11
15.3.2 鍢у暥鍙婂叾琛嶇敓鐗╋細灏垮槯鍟躲€佽優鍢у暥銆佽兏鑵哄槯鍟�
15.4 涓€鑸簡瑙ｇ闆滅挵(hu谩n)鍖栧悎鐗╋細鍚插摎鍙婂叾琛嶇敓鐗�銆佸柟鍟夊強鍏惰鐢熺墿锛堟柉鍏嬪ェ娴� Skraup 鍚�
鎴愭硶锛夈€�
绗崄鍏珷 鍛ㄧ挵(hu谩n)鍙嶆噳
16.1 闆荤挵(hu谩n)鍖栧弽鎳�
16.2 鐔熸倝骞舵帉鎻 2+2], [2+4] Diels-Alder 鐠�(hu谩n)鍔犳垚鍙嶆噳
16.3 鐔熸倝蟽 -閬风Щ鍙嶆噳锛圕laisen 鍏嬩締妫噸鎺�銆丆ope 閲嶆帓銆佹矮鍘熷瓙鍙冨姞鐨勶蓟l, i锛介伔绉�銆�
纰冲師瀛愬弮鍔犵殑锛籰, i锛介伔绉伙級
绗崄涓冪珷 纰虫按鍖栧悎鐗╋紙鍠硸锛屽绯栵級
浜嗚В纰虫按鍖栧悎鐗╋紙绯栵級鐨勬兜缇�銆佸垎椤炪€佸瓨鍦�
鎺屾彙 D鈥旂郴鍒楀柈绯栫殑閲嶈鐗╃悊鎬ц唱(zh矛)鍙婂寲瀛告€ц唱(zh矛)
鐔熸倝鍠硸鐨勭挵(hu谩n)鐙€绲�(ji茅)妲�(g貌u)鍜岄張鐙€绲�(ji茅)妲�(g貌u)浠ュ強宸悜鐣板寲浣滅敤鍜岃畩鏃嬪師鐞�
浜嗚В骞剧ó纰虫按鍖栧悎鐗╋紙钁¤悇绯�銆佹灉绯�銆佽敆绯栦互鍙婃穩绮夈€佺簴缍礌锛夌殑閲嶈鎬ц唱(zh矛)鍜岀敤閫�
17.1 鐔熸倝鍠硸绲�(ji茅)妲�(g貌u)鑸囩墿鐞嗗寲瀛告€ц唱(zh矛)
17.1.1 鍠硸鐨勭⒊鏋剁祼(ji茅)妲�(g貌u): 鍠硸鐨勬(g貌u)閫犲紡鐨勭⒑瀹�銆佺珛楂旀(g貌u)鍨�銆佺挵(hu谩n)鐙€绲�(ji茅)妲�(g貌u)[鍝堟鏂�
锛圚aworth锛夐€忚寮�銆佹(g貌u)璞″紡
17.1.2 鍠硸鐨勬€ц唱(zh矛)锛氱硸閰哥殑宸悜鐣版(g貌u)鍖�銆佹哀鍖栬垏閭勫師锛堝悙鍊拰鑿叉灄瑭﹀姂锛屾捍姘存垨闆�
瑙ｆ哀鍖�锛岀閰告哀鍖�锛屽偓鍖栨矮鍖�锛岄垑姹為倓鍘燂級銆佹垚鑴庡弽鎳�銆佹垚鑻峰弽鎳�銆佸柈绯栫殑閬�
闄嶏紙Ruff 闄嶈В锛學ohl 闄嶈В锛�銆佺硸鑴庤垏绯栬厵
17.1.3 閲嶈鐨勫柈绯栵細钁¤悇绯�銆佹灉绯�銆佸崐涔崇硸銆佹牳绯�銆佽劔姘ф牳绯�
17.1.4 璁婃棆鍏夊強姘х挵(hu谩n)鐨勬脯瀹�
17.2 浜嗚В闆欑硸锛� 閭勫師鎬ч洐绯栵細楹ヨ娊绯�銆佺簴缍簩绯�銆佷钩绯�锛涢潪閭勫師鎬ч洐绯栵細钄楃硸锛堢祼(ji茅)妲�(g貌u) 娓�
瀹氾級
17.3 浜嗚В澶氱硸锛� 娣€绮夛紙鍒嗛銆佺祼(ji茅)妲�(g貌u)鍜屾€ц唱(zh矛)锛�銆佺簴缍礌锛堢祼(ji茅)妲�(g貌u)鍜屽埄鐢細閫犵礄銆佷汉閫犵簴缍�銆�
缇х敳鍩虹簴缍礌锛夈€佸崐绾栫董绱�銆佸彸鏃嬬硸閰�
绗崄鍏珷 姘ㄥ熀閰搞€佸鑲借泲鐧借唱(zh矛)
鐔熸倝姘ㄥ熀閰哥殑绲�(ji茅)妲�(g貌u)銆佸懡鍚嶅拰甯歌(gu墨)鐨勫寲瀛告€ц唱(zh矛)
浜嗚В澶氳偨鐨勭祼(ji茅)妲�(g貌u)鐗瑰緛銆佺祼(ji茅)妲�(g貌u)鐨勬脯瀹氭柟娉�銆佹€ц唱(zh矛)
浜嗚В铔嬬櫧璩�(zh矛)鐨勪富瑕佸寲瀛告€ц唱(zh矛)锛屼簡瑙ｈ泲鐧借唱(zh矛)鐨勪竴绱�銆佷簩绱�銆佷笁绱氥€佸洓绱氱祼(ji茅)妲�(g貌u)
18.1 姘ㄥ熀閰革細绲�(ji茅)妲�(g貌u)銆佸垎椤炲拰鍛藉悕銆佸埗娉曘€愭皑鍩洪吀鐨勫悎鎴愶細Strecker 鍚堟垚銆佅� -楣典唬閰告皑瑙�銆�
Gabriel 鍚堟垚銆佷笝浜岄吀閰硶銆�銆佹€ц唱(zh矛)銆愬叐鎬у拰绛夐浕榛�銆佹皑鍩虹殑鍙嶆噳锛堣垏浜炵閰�銆佺敳閱�銆�
浜岀鍩烘盁鑻弽鎳夛級銆佽劔缇у弽鎳夈€佽垏姘村悎鑼氫笁閰弽鎳夈€�
18.2 浜嗚В澶氳偨锛氬鑲界祼(ji茅)妲�(g貌u)纰哄畾鍜屽悎鎴愬師鐞嗙啊浠�銆佸鑲藉悎鎴愩€愮晶鍩虹殑淇濊銆佹皑鍩虹殑淇濊銆�
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