isoapiole | 484-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: isoapiole
• 英文别名: 4,7-Dimethoxy-5-(prop-1-en-1-yl)-2H-1,3-benzodioxole；4,7-dimethoxy-5-prop-1-enyl-1,3-benzodioxole
• CAS: 484-52-6
• 化学式: C₁₂H₁₄O₄
• mdl: MFCD09028317
• 分子量: 222.241
• InChiKey: XKCIPTFOQRVXGG-UHFFFAOYSA-N

物化性质

• 沸点：
  327.9±37.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isoapiole 在 吡啶 、 sodium tetrahydroborate 、 二苯并-18-冠醚-6 、 氯化亚砜 、 盐酸肼 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 氯仿 、 乙腈 、 mineral oil 、 苯 为溶剂， 反应 11.17h， 生成 5-(4-methoxyphenyl)-4-(2,5-dimethoxy-3,4-methylenedioxyphenyl)-1H-pyrazol-3-amine
  参考文献：
  名称：

  cis-Restricted 3-Aminopyrazole Analogues of Combretastatins: Synthesis from Plant Polyalkoxybenzenes and Biological Evaluation in the Cytotoxicity and Phenotypic Sea Urchin Embryo Assays

  摘要：

  We have synthesized a series of novel cis-restricted 4,5-polyalkoxydiaryl-3-aminopyrazole analogues of combretastatins via short synthetic sequences using building blocks isolated from dill and parsley seed extracts. The resulting compounds were tested in vivo in the phenotypic sea urchin embryo assay to reveal their antimitotic and antitubulin effects. The most potent aminopyrazole, 14a, altered embryonic cell division at 10 nM concentration, exhibiting microtubule-destabilizing properties. Compounds 12a and 14a displayed pronounced cytotoxicity in the NCI60 anticancer drug screen, with the ability to inhibit growth of multidrug-resistant cancer cells.

  DOI：

  10.1021/np400310m
• 作为产物：
  描述：

  洋芹脑 在 potassium hydroxide 作用下， 反应 0.67h， 生成 isoapiole
  参考文献：
  名称：

  植物聚烷氧基苯衍生物的氢化：方便获得辅酶Q0类似物

  摘要：

  已经开发出技术上先进的方案，用于将植物烯丙基（聚烷氧基）苯转化为甲基和丙基（聚烷氧基）苯，它们是辅酶Q0类似物合成中的中间体。烯丙基和苯甲醛部分氢化的关键阶段是以周期性的高压釜模式在高度多孔的陶瓷嵌段Pd催化剂上进行的。这些催化剂具有大的表面积，低的水力阻力，显着的热稳定性和机械稳定性，多次循环和易于再生，可显着减少Pd的消耗。

  DOI：

  10.1016/j.mencom.2020.09.015

文献信息

• Synthesis of functionalized 1-methylchromeno[3,4-b]pyrrol-4(3H)-ones via the Barton–Zard reaction starting from pseudonitrosites
  作者：Daniil А. Rusanov、Alexander V. Samet、Vyacheslav V. Rusak、Victor V. Semenov

  DOI：10.1007/s10593-021-03004-3

  日期：2021.9

  A method for the preparation of chromeno[3,4-b]pyrrol-4(3H)-ones via the synthesis of the corresponding 3-arylpyrrole-2-carboxylates from pseudonitrosites by the Barton–Zard reaction was developed. As a result of selective O-demethylation upon exposure to BBr3, the lactone ring closes with the formation of substituted chromeno[3,4-b]pyrrolones in moderate yields.

  一种色烯的制备方法[3,4 b ]吡咯-4-（3 ħ） -酮通过相应的从由巴顿ZARD反应pseudonitrosites 3-芳基吡咯-2-羧酸酯的合成被开发。由于在暴露于 BBr 3时选择性O-去甲基化，内酯环闭合，形成中等产率的取代的色诺[3,4- b ]吡咯酮。
• Pseudonitrosites as masked nitroalkenes in the Barton–Zard pyrrole synthesis
  作者：Daniil A. Rusanov、Andrey B. Myshlyavtsev、Eugenia A. Silyanova、Alexander V. Samet、Victor V. Semenov

  DOI：10.1016/j.mencom.2020.07.026

  日期：2020.7

  3-Aryl-4-methylpyrrole-2-carboxylates were prepared via the Barton–Zard reaction using pseudonitrosites as a source of the corresponding nitroalkenes. The starting pseudonitrosites were, in turn, obtained via addition of N2O3 to propenylbenzenes available from the natural plant essential oils.

