第12章杂环化合物与生物碱 掌握杂环分类和命名 单杂环化合物主要化学性质 冬生物碱提取和鉴别方法nic chemistr By Junru Wang Email:wangjr07@163.com 西北农林科技大堂理堂院
Organic chemistry By Junru Wang Email: wangjr07@163.com 西北农林科技大学理学院 第12章 杂环化合物与生物碱 ❖掌握杂环分类和命名 ❖单杂环化合物主要化学性质 ❖生物碱提取和鉴别方法
一些典型的例子 叶绿素、血红素、 维生素B12 花色苷（花色素） 可卡因尼古丁吗啡海洛因马钱子碱
西北农林科技大学理学院 一些典型的例子 叶绿素、血红素、维生素B12 花色苷（花色素） 可卡因 尼古丁 吗啡 海洛因 马钱子碱
2、咣路色素（册族化合物 3 卟啉 8
西北农林科技大学理学院 2、吡咯色素（口 口 口 口 族化合物） NH N N HN 1 2 3 4 5 7 6 8 α β γ δ 卟 啉
王 血红素 CH2-CH CH3 CH3T CH=CH2 血红素 CH3 CH3 HOOCCH2CH2 CH2CH2COOH
西北农林科技大学理学院 血红素 N N N N Fe CH2 CH CH3 CH3 CH2 CH3 CH CH2 CH3 HOOCCH2 CH2 CH2 COOH 血红素
CH2=CH 叶绿素 CH2CH3 2+ a/b/c/d 4 g R=CH3叶绿素a 种 R=CHO叶绿素b CH3 CH3 CH(CH2)3C CHCHQCCH2CH COOMe (CH2)3CH(CH2)3CH(CHa)2 植物醇 叶绿素甲酯 CH3 >叶绿素a存在于所有的高等植物藻类和蓝细菌中。叶绿素b主要 存在于高等植物、绿藻中。叶绿素c则存在于硅藻、褐、甲藻中， 叶绿素d仅在红藻中发现。 >叶绿素a为兰黑色的晶体，在乙醇溶液中为蓝绿色，b为黄绿 色的粉末，再乙醇溶液中为黄绿色
2+ OOMe N N N N Mg R CH2CH3 CH3 O H C H H CHCH2OCCH2CH2 O CH(CH2 ) 3C CH3 CH3 (CH2 ) 3CH(CH2 ) 3CH(CH3 ) 2 CH3 CH3 CH3 CH2 CH R = CH3 叶绿素a R = CHO 叶绿素b 植物醇 叶绿素甲酯 ➢叶绿素a存在于所有的高等植物藻类和蓝细菌中。叶绿素b主要 存在于高等植物、绿藻中。叶绿素c则存在于硅藻、褐、甲藻中， 叶绿素d仅在红藻中发现。 ➢叶绿素ａ为兰黑色的晶体，在乙醇溶液中为蓝绿色，ｂ为黄绿 色的粉末，再乙醇溶液中为黄绿色。 叶绿素 ａ/ｂ/c/d 4 种
CH2CONH2 CH2 CHa HaC CH2CONH2 H2NCCH2 CH2CH2CONH2 CH3 H2NCCH CH3 维生素B12 CH2CH2CONH2 CH3 CH3 H CH2HNCCH2CH CHCH3 HOH2C
西北农林科技大学理学院 维生素B12 N N N H N Co CN CH3 H CH2 CH2 CONH2 H2 NCCH2 O CH3 H H H2 NCCH2 O CH3 CH3 CH2 CH2 CONH2 CH3 CH3 H CH2 CH2 CONH2 H3 C CH2 CONH2 CH2 HNCCH2 CH2 O CHCH3 O O O - P H C O H H OH H O N N HOH2
OH OH OH OH OH OH OH OH cr OH 氯化青芙蓉素 氯化飞燕草素 0C6H11O5 OC H1Os 花色苷 OH 青芙蓉苷色素 (紫色pH=7-9) OH OC6HnOs OH OH H HO OH 青类蓉苷阳离子（红色11)
西北农林科技大学理学院 O OH OH OH O OH HO OH OH + Cl - + Cl - OH HO OH OH 氯化青芙蓉素 氯化飞燕草素 花色苷
Alkaloids 日十带 Extractions from bark,leaves,berries and fruits yields nitrogen containing bases called alkaloids Name comes from "alkali or base-like"-most react with acids to give soluble salts. Most produce striking physiological effects that vary from alkaloid to alkaloid. 3 Nicotine Nicotinic Acid small doses its a stimulant in9 operated into NA的的 larger doses its a poison Nicotine salts are insecticides nicotinamide adenine dinucleotide
西北农林科技大学理学院 Alkaloids Extractions from bark, leaves, berries and fruits yields nitrogen containing bases called alkaloids Name comes from “alkali or base-like” – most react with acids to give soluble salts. Most produce striking physiological effects that vary from alkaloid to alkaloid. N N CH3 H Nicotine N C O OH Nicotinic Acid small doses its a stimulant larger doses its a poison Nicotine salts are insecticides incoperated into NAD + nicotinamide adenine dinucleotide
A3 OCH: Ph HOH2C Cocaine Atropine small doses -stimulant Intense Poison causes physical addiction and 0.5-1%solutions are depression used to dilute the pupils was used medically as an derivatives used against anesthetic the common-cold CH2CH2CH3 Erythroxylum coca 1%is cocaine Coniine (conium maculatum) poison from hemlock
西北农林科技大学理学院 N H H CH2CH2CH3 Coniine (conium maculatum) poison from hemlock N H3C O H C O C Ph H HOH2C Atropine Intense Poison 0.5-1% solutions are used to dilute the pupils derivatives used against the common-cold N H3C H O Cocaine small doses - stimulant causes physical addiction and depression was used medically as an anesthetic C O Ph H O OCH3 Erythroxylum coca 1% is cocaine
Papaver somniferum(opium poppy) Morphine is a potent analgesic Used in medicine to relieve "deep"pain Addiction depression respiratory falure Papaverine H2CO Isoquinoline Morphine,R H Codeine,R CH Professor Marshall Gates-In 1952 First Synthesis Conformation of the structure of morphine
西北农林科技大学理学院 Professor Marshall Gates – In 1952 First Synthesis + Conformation of the structure of morphine Papaver somniferum (opium poppy) N Isoquinoline N H3CO H3CO H3CO H3CO Papaverine O HO RO N H H CH3 Morphine, R = H Codeine, R = CH3 Morphine is a potent analgesic Used in medicine to relieve “deep” pain Addiction + depression + respiratory falure