2,4,5-Trimethoxyphenylacetone | 2020-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4,5-Trimethoxyphenylacetone
• 英文别名: 1-(2',4',5'-trimethoxyphenyl)-2-propanone；1-(2,4,5-trimethoxyphenyl)-2-propanone；1-(2,4,5-trimethoxyphenyl)propan-2-one；1-(2,4,5-trimethoxyphenyl)acetone；acoramone
• CAS: 2020-90-8
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: AQZHZTTUVYQMIN-UHFFFAOYSA-N

物化性质

• 熔点：
  47-48 °C
• 沸点：
  323.1±37.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)
• LogP：
  1.020 (est)
• 保留指数：
  1751.1

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  2,4,5-Trimethoxyphenylacetone 在 氢溴酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 (+/-)-2,4,5-trihydroxymethamphetamine hydrobromide
  参考文献：
  名称：

  Synthesis and Neurotoxicity Profile of 2,4,5-Trihydroxymethamphetamine and Its 6-(N-Acetylcystein-S-yl) Conjugate

  摘要：

  The purpose of the present study was to determine if trihydroxymethamphetamine (THMA), a metabolite of methylenedioxymethamphetamine (MDMA, "ecstasy"), or its thioether conjugate, 6-(N-acetylcystein-S-yl)-2,4,5-trihydroxymethamphetamine (6-NAC-THMA), play a role in the lasting effects of MDMA on brain serotonin (5-HT) neurons. To this end, novel high-yield syntheses of THMA and 6-NAC-THMA were developed. Lasting effects of both compounds on brain serotonin (5-HT) neuronal markers were then examined. A single intraventricular injection of THMA produced a significant lasting depletion of regional rat brain 5-HT and 5-hydroxyindoleacetic add (5-HIAA), consistent with previous reports that THMA harbors 5-HT neurotoxic potential. The lasting effect of THMA on brain 5-HT markers was blocked by the 5-HT uptake inhibitor fluoxetine, indicating that persistent effects of THMA on 5-HT markers, like those of MDMA, are dependent on intact 5-HT transporter function. Efforts to identify THMA in the brains of animals treated with a high, neurotoxic dose (80 mg/kg) of MDMA were unsuccessful. Inability to identify THMA in the brains of these animals was not related to the unstable nature of the THMA molecule because exogenous THMA administered intracerebroventricularly could be readily detected in the rat brain for several hours. The thioether conjugate of THMA, 6-NAC-THMA, led to no detectable lasting alterations of cortical 5-HT or 5-HIAA levels, indicating that it lacks significant 5-HT neurotoxic activity. The present results cast doubt on the role of either THMA or 6-NAC-THMA in the lasting serotonergic effects of MDMA. The possibility remains that different conjugated forms of THMA or oxidized cyclic forms (e.g., the indole of THMA) play a role in MDMA-induced 5-HT neurotoxicity in vivo.

  DOI：

  10.1021/tx2001459
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 2,4,5-Trimethoxyphenylacetone
  参考文献：
  名称：

  270.β-Asarone

  摘要：

  DOI：

  10.1039/jr9370001338

文献信息

• Role of the methoxy group in product formation via TiCl4 promoted 4-phenyldioxolane isomerizationsons
  作者：Ivan Robert Green、Natasha October

  DOI：10.3998/ark.5550190.0011.206

  日期：——

  The product distribution obtained from the TiCl4 initiated intramolecular isomerizations of 4methoxyphenyland trimethoxyphenyldioxolanes at -78 C, -30 C and 0 C provided insights into the important regiochemical role played by these groups in such Mukaiyamatype rearrangements through their resonance effects on the aryl ring of the dioxolanes.

  从 TiCl4 引发的 4-甲氧基苯基和三甲氧基苯基二氧戊环在 -78°C、-30°C 和 0°C 的分子内异构化获得的产物分布提供了对这些基团在此类 Mukaiyama 型重排中发挥的重要区域化学作用的见解，通过它们对二氧戊环的芳环的共振作用.
• Welkstoffe und Antibiotika. 30. Mitteilung. Ausgangsprodukte zur Totalsynthese des Javanicins
  作者：E. Hardegger、K. Steiner、E. Widmer、H. Corrodi、Th. Schmidt、H. P. Knoepfel、W. Rieder、H. J. Meyer、F. Kugler、H. Gempeler

  DOI：10.1002/hlca.19640470740

  日期：——

  Zur Herstellung von Ausgangsprodukten zur Synthese des Javanicins wurden, ausgehend von Vanillin (1) über Methoxyhydrochinon (2), dessen Ester 2a, b und 1, 2, 4-Trimethoxybenzol (2c) mit FRIES'scher Verschiebung, FRIEDEL-CRAFTS-Reaktion und MANNICH-Kondensation eine grössere Anzahl Verbindungen vom Typus 3, 4, 5, 6 hergestellt, welche die neu eingeführten Substituenten in o-, m-, p-Stellung zu den

