2,5-dimethoxy-3,4-(methylenedioxy)benzyl alcohol | 778-54-1

• 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: 2,5-dimethoxy-3,4-(methylenedioxy)benzyl alcohol
• 英文别名: (4,7-Dimethoxy-2H-1,3-benzodioxol-5-yl)methanol；(4,7-dimethoxy-1,3-benzodioxol-5-yl)methanol
• CAS: 778-54-1
• 化学式: C₁₀H₁₂O₅
• mdl: MFCD11983301
• 分子量: 212.202
• InChiKey: ZLSWEPWEUPHLBJ-UHFFFAOYSA-N

物化性质

• 熔点：
  85 °C
• 沸点：
  341.3±37.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-dimethoxy-3,4-(methylenedioxy)benzyl alcohol 在 二苯并-18-冠醚-6 、 氯化亚砜 、 盐酸肼 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 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 吡啶 、 sodium tetrahydroborate 、 臭氧 、 potassium hydroxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.67h， 生成 2,5-dimethoxy-3,4-(methylenedioxy)benzyl alcohol
  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

文献信息

• Reprint of: Antiproliferative activity of the Antrodia camphorata secondary metabolite 4,7-dimethoxy-5-methylbenzo[d][1,3]dioxole and analogues
  作者：Sing Yee Yeung、Matthew J. Piggott

  DOI：10.1016/j.fitote.2018.04.001

  日期：2018.4

  secondary metabolite, 4,7-dimethoxy-5-methylbenzo[d][1,3]dioxole, have been reported to possess promising anticancer activity. In this work the natural product and analogues bearing more polar substituents were synthesised and assessed for antiproliferative activity in the NCI-60 screen. Although each compound inhibited the growth of some cell lines at 10μM, none had sufficient activity to warrant

  据报道，传统中药真菌樟脑樟及其次级代谢产物4,7-二甲氧基-5-甲基苯并[d] [1,3]二恶唑均具有良好的抗癌活性。在这项工作中，合成了带有更多极性取代基的天然产物和类似物，并在NCI-60筛选中评估了其抗增殖活性。尽管每种化合物均以10μM抑制某些细胞系的生长，但没有一种具有足够的活性值得进一步研究。
• Preparation of Ring-Methoxylated Arylnitromethanes by the Victor Meyer Reaction
  作者：Victor P. Kislyi、Anna S. Maksimenko、Petr A. Buikin、Elena D. Daeva、Victor V. Semenov

  DOI：10.1055/s-0041-1737534

  日期：2022.6

  arylnitromethanes and nitrite esters. A modified approach for the isolation of arylnitromethanes is described, which represents a valuable improvement of the established Victor Meyer reaction. The isolation technique, which involves reaction of the nitrite ester with urea in methanol, allows the desired arylnitromethanes to be isolated, without loss, in 29–75% yields, and generates the corresponding recyclable

  易于获得且稳定的环甲氧基化苄基氯与 AgNO2 反应生成相应的芳基硝基甲烷和亚硝酸酯的混合物。描述了一种改进的芳基硝基甲烷分离方法，它代表了对已建立的 Victor Meyer 反应的有价值的改进。该分离技术涉及亚硝酸酯与脲在甲醇中的反应，可以以 29-75% 的收率无损失地分离出所需的芳基硝基甲烷，并生成相应的可回收苯甲醇。出乎意料的是，环甲氧基化苄基碘不能使用，因为它们不够稳定并且在开发的反应条件下会产生焦油。
• 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
• Synthesis of a new apiol-derived cyclotriveratrylene analog
  作者：Alexander V. Samet、Dmitry V. Tsyganov、Viktor P. Kislyi、Egor I. Tujarov、Victor V. Semenov

  DOI：10.1016/j.mencom.2023.10.011

  日期：2023.11
• JP2023/151880
  申请人：——

  公开号：——

  公开（公告）日：——