异喹啉

异喹啉是无色低熔点片状结晶、固体或液体，有类似茴香油和苯甲醛混合物的香味，通常存放后颜色会发黄。存在于煤焦油和骨油中。微溶于水，溶于稀酸，能与多种有机溶剂混溶。能随水蒸气蒸发。具吸水性。有碱性，pK_a=5.4，碱性较喹啉强，比吡啶略强，能与各种酸成盐，其盐酸盐熔点 209°C。

Iridium is a non-coloured, low-melt-point tablet crystalline, solid or liquid, with fragrances similar to the alfon and berylldehyde blends, usually with yellow colours. It is found in kerosene and osteoporium oil. It is soluble in water, soluble in rare acids, soluble with a variety of organic solvents. It can evaporate with water vapour. It is water-sortious. It is alkaline, pK_a= 5.4, it is more alkaline, it is slightly stronger, it can melt with a variety of acids, its hydrochloric smelting point 209°C.

1885年 Hoogewerff 和 van Dorp从煤焦油喹啉馏分中用分级结晶法获得了硫酸异喹啉。同年 Gabriel完成了异喹啉的合成。1914年 Wei?gerber利用异喹啉和喹啉之间的碱性差异，发展了一种更为有效的分离方法。

Hoogewerff and van Dorp obtained sulphate sulphate from a graded crystallization of the kerosene distillation in 1885. Gabriel completed the sulphate synthesis in the same year. Wei?gerber developed a more effective separation method in 1914, using the alkaline differences between peas and pea.

工业上主要以煤焦油粗喹啉馏分为原料，通过磺化、分级结晶、过滤、重结晶、氨水分解、洗涤和精馏生产异喹啉。

Industrially, the raw material is divided mainly into coal tar rough distillation, which is produced by sulfurization, grade crystallization, filtering, recrystalization, ammonia decomposition, washing and distillation.

异喹啉的化学性质与吡啶和喹啉相似，质子化、烷基化、酰化以及被过氧酸氧化都在 N 原子上进行，亲电芳香取代和亲核芳香取代反应主要在环上的 C 原子上进行。

The chemical properties of the ammonium are similar to those of the titanium and titanium, with protonization, alkylization, odification and peroxyacetic acid oxidation occurring on N atoms, with in vitro aromatic replacement and pronunciation replacing the aromatic reaction mainly on the ring C atoms.

异喹啉的亲电芳香取代活性高于吡啶，优先发生在异喹啉环的 5- 和 8-位，以 5-位产物为主。通过N-质子化进行苯环上C-质子化然后进行质子交换，需要硫酸这样的强酸，而且反应在 C-5 上比 C-8 上快。亲核芳香取代在异喹啉的杂环进行，优先发生在 1-位。例如，异喹啉经过 Chichibabin反应可得1-氨基异喹啉；与正丁基锂发生 Ziegler反应得到1-正丁基异喹啉，这个反应的一级加成产物1-正丁基-1,2-二氢异喹啉受稠合苯环的影响而得到稳定，可被分离出来，经硝基苯氧化可在碳上取代，并恢复异喹啉环的芳香性。

The aromatic aromatic fragrance of the amphiboles replaces the activity with the activity above the activity of the thorium, giving priority to 5- and 8-bit of the ammonium ring, dominated by the 5-bit product. A strong acid, such as sulphate, is required to be exchanged for the C-protonization of the benzene ring through N-protonization, and reacts faster than the C-8 on C-5. The fragrance of the aromatic aromatic aromatic aromatics replaces the coils, giving priority to 1-bits in 1-bits. For example, the reaction of the ammonium via Chichibabin is likely to be 1-aminos; and the reaction of the Ziegler with the n-butyl lithium has received 1- or pyrinthonyloids, the first stage of which is stabilized by adding the product 1- or pyretyl-1, and the second-dihydrogen is subject to the dense benzene ring, and can be separated by the nitrobenzen oxide oximation of the ring.

异喹啉可以在高温下通入氢气流与氢氧化钾反应而直接羟基化，产物是1-异喹啉酮。

The aphids can react directly to potassium hydroxide by introducing hydrogen into the hydrogen current at high temperatures, with a product of 1-i-thioketone.

异喹啉 3-位的卤素表现出与卤代苯相似的性质，但 1-位的卤素具有与 α- 和 γ-卤代吡啶相似的敏感性，很容易发生亲核芳香取代。例如，1,3-二氯异喹啉可选择性地被甲氧基取代为 1-甲氧基-3-氯异喹啉。然而，3-卤代异喹啉惰性的一个明显例外是 3-溴代异喹啉与氨基钠通过ANRORC机理发生的取代反应，在这个反应中环氮原子变为取代基上的氮原子，生成3-氨基异喹啉。

Iridium 3-bit halogens display properties similar to halogens, but 1-bit halogens have similar sensitivities to alpha- and gamma-halogenated aromatic aromatics, which can easily be replaced by in-kind aromatic aromatics. For example, 1,3-dichloroisomers can be selectively replaced by methyloxy-baseds with 1-methyloxy-3-chloroxone. However, a clear exception to the 3-halogen helium inertity is a 3-brominated helium and sodium amino by ANRORC machines, in which the cyclin nitrogen atoms are replaced by substrate nitrogen atoms, producing 3-aminoygens.

