diethyl 2-[2-oxo-2-(3,4,5-trimethoxyphenyl)ethylidene]malonate | 1593957-83-5

• 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: diethyl 2-[2-oxo-2-(3,4,5-trimethoxyphenyl)ethylidene]malonate
• 英文别名: Diethyl 2-[2-oxo-2-(3,4,5-trimethoxyphenyl)ethylidene]propanedioate；diethyl 2-[2-oxo-2-(3,4,5-trimethoxyphenyl)ethylidene]propanedioate
• CAS: 1593957-83-5
• 化学式: C₁₈H₂₂O₈
• 分子量: 366.368
• InChiKey: NGUFMUSYPXCBTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl 2-[2-oxo-2-(3,4,5-trimethoxyphenyl)ethylidene]malonate 、 硫代乙酰胺 以67 %的产率得到diethyl 2-[2-methyl-4-(3,4,5-trimethoxyphenyl)thiazol-5-yl]malonate
  参考文献：
  名称：

  SnCl4 介导的硝基取代供体-受体环丙烷和硫代酰胺一锅法合成 2,4,5-三取代噻唑

  摘要：

  用 SnCl 4处理硝基取代的供体-受体环丙烷 (DAC)以及随后与硫代酰胺的反应提供了各种噻唑衍生物的一锅法。芳酰亚甲基丙二酸酯作为反应的中间体产生，它们经过共轭加成，然后与硫代酰胺环化缩合，得到产物。这项工作证明了这类环丙烷在合成所有三种 1,3-唑类方面的多功能性。

  DOI：

  10.1039/d2ob01604d
• 作为产物：
  描述：

  在 三氟化硼乙醚 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 10.25h， 生成 diethyl 2-[2-oxo-2-(3,4,5-trimethoxyphenyl)ethylidene]malonate
  参考文献：
  名称：

  Boron Trifluoride Mediated Ring-Opening Reactions of trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates. Synthesis of Aroylmethylidene Malonates as Potential Building Blocks for Heterocycles

  摘要：

  trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates, upon treatment with BF3 center dot OEt2, undergo ring-opening rearrangement and the Nef reaction to give aroylmethylidene malonates. The products are found to be potential precursors for heterocycles, such as imidazoles, quinoxalines, and benzo[1,4]thiazines.

  DOI：

  10.1021/jo402848v

文献信息

• Synthesis and biological evaluation of new 1, <scp>4‐benzothiazine</scp> derivatives as potential <scp>COX</scp> ‐2 inhibitors
  作者：Maniarasu Meenakshi、Panneerselvam Antojenifer、Muthusamy Karthikeyan、Chidambaram Prahalathan、Kannupal Srinivasan

  DOI：10.1002/jhet.4389

  日期：2022.2

  A series of new 2H-benzo[1,4]thiazine derivatives were synthesized from aroylmethylidene malonates and o-aminothiophenols by condensation/cyclization methodology in order to evaluate their COX-2 inhibitory activity. In-silico studies indicated that among the synthesized compounds, 5i could serve as a potential candidate for the task. So, compound 5i was taken as a model ligand for in vitro studies

  以芳酰基亚甲基丙二酸酯和邻氨基苯硫酚为原料，采用缩合/环合方法合成了一系列新的 2H-苯并[1,4]噻嗪衍生物，以评估其对 COX-2 的抑制活性。计算机研究表明，在合成的化合物中，5i可以作为该任务的潜在候选者。因此，化合物5i被用作体外研究的模型配体。研究的有利结果表明，化合物5i确实是一种极好的 COX-2 抑制剂。
• Sequential One-Pot Synthesis of β-Amino-γ-keto-malonates from Nitro-Substituted Donor–Acceptor Cyclopropanes
  作者：Subramani Selvi、Maniarasu Meenakshi、Kannupal Srinivasan、Chidambaram Visalini

  DOI：10.1055/a-2206-3750

  日期：2024.3

  A sequential one-pot procedure has been developed to access β-amino-γ-keto-malonates from nitro-substituted donor–acceptor cyclopropanes and four different nitrogen heterocycles. The reaction proceeds through in situ generation of aroylmethylidene malonates from 1-aryl-2-nitrocyclopropanes via Kornblum-type ring-opening oxidation using DMSO and subsequent aza-Michael addition with the nitrogen heterocycles

  已经开发出一种连续的一锅法，可以从硝基取代的供体-受体环丙烷和四种不同的氮杂环中获得β-氨基-γ-酮基丙二酸酯。该反应通过使用DMSO 的 Kornblum 型开环氧化和随后与氮杂环的氮杂迈克尔加成，从 1-芳基-2-硝基环丙烷原位生成芳酰基亚甲基丙二酸酯。为了证明所得产物的合成效用，其中一种被转化为哒嗪酮衍生物。
• Boron Trifluoride Mediated Ring-Opening Reactions of <i>trans</i>-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates. Synthesis of Aroylmethylidene Malonates as Potential Building Blocks for Heterocycles
  作者：Thangavel Selvi、Kannupal Srinivasan

  DOI：10.1021/jo402848v

  日期：2014.4.18

  trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates, upon treatment with BF3 center dot OEt2, undergo ring-opening rearrangement and the Nef reaction to give aroylmethylidene malonates. The products are found to be potential precursors for heterocycles, such as imidazoles, quinoxalines, and benzo[1,4]thiazines.
• SnCl₄-mediated one-pot synthesis of 2,4,5-trisubstituted thiazoles from nitro-substituted donor–acceptor cyclopropanes and thioamides
  作者：Maniarasu Meenakshi、Kannupal Srinivasan

  DOI：10.1039/d2ob01604d

  日期：——

  The treatment of nitro-substituted donor–acceptor cyclopropanes (DACs) with SnCl4 and the subsequent reaction with thioamides provide one-pot access to various thiazole derivatives. Aroylmethylidene malonates were produced as intermediates in the reactions and they underwent conjugate addition followed by cyclocondensation with thioamides to afford the products. This work demonstrates the versatility

  用 SnCl 4处理硝基取代的供体-受体环丙烷 (DAC)以及随后与硫代酰胺的反应提供了各种噻唑衍生物的一锅法。芳酰亚甲基丙二酸酯作为反应的中间体产生，它们经过共轭加成，然后与硫代酰胺环化缩合，得到产物。这项工作证明了这类环丙烷在合成所有三种 1,3-唑类方面的多功能性。