  从香兰素（1）经由甲氧基氢醌（2），其酯2a，b和1,2,4-三甲氧基苯（2c）起具有FRIES的scher位移，FRIEDEL-CRAFTS反应，用于生产合成苦参碱的起始产物曼尼希缩合反应和曼尼希缩合反应产生了大量的3、4、5、6型化合物，这些化合物在o，m，p位置上已引入的氧官能团带有新引入的取代基。使用丙二酸酯合成的进一步积累反应产生了类型为20、21的单环制剂，其中z为。它们中的一些已经以正确的顺序包含了javanicin的所有C和O原子，但是到目前为止，它们还不能被环化以形成javanicin的衍生物。
• Hepatic Metabolism of Carcinogenic β-Asarone
  作者：Alexander T. Cartus、Simone Stegmüller、Nadine Simson、Andrea Wahl、Sylvia Neef、Harald Kelm、Dieter Schrenk

  DOI：10.1021/acs.chemrestox.5b00223

  日期：2015.9.21

  1′-Oxoasarone (3) was probably also formed in incubations with 1 but was not detectable, possibly due to its rapid reaction with nucleophiles. Eventually, three mono-O-demethylated metabolites of 1 were detected in minor concentrations. The time course of metabolite formation and determined kinetic parameters show little species-specific differences in the microsomal metabolism of 1. Furthermore, the

  β-Asarone（1）属于天然存在的丙烯丙烯类，如丁子香酚或茴香脑。化合物1存在于几种植物中，例如A蒲或欧洲细辛。含化合物1的植物材料及其精油用于调味食品和含酒精的饮料，并用作传统植物药中许多药物的成分。尽管有人声称1具有几种积极的药理作用，但已发现它在啮齿动物（肝脏和小肠）中具有遗传毒性和致癌性。致癌烯丙基的作用机理苯丙烯包括通过细胞色素P450酶和磺基转移酶的代谢活化。体内实验表明，与其他丙烯基化合物（如茴香脑）一样，该途径在丙烯基化合物1的致癌性中不发挥主要作用。由于尚未研究1的代谢途径，并且尚不清楚其致癌作用方式，因此我们使用1研究了大鼠，牛，猪和人的肝微粒体中1的代谢。1 H NMR，HPLC-DAD和LC-ESI-MS / MS技术。我们合成了大多数鉴定出的代谢物，这些代谢物用作定量和最终验证代谢物的参考化合物。1的侧链的微粒体环氧化大概会产生（Z）-asarone-1'，2
• [EN] A PROCESS FOR THE PREPARATION OF PHARMACOLOGICALLY ACTIVE ALPHA-ASARONE FROM TOXIC BETA-ASARONE RICH ACORUS CALAMUS OIL<br/>[FR] PROCEDE DE PREPARATION DE ALPHA-ASARONE A ACTIVITE PHARMACOLOGIQUE A PARTIR D'UNE HUILE D'ACORE ODORANT RICHE EN BETA-ASARONE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2003082786A1

  公开（公告）日：2003-10-09

  The present invention relates to a process for the preparation of high purity and yield α-asarone, trans 2,4,5-trimethoxy cinnamaldehyde, 2,4,5-trimethoxy-phenyl propionone, from β-asarone or β-asarone rich Acorus calamus oil containing α and η-asarone by hydrogenating, followed by treatment with DDQ with or without solid support of silica gel or alumina in dry organic solvent and α-asarone can also be obtained by treating the hydrogenated product of β-asarone or β-asarone rich Acorus calamus with DDQ in an aqueous organic solvent to obtain an intermediate 2,4,5-trimethoxy phenyl propionone, which in turn is reduced with sodiumborohydride to obtain the corresponding 2,4,5-trimethoxy-phenyl propanol and followed by final treatment with a dehydrating agent.

  本发明涉及一种从含有α和η-芳香烃的β-芳香烃或β-芳香烃丰富的菖蒲油中通过加氢后用DDQ处理的高纯度和高产率α-芳香烃、顺式2,4,5-三甲氧基肉桂醛、2,4,5-三甲氧基苯丙酮的制备方法，其中可以在干有机溶剂中使用硅胶或氧化铝固体载体，也可以通过在水有机溶剂中处理β-芳香烃或β-芳香烃丰富的菖蒲油的加氢产物以获得中间体2,4,5-三甲氧基苯丙酮，然后用氢硼酸钠还原获得相应的2,4,5-三甲氧基苯丙醇，最后用脱水剂进行最终处理以获得α-芳香烃。
• Synthetic and preliminary hemodynamic and whole animal toxicity studies on (R,S)-, (R)-, and (S)-2-methyl-3-(2,4,5-trihydroxyphenyl)alanine
  作者：D. G. Musson、D. Karashima、H. Rubiero、K. L. Melmon、A. Cheng、N. Castagnoli

  DOI：10.1021/jm00186a007

  日期：1980.12

  The synthesis, resolution, and absolute configuration assignment of 2-methyl-3-(2,4,5-trihydroxphenyl)alanine (6-OH-alpha-Me-Dopa) are reported. Hemodynamic studies in the rat have shown that this structural analogue and potential metabolite of the clinically useful drug (S)-alpha-Me-Dopa possesses weak hypotensive activity which resides in the R enantiomer. LD50 studies in mice have established that 6-OH-alpha-Me-Dopa is over four times more toxic than alpha-Me-Dopa. Chronic exposure to 6-OH-alpha-Me-Dopa leads to renal and hepatic lesions. The case of oxidation of this hydroquinone to the electrophilic quinone species may contribute to its enhanced toxicity compared to alpha-Me-Dopa.