异喹啉在苯甲酰氯等酰化试剂的作用下，与氰化钾或三甲基氰硅烷发生 Reissert反应，生成 Reissert 化合物 2-酰基-1-氰基-1,2-二氢异喹啉。Reissert 化合物可以发生一系列在合成上有用的转换。

Reissert reacts with potassium cyanide or trimethyl cyanide, producing Reissert compounds 2-Fyl-1-Cyanyl-1,2-dihydrazepine. Reissert compounds can undergo a range of useful synthetic transformations.

异喹啉可以与过氧化苯甲酰作用，生成多种苯基异喹啉的混合物。如果用异喹啉正离子为作用物，则可通过它在酸性溶液中与亲核性更强的自由基的取代反应，在异喹啉的 1-位引入酰基和酰胺基。

Iridium can be used with phenylacetyl peroxide to produce a mixture of several benzyl isomers. If the iridium is used as an active substance, it can be introduced into the iridium and ammonium at 1-bit of the iridium by replacing it with the more nuclear free radicals in the acid solution.

异喹啉被碱性高锰酸钾氧化，两个环都可被降解，得到的是吡啶-3,4-二甲酸和邻苯二甲酸的混合物。而在中性介质中用高锰酸钾氧化，不氧化苯环，只生成邻苯二甲酰亚胺。苯环上的取代基可以影响氧化反应的结果。

Heptachlor is oxidized by potassium permanganate of alkaline type, both rings are degradable, with a mixture of thallium-3,4-dimethyl acid and periphenyldipic acid. In the neutral medium, potassium permanganate is oxidized, not oxidized, producing only phenylmethamphetamine. Substitution bases on the benzene ring can influence the oxidation response.

用过氧酸氧化异喹啉，得异喹啉N-氧化物。

Oxygen oxide with peroxyacetic acid, different from N-oxidant.

异喹啉可以被催化氢化、氢化试剂或金属还原；也可以实现选择性完全还原或部分还原异喹啉的吡啶环或苯环。催化氢化的产物受反应介质酸性的影响很大：在乙酸中，吡啶环选择性还原生成1,2,3,4-四氢异喹啉；而在浓盐酸中，苯环被选择性还原生成5,6,7,8-四氢异喹啉，进一步还原则生成顺式和反式十氢异喹啉的混合物。

The product of catalytic hydrogenation is highly influenced by the acidity of the reaction medium: in acetic acid, the thallium thallium selective reduction produces 1,2,3,4-tetrahydrothyridium; in americ acid, the benzene ring is selectively reduced by 5,6,7,8-tetrahydrothiolyptone, and further by the principle of producing a mixture of pro- and transgenic decahydrazine.

异喹啉用二乙基氢化铝或氢化铝锂还原可以得到很活泼的1,2-二氢异喹啉；在液氨中用锂还原则得到3,4-二氢异喹啉。异喹啉离子被质子溶剂中的硼氢化钠迅速还原生成1,2,3,4-四氢异喹啉，该反应是确定生物碱结构的一个重要反应。杂环部分迅速被还原，其它可被还原的官能团如羰基可以不受影响。

Diethyl aluminum or lithium hydrogenated aluminium can be retrenched to lively 1,2-dihydrazine; lithium in liquid ammonia is returned to 3,4-dihydrazine. Sodium hydrazine is rapidly retrenched to 1,2,3,4-tetrahydrogen azidone in a proton solvent, a response that is an important reaction in determining the structure of the biomass. The hybrid parts are quickly restored, and other functional groups that can be retrenched can be unaffected if the base is not affected.

异喹啉杂环上的甲基具有 CH 酸性，1-位甲基氢酸性大于3-位，因此能够发生酸或碱催化的 C-C 键形成反应。

The methyl in the amphiboles has a CH-acid properties, with 1-bit methyl-hydro-acid properties greater than 3-bit, and therefore has the ability to react with acid or alkali-catalytic C-C keys.

异喹啉盐中的吡啶环较容易进行亲核加成，可与富电子的亲双烯体如乙烯基乙醚发生环加成反应。

The ammonium ring in the iridium salt is easier to perform by-productation, which can be associated with a rich electron parent biene, e.g. ethylene ether.