  3-Baryl-4-吡咯-2-甲酸3-芳基酯是通过使用伪亚硝酸盐作为相应硝基烯烃的来源的Barton-Zard反应制备的。反过来，通过将N2O3加到可从天然植物精油中得到的丙烯基苯中获得起始假亚硝酸盐。
• Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents
  作者：Alexander V. Samet、Oksana G. Shevchenko、Vyacheslav V. Rusak、Eduard M. Chartov、Andrey B. Myshlyavtsev、Daniil A. Rusanov、Marina N. Semenova、Victor V. Semenov

  DOI：10.1021/acs.jnatprod.8b00878

  日期：2019.6.28

  groups in the aromatic ring were evaluated using several in vitro models. These included the DPPH assay, inhibition of lipid peroxidation products accumulation, inhibition of H2O2-induced hemolysis, and oxidation of oxyhemoglobin. A synthetic protocol for the synthesis of natural nothoapiol (9) from a parsley seed metabolite, apiol (7), was developed. A structure–activity relationship study revealed

  使用几种体外模型评估了芳环中具有不同数量的烷氧基/甲氧基的天然和相关合成烯丙基聚烷氧基苯的自由基清除能力抗氧化和膜保护特性。这些包括 DPPH 测定、脂质过氧化产物积累的抑制、H 2 O 2诱导的溶血的抑制和氧合血红蛋白的氧化。开发了从欧芹种子代谢物芹菜酚 ( 7 )合成天然芹菜酚 ( 9 ) 的合成方案。构效关系研究表明，芳环中的亚甲二氧基片段和甲氧基均有利于抗氧化活性。羟基芹菜醇 ( 14)，在芳香核中含有一个羟基，被确定为最有效的化合物。五烷氧基取代的 nothoapiol ( 9 ) 在小鼠脑匀浆中表现出抗氧化活性，而在小鼠红细胞中表现出显着的促氧化作用。尽管自由基清除能力低，但烯丙基聚烷氧基苯可以提高植物精油的总抗氧化能力。
• Polyalkoxybenzenes from plant raw materials 1. Isolation of polyalkoxybenzenes from CO2 extracts of Umbelliferae plant seeds
  作者：V. V. Semenov、V. V. Rusak、E. M. Chartov、M. I. Zaretskii、L. D. Konyushkin、S. I. Firgang、A. O. Chizhov、V. V. Elkin、N. N. Latin、V. M. Bonashek、O. N. Stas’eva

  DOI：10.1007/s11172-007-0389-1

  日期：2007.12

  For the search for a domestic natural source of allylpolyalkoxybenzenes and development of an effective process for their isolation, CO2 extracts of several varieties of parsley, dill, celery, caraway, and nutmeg were analyzed systematically for the first time by GC/MS and GLC techniques. The varieties with high contents of myristicin, elemicin, allyltetramethoxybenzene, apiol, and dillapiol were identified. The conditions of CO2 extraction for obtaining concentrates with minimum contents of the distillation residues were selected. Using high performance fractional distillation, polyalkoxyallylbenzenes with 98–99% purity were isolated from the concentrates on a pilot unit. By isomerization of some allylbenzenes followed by ozonolysis under specially selected conditions, apiol-and dillapiolaldehydes were obtained in 75–80% yields.

  为了寻找烯丙基聚烷氧基苯的国内天然来源并开发有效的分离工艺，我们首次采用 GC/MS 和 GLC 技术对香芹、莳萝、芹菜、胡罗卜素和肉豆蔻等多个品种的二氧化碳提取物进行了系统分析。确定了肉豆蔻苷、榄香苷、烯丙基四甲氧基苯、芹醇和莳萝酚含量较高的品种。选定了二氧化碳萃取条件，以获得蒸馏残留物含量最低的浓缩物。利用高效分馏技术，在试验装置上从浓缩物中分离出了纯度为 98-99% 的多烷氧基烯丙基苯。通过对一些烯丙基苯进行异构化，然后在特别选定的条件下进行臭氧分解，可以得到产率为 75-80% 的芹醇和莳萝酚醛。
• Synthesis of Antimitotic Polyalkoxyphenyl Derivatives of Combretastatin Using Plant Allylpolyalkoxybenzenes
  作者：Victor V. Semenov、Alex S. Kiselyov、Ilia Y. Titov、Irina K. Sagamanova、Natalie N. Ikizalp、Natalia B. Chernysheva、Dmitry V. Tsyganov、Leonid D. Konyushkin、Sergei I. Firgang、Roman V. Semenov、Irina B. Karmanova、Mikhail M. Raihstat、Marina N. Semenova

  DOI：10.1021/np1004278

  日期：2010.11.29