香豆素
香豆素
基本信息
香豆素（Coumarin）是一类具有独特芳香气味的化合物，化学式为C9H6O2。它们属于苯骈α-呋喃酮类化合物，在自然界中广泛存在。
结构特征香豆素的基本结构由苯环和呋喃酮构成，其中苯环与四个碳原子相连的呋喃酮单元形成独特的“香豆素环”。
自然来源香豆素存在于多种植物、真菌及动物体内。在植物界中，它主要作为天然防御机制的一部分，用作对昆虫的化学信号。著名的例子包括：天竺葵科（如紫花苜蓿）、唇形科（如薄荷）和芸香科（如柑橘属果实）。此外，在真菌、苔藓及藻类中也有发现。
化学性质 稳定性由于其独特的结构，香豆素表现出良好的化学稳定性。它们不易被氧化或还原，但可以与其他化合物发生多种类型的反应，包括缩合、取代等。
生物活性许多香豆素衍生物具有生物活性，能够引起抗菌、抗炎、抗氧化等多种作用。这些特性使它们成为医药、食品添加剂等多个领域的重要研究对象。
应用领域 医药行业在制药业中，某些结构类似物被开发为药物先导化合物。例如，香豆素类抗生素是最早的广谱抗生素之一；一些香豆素衍生物还表现出抗癌潜力。
食品工业由于其独特的香气和味道，在食品加工中也得到了广泛应用，常作为香精成分使用。
其他应用此外，它们还在染料生产、农药开发等多个领域展现出潜在价值。
生产方法香豆素可通过多种合成路径获得。传统的化学合成涉及从苯甲醛出发的反应；而近年来，通过生物转化技术，利用微生物发酵过程制备天然香豆素也成为一种可持续的方法。
总之，香豆素因其独特的结构和广泛的生物学应用，在多个领域中发挥着重要作用，并且仍然是有机化学研究中的一个重要课题。
相关化合物
| 中文名称 | 英文名称 | CAS号 | 化学式 | 结构式图片 |
|---|---|---|---|---|
| —— | (3R,4S,4aS,9bS)-3-[dodecanoyl(hexyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C35H54N2O7 |
|
| —— | (3R,4S,4aS,9bS)-3-[3-ethoxypropyl(propanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H34N2O8 |
|
| —— | (3R,4S,4aS,9bS)-8-formyl-3-[hexyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O7 |
|
| —— | (3R,4S,4aS,9bS)-8-formyl-3-[hexyl-(2-methoxyacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[3-cyclopentylpropanoyl(3-ethoxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H42N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclobutanecarbonyl(3-ethoxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-(3-propan-2-yloxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H42N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[3-cyclopentylpropanoyl(cyclopropylmethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H38N2O7 |
|
| —— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[(2-methoxyacetyl)-(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O9 |
|
| —— | (3R,4S,4aS,9bS)-3-[3-ethoxypropyl(2-methylpropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[3-ethoxypropyl(5-oxohexanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O9 |
|
| —— | (3R,4S,4aS,9bS)-8-formyl-3-[hept-6-enoyl(hexyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H42N2O7 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclopropylmethyl(propanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H30N2O7 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclopropylmethyl(3-methylbut-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H32N2O7 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclopropylmethyl(pent-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H32N2O7 |
|
| —— | (3R,4S,4aS,9bS)-3-[3-ethoxypropyl(oxolane-2-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O9 |
|
| —— | (3R,4S,4aS,9bS)-3-[butanoyl(3-propan-2-yloxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O8 |
|
| —— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[propanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O8 |
|
| —— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[oxolane-3-carbonyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O9 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclobutanecarbonyl(hexyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O7 |
|
| —— | (3R,4S,4aS,9bS)-3-[butanoyl(3-ethoxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[3-ethoxypropyl(octanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H44N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[3-ethoxypropyl(pent-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclopropylmethyl(2-methylpropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H32N2O7 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclopropanecarbonyl(3-ethoxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O8 |
|
| —— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[pentanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H40N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[3-ethoxypropyl(2-oxobutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O9 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclopropylmethyl(3-methoxypropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H32N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[acetyl(3-propan-2-yloxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H34N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-(3-ethoxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H40N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclopropanecarbonyl(3-propan-2-yloxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O8 |
|
| —— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[pent-4-enoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclopentanecarbonyl(cyclopropylmethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H34N2O7 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclobutanecarbonyl(cyclopropylmethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H32N2O7 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclopropylmethyl(pent-4-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H32N2O7 |
|
| —— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-methylpropanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[acetyl(3-ethoxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H32N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[3-cyclopentylpropanoyl(hexyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H44N2O7 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclopropylmethyl(pentanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O7 |
|
| —— | (3R,4S,4aS,9bS)-3-[3-ethoxypropyl(3-methoxypropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O9 |
|
| —— | (3R,4S,4aS,9bS)-3-[butanoyl(cyclopropylmethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H32N2O7 |
|
| —— | (3R,4S,4aS,9bS)-8-formyl-3-[hexyl(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[(2-ethoxyacetyl)-(3-propan-2-yloxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O9 |
|
| —— | (3R,4S,4aS,9bS)-3-[3-ethoxypropyl(oxolane-3-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O9 |
|
| —— | (3R,4S,4aS,9bS)-8-formyl-3-[hexyl(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O8 |
|
| —— | (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-(cyclopropylmethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H36N2O7 |
|
| —— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methoxypropanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O9 |
|
| —— | (3R,4S,4aS,9bS)-3-[cyclopropylmethyl(dodecanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H48N2O7 |
|
| —— | (3R,4S,4aS,9bS)-3-[3-cyclopentylpropanoyl(3-propan-2-yloxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H44N2O8 |
|
| —— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[oxolane-2-carbonyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O9 |
|
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