从异喹啉 1 的逆合成分析可以看出，如果从亚胺键的断裂回推，可以通过二羰基化合物 10 作为环合原料。如果算上还原步骤，可用氨基羰基化合物 8 和 4 作为二氢异喹啉的制取原料。另一方面，3,4-二氢异喹啉 5 的 C-1 和 C-4 键断裂可以产生合成子 α-亲电性烯胺 7 以及 β-亲电性烯胺 6，它们也可用作亲电芳香取代环化的原料。

A reverse synthesis analysis of ammonium 1 shows that, if pushed back from the break of the ammonium key, it can be used as a cyclic feedstock. If the steps are taken to restore it, it can be used as a raw material for dihydrogenisium. On the other hand, C-1 and C-4 key fractures of 3,4-dihydrazepines 5 can produce synthetics alpha-promotive enzymide7 and beta-promotive enzymes6 which can also be used as a feedstock to replace cyclicization with pyromatic aromatic aromatic fragrances.

因此，异喹啉及其衍生物的合成方法有：

Thus, the method of synthesizing the ammonium and its derivatives is as follows:

1、(2-甲酰苯基)乙醛及类似的二羰基化合物与氨发生环化反应生成异喹啉（合成子 10）。如果用羟胺、肼或伯胺代替氨，则可分别得到异喹啉N-氧化物、N-内铵盐和N-取代的异喹啉离子。

1, 2-(2-methylbenzenyl)acetyldehyde and similar diazole compounds have been cyclic with ammonia to produce diazine (synthesis 10). If ammonia is replaced with hydrazine, hydrazine or permethrin, a hemolymethrin ion may be replaced by iridium N-oxidide, N-magnetium salt and N-, respectively.

2、Bischler-Napieralski反应：2-芳基乙胺与酰氯或酸酐反应生成酰胺，然后在失水剂作用下环化生成3,4-二氢异喹啉，然后脱氢生成1-取代的异喹啉（合成子 7）。

2. Bischler-Napieralski reaction: 2- aromatic ethylamide reacts with arydyl chloride or anhydride to produce anamide, and then cyclisses 3,4-dihydrazepines under water loss, and dehydrates to produce 1-to-replace apes (synthesis 7).

Pictet-Gams反应：上述反应的改进法，用 β-甲氧基或 β-羟基芳乙胺进行反应，可不经氧化或脱氢，直接得到异喹啉类化合物。反应中有唑啉中间体生成。

Pictet-Gams Reaction: An improved response method as described above, with beta-methyloxy or beta-hydroxy alamine, can be obtained directly from ammonium compounds without oxidation or dehydration.

3、Pictet-Spengler反应：2-芳基乙胺与醛在酸催化下生成亚胺，然后亚胺在酸催化下环化生成1,2,3,4-四氢异喹啉，脱氢得到异喹啉（合成子 7）。

3. Pictet-Spengler reacts: 2- aromatic ethylamine and formaldehyde produce alamine under acid-catalysing, followed by the cycling of 1,2,3,4-tetrahydrogen azidone, dehydrated to diazepine (synthesis 7).

4、Pomeranz-Fritsch合成：芳醛与氨基乙缩醛缩合生成亚胺，亚胺在酸催化下环化为杂环上无取代基的异喹啉（合成子 6）。

4. Pomeranz-Fritsch synthesis: aromatic and aminoacetic astrates produce alamine, which is cycling into an acid-catalysed ring with no substrate (synthesis 6).

用作合成药物、染料、杀虫剂的中间体及气相色谱固定液。

Intermediates used as synthetic drugs, dyes, insecticides and gas chromatography fixes.

异喹啉衍生物广泛存在于自然界中，目前已知的异喹啉生物碱有1000多种，是已知生物碱中最大的一类。它们多以异喹啉或四氢异喹啉为母核，又可根据连接基团而细分为异喹啉类、苄基异喹啉类、双苄基异喹啉类、阿扑芬类、原小檗碱类、普罗托品类、吐根碱类、α-萘菲啶类和吗啡类生物碱等九类。

Iridium derivatives are widely present in nature, and there are currently more than 1,000 known alkaloids, the largest of which are known to be alkaloids. Most of them are pyridium or tetrahydrothyridium as the mother core, and can be broken down into nine groups of iridium, pyridium-based syridium, bitropium-based amphipodium, atropine, primary pyrome, Prototon, Tshogen, alpha-pyridium and morphine.

有许多药物是异喹啉的衍生物。著名的异喹啉类生物碱罂粟碱，至今仍是重要的解痉药。抗抑郁药诺米芬辛和抗血吸虫药吡喹酮是从四氢异喹啉衍生而来。

There are a lot of drugs that are derivatives of the aphrodisiac. The famous iridium-based alkaline is still an important antidote today. The antidepressants Nomefensyn and antiseptic ketone are derived from the tetrahydrogenis.