N-(3-oxodecanoyl)pyrrolidine | 217812-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-(3-oxodecanoyl)pyrrolidine
• 英文别名: 1-Pyrrolidin-1-yldecane-1,3-dione
• CAS: 217812-93-6
• 化学式: C₁₄H₂₅NO₂
• 分子量: 239.358
• InChiKey: PCSSQFKTTZPNLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-oxodecanoyl)pyrrolidine 在 四丁基对甲苯磺酸铵 、 silica gel 、 sodium hydride 作用下， 反应 3.42h， 生成 1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldecane-1,3-dione
  参考文献：
  名称：

  Isolation, Structural Assignment, and Synthesis of N-(2-Methyl-3-oxodecanoyl)-2-pyrroline, a New Natural Product from Penicillium brevicompactum with in Vivo Anti-Juvenile Hormone Activity

  摘要：

  A new natural product with in vivo anti-juvenile hormone (JK) activity, N-(2-methyl-3-oxodecanoyl)-2-pyrroline (2), has been isolated from Penicillium brevicompactum Dierckx. Its structure has been tentatively assigned based on spectral data and unambiguously confirmed by alternative syntheses. Compound 2 has been prepared by means of a sequence of reactions beginning with acylation of Meldrum's acid by octanoyl chloride. The subsequent steps have been aminolysis of the resultant intermediate with pyrrolidine,;alkylation of the active position with iodomethane, introduction of a methoxy group in the pyrrolidine ring by anodic oxidation, and final elimination of methanol through adsorption on SiO2 and heating. The natural product 2 and its bicyclic isomer 2-heptyl-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo [2,1-b]-1,3-oxazine (3) are also obtained. This reveals that 2 can be biogenetically related to the recently discovered brevioxime (1). Compound 2 and the synthetic precursors of 2 have shown important biological activities as insecticides (against Oncopeltus fasciatus Dallas) and fungicides. The natural product induces precocious metamorphosis in the target insect (70% precocious adults at 10 mu g/nymph). In view of the above results, these products could be useful as lead molecules for the synthesis of analogues with enhanced biological activities.

  DOI：

  10.1021/jo972267v
• 作为产物：
  描述：

  四氢吡咯 、 5-(1-hydroxyoctylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 以 苯 为溶剂， 反应 12.0h， 以4.50 g的产率得到N-(3-oxodecanoyl)pyrrolidine
  参考文献：
  名称：

  Isolation, Structural Assignment, and Synthesis of N-(2-Methyl-3-oxodecanoyl)-2-pyrroline, a New Natural Product from Penicillium brevicompactum with in Vivo Anti-Juvenile Hormone Activity

  摘要：

  A new natural product with in vivo anti-juvenile hormone (JK) activity, N-(2-methyl-3-oxodecanoyl)-2-pyrroline (2), has been isolated from Penicillium brevicompactum Dierckx. Its structure has been tentatively assigned based on spectral data and unambiguously confirmed by alternative syntheses. Compound 2 has been prepared by means of a sequence of reactions beginning with acylation of Meldrum's acid by octanoyl chloride. The subsequent steps have been aminolysis of the resultant intermediate with pyrrolidine,;alkylation of the active position with iodomethane, introduction of a methoxy group in the pyrrolidine ring by anodic oxidation, and final elimination of methanol through adsorption on SiO2 and heating. The natural product 2 and its bicyclic isomer 2-heptyl-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo [2,1-b]-1,3-oxazine (3) are also obtained. This reveals that 2 can be biogenetically related to the recently discovered brevioxime (1). Compound 2 and the synthetic precursors of 2 have shown important biological activities as insecticides (against Oncopeltus fasciatus Dallas) and fungicides. The natural product induces precocious metamorphosis in the target insect (70% precocious adults at 10 mu g/nymph). In view of the above results, these products could be useful as lead molecules for the synthesis of analogues with enhanced biological activities.

  DOI：

  10.1021/jo972267v

文献信息

• Isolation, Structural Assignment, and Synthesis of <i>N</i>-(2-Methyl-3-oxodecanoyl)-2-pyrroline, a New Natural Product from <i>Penicillium </i><i>b</i><i>revicompactum</i> with in Vivo Anti-Juvenile Hormone Activity
  作者：Pilar Moya、Ángel Cantín、Maria-Angeles Castillo、Jaime Primo、Miguel A. Miranda、Eduardo Primo-Yúfera

  DOI：10.1021/jo972267v

  日期：1998.11.1

  A new natural product with in vivo anti-juvenile hormone (JK) activity, N-(2-methyl-3-oxodecanoyl)-2-pyrroline (2), has been isolated from Penicillium brevicompactum Dierckx. Its structure has been tentatively assigned based on spectral data and unambiguously confirmed by alternative syntheses. Compound 2 has been prepared by means of a sequence of reactions beginning with acylation of Meldrum's acid by octanoyl chloride. The subsequent steps have been aminolysis of the resultant intermediate with pyrrolidine,;alkylation of the active position with iodomethane, introduction of a methoxy group in the pyrrolidine ring by anodic oxidation, and final elimination of methanol through adsorption on SiO2 and heating. The natural product 2 and its bicyclic isomer 2-heptyl-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo [2,1-b]-1,3-oxazine (3) are also obtained. This reveals that 2 can be biogenetically related to the recently discovered brevioxime (1). Compound 2 and the synthetic precursors of 2 have shown important biological activities as insecticides (against Oncopeltus fasciatus Dallas) and fungicides. The natural product induces precocious metamorphosis in the target insect (70% precocious adults at 10 mu g/nymph). In view of the above results, these products could be useful as lead molecules for the synthesis of analogues with enhanced biological activities.