methyl 3-ethyl-6-phenyl-2-propyl-2H-pyran-5-carboxylate | 1341233-97-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 3-ethyl-6-phenyl-2-propyl-2H-pyran-5-carboxylate
• CAS: 1341233-97-3
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: MEGHIYGCXUNHGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-ethyl-6-phenyl-2-propyl-2H-pyran-5-carboxylate 在 氧气 、 rose bengal 作用下， 以 甲醇 为溶剂， 以88%的产率得到methyl 1-ethyl-4-phenyl-6-propyl-2,3,5-trioxabicyclo[2.2.2]oct-7-ene-8-carboxylate
  参考文献：
  名称：

  取代基控制的 2,4-二烯酮电环化：2,3,6-三取代 2H-Pyran-5-carboxylates 的合成及其转化

  摘要：

  通过使用 2-烷基-2-烯醛作为与乙酰乙酸酯的反应物，可以轻松获得 2,3,6-三取代的 2H-吡喃-5-羧酸酯。该反应涉及 Knoevenagel 缩合，然后是 6π-电环化，其中烯醛中 C2 烷基取代基的存在有利于形成 (E)-Knoevenagel 加合物，用于随后的电环化。所得的 2H-吡喃被氢化形成 3,4-二氢-2H-吡喃并通过单线态氧环加成转化为内过氧化物。

  DOI：

  10.1002/ejoc.201100780
• 作为产物：
  描述：

  2-乙基-2-己烯醛 、 苯甲酰乙酸甲酯 在 哌啶 、 溶剂黄146 作用下， 以 四氢吡喃 为溶剂， 以39%的产率得到methyl 3-ethyl-6-phenyl-2-propyl-2H-pyran-5-carboxylate
  参考文献：
  名称：

  取代基控制的 2,4-二烯酮电环化：2,3,6-三取代 2H-Pyran-5-carboxylates 的合成及其转化

  摘要：

  通过使用 2-烷基-2-烯醛作为与乙酰乙酸酯的反应物，可以轻松获得 2,3,6-三取代的 2H-吡喃-5-羧酸酯。该反应涉及 Knoevenagel 缩合，然后是 6π-电环化，其中烯醛中 C2 烷基取代基的存在有利于形成 (E)-Knoevenagel 加合物，用于随后的电环化。所得的 2H-吡喃被氢化形成 3,4-二氢-2H-吡喃并通过单线态氧环加成转化为内过氧化物。

  DOI：

  10.1002/ejoc.201100780

文献信息

• Substituent-Controlled Electrocyclization of 2,4-Dienones: Synthesis of 2,3,6-Trisubstituted 2H-Pyran-5-carboxylates and Their Transformations
  作者：Wei Peng、Toshiaki Hirabaru、Hiroyuki Kawafuchi、Tsutomu Inokuchi

  DOI：10.1002/ejoc.201100780

  日期：2011.10

  A facile access to 2,3,6-trisubstituted 2H-pyran-5-carboxylates is developed by employing 2-alkyl-2-enals as reactants with acetoacetates. The reaction involves Knoevenagel condensation followed by a 6π-electrocyclization, in which the presence of the C2 alkyl substituent in the enals favors the formation of (E)-Knoevenagel adducts for the ensuing electrocyclization. The resulting 2H-pyrans are hydrogenated

  通过使用 2-烷基-2-烯醛作为与乙酰乙酸酯的反应物，可以轻松获得 2,3,6-三取代的 2H-吡喃-5-羧酸酯。该反应涉及 Knoevenagel 缩合，然后是 6π-电环化，其中烯醛中 C2 烷基取代基的存在有利于形成 (E)-Knoevenagel 加合物，用于随后的电环化。所得的 2H-吡喃被氢化形成 3,4-二氢-2H-吡喃并通过单线态氧环加成转化为内过氧化物。
• Design, synthesis, and in vitro cancer cell growth inhibition evaluation and antimalarial testing of trioxanes installed in cyclic 2-enoate substructures
  作者：Md. Imran Hossain、Marta Świtalska、Wei Peng、Mariko Takashima、Ning Wang、Marcel Kaiser、Joanna Wietrzyk、Shingo Dan、Takao Yamori、Tsutomu Inokuchi

  DOI：10.1016/j.ejmech.2013.08.008

  日期：2013.11

  A novel series of 1,2,4-trioxanes were synthesized from 2H-pyrans via photooxidation, and their antiproliferative and growth factor inhibitory activity has been investigated across a variety of human cancer cell lines. Compounds 5k, 51, 5s, 7a and 7c exhibited the highest activity and selectivity against a human leukemia (MV4-11) cell line (IC50 = 0.5 mu M). Compound 5o showed the highest growth factor inhibitory activity against a melanoma (LOX-IMVI) cancer cell line (GI(50) = 1.0 mu M). A SAR study has confirmed the importance of the 1,2,4-trioxane unit as a pharmacophore for anticancer activity. The computer-assisted database analysis, COMPARE, has suggested that the compounds have unique mechanisms of actions that were different from those of known anticancer drugs. Some of the selected trioxanes were tested against the NF54 strain, albeit showing weak antiplasmodial activity. The molecular docking of trioxanes and hemin reveals that a short distance (130 angstrom) leads to their physical contact. The UV-vis spectroscopic analysis ensured the definite complexation between 1,2,4-trioxanes and hemin. The role of hemin-trioxane interaction in the hemin-induced oxidative damage has been studied using methylene blue as a substrate by UV-vis spectroscopy. (C) 2013 Elsevier Masson SAS. All rights reserved.