1-(furan-2-ylmethyl)-2-oxopropyl 4-nitrobenzoate | 1040375-89-0

• 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: 1-(furan-2-ylmethyl)-2-oxopropyl 4-nitrobenzoate
• 英文别名: 1-(furan-2-yl)-3-oxobutan-2-yl 4-nitrobenzoate；[1-(Furan-2-yl)-3-oxobutan-2-yl] 4-nitrobenzoate
• CAS: 1040375-89-0
• 化学式: C₁₅H₁₃NO₆
• 分子量: 303.271
• InChiKey: ZSPPHIZFXKWOGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(furan-2-ylmethyl)-2-oxopropyl 4-nitrobenzoate 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 72.83h， 生成 5-(furan-2-ylmethyl)-4-methylene-5-(3-oxobutyl)-3-phenyloxazolidin-2-one
  参考文献：
  名称：

  Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products

  摘要：

  Captodative alkene 1-acetylvinyl p-nitrobenzenecarboxylate 1a was evaluated for its reactivity in Lewis acid-catalyzed Michael additions with functionalized benzene rings and heterocycles, leading to diverse conjugated addition adducts. The hydrolysis of the latter resulted in the desired functionalized a-ketols, including natural alkaloid actinopolymorphol B (24a). The alpha-ketol core structure of these compounds was used as the building block for the synthesis of the natural alkaloid tanakine (25) and for the divergent construction of highly substituted heterocycles, such as 4-oxazolin-2-ones and butenolides, and their respective fused polycyclic derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.010
• 作为产物：
  描述：

  呋喃 、 3-(p-nitrobenzoyloxy)-3-buten-2-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到1-(furan-2-ylmethyl)-2-oxopropyl 4-nitrobenzoate
  参考文献：
  名称：

  天然呋喃衍生物地黄酮 A、B 和 C 的全合成

  摘要：

  描述了天然存在的呋喃衍生物地黄酮 A、B 和 C 的合成。为制备这些天然产物开发了多种替代合成策略。在路易斯酸催化下，呋喃与捕获的烯烃 1-乙酰基乙烯基 4-硝基苯甲酸酯共轭加成得到相应的加合物，分别通过三步和两步转化为地黄酮 B 和 C。它们还通过丙酮与关键的呋喃-2-碳水化合物-醛中间体缩合制备，这些中间体可以很容易地从 D-果糖中获得。双呋喃地黄酮 A 不仅通过丙酮与 5-(甲氧基甲基)呋喃-2-甲醛的双重缩合在一步程序中获得，而且通过将后者与地黄酮 B 以高总产率缩合获得。

  DOI：

  10.1055/s-2008-1066987

文献信息

• Total Syntheses of Natural Furan Derivatives Rehmanones A, B, and C
  作者：Joaquín Tamariz、Héctor Quiroz-Florentino、Raúl Aguilar、Blanca Santoyo、Francisco Díaz

  DOI：10.1055/s-2008-1066987

  日期：——

  The synthesis of naturally occurring furan derivatives rehmanones- A, B, and C is described. Diverse alternative synthetic strategies were developed for the preparation of these natural products. Conjugate addition of a furan to captodative alkene 1-acetylvinyl 4-nitrobenzoate was carried out under Lewis acid catalysis to give the corresponding adduct, which was transformed into rehmanones B and C

  描述了天然存在的呋喃衍生物地黄酮 A、B 和 C 的合成。为制备这些天然产物开发了多种替代合成策略。在路易斯酸催化下，呋喃与捕获的烯烃 1-乙酰基乙烯基 4-硝基苯甲酸酯共轭加成得到相应的加合物，分别通过三步和两步转化为地黄酮 B 和 C。它们还通过丙酮与关键的呋喃-2-碳水化合物-醛中间体缩合制备，这些中间体可以很容易地从 D-果糖中获得。双呋喃地黄酮 A 不仅通过丙酮与 5-(甲氧基甲基)呋喃-2-甲醛的双重缩合在一步程序中获得，而且通过将后者与地黄酮 B 以高总产率缩合获得。
• Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products
  作者：Daniel Zárate-Zárate、Raúl Aguilar、R. Israel Hernández-Benitez、Ehecatl M. Labarrios、Francisco Delgado、Joaquín Tamariz

  DOI：10.1016/j.tet.2015.07.010

  日期：2015.9

  Captodative alkene 1-acetylvinyl p-nitrobenzenecarboxylate 1a was evaluated for its reactivity in Lewis acid-catalyzed Michael additions with functionalized benzene rings and heterocycles, leading to diverse conjugated addition adducts. The hydrolysis of the latter resulted in the desired functionalized a-ketols, including natural alkaloid actinopolymorphol B (24a). The alpha-ketol core structure of these compounds was used as the building block for the synthesis of the natural alkaloid tanakine (25) and for the divergent construction of highly substituted heterocycles, such as 4-oxazolin-2-ones and butenolides, and their respective fused polycyclic derivatives. (C) 2015 Elsevier Ltd. All rights reserved.