isodillapiole | 23731-63-7

• 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: isodillapiole
• 英文别名: 4,5-dimethoxy-6-(prop-1-en-1-yl)-2H-1,3-benzodioxole；4,5-dimethoxy-6-prop-1-enyl-1,3-benzodioxole
• CAS: 23731-63-7
• 化学式: C₁₂H₁₄O₄
• mdl: MFCD09028316
• 分子量: 222.241
• InChiKey: OEDZKYGAFWDLGE-UHFFFAOYSA-N

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

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  isodillapiole 在 吡啶 、 氯化亚砜 、 过氧化脲素 、 臭氧 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.5h， 生成 2,3-dimethoxy-4,5-methylenedioxybenzoic acid methyl ester
  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：

  dihydrodillapiole 在 potassium hydroxide 作用下， 以 正丁醇 为溶剂， 反应 24.0h， 以85%的产率得到isodillapiole
  参考文献：
  名称：

  Dillapiole 作为抗利什曼原虫药物：Dillapiole 类似物的发现、细胞毒活性和初步 SAR 研究

  摘要：

  在本文中，报道了从花椒中分离 dillapiole (1) 以及通过还原和异构化反应半合成两种苯丙烷衍生物 [di-hydrodillapiole (2), isodillapiole (3)]。此外，还计算并研究了化合物的分子特性（结构、电子、疏水和空间），以建立一些初步的结构-活性关系 (SAR)。评估了化合物的体外抗利什曼原虫活性和对成纤维细胞的细胞毒性作用。化合物 1 对 Leishmania amazonensis (IC50 = 69.3 µM) 和 Leishmania brasiliensis (IC50 = 59.4 µM) 具有抑制活性，并主要在高浓度下对成纤维细胞产生细胞毒作用。化合物 2（亚马逊乳杆菌的 IC50 = 99.9 µM，巴西乳杆菌的 IC50 = 90.5 µM）和 3（IC50 = 122。L. amazonensis 为 9 µM，L. brasiliensis

  DOI：

  10.1002/ardp.201200212

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。
• Hydrogenation of plant polyalkoxybenzene derivatives: convenient access to coenzyme Q0 analogues
  作者：Alexander E. Varakutin、Egor A. Muravsky、Ilia Yu. Shinkarev、Victor N. Khrustalev、Victor V. Semenov

  DOI：10.1016/j.mencom.2020.09.015

  日期：2020.9

  A technologically advanced protocol has been developed for converting plant allyl(polyalkoxy)benzenes to methyl- and propyl(polyalkoxy)benzenes being intermediates in the syntheses of coenzyme Q0 analogues. The key stage of allyl and benzaldehyde moieties hydrogenation was carried out in a periodical autoclave mode on highly porous ceramic block Pd-catalysts. These catalysts possess large surface area

  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。
• [EN] A PROCESS FOR THE PREPARATION OF VANILLIN AND OTHER SUBSTITUTED PHENYLALDEHYDES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE VANILLINE ET D'AUTRES PHÉNYLALDÉHYDES SUBSTITUÉS
  申请人：COUNCIL OF SCIENT AND INDUSTRIAL RESEARCH AN INDIAN REGISTERED BODY INCORPORATED UNDER THE REGN OF S

  公开号：WO2022003710A1

  公开（公告）日：2022-01-06

  The present invention relates to a chemical process for the production of substituted phenylaldehydes such as vanillin (1a) from substituted phenylpropenes or substituted phenylpropenes enriched essential oils such as eugenol (2a) or eugenol rich essential oils indiscriminately through either cis or trans or a mixture of cis and trans isomer(s) of substituted phenylprop-2-enes such as isoeugenol, an intermediate compound. The invention relates to the conversion of substituted phenylpropenes to other substituted phenylaldehydes, particularly vanillin without the protection of the phenolic group, therefore, it offers a step economy. The present chemical process involves the use of class 3 and 4 solvents thereby devoid of the use of any chlorinated solvent.

  本发明涉及一种化学过程，用于从取代苯丙烯或富含取代苯丙烯的精油（如丁香酚或丁香酚富含精油）中无差别地通过顺式或反式或顺反异构体的取代苯丙烯（如异丁香酚）的中间化合物，生产取代苯基醛类化合物，如香草醛（1a）。本发明涉及将取代苯丙烯转化为其他取代苯基醛，特别是香草醛，而无需保护酚基，因此提供了一种步骤经济性。本化学过程涉及使用3级和4级溶剂，因此不需要使用任何氯化溶剂。
• 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。
• 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。