4-甲基-1,4-二氢-3,5-吡啶二甲醛 | 71970-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-甲基-1,4-二氢-3,5-吡啶二甲醛
• 英文名称: 4-methyl-1,4-dihydro-3,5-pyridinedicarboxaldehyde
• 英文别名: 4-methyl-1,4-dihydropyridine-3,5-dicarboxaldehyde；4-Methyl-1,4-dihydro-3,5-pyridinedicarbaldehyde；4-Methyl-1,4-dihydropyridin-3,5-dicarbaldehyde；4-methyl-1,4-dihydro-pyridine-3,5-dicarbaldehyde；3,5-Diformyl-4-methyl-1,4-dihydropyridin；4-Methyl-1,4-dihydropyridine-3,5-dicarbaldehyde
• CAS: 71970-43-9
• 化学式: C₈H₉NO₂
• 分子量: 151.165
• InChiKey: GHUJOXJDUAROKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4-dihydroxymethylene-3-methylglutaraldehyde Na salt 在 氨 作用下， 以 水 为溶剂， 以16%的产率得到4-甲基-1,4-二氢-3,5-吡啶二甲醛
  参考文献：
  名称：

  Cleavage and oligomerization of malondialdehyde under physiological conditions

  摘要：

  DOI：

  10.1016/s0040-4039(00)94504-0

文献信息

• Reaction of malondialdehyde with amine neurotransmitters. Formation and oxidation chemistry of fluorescent 1,4-dihydropyridine adducts
  作者：Marco d'Ischia、Alessandra Napolitano、Claudio Costantini

  DOI：10.1016/0040-4020(95)00552-j

  日期：1995.8

  Under physiologically relevant conditions, malondialdehyde reacts smoothly with amine neurotransmitters, i.e. dopamine, norepinephrine and serotonin, to give the fluorescent dihydropyridines 1, 4 and 5, respectively, as the relatively most abundant products. Small amounts of enaminal derivatives, such as 2 and 6, could also be obtained in the reactions with dopamine and serotonin. Oxidation of 1 with

  在生理相关条件下，丙二醛与胺神经递质（即多巴胺，去甲肾上腺素和5-羟色胺）平稳反应，分别得到荧光二氢吡啶1、4和5，这是相对最丰富的产物。在与多巴胺和5-羟色胺的反应中也可以获得少量的烯胺衍生物，例如2和6。用过氧化氢/过氧化物酶氧化1会导致形成不稳定产物的复杂模式，不稳定产物的主要成分已被分离并鉴定为邻醌环氧化物7。类似的4和5氧化主要得到二氢吡啶8和4,4 ′-二吲哚基9。这些结果为丙二醛在神经元变性和脂褐素形成中的作用提供了新的线索。
• Fluorescence of 1,4-dihydropyridine derivatives relevant to age pigments.
  作者：KIYOMI KIKUGAWA、TAKAMI NAKAHARA、KEIZO SAKURAI

  DOI：10.1248/cpb.35.4656

  日期：——

  1, 4-Disubstituted-1, 4-dihydropyridine-3, 5-dicarbaldehydes, models of fluorogens in age pigments, show a high intensity of fluorescence comparable to that of quinine sulfate. Relationships between the structures and fluorescence emission of the 1, 4-dihydropyridine derivatives were studied. Loss of substituents at the 1- or 4-positions had little effect on the fluorescence. Reduction of one of the aldehyde groups to an alcoholic group greatly decreased the fluorescence intensity. When the aldehyde groups were replaced by acetyl groups, the fluorescence was greatly decreased. A derivative without aldehyde or carbonyl groups at the 3- and 5-positions was virtually nonfluorescent. Thus, the aldehyde groups at the 3- and 5-positions are requisite for the high intensity of fluorescence of the 1, 4 dihydropyridines.

  1,4-二取代-1,4-二氢吡啶-3,5-二羰基醛是老年颜料中荧光剂的模型，其荧光强度与硫酸奎宁相当。研究人员对 1，4-二氢吡啶衍生物的结构与荧光发射之间的关系进行了研究。在 1 位或 4 位失去取代基对荧光的影响很小。将其中一个醛基还原成醇基会大大降低荧光强度。当醛基被乙酰基取代时，荧光强度也大大降低。3 位和 5 位没有醛基或羰基的衍生物几乎没有荧光。因此，3-和 5-位上的醛基是 1，4-二氢吡啶产生高强度荧光的必要条件。
• Cleavage and Oligomerization of Malondialdehyde
  作者：Antonio Gómez-Sánchez、Isidro Hermosín、Jose-María Lassaletta、Inés Maya

  DOI：10.1016/s0040-4020(01)85814-2

  日期：1993.2

  Malondialdehyde (MDA) slowly self-condensates in aqueous solution at pH 4.5-6 and room temperature yielding (E)-(3'-oxo-1'-propenyl)malondialdehyde and 2,4-dihydroxymethylene-3-(2'-oxoethyl)glutaraldehyde. The latter compound exists in solution in equilibrium with 4-(1,3-dioxopropan-2-yl)-5-formyl-2-hydroxy-3,4-dihydro-2H-pyran, the trans-form of which can be readily isolated as a crystalline hemipotassium salt. Cleavage of MDA also occurs under these conditions leading to acetaldehyde, which further reacts with the excess of MDA to form 2,4-dihydroxymethylene-3-methylglutaraldehyde.
• Influence of malondialdehyde on the Maillard degradation of Amadori compounds
  作者：Antonio Gómez-Sánchez、Isidro Hermosín、Inés Maya

  DOI：10.1016/s0008-6215(00)90577-9

  日期：1992.5

  1-Amino-1-deoxy-D-fructose (7), and its N-butyl derivative (8), reacted with malondialdehyde to yield the 1-deoxy-1-(3-oxo-1-propenylamino)-D-fructoses 9 and 10, respectively. Small proportions of 4-methyl-1,4-dihydro-3,5-pyridinedicarbaldehyde (12) and 1-deoxy-1-(3.5-diformyl-4-methyl-1,4-dihydro-pyridin-1-yl)-D-fructose (14) were also formed in the reaction with 7, and of 1-butyl-4-methyl-1,4-dihydro-3,5-pyridinedicarbaldehyde (13) in the reaction with 8. The reaction of 7 with methylmalondialdehyde afforded 1-deoxy-1-(2-methyl-3-oxo-1-propenylamino)-D-fructose (11). The enaminals 9 and 10 cyclised, in neutral or weakly alkaline aqueous solution, into a mixture of 4-(D-arabino-tetritol-1-yl)-3-pyrrolecarbaldehyde pyrrolecarbaldehyde (15 and 17, respectively) and 3-(D-arabino-tetritol-1-yl)-4-pyridone (19 and 21, respectively). Small proportions of 4-(hydroxymethyl)-3-pyrrolecarbaldehyde (16) and 3-(hydroxymethyl)-4-pyridone (20) were also formed in the cyclisation of 9, and of 1-butyl-4-(alpha,beta-D-erythrofuranosyl)-3-pyrrolecarbaldehyde (18-alpha,beta) in the cyclisation of 10. All of the heterocyclic compounds were unstable.
• GOMEZ-SANCHEZ, ANTONIO;HERMOSIN, ISIDRO;MAYA, INES, TETRAHEDRON LETT., 31,(1990) N8, C. 4077-4080
  作者：GOMEZ-SANCHEZ, ANTONIO、HERMOSIN, ISIDRO、MAYA, INES

  DOI：——

  日